As summer fades away and the crisp air of autumn rolls in, Chicago transforms into a picturesque wonderland. With the changing leaves and cooler temperatures, fall in Chicago is a magical time to explore the city. There's no shortage of exciting and unforgettable fall activities for those visiting the city or for locals who are planning a fun weekend. From pumpkin patches to cool night activities and seasonal flavors, there's something for everyone. Get ready to immerse yourself in the beauty of the season as we unveil the top activities and sights when you're in Chicago in fall.
Fall in Chicago is brimming with arts and culture, and it's just waiting to be explored. Immerse yourself in the world-renowned collections at the Art Institute of Chicago, where the vibrant hues of fall are matched by the masterpieces inside.
Famous museums, including the Shedd Aquarium, Field Museum,
and the Museum of Science & Industry offer free admission days throughout the season.
For a celestial experience, Adler Planetarium opens its doors for free entry on Wednesdays, letting you gaze into the autumn sky. Embrace the cooler weather with a scenic fall boat tour along Chicago's picturesque waterways, offering a unique perspective of the city's stunning architecture draped in autumn colors.
The best shows hit the Chicago Fall theaters with plays and live performances for every kind of visitor. Some popular favorites include:
Find more information about what's on in Chicago on the stage here.
For film enthusiasts, make an outdoor movie part of your Chicago fall activities. ChiTown Movies provides a nostalgic drive-in movie experience featuring blockbusters and classic movies under the stars in the Pilsen neighborhood. Order some food and beverages from the ChiTown Grille to make it a complete night out.
Enjoy an urban open-air cinema experience at the Rooftop Cinema Club at Fulton Market. This venue offers a selection of classic and new films with a starry night sky backdrop. It's a fun blend of cinematic joy with crisp fall evenings.
While exploring the city's vibrant cultural offerings, take in its outdoor architecture and landscapes from a unique vantage point with a fall boat tour. Gliding along the Chicago River provides an unparalleled skyline view, and the fiery fall colors accentuate the city's exceptional landmarks & architecture.
Art and literature fans should attend the Printers Row Lit Fest, September 7-8th, celebrating literature and the written word. Stroll around in the beautifully lined book stalls under the canopy of fall-colored trees in Lincoln Park, marking a day for self-proclaimed bibliophiles.
Get captivated by the musical performances that take center stage during the fall, presenting a spectrum of musical genres embracing the fall rhythm in Chicago.
Riot Fest in Douglas Park, from September 20-22nd, offers a unique opportunity to immerse in Chicago's chaos (in a legal way!) This event merges the raw energy of live alternative rock music (with headliners including Slayer, The Offspring, and Public Enemy) and a vibrant carnival atmosphere complete with festivities and local food and beverage. While the headlining artists draw you in, the enticing carnival rides will make you want to stay!
World Music Festival Chicago from September 20-29th. This annual festival showcases diverse artists from numerous countries. The World Music Festival offers a captivating blend of traditional and contemporary music with free and ticketed performances. Experience the global sounds that this extraordinary event brings to our city.
The Hyde Park Jazz Festival runs September 28- 29th to celebrate the ongoing development of jazz on the south side of Chicago. The event creates opportunities for a diverse group of listeners and creators to support the craft. Attendance is free, but a $10 donation at the entrance is greatly appreciated.
As the leaves change color and the air is cool and crisp, Chicago's culinary scene heats up with the season's flavors. Embrace the essence of fall by visiting one of the city's many breweries, such as Revolution Brewing's Tap Room, where seasonal ales and ciders abound. These local establishments often create special drinks that encapsulate the spirit of autumn.
For heartier fare, dive into a slice of deep-dish pizza, a Chicago staple that tastes especially comforting when the temperatures drop. The city's renowned pizzerias, like the famous Lou Malnati's Pizzeria, can be found in multiple locations across the city, regardless of where you are wandering.
To fully immerse yourself in Chicago's culinary diversity in the fall, consider joining a food tour from Chicago Food and City Tours. These guided tours provide a curated experience of the city's best restaurants and hidden gems, letting you savor various seasonal flavors while exploring Chicago's vibrant neighborhoods.
The Chicago fall food and drink festivals are equally delicious. Check out the Lincoln Park Wine Festival, October 4-6th, for a taste of international wines and live music while you stroll through the eclectic art market.
Whether you're a local or a visitor, indulging in these culinary delights across the city is a must-do to experience the authentic taste of fall in Chicago.
Chicago transforms into a kaleidoscope of fiery hues during the fall, making it the perfect time to explore the city's natural beauty. Lincoln Park is an expansive green space and neighborhood that has become a vibrant canvas of yellows, oranges, and reds. Wander through the park's winding paths to fully appreciate this seasonal spectacle. The Morton Arboretum, a bit farther from the city's hustle and bustle, offers an immersive fall experience with its vast collection of trees from around the world, each adding its unique color to the autumnal mosaic.
For an exceptional view, ascent to 360 CHICAGO witness the splendor of autumn from every angle. Marvel at the panoramic views of the cityscape, downtown, and parks as the foliage bursts into vibrant hues. Fall is the ideal time to visit this attraction with fewer crowds. Book your 360 CHICAGO ticket today.
For an outdoor experience in the urban parks, visit Promontory Point in Burnham Park, where the striking skyline juxtaposes Lake Michigan's calm backdrop. Stroll through Millennium Park & Lurie Garden, where the iconic Cloud Gate ('The Bean') reflects the changing leaves, providing a stunning photo opportunity in one of the best places to see the changing fall colors.
These locations offer a distinct way to experience the glory of fall in Chicago, inviting locals and visitors alike to revel in the season’s beauty.
The scenic trails beckon outdoor enthusiasts the opportunity to hike, bike, and run amidst the stunning backdrop of Chicago's fall colors. The Lakefront Trail, an 18-mile stretch along the shores of Lake Michigan, offers panoramic views of the city skyline and vibrant autumn hues. It's perfect for a leisurely bike ride, a brisk run, or a peaceful hike.
For a more nature-immersed experience, the North Branch Trail delivers 16 miles of winding paths through forests and preserves, showcasing the region's rich biodiversity.
The 606, an elevated trail stretching 2.7 miles, provides a unique urban perspective, connecting four neighborhoods with art installations and green spaces.
Embrace the quintessential fall activity by visiting a pumpkin patch, ideal for families and friends looking for seasonal fun. In the heart of Chicago, JoJo’s Shake Bar transforms an outdoor space into a delightful pop-up pumpkin patch, offering a whimsical backdrop for your autumnal photos along with seasonal treats such as caramel apples, pumpkin pie, apple pie, spiked ciders, and hot chocolate.
Another seasonal option is Jack’s Pumpkin Pop-Up, which opens in September and features many pumpkins and activities like corn mazes and games.
For those willing to venture further into the city, the Night of 1000 Jack-o-Lanterns on the Chicago Botanic Garden grounds illuminates the night with artistically carved pumpkins, creating a mesmerizing spectacle. Carving demonstrations and costumed entertainers also take place.
The Richardson Adventure Farm, known for its epic corn maze, also boasts a sprawling pumpkin patch where you can pick your perfect pumpkin directly from the field.
These seasonal attractions are typically open from September through October, giving you ample opportunity to soak in the fall ambiance, find your ideal pumpkin, and enjoy the flavors of delicious pumpkin goodness.
Oktoberfest, which takes place from September 27 to 29, brings a taste of Bavarian tradition to the heart of the city, complete with authentic German beers, food, and lively music.
The Lincoln Square Apple Festival, on October 5 and 6, celebrates the harvest season with apple-themed treats, crafts, and family-friendly activities.
Open House Chicago, occurring on October 19 and 20th, invites locals and visitors to explore the city's architectural wonders, offering rare access to historic sites and landmarks not typically open to the public. Each festival provides a unique way to enjoy fall, catering to various tastes and interests.
Autumn in Chicago isn't just about the changing leaves and pumpkin patches; it's also a prime time for sports enthusiasts. The sports scene heats up as the city cools down, offering exciting opportunities to catch a game in person.
Football fans can rally behind the Chicago Bears at Soldier Field, experiencing the thrill of NFL action amidst the crisp fall air. For those who prefer the indoor excitement of basketball, the Chicago Bulls begin their season showcasing high-flying dunks and intense competition at the United Center.
Fall in Chicago also includes the opening season of the Chicago Blackhawks as the players lace up their skates and hit the ice, bringing the fast-paced action of the NHL to fans eager for the puck to drop.
Each game provides a unique way to experience Chicago's sports culture. Whether you're a die-hard sports fanatic or just looking for a lively evening, heading out for a game is a perfect fall activity in Chicago.
Chicago turns into a city of haunts and thrills every Halloween, offering a variety of activities that promise unforgettable spooky fun.
Navy Pier becomes a hub of spooky festivities during Halloween, with its array of costumes, decorations, and events suitable for all ages.
For those who dare, the 13th Floor Haunted House presents a chilling adventure with its intricately designed sets and professional actors that guarantee to spook even the bravest souls.
The Haunted Halsted Halloween Parade is an iconic event where creativity shines. It features elaborate costumes and vibrant floats that parade down Halsted Street, celebrating the community and LGBTQ+ culture.
Arts in the Dark is a unique Halloween parade that transforms the city's streets into an open-air gallery of luminous art, showcasing the city's diverse artistic community.
Each Halloween activity offers a different way to experience the eerie beauty of fall in Chicago, perfect for those looking to enjoy the season with a mix of fun and frights.
As the vibrant tapestry of autumn unfolds, it's clear that Chicago in the fall is more than just a season; it's an experience brimming with culture, flavor, and adventure. For more tips, insights, and information on making the most of your visit to Chicago, no matter the season, visit our blog. Discover more ways to fall in love with Chicago, and let the Windy City sweep you off your feet this autumn.
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Chicago is a city that truly has it all! Immerse yourself in an array of world-class museums, vibrant comedy clubs, exciting outdoor adventures, and captivating live shows. Perhaps you’d prefer to experience the most exhilarating attractions Chicago has to offer from different perspectives. Catch a baseball game at the iconic Wrigley Field, enjoy family-friendly outdoor fun at Millennium Park, marvel at the stunning skyline from the 360 CHICAGO Observation Deck at sunset, and discover countless other delights.
Explore our curated list of top Chicago attractions that promise to enchant every visitor and make your stay in this mesmerizing city unforgettable.
875 N. Michigan Avenue 94th Floor
Daily 9 am - 11 pm. The last entry is at 10 pm.
360 CHICAGO, one of the top attractions in Chicago, is an Observation Deck full of activities located on the 94th floor of the former John Hancock building.
Elevate your Chicago experience with a visit to 360 CHICAGO. This attraction has something for all ages and interests. Enjoy incredible panoramic city views of the city skyline, day or night. For those seeking a thrill, try TILT, one of the world's highest thrill rides. Relax, grab a beverage, and enjoy the views at CloudBar—the all-ages and highest bar in Chicago. View the local art installations, the newly upgraded multimedia concourse, and more. Once you arrive, stay on the Observation Deck as long as you like! Book your 360 CHICAGO ticket today.
North Michigan Avenue
Daily 9 am - 10 pm
The Magnificent Mile is Chicago’s famous and premier commercial district. This mile is home to over 450 retailers (including flagship department stores and boutiques), 275 restaurants, entertainment, and attractions. This area includes famous landmarks such as the Chicago Water Tower and the former John Hancock Center, which features the 360 CHICAGO Observation deck.
Visit the "Mag Mile" for a shopping lover's paradise. You can find the most up-to-date fashion trends, innovative technologies, home goods, and more here. You'll literally find something for everyone in your group, plus lots of incentives and premier savings opportunities.
Want to learn about specific things to do on the Mag Mile? Check out this blog post!
1200 S DuSable Lake Shore Drive
Daily 9 am - 6 pm
Embark on a mesmerizing underwater journey at Shedd Aquarium, where over 32,000 marine creatures, from beluga whales and bluegills to stingrays, penguins, and sea otters, await your discovery. Check out the 75-minute guided tour highlighting the aquarium's most extraordinary features. Experience the behind-the-scenes magic as you enjoy prime seating for an Animal Spotlight and converse with an animal care manager. You can also explore the exhibits at your own pace with the Shedd Go app, which allows you to navigate the aquarium effortlessly.
Washington (George) Park, 740 East 56th Place
Wed-Sun, 11:00 am - 4:00 pm
The DuSable Museum of African American History boasts over 15,000 diverse pieces, including paintings, sculptures, prints, and historical memorabilia. It hosts special exhibitions, workshops, and lectures highlighting artists and historical events. Key exhibitions include Freedom: Origin and Journey, honoring lives dedicated to freedom and equality; The Harold Washington Story, chronicling Chicago's first African American mayor; and South Side Stories, showcasing Dr. Margaret T. Burroughs' artistic and activist legacy.
Check the admission page to see if you qualify for free admission.
1805 N. Ridgeway Avenue
Daily 6 am - 11 pm
The 606 is an abandoned railway transformed into a 2.7-mile elevated park and trail on Chicago's northwest side. Built on an old industrial train line, the 606 features street-level parks, scenic look-out points, an observatory, and public art. Officially named the Bloomingdale Trail, it derives its name from the numbers in Chicago's zip codes. Spanning Wicker Park, Bucktown, Logan Square, and Humboldt Park, the trail is a favorite among walkers, runners, bikers, and families. With bike rentals from Divvy stations and year-round events like community bonfires, the 606 offers something for everyone.
337 E. Randolph Street
Starting at 6 am - 9 pm. Times vary according to the activity.
During the winter, Maggie Daley Park transforms into a fun winter Ice Skating Ribbon that offers stunning skyline views and a lively ambiance. Lace up your skates (rentals are available) and glide through one of the most unique rink parks. In the summer, the park is the perfect rollerblading destination. The park is brimming with more activities for those who enjoy the outdoors, like a climbing wall, mini golf, tennis, and more. Discover the myriad of attractions at Maggie Daley Park throughout the year.
111 E. Wacker Drive, Suite 1321
Sun - Thu, 9 am - 5 pm
Fri & Sat, 9 am - 7 pm
The Chicago Architecture Center's riverfront location is nearly 10,000 square feet of exhibition space filled with super-sized models and views of iconic skyscrapers. The Center exhibits focus on Chicago’s diverse neighborhoods, housing types, leading architects, and future projects. Among the highlights is the largest scale model of the city, with more than 4,250 miniature buildings, interactive touchscreens, and a cinematic backdrop animating key moments in its history. Alternatively, join a CAC walking tour or River Cruises aboard Chicago’s First Lady. Learn the stories behind the buildings and how the CAC inspires people to discover why design matters.
22 E Wacker Drive
Daily 6 am - 11 pm
The Chicago Riverwalk, located on the south bank of the Chicago River, is a must-visit destination stretching 1.25 miles from Lake Michigan to Lake Street. This award-winning, pedestrian-friendly area offers a rich tapestry of experiences, from intimate coves and breezy cafes to wineries and bars. Visitors can immerse themselves in public art, monuments, and nearby museums or embark on various water excursions, including boat tours and kayaking. The Chicago Riverwalk provides a picturesque backdrop for those who seek culinary delights or cultural enrichment.
Things to do on or along the Riverwalk:
1614 E. 113th Street
Thu-Sun, 11 am - 3 pm
In 1880, George M. Pullman established a model industrial town to bolster his luxury railcar business, creating a unique intersection of history, architecture, railroad innovation, urban planning, labor milestones, and civil rights.
The Historic Pullman Foundation now safeguards these historic buildings, documents, and artifacts, acting as the official friends group of Pullman National Historical Park. Visitors, including history aficionados, national park devotees, train enthusiasts, and curious families, can enjoy captivating tours, exhibits, and events at Chicago's inaugural national park.
5700 S. DuSable Lake Shore Drive
Daily, 9:30 am - 5:30 pm
Adventure through a multi-sensory experience at the Griffen Museum of Science and Industry! With its award-winning exhibits, the museum promises to captivate every visitor through immersive experiences, giant-screen films, and engaging events. Don’t miss the groundbreaking exhibit 007 Science: Inventing the World of James Bond, which delves into the science and technology behind the film series' legendary gadgets, vehicles, and stunts. Each exhibit at MSI is designed to ignite curiosity and inspire a passion for learning, making it the perfect destination to explore the world's marvels during your cherished time off.
See exciting new exhibits always on display
1300 S DuSable Lake Shore Drive
Daily 9 am - 4 pm
The Adler Planetarium is a pioneering institution devoted to the wonders of astronomy and astrophysics since 1930. Perched at the northeastern edge of Northerly Island by Lake Michigan, it is considered America's first planetarium. Its core mission is to ignite curiosity and foster a deeper understanding of the cosmos. The Planetarium includes three state-of-the-art theaters, a series of space science exhibits, and a remarkable collection, including the Gemini 12 space capsule and various antique scientific instruments and printed works.
78 E. Washington Street
Daily 10 am - 5 pm
The Chicago Cultural Center, inaugurated in 1897, spans an entire city block across Michigan Avenue from Millennium Park in the Chicago Loop Neighborhood. This magnificent architectural gem, managed by the Department of Cultural Affairs and Special Events, serves as the city's official reception venue. The Mayor of Chicago has welcomed presidents, royalty, and diplomats here. The center is also accessible to the public, who can admire its grand architecture featuring Tiffany stained glass domes and enjoy over 700 exhibits and humanities programs annually, many of which are entirely free.
1616 N Wells Street, 2nd Floor
Mon-Thu, 10 am - 11 pm
Fri-Sun, 10 am - 12 am
A visit to Chicago wouldn’t be complete without diving into its iconic comedy scene. Many of America's top comedians launched their careers in the Windy City through improv and sketch comedy. The renowned Second City serves as a breeding ground for some of the biggest stars in the industry. Legendary figures such as John Belushi, Tina Fey, and Steve Carell began their journeys here, leaving an indelible mark on comedy. Attending one of Second City's main stage performances is an absolute must.
1852 W. 19th Street
Tue-Sun, 10 am - 5 pm
This sprawling 48,000-square-foot, cutting-edge museum is dedicated to deepening the understanding and appreciation of Mexican art and culture on both sides of the border. The museum boasts an impressive permanent collection of Mexican art, complemented by visual and performing arts programs, top-tier arts education initiatives, and resources for the professional growth of Mexican artists. Check out one of the largest collections of Mexican art in the US (over 22,000 pieces) and cultural programs—including theater, dance, music, and literary events- that celebrate the rich tapestry of Mexican heritage.
Cermak Road and Wentworth Avenue
24 hours
Since 1912, this tight-knit community has flourished in Chicago's South Side, spanning Wentworth Avenue and attracting residents and tourists. The neighborhood offers a lively experience with its authentic cuisine, captivating architecture, and numerous shops, cafes, dim sum spots, and teahouses. For a more extensive shopping experience, explore the Chinatown Square outdoor mall. To delve into the rich history, visit the Chinese-American Museum.
1060 W. Addison Street
See the game and tour schedule.
Ignite your passion for sports and history by visiting Wrigley Field, a Chicago treasure steeped in over a century of heritage. Whether you catch a game, stroll among the seats and concession stands, or take a full stadium tour, the experience will be captivating. Every Cubs enthusiast, regardless of age, will delight in standing on the same field graced by legendary players, relaxing in the dugouts, and exploring much more.
The Loop Community Area
Daily, 6 am - 11 pm
Millennium Park is a must-visit attraction in the heart of downtown Chicago, offering diverse activities and sights. The lakefront campus features the iconic Cloud Gate statue, interactive fountains, serene gardens, free events, public art, skating rinks, rock climbing, and expansive green spaces. Don’t miss the Jay Pritzker Pavilion, where a state-of-the-art sound system mimics indoor theater acoustics. Enjoy events like the Summer Music and Film Series on the Great Lawn and visit Lurie Garden, an award-winning botanical masterpiece that provides a peaceful oasis with native plants year-round.
1601 N. Clark Street
Tues–Sat, 9:30 am - 4:30 pm
Sun, 12:00 pm - 5:00 pm
Immerse yourself in the rich tapestry of Chicago's history at the Chicago History Museum. There are many stories to uncover, from the city's sports legacy and political milestones to the iconic Union Stockyards and the infamous Great Chicago Fire. Engage with c exhibitions and dynamic programs within the museum's walls, or experience the city's history firsthand through guided tours and special events. Established in 1856, the museum stands as a beacon of knowledge, inspiration, and civic participation, illuminating Chicago's past, present, and future.
111 S Michigan Avenue
Thu-Mon, 11 am - 8 pm
Tue-Wed, Closed
The Art Institute of Chicago is a world-renowned museum boasting one of the largest permanent collections in the United States. This encyclopedic institution collects, preserves, and exhibits works across all mediums, cultures, and historical periods while hosting unique exhibitions. With over 260,000 pieces of artwork, the museum excels in Impressionist and Post-Impressionist art, early 20th-century European pieces, contemporary art, Japanese prints, and photography. The Art Institute also offers about forty special exhibitions annually and daily lectures, tours, and performances.
From Ardmore Ave. on the north to 71st St. on the south, Chicago
Open Daily
One of the hallmark characteristics of Chicago is its iconic setting along the shores of Lake Michigan, encompassing 26 miles of breathtaking coastline. Integral to this waterfront is the Lakefront Trail, a charming pedestrian route extending over 18 miles. This trail provides awe-inspiring vistas of the lake and the city’s skyline. Throughout the year, it attracts walkers, cyclists, and runners alike. The Lakefront Trail seamlessly links numerous lakefront parks, beaches, museums, neighborhoods, and waterfront dining spots, making it a vibrant artery of urban life.
4802 N Broadway Avenue
Daily 4 pm - 1 am
Celebrating a centennial milestone, the Green Mill Jazz Club is the city's quintessential jazz venue. With its doors first opening in 1907, this establishment has earned the title of the oldest jazz club in the United States. Once a favored spot for the infamous Al Capone, it exudes the charm and secrecy of Prohibition-era speakeasies. Styled after the 1940s, the club offers live performances every night of the week. Even if jazz isn't your usual scene, the club's history and roster of legendary performers and patrons make it a must-visit. True to its roots, it remains a cash-only bar, just as it was in the 1940s.
1400 S Lakeshore Drive
Daily 9 am - 5 pm
The Field Museum of Natural History is the attraction in Chicago offering a treasure trove of wonders to captivate visitors of all tastes. Since its establishment in 1894, the museum has amassed a staggering collection of over 40 million specimens and artifacts from around the globe. The museum's architecture narrates an extraordinary history. With ever-changing exhibits, there's always something new and exciting to discover.
600 E. Grand Avenue
Sun-Thu, 11 am - 9 pm
Fri-Sat, 11 am - 10 pm
Navy Pier spans 50 picturesque acres along the waterfront, offering an array of dining, exhibitions, shops, and entertainment. Revel in the breathtaking views of Lake Michigan and the Chicago skyline as you ride the 200-foot Ferris wheel, explore the hands-on exhibits at the Chicago Children's Museum, attend a free concert, or embark on a quest to discover art and murals. Thrill-seekers can indulge in exhilarating speedboat tours, while those looking to relax can opt for a serene sightseeing cruise.
Whatever Chicago Attractions you choose to visit, your visit will be incredible. For more tips and ideas for enjoying Chicago, follow our blog.
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Location: 201 E Randolph Street
Proposal Photography Permit: Required
Permit Fee: $35 application fee +$45 photography fee/hour
In the heart of downtown Chicago lies Millennium Park, a favorite spot for a proposal amidst iconic city landmarks. The park's famed Cloud Gate sculpture, affectionately known as "The Bean," provides a reflective, mesmerizing backdrop perfect for the occasion. Beyond The Bean, the park's beautifully landscaped gardens and impressive cityscape views offer various romantic spots for getting down on one knee. Even more, you can heighten the ambiance by timing your proposal with one of the park's regular concerts or public events. While Millennium Park operates from 6 am to 11 pm, you'll want to keep in mind that peak hours and events may increase the number of spectators to your special moment.
Location: 201 E. Randolph St., between Monroe St. and Columbus Ave
Proposal Photography Permit: Required
Permit Fee: $35 application fee +$45 photography fee/hour
Pop the question at Lurie Garden, a magnificent five-acre sanctuary famed for its sustainable design and gorgeous perennial garden located at Millenium Park. This spot would offer a peaceful and visually striking setting for your marriage proposal. The contrasting scenery of native plants against the city's towering skyline provides a gorgeous backdrop, blending nature's beauty with architectural grandeur. Planning your proposal during the blooming season, from late spring through early fall, will showcase the garden at its most vibrant, making it a great choice for your special moment. In one word? Beautiful.
Location: 500 N Lake Shore Dr, Chicago
Proposal Photography Permit: Not Required
Permit Fee: None
Step into Milton Lee Olive Park, a hidden gem away from the hustle and bustle, waiting to be the stage for your grand proposal moment! This isn’t just any spot; it’s where Lake Michigan meets the vibrant Chicago skyline, creating a magnificent canvas that's both wildly natural and unmistakably urban. For couples who chase extraordinary experiences, this park is the perfect spot for you to declare your love. Imagine—the privacy, the secluded paths, all leading to that one magical moment where you pop the question against a backdrop nothing short of spectacular. No permits, no fuss, just ensure you make your move before the clock strikes 11 pm. Here’s your chance to step up, embrace the moment, and mark the beginning of your forever.
Location: 875 N Michigan Avenue
Proposal Photography Permit: Not Required
Permit fee: None
See Proposal Package
Transform your proposal into a landmark moment at 360 CHICAGO! Perched on the 94th floor of the former John Hancock Building, this observation deck gifts you a breathtaking 360-degree panorama that sprawls over Chicago and spills into the majestic Lake Michigan. Envision taking your love to new heights, proposing amidst a canvas of sunset or the city's luminous night lights. The Chicago Proposal Package is designed to fuel that romance with all the right touches. It offers you a private space with unmatched views, captivating "Marry Me" lights, a trail of rose petals, adrenaline-pumping TILT thrill ride tickets for two, and a duo of drinks from CloudBar's Sip Menu. Once there, you're invited to immerse yourselves entirely and stay as long as you like. Seize this opportunity to etch your moment in eternity, showcasing the unstoppable force of your love. Let 360 CHICAGO be the launchpad for your journey together. Propel your love story into the stratosphere, where it rightfully belongs!
Location: 2001 N Clark St, Chicago
Proposal Photography Permit: Yes
Permit Fee: $150 /hr photo session
Lincoln Park Zoo offers a whimsically romantic setting for those looking to pop the question amidst gardens, animals, architecture, and Chicago's skyline view. The enchanting backdrop of exotic animals and beautifully landscaped grounds provides a unique and lively atmosphere for a proposal. Whether you choose to kneel beside the tranquil swan pond, under the leafy embrace of the conservatory, or in front of your partner’s favorite animal exhibit, this location ensures an unforgettable moment. The zoo offers a playful setting that speaks to the adventurous spirit of love.
Location: Southern end of the zoo, east of Café Brauer 2121 N Stockton Drive
Proposal Photography Permit: Yes
Permit Fee: $150 /hr photo session
Lincoln Park is a haven for nature lovers and a picturesque choice for a proposal. This expansive park is adorned with sprawling gardens, tranquil ponds, and scenic pathways, offering a variety of enchanting settings. Opt for a bridge overlooking the South Pond for a beautiful view that encapsulates the essence of nature in the city. Beyond its natural charm, this idyllic park is known for its peaceful ambiance that invites lovers to express their heartfelt feelings. Plus, with its proximity to neighboring eateries and fantastic cityscape views, your proposal can easily be extended into a romantic date, marking an unforgettable chapter in your love story.
Location: 125 W Fullerton Parkway Suite 4800
Proposal Permit: Required
Permit Fee: $150.00
Immerse yourself in nature's serenity at The Alfred Caldwell Lily Pool within Lincoln Park. This tranquil oasis is characterized by its meandering stone pathways, native plants, and, most notably, the picturesque lily pool that provides a serene and intimate location to pop the question. The Lily Pool is open to visitors from mid-April through early November, from sunrise to sunset.
Location: Southernmost end of the zoo, east of Café Brauer and Farm-in-the-Zoo 2121 N Stockton Drive
Proposal Photography Permit: Required
Permit Fee: $125.00
This architectural beauty in Lincoln Park creates a gorgeous setting for an engagement. The Honeycomb Structure, officially known as the People's Gas Pavilion, is a marvel of modern design, featuring a lattice-like steel network forming an expansive canopy above a lush green landscape. The interplay of light and shadow through its geometric patterns provides a visually stunning setting. Picture the moment you ask your person to marry you, enveloped by this architectural masterpiece, with nature as your witness. This spot not only offers a unique backdrop for such a pivotal moment, and also symbolizes the interconnectedness of your future together.
Location: 5700 S Lake Shore Drive
Proposal Photography Permit: Inquire
Permit Fee: Inquire
Ignite a spark of discovery and innovation at the Museum of Science and Industry for your proposal. This place is especially appealing to couples who share a passion for science, exploration, and learning. This iconic venue, one of the largest science museums in the world, offers an extraordinary array of exhibits that provide a dynamic and interactive backdrop for popping the question. Imagine the excitement of proposing amidst groundbreaking scientific achievements, from standing under a massive suspended aircraft to the shadows of a towering dinosaur skeleton! It will be a moment that your loved one least expects. Check with Museum staff for any required permissions or fees related to events or photography. Operating hours vary, so make sure to plan your surprise around a time when your favorite exhibits are accessible.
Location: 1601 N. Lake Shore Drive
Proposal Photography Permit: Not Required
Permit Fee: None
It's one of the city's most popular beaches, with some of the best views of the city and Lake Michigan, hands down! Imagine walking hand in hand along the sandy shores of North Avenue Beach, pausing as the sky is painted in orange and purple hues. At this moment, as the bustling city seems to stand still, presenting your beloved with the ultimate question here makes for an exceptionally picturesque and heartfelt moment. Not only is this location easily accessible, but it also does not require a permit for proposals, making it a cost-effective yet heartwarming choice. Keep in mind, though, that this public space is most peaceful during early mornings or late evenings.
Location: South bank of the Chicago River
Proposal Photography Permit: Not Required
Permit Fee: None
Take a stroll along the Chicago Riverwalk for an enchanting proposal experience. This waterside promenade weaves through the heart of the city with its captivating views. Lined with impressive skyscrapers and bridged by historic walkways, the Riverwalk provides a unique blend of natural beauty and architectural marvels. Choose a spot near one of the many iconic landmarks to pop the question, which will likely be very unexpected! The ideal time for a more serene moment would be in the early morning or late evening, avoiding significant crowd times, typically in the mid-afternoon and on weekends.
Location: 1200 W Randolph Street
Proposal Permit: None
Permit Fee: None; inquire about private space/dining and drink experience
Do you and your partner love fine wines and an intimate setting? Look no further than the City Winery Chicago, which offers a lovely proposal location. Located on the vibrant Chicago Riverwalk, this venue combines urban sophistication with the charm of wine country, making it an idyllic spot for this special moment. With its customizable event spaces, you can curate an ambiance that reflects your love story, whether it's a private barrel room illuminated by candlelight or a scenic outdoor patio with river views. Although the City Winery does not require permits for small, informal gatherings, securing a private space for your proposal might involve a reservation fee and should be arranged directly with the venue. This ensures your moment is as seamless as it is memorable. Whether over a glass of their finest vintage or a custom dining experience, proposing at City Winery promises romance and tasty libations.
Location: Center of Grant Park, 301 S Columbus Drive
Proposal Permit: Required
Permit Fee: $35 application fee + $45 photography fee
This historic fountain (Remember the opening scene of Married With Children?) is one of the largest in the world and provides a visually stunning background for your special moment with your love because of its rococo-style design and dazzling water displays. The fountain's water shows and Chicago's skyline in the background create a romantic atmosphere, especially during the evening light and music performances from April to October. For an added wow factor, plan for the proposal to happen when the fountain's water display is in full swing. The park is open from 6 am to 11 pm, offering flexibility for your proposal plans. However, be mindful of public events that might coincide with your planned date. Visiting the Buckingham Fountain will deliver a visually spectacular moment.
Location: 1000 Lake Cook Rd, Glencoe, IL (20 miles from Chicago)
Proposal Photography Permit: Required
Available daily 10 a.m., 12 p.m., and 2 p.m.
Permit Fee: $250 Includes parking for two passenger vehicles
Escape to a world where nature's beauty unfolds at every turn at the Chicago Botanic Garden. This sprawling sanctuary offers an idyllic setting for your proposal if your partner loves meticulously curated gardens and tranquil water features. Its vast array of landscapes, from the romantic English Walled Garden to the serene Japanese Garden, provides a variety of locations perfect for dropping to one knee. Choosing this location for your special moment ensures a backdrop filled with natural beauty and a tranquil atmosphere.
Location: 600 E Grand Ave
Proposal Photography Permit: Not required
Permit Fee: Not required
Looking for an engagement location that will deliver fun and energy? Navy Pier, stretching into Lake Michigan, offers a captivating backdrop for your proposal. This iconic Chicago landmark is home to the Centennial Wheel, providing a unique opportunity to pop the question high above the city with panoramic views of the skyline and lake. The pier's lively atmosphere, filled with gardens, restaurants, and attractions, adds a festive touch to your special moment. You won't have a private location, but you will have a blast for your big day.
Location: 23rd Floor, London House Chicago. 85 E Wacker Drive
Proposal Permit: Required
Permit Fee: Inquire
Perched atop the luxurious London House Chicago, The Cupola (a private outdoor section on the roof of London House) offers an intimate and breathtaking venue for a marriage proposal. This exclusive space boasts Chicago skyline views of the Chicago River, creating a dramatic and unforgettable scene. The Cupola's elegance and privacy make it ideal for a special moment away from the city below. The team at London House can top off your evening with a special dinner menu to celebrate your special occasion.
This is one of the classic summer activities in Chicago. Every Wednesday at 9 pm and Saturday at 10 pm, starting Memorial Day weekend through to Labor Day weekend, marvel at the dazzling fireworks spectacle put on all summer long at Chicago’s famous Navy Pier. Take in the show from any of the beaches along the lake, from the pier itself, or book a romantic dinner cruise to see them from the water in style.
For the most stunning vantage point (like in this photo),head to the 360 CHICAGO Observation Deck to catch the fireworks from 94 floors up!
The boys of summer are in full swing as the Cubbies take to the diamond this summer in front of their loyal fans at Wrigley Field. Even if you’re not into baseball, Wrigley Field is designated as a historic landmark, and is one of the two oldest operating Major League parks in the country. Can you guess the other one?
Get your Cubs tickets now!
Situated in the lush Logan Square neighborhood, the 606 Trail is Chicago’s answer to the High Line, and summer in Chicago is the perfect backdrop. At almost three miles long, the beautiful elevated park used to be a railroad track for the city’s famous “L” Train. Walk, skate, or ride your bike and discover art installations, murals, and other community engagement projects. The 606 is also a great place to bring a picnic!
The incredible story of Chicago might best be told through its captivating architecture. These guided cruises are the perfect way to relax, take in the sights, and learn some of the amazing history behind the city’s most iconic buildings.
Reserve your Architecture Cruise in advance, these are popular tours!
Chicago has miles of lakefront beaches and spots like this to enjoy the gorgeous skyline from literally every angle. Plan a drink on a boat, head to the beach such as Foster Beach, North Avenue Beach, or Rainbow Beach, or find somewhere to dine al fresco with views from above. You've got options in Chicago!
If big adventure is what you’re after, head just 22 miles outside of Chicago to The Forge: Lemont Quarries, where you’ll find outdoor activities for the whole family. No matter your age or fitness level, there’s something for everyone at The Forge, including climbing, ziplining, competitive activities like laser tag, hiking, kayaking, and so much more. There are even several dining options to refuel after your adventure.
Check out all the fun at The Forge, and book your adventure now!
The Forge also features a full summer schedule of concerts, live music, and events too.
Take in breathtaking panoramic views of the whole city from 1,030 feet above the famed Magnificent Mile at the 360 CHICAGO Observation Deck at the top of the former John Hancock Center. Visit CloudBar for a Sip and View, and if excitement is what you’re after, step into TILT, the world’s highest thrill ride. It's no surprise why its one of the top things to do in Chicago in summer.
Get your tickets now for 360 CHICAGO and skip the line!
From June 26, 2025, to August 7, 2025 (every Monday and Thursday) at Millennium Park’s Jay Pritzker Pavilion, enjoy music from around the world and right here in Chi-town, featuring artists both emerging and established. This summer’s series always kicks off with a renowned music artist, so check back to see who is headlining the series this year.
Admission to concerts is always free, and the park is open from 6:30 p.m. to 11 p.m. View the summer events schedule for super helpful information about planning your visit
Spend your summer exploring the City of Chicago's wide array of farmer's markets! Stocking up on freshly grown produce, aromatic flowers, pre-prepared meals, handmade goods, and uncommon trinkets is just a short journey away. From May to October, you can visit the longest-running market in Chicago - the iconic Daley Plaza Farmers Market - as well as the storied Maxwell Street Market and numerous community markets. For a full list of markets, check out the map and date schedule for more information.
Summer in Chicago isn't complete without a good festival. Grant Park is home to the only free outdoor classical music festival in the country. Featuring the Grant Park Symphony Orchestra and Chorus, along with a bevy of guest musicians and conductors, performances take place throughout the summer, and the lineup of performances this year look fantastic. The music festival starts in June toAugust.
Since 1980, Chicago's food scene has come alive during summertime with a fantastic range of restaurants and eateries showcasing the city's incredible culinary art and diversity. The festival gets going in Marquette Park on June 28th, 2025, then to Pullman Park on July 19th, 2025, then Albany Park on August 9th, 2025. The final weekend returns to Grant Park on September 5th - 7th, 2025. Don't forget, entry is free! For more details, please visit the Taste of Chicago.
Mark your calendars for Sunday, June 29th, 2025 for the most joyous, colorful, fun events of the year. The Chicago Pride Parade is one of the biggest Pride festivals in the world. This year’s theme, United in Pride, showcases the power of diversity, unity, and the power of love as an unstoppable force for good. For more details, please visit the Chicago Price Parade.
The City of Chicago is delighted to present the Air and Water Show on August 16th & 17th, 2025, with a rehearsal on Friday August 15th. Now in its 63rd year, with a reported attendance of up to two million annually, you’ll see performances from a selection of top civilian and military pilots and aircraft, such as the U.S. Navy Blue Angels, the U.S. Air Force Thunderbirds, and the U.S. Army Parachute Team Golden Knights. There’s no public seating areas available at the event, so you’re encouraged to stake out their viewing spots early along the lakefront from Fullerton to Oak Street, with North Avenue Beach as the focal point.
To make the most of the show, consider taking in the views from 360 CHICAGO, with its prime and uninterrupted panoramic views of the show.
The world-renowned Lollapalooza music festival returns to its permanent home in Chicago on July 31st to August 3rd, 2025, taking over Grant Park with 9 stages and over 170 bands. Fans can look forward to spectacular performances from Tyler, The Creator, Luke Combs, Olivia Rodrigo, Kron, Rüfüs Del Sol, Sabrina Carpenter, A$AP Rocky, and so many more.
Available ticketing options include General Admission, VIP, and Platinum, as well as one-day, two-day, and four-day passes. For the complete lineup and ticket information, check out Lollapalooza's official website. Get your hands on the Lolla lineup, details, and tickets now!
There’s so much to do this time of year in the windy city! We hope this Chicago Summer Guide is helpful as you and your loved ones get out into the warm weather and take in all the city has to offer. While you're here, explore the vibrant Chicago Neighborhoods using this handy guide for fun things to do, cultural flavors, and great views of the city.
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Streeterville
Enjoy the highest bar in Chicago and the most exceptional views of the city skyline, hands down! Located at the 360 CHICAGO Observation Deck on the 94th floor of the former John Hancock Building, you’ll get unparalleled 360-degree views of the Chicago skyline and Lake Michigan. Get the best seat in the house at CloudBar, a modern, sleek lounge where European design meets Chicago flare. Peruse the snack list, or order a unique cocktail (or mocktail) from the menu. Try a Wild and Personable, a Gold Coast Manhattan, or other drinks inspired by the culture and energy of the Chicago neighborhoods.
CloudBar, the top bar in Chicago with a view, is open from 9 am-11 pm daily. Special tickets are available for admission on the Observation Deck, which include a drink from a select menu (Sip & View Ticket) or a Sip, TILT, and View Ticket, which includes a ride on TILT— one of the highest thrill rides in the world. Enter with an admission ticket and stay as long as you like!
Streeterville
Z Bar, in one word, is classy. It is a luxury, upscale rooftop bar concept located on the 6th floor of The Peninsula Chicago Hotel on Michigan Avenue. Z Bar combines the allure of global cuisine and drinks with a view along downtown's Magnificent Mile. World-renowned mixologists curate the bar's inventive cocktail menu that guarantees a great hangout whether you're enjoying the environment amid the chic, cosmopolitan interior or basking in the open air on the terrace.
Streeterville
Imagine 36,000 square feet of indoor and outdoor rooftop and bar space! You can find it at Offshore Rooftop & Bar, America's largest rooftop venue at Navy Pier. Visit this place during a trip to the iconic pier to sample from the list of inventive bar snacks, shared plates, wine, cocktails, and craft beers. The bar juts out into Lake Michigan and offers fantastic views of the Chicago skyline and the lake. The space is modern and sleek, and for chilly days, its fire pits and comfortable seating areas will make you want to linger here a little longer.
Downtown-The Loop
Enjoy the culture and flavors of South America without ever leaving Chicago's financial district! Boleo lives on the 15th floor of the Kimpton Gray Hotel and is known for its rain-or-shine retractable glass roof. Inspired by South America's vibrant colors and textures, the bar's design creates a warm and inviting ambiance, perfect for lively evenings with friends or intimate nights out. The space is infused with the sounds of live Latin music that complements the rich flavors of the Peruvian and Argentinean-inspired street food menu. Sip on a Pisco Sour or a Smoky Paloma crafted by expert mixologists. Whether you're here to enjoy the music or to savor the intricately designed cocktails, Boleo is an exciting destination among the rooftop bars in Chicago.
Downtown-The Loop
Discover Raised, located in the heart of the Loop. This inviting space blends the city's architectural grandeur in an industrial chic ambiance with garden-inspired decor, which gives this open-air venue an urban yet relaxed vibe after a busy day in the city. With views that stretch over the Chicago River and into the city's sprawling skyline, Raised offers a picturesque setting for enjoying its extensive food and drink menu. Here, local craft brews, imaginative cocktails, and a curated selection of American dishes take center stage. Raised is a popular destination for those looking to embrace Chicago's rooftop culture.
Downtown-The Loop
Roof on the Wit, a pioneering rooftop lounge, is perched on the 27th floor of the Wit Hotel, steps away from the iconic Chicago Theatre. Guests are welcomed into a space that combines the allure of an elegant cocktail party with the energy of a premier nightclub. The Roof on the Wit has a retractable roof that guarantees an unforgettable experience regardless of the weather. The menu is equally interesting, with an impressive array of drinks and a vast food menu of shareable plates, pizza, sushi, and more. This rooftop bar not only captivates with its panoramic views of the city's skyline but also its unique design, featuring fire pits and sleek, modern seating areas.
Downtown-The Loop
Nestled within the historic Chicago Athletic Association Hotel, Cindy's Rooftop is a beacon of culinary and mixology excellence. This rooftop bar features a glass atrium and airy open-air sections with fantastic panoramic views of Millennium Park, the Art Institute, and the shimmering waters of Lake Michigan. This spot features a menu emphasizing fresh, seasonal ingredients in its food and drink offerings. The venue has become renowned for its delectable brunch options, making it a favorite for early risers and afternoon loungers. Head to this spot for a relaxed atmosphere and a memorable rooftop experience in Chicago.
Downtown-The Loop
Cerise, a bar at the Virgin Hotels Chicago in the Loop neighborhood, offers a refreshing take on the rooftop bar experience with its energetic atmosphere and eclectic design. This 26th-floor bar commands an impressive view of downtown, serving as a perfect backdrop for evening escapades. Cerise is known for its bold cocktails, nightclub atmosphere, and a rotating roster of DJs that keep the atmosphere alive.
Downtown-The Loop
Upstairs at the Gwen can be found on the 5th floor of the Gwen Hotel on the Magnificent Mile. This art deco-designed bar has sleek and contemporary lines and offers comfortable seating, cozy firepits, and large umbrellas and monitors to function in any season in the Windy City. The menu celebrates innovation and tradition in handcrafted cocktails like the Creole Maple Old Fashioned and the Mayan Mule. Upstairs at the Gwen is ideal for intimate gatherings and larger social outings.
The Loop - River North
Head to the 24th floor of the Hyatt Centric The Loop Chicago and find Aire Rooftop Bar, a refreshing retreat in the bustling River North neighborhood. This open-air bar boasts fantastic skyline views of the city and an exciting menu of Midwestern favorites, cocktails, and slushes for those hot summer days. Aire offers seasonal events and themed nights, transforming the space into an ever-evolving entertainment hub. Nestled amidst the architectural grandeur of Chicago, just moments away from Michigan Avenue, this rooftop bar is the place for a lively atmosphere.
The Loop - River North
Terrace 16, located at the top of the Trump International Hotel & Tower boasts an enviable position overlooking the winding Chicago River and the city's skyline. This bar and restaurant celebrates American culinary flavors with dishes like the Terrace 16 Burger. You can explore a diverse selection of wines and inventive cocktails that perfectly complement the gastronomic offerings. With its contemporary aesthetics and sprawling indoor and outdoor space, Terrace 16 offers a refined ambiance perfect for any time in the day or evening. With a visit here, you'll feel like you're in the heartbeat of Chicago from this exciting vantage point.
The Loop - River North
At the epicenter of Chicago's downtown, LH (LondonHouse) Rooftop sets the stage for an unmatched luxurious outing at the junction of Michigan Avenue and Wacker Drive. Get ready for a fantastic view of the Chicago River and the Magnificent Mile from its open-air rooftop on the 22nd floor. Service here is reserved for dining, so be sure to come hungry and make it a night of dinner and drinks with a view. Don’t forget to take advantage of the incredible Margarita menu. A visit to the LH Rooftop is an opportunity to bask in the grandeur of Chicago's outstanding architecture.
The Loop - River North
Tanta gives guests an indoor and outdoor experience that brings Peru's tasteful flavors and spirit to Chicago. Get ready for a genuine Peruvian dining and drinking experience, highlighted by signature Pisco Sours and Chilcanos cocktails, complemented by rich and flavorful dishes like Ceviches, Empanadas, and Arroz Mariscos. Located just a short distance from Michigan Avenue, Tanta provides a great spot that combines Latin energy with wonderful skyline views in one exciting rooftop bar in Chicago.
The Loop - River North
Celeste is a multi-level establishment built in 1888 that marries the charm of a classic cocktail lounge with the allure of a modern bar. This historic building allows guests to traverse different atmospheres, from the intimate ground floor Whiskey Lounge to the vibrant rooftop garden, each floor designed with Victorian-era decor and contemporary touches to give it a timeless elegance. This Chicago rooftop bar, known as The Garden, is a calming retreat amidst the urban landscape of Chicago, offering a serene spot to enjoy drinks (a.k.a. top-end bottle service) under the stars.
The Loop - River North
Joy District stands as a beacon of nightlife and social gatherings. It's part sports bar, dance bar, and rooftop patio for people who want to party. The rooftop bar offers a lit-up nighttime space for gatherings with friends for cocktails, music, and nibbles on classic American small and large plates. Looking to elevate your night with a lot of energy and great skyline views in the distance? This is one of the Chicago rooftop bars to check out!
The Loop - River North
Looking for an upscale lounge with a view? Head to the Godfrey Hotel's Rooftop for an elegant lounge with an indoor/outdoor space, including a sleek, retractable roof system, ensuring the party continues regardless of the weather. Sip as the city lights twinkle below on modern variations of lemonades, mojitos, and sangrias, and complement them with small plates like sushi rolls and shrimp tacos. The Godfrey hosts Kentucky Derby Parties, special events, or regular gatherings, day or night.
Wicker Park
The UP Room at The Robey Hotel provides an elevated drinking experience that mirrors the sophistication and style of Chicago itself. Situated on the 13th floor, the interior blends art déco elegance and contemporary comfort, providing a cozy yet stylish setting for intimate dates and casual gatherings. The velvet seating and warm lighting set against the backdrop of the Chicago skyline create an almost cinematic experience. Enjoy expertly crafted cocktails that blend classic Mixology with innovative twists. The UP Room at The Robey Hotel promises an unmatched atmosphere that captures the essence of rooftop bars in Chicago.
Wicker Park
Wicker Park's Kennedy Rooftop, located at the top of the Hyatt Place Wicker Park, offers a fun and artsy atmosphere with great views of the Chicago Skyline. Head on the patio and play a giant game of Jenga with friends while sipping on a cocktail from its Oval Office and Presidential drink menu, or drop by for Happy Hour from 4-6 pm Monday through Friday. The Kennedy offers sharable plates and a sizeable Charcuterie Platter to satisfy the hunger and keep the fun going well into the night.
Wicker Park
Whisky Business is a haven for those who cherish a good dram and a great view. This Chicago rooftop bar, known for its laid-back atmosphere and an impressive selection of over 100 whiskies, sits comfortably atop the second floor, making it the perfect spot to gaze at the Chicago skyline while enjoying a spirit or two. This casual spot is easy on the wallet, making it great for any kind of budget. Whisky Business has an expansive rooftop patio filled with neon lights and offers ample seating for both small and large gatherings. While you are here, try their Brunch Sammies or Mac and Cheese bites.
Besides its focus on whiskey, this bar doesn't shy away from providing a full experience with its themed movie nights, which pair perfectly with its creative cocktail offerings. If you are looking for a casual yet energetic rooftop bar in Chicago and a fun tribute to the 1980s, this one is for you.
Lincoln Park
Perched atop Hotel Lincoln in the beautiful Lincoln Park neighborhood is The J. Parker, one of the popular Chicago rooftop bars. This spot has some of the best views of Chicago that sweep across the city skyline and the vast expanse of Lake Michigan. This spot strikes a harmonious balance between elegance and affordability, with a diverse menu that caters to various tastes. J. Parker is known for its bottomless Mimosa and Bloody Mary's paired with its classic brunch. This spot is for you if you want food, drink, and views in a stylish yet laid-back setting.
Lincoln Park
North Pond can easily claim the award for one of the best Chicago bars with a view. This restaurant/lounge in the city's beloved Lincoln Park shows off the beauty of Chicago and its natural landscape. This location is near the Lincoln Park Zoo, next to the North Pond, with dramatic views of the Chicago skyline in the distance. It's a place for a serene dining and drinking experience tucked away in nature, with farm-to-table dishes highlighting the freshest ingredients and a seasonally relevant menu. You won't find skyscrapers here, but you will find a picturesque escape with delicious food and drink in a beautiful building that dates back to the early 20th century.
Bronzeville-Southloop
Elevating the dining and drinking scene in the South Loop, VU Rooftop Bar proudly stands 22 stories high, offering excellent views of Lake Michigan and the Chicago skyline. The bar's contemporary design, indoor lounge, and outdoor terrace make it the perfect spot to enjoy the city views and stay to indulge in a drink or dinner. The drink menu is overflowing with creative cocktails that can all be customized with or without spirits. For those with a sweet tooth, the Dessert Cocktail selections are sure to satisfy. Even on a chilly night, it's the spot to cozy up in front of the fire pit on the comfy couches and take in sparkling city lights.
West Loop- Fulton Market
Transport yourself into a Mediterranean-meets California-inspired oasis on this 3rd-floor bar/restaurant, which offers an escape into a lush, botanical setting where olive trees and greenery frame the skyline views. Aba's menu is a celebration of Mediterranean flavors, with a focus on mezze, the shared plates that invite conversation and connection. The Smoky Garlic Hummus and Shawarma-Spiced Skirt Steak are just a taste of the culinary delights that await. Whether you're here for a delicious brunch or a serene evening, Aba's rooftop is a testament to the beauty of dining al fresco in Chicago.
West Loop
Rooftop at Nobu Hotel offers an upscale experience that includes world-class mixology and a Japanese-inspired menu that reflects Nobu's renowned culinary excellence. Visitors can indulge in signature Nobu cocktails, with the "Nobu Sidecar" being a particular highlight, showcasing the mixologists' prowess in creating a modern twist on classic drinks or exotic plates like Lobster Tempura Truffle Amazu or Wagyu Dumplings or Sliders. The rooftop also hosts a variety of special events, ranging from brunch to evening DJ sessions, offering an unmatched ambiance for both daytime and nighttime entertainment.
Old Town
Utopian Tailgate, is known for its color! Located above the home of comedy—Second City, this bar offers an eclectic mix of games, colorful décor, and sweeping views of the Chicago skyline from its spacious terrace. Bring some friends to play from an array of entertainment options, including ping pong tables, bocce ball, and giant Jenga, setting the stage for an unforgettable outing. The bar's menu is a testament to creativity, featuring a diverse selection of cocktails that are as visually appealing as they are delicious. Ask about the Playpen Playdate cocktail that serves 6-8 friends!
Logan Square
Lonesome Rose graces two neighborhoods in Chicago with its relaxed, Texan-inspired ambiance. It offers indoor and outdoor spaces to relax, have fun, and enjoy the welcoming environment. At Lonesome Rose, the culinary and cocktail offerings stand out, featuring a blend of traditional American and Tex-Mex flavors with its extensive taco and burrito menu and its take on Southwest Chicken Empanadas. Take advantage of the rooftop patio and bar in Logan Square for an afternoon or evening of fun in one of the coolest neighborhoods in the city.
Looking for more tips, guides, and information about the Windy City? Check out our Chicago blog for things to do in Chicago at any time of the year.
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Kick off your Chicago Spring Break at Navy Pier, a destination that caters to every family member's interests. The pier typically hosts a week-long Spring Break itinerary in March with interactive events, performances, and artisan markets. Keep an eye on the Navy Pier events calendar for details. Combine these seasonal activities with the thrill of a Ferris Wheel ride or a leisurely meal at one of the many family-friendly eateries.
Immerse your family in a world of color! Enjoy the first glimpses of spring flowers in bloom and check out the 2024 event called "What's In A Name?" which explains the history and science of the botanical naming of flowers and plants. It's a vibrant and educational show during spring break in Chicago, IL. Be sure to charge your phone or bring a camera to capture your family amidst the stunning floral displays.
Venture into the diverse neighborhoods of Chicago for a truly local experience. Each neighborhood has its own unique charm, from the vibrant murals in Pilsen to the lively music scene in Wicker Park. Families can enjoy a variety of cuisines, local shops, and community events that reflect the city's rich cultural tapestry. Exploring these neighborhoods offers a different perspective of the city, making it a valuable addition to your spring break in Chicago.
Looking to relax and unwind as a family in Chicago this spring break? Experience serenity at the Lincoln Park Conservatory's North Pond Nature Sanctuary. It's great for a relaxing family stroll, featuring the sights and smells of native plants and an idyllic pond. Kids will love spotting the birds, tadpoles, and turtles that inhabit the pond. Additionally, visit the beautiful Conservatory and Gardens full of blooming plants. Entry to this tranquil oasis is free, but it's recommended to make a reservation, especially during this busy time of year.
Elevate your Chicago spring break experience at the 360 CHICAGO Observation Deck. This destination delivers panoramic city views that the whole family will love. Those seeking a thrill should try TILT, one of the world's highest thrill rides that provides an awesome perspective of the city from above. Check out the Sip, TILT, and View ticket to save and enjoy a beverage while you enjoy the view. Once you arrive, stay on the Observation Deck as long as you want! Your trip to 360 CHICAGO will surely be a high point of your spring break adventure.
Spend your spring break at Great Wolf Lodge, the popular family-focused resort that offers a myriad of fun, with an expansive indoor water park, adventurous MagiQuest game, and multiple dining options. Best of all, the resort is offering Spring Break deals at 30-35% OFF 2 and 3-night stays in Chicago. A stay at Great Wolf Lodge is a guaranteed crowd-pleaser and a great home base to explore the Chicago sights.
Dive into a world of imagination with your kids at American Girl Place. This delightful shop and attraction, in one, offers immersive experiences for doll enthusiasts. Your little ones can pamper their dolls with a visit to the Doll Hair Salon, enjoy a special meal with their doll, or book tea time. With various themed events and interactive displays, this store can take playtime to a new level during your Chicago spring break.
Step into the vibrant world of the Sloomoo Institute Chicago, where fun and creativity collide! It's a slime wonderland filled with various hand-crafted slimes in multiple colors, scents, and textures that delight all the senses. It's not just about the slime, though. The Institute offers a sensory journey like no other, known as the Sloomooverse! Sloomoo Institute is no ordinary attraction; it’s a tactile exploration of a fun, immersive universe that kids (and adults!) will adore. Add a visit to this place to your family's spring break itinerary.
The Chicago Children's Museum, located within Navy Pier, is a hotspot for youthful exploration and learning. Each exhibit is ingeniously engineered to inspire young minds, creating specific sections to suit children of different ages, such as the new Circusville: Play Under the Big Top and popular favorites like Water City and the Tinkering Lab. Make sure the Children's Museum is on your itinerary!
Unleash your inner builder at Legoland Discovery Center with hands-on exhibits like the Lego Build and Inspire area, a meet-and-greet LEGO characters exhibit, and more. The center ensures endless fun for all ages of Lego enthusiasts (parents love spending time here too)! We recommend you book tickets in advance as this is a popular spring break Chicago activity.
Ignite your children's curiosity at the Sensing Chicago exhibit in the Chicago History Museum. This unique display encourages kids to use their senses to explore the city's history, fostering an immersive (and fun) learning experience. The exhibit features activities like a giant Chicago-style hot dog that kids can dive into! The interactive approach of this museum makes history come alive for young learners, making it an excellent addition to your family's Chicago agenda.
It's a multi-sensory exploration! The award-winning exhibits at the Museum of Science and Industry will surely excite every family member with endless experiences, films featured on a giant screen, and events. Starting this March, explore the first-ever exhibit called 007 Science: Inventing the World of James Bond. This exhibit showcases the science and technology behind the film series's iconic gadgets, cars, and stunts. All the exhibits at the MSI will captivate your family, sparking curiosity and fostering a love for learning. Explore the wonders of the world during your valuable time off.
Your spring break staycation or visit to Chicago is only complete with a visit to Lincoln Park Zoo. This place isn't just about seeing animals; it includes activities to understand the animals and their challenges, like a ride on the Endangered Species Carousel, experiencing Gorilla Trek: The virtual reality ride, or visiting the zoo when the animal caretakers are attending to and feeding the animals. There is something to discover all over the zoo!
Unleash your family's wild side at the Brookfield Zoo. Home to a diverse array of animals, the zoo's interactive exhibits, like Hamill Family Wild Encounters and the captivating Dolphin Show, will engage and delight the whole family. Check the event schedule while planning your visit, as regular seasonal activities are planned that can easily complement your family's spring break itinerary.
Delve into an underwater adventure at Shedd Aquarium. Housing over 32,000 aquatic species it's a visual spectacle for the entire family. Along with the many engaging exhibits, the aquarium offers a tour specifically for families—The Best of the Shedd—a 75-minute guided tour. Go behind the scenes at Shedd with a guide, sit in the best seats in the house for an Animal Spotlight, chat with an animal care manager, and touch a slimy, soft sea jelly! Experience the magic of aquatic life during your Chicago spring break!
Experience the wonder of nature at the Peggy Notebaert Nature Museum. Top highlights like the Butterfly Haven, a 2700-square-foot greenhouse where over 1,000 colorful butterflies flutter freely, will captivate your family!
Kickstart your Chicago journey in and around the Chicago Loop Neighborhood. This area is the heart of downtown Chicago and the central business district. One may think it's quiet after 5 pm and a ghost town on weekends, but its events, theaters, and parks make it an exciting destination any time of the year.
Start with a hearty breakfast at the Goddess and the Baker, located at the intersection of Wacker & LaSalle. This café is renowned for its extensive coffee selection and creative brunch menu featuring classic and innovative dishes. Fuel up for the day with one of their artisanal sandwiches or decadent pastries.
After breakfast, take a stroll along the Chicago River Walk.
The river walk is a 1.25-mile-long path along the Chicago River to see the city's infamous architecture and attractions and get a first-hand perspective of areas you may want to see again during your visit. There is much to see along the pathway; it is continuous from Lake Street to the lakefront, or you can take the vertical stretch from Upper Wacker Drive to the waterway.
Another way to see Chicago's outstanding architecture and the main sites is on a Chicago River Cruise. Join a tour with exciting narration and details of the legendary people who designed and built Chicago. Even if the weather isn't cooperating, this cruise allows you to sit indoors or outdoors. Relax and enjoy the 90-minute tour for an exciting sightseeing tour in the city.
Lunch
When hunger strikes, head to Revival Food Hall for lunch. This all-local dining concept spotlights the best of Chicago’s culinary scene under one roof. Whether you're craving ramen, tacos, or something vegan, you'll find something to satisfy your taste buds here.
Museum of your Choice
As the afternoon rolls in, choose an indoor activity from three of the best museums in the United States, such as the Art Institute of Chicago, one of the oldest and largest art museums in the United States and home to over 300,000 works of art. You'll find pieces from every era, from ancient times to the contemporary period. Alternatively, visit the Field Museum, which boasts the status of one of the world's leading natural history museums. Its exhibits are immersive and span from ancient cultures to modern-day scientific discoveries, with a staggering collection of over 24 million objects, contributing to the museum's status as a global destination for educational and informative experiences.
If museums aren't your thing and you would rather be outside and enjoy some sports, head to a baseball game or take a tour of Wrigley Field, one of Chicago’s gems with over 100 years of history! You can watch a game, wander through the seats and concessions, or tour the stadium. Every Cub fan—big or small—will love stepping onto the field where so many greats have played, sitting in the dugouts, and more!
Wander Millennium Park
If you are craving a little more outdoor time after your museum visit, wander around Millennium Park and check out the Lurie Gardens and the Crown Fountain, and if you are lucky, there may be a free concert at the Jay Pritzker Pavilion. When you visit Chicago, you may see The Bean, officially known as Cloud Gate, the stainless steel sculpture that reflects the city's skyline and the clouds above and has become an iconic symbol of Chicago. The Bean is closed for renovations until Spring 2024, but we have some exciting options for you to enjoy in and around the park if the upgrades are still in progress.
As evening falls, indulge in an unforgettable dining experience at Acanto restaurant, an award-winning Italian restaurant near Millennium Park. With a menu that beautifully balances traditional and contemporary Italian cuisine, it's the perfect setting for a sophisticated yet relaxed dinner.
Round off your day with a show at one of Chicago's World-Famous Theaters.
Take advantage of the thriving theater scene; the most famous is the iconic Chicago Theater in downtown Loop. Alternatively, choose a theater slightly off the beaten path. The Chicago Magic Lounge, in the Andersonville neighborhood, offers a unique blend of a speakeasy, magic show, and theatrical production that you won't find anywhere else. Enter through the secret door to a laundromat and be transported into a mysterious location. Find a list of the top Chicago theaters here.
With two more days to go, rest well, knowing you have plenty more exciting adventures to look forward to!
Rise and shine for your second day in Chicago and gear up for another round of adventures. Begin your day with a special cup of coffee and breakfast at Starbucks Reserve - The Chicago Roastery, the largest Starbucks in the world, located on the Magnificient Mile. With four stories and more than 35,000 square feet of space, the cafe is a must-visit for coffee lovers and is known for its immersive coffee experience and impressive selection of unique drinks, pastries, and food selections.
Once you've sufficiently caffeinated, it's time to indulge in a shopping spree on the Magnificent Mile. This bustling district offers a blend of high-end stores, trendy fashion outlets, and major department stores, making it a shopper's paradise. While window shopping around the area, visit the iconic Water Tower, one of the few structures that survived the Great Chicago Fire of 1871 and an important symbol of the city's resilience.
As the clock strikes lunch hour, take a ten-minute walk to refuel at Sayat Nova, an award-winning Armenian restaurant serving authentic and flavorful dishes since 1970. Their diverse menu includes meat and vegetarian options to tantalize your taste buds.
After lunch, soak in some culture at the nearby Museum of Contemporary Art, which houses a vast collection of artwork dating from 1945 to the present. Take your time to admire the thought-provoking exhibits and installations, and engage in a dialogue with the art.
In the late afternoon, make your way to 360 CHICAGO, the Observation Deck on the 94th floor of the former John Hancock Center. Witness one of the best places in the city for sunset when the breathtaking 360 panoramic view of the cityscape transforms under the golden hues. For an extra jolt of adrenaline, add a ride on TILT to your ticket— one of the highest thrill rides in the world, for a unique and thrilling view of the city. Participants can lean outwards on a glass window that tilts forward to a 30-degree angle, offering an exciting perspective of the Windy City.
With your 360 CHICAGO entrance ticket, stay as long as you like. As the night descends, raise a toast to your second day in Chicago at CloudBar, a stylish lounge offering exquisite cocktails, snacks, and more views of Chicago's brilliant skyline.
Post-drinks, treat yourself to a sumptuous dinner at either Nomi Kitchen, known for its upscale American fare and stunning views, or opt for a more casual dining experience at Navy Pier, which offers a diverse range of food options from pizza to seafood.
End your day on a fun note by enjoying the various games at Navy Pier; there are always fun things to do at the Pier, like free concerts, cultural attractions and games and rides like the iconic Ferris wheel. Wrap up the day with a sweet treat (like ice cream) with the backdrop of the summer fireworks lighting up the sky.
Remember, your trip to Chicago is more than halfway over - the city still has plenty more to offer, so save some energy for what's coming next!
Get ready to embrace the final day of your Chicago trip with the same enthusiasm you started with. Start your day right with breakfast at Wheat's End Cafe and Bakery; located near the Lincoln Park Zoo, this bakery cafe offers a mouth-watering selection of breakfast dishes and artisanal baked goods that are sure to fuel you up for the day's adventure.
After breakfast, spend your morning at the Lincoln Park Zoo. This all-ages attraction is home to more than 200 species of animals and home to one of the last free admission zoos in the country. Built in 1868, it’s also one of the oldest. Beyond the amazing exhibits, the summer months are filled with special events like picnics, block parties, and wine tastings.
After your zoo visit, take a leisurely stroll along the Lincoln Park nature boardwalk and enjoy stunning views of the Chicago skyline. Along the boardwalk, make a stop at The Honeycomb—a gorgeous piece of contemporary art that makes an interesting shot in all kinds of lighting, both day and night. If the weather is not cooperating, don't worry! There are plenty of indoor options. The Peggy Notebaert Nature Museum and the Chicago History Museum are both fantastic nearby alternatives offering interesting facts, knowledge and interactive exhibits.
Lunch
Before you leave the Lincoln Park area, grab lunch at the Patio at Café Brauer right off the Nature Park Boardwalk or head to Nookies on Wells, a 50-year-old establishment serving up American and Classic Diner comforts.
Visit the Old Town Neighborhood
In the afternoon, immerse yourself in the history and charm of the Old Town Triangle neighborhood to the north on Division Street on the south side and on Wells and Clark Streets. This historic area is best known for its well-preserved Victorian homes, tree-lined streets, quaint shops and quality restaurants. Consider taking a walking tour to appreciate the area's rich history and unique character fully. If the weather doesn't cooperate, consider visiting the Shedd Aquarium. This exciting indoor public aquarium, with a diverse collection of over 32,000 marine animals and creatures worldwide, offers a rare and fascinating opportunity to discover marine life and its preservation.
Unwind at the Old Town Ale House
As evening approaches, take a load off your weary feet and unwind with a drink at the Old Town Ale House. Known as the "Best Dive Bar in Chicago," this watering hole has been serving patrons since 1958 and offers an impressive selection of beers. It's colorful history and quirky art collection make it an ideal place to relax and soak in the local culture.
Dinner
For your final dinner in Chicago, Bring your appetite to one of the best Italian restaurants in Chicago and an Old Town staple—Topo Gigio. Book ahead in the cozy dining room, or find a spot in the garden during the summer months. It's the perfect place to reminisce about your Chicago adventure over a delicious meal.
Catch a Comedy Show
No Chicago itinerary would be complete without experiencing its legendary comedy scene. The greatest comedians in America got their start with improv and sketch comedy in Chicago. So, wrap up your night and three-day Chicago journey with laughter at two of Chicago's Comedy Clubs in the area. The first option is Zanies Comedy Club—a staple of Chicago's comedy scene since 1978. The club hosts local and national acts and has seen the likes of Joan Rivers, Jerry Seinfeld, and Ellen DeGeneres grace its stage. Alternatively, check out Second City, the club that is a training ground for some of the biggest names in comedy. From John Belushi to Tina Fey and Steve Carell, Second City alumni have made their mark on the world of comedy. The club's mainstage shows are a must-see.
And just like that, your 3-day whirlwind tour of Chicago comes to an end. But remember, this is just a taste of what The Windy City has to offer. Whether it's the food, the history, the architecture, or the vibrant nightlife, there's always more to explore in Chicago!
When to Visit Chicago
Deciding on what time of year to visit Chicago largely depends on what you want to experience.
Winter: The city turns into a magical winter wonderland from December to February; though quite cold, there's holiday charm with Christmas markets and ice skating.
Spring (March-May) tends to be rainy, but the city’s parks are stunningly verdant.
Summer (June - August) is vibrant and filled with numerous events, including popular summer festivals such as the Lollapalooza Music Festival, Taste of Chicago Food Festival, and city-wide beach openings.
Autumn (September - November) is great for its fall foliage and the comfortable weather.
Getting Around Chicago
Getting around the city of Chicago is quite convenient due to its extensive and well-run public transportation system.
The 'L' train (short for 'Elevated') operates across eight lines, servicing all parts of the city and even reaching into neighboring suburbs. Buses run throughout the city as well. Alternatively, there are many options for bike rentals, which are quite popular for leisurely rides along Lake Michigan or through the many city parks. Of course, traditional taxis and Uber are widely available. Find all the popular maps, including transit, bike paths, attractions and more, to help you get around Chicago.
Save Money on Attractions with a Chicago City Pass or Go City®
To save time and money on attractions in Chicago, a Chicago Attractions Pass is the perfect way to visit the renowned sights and, plan activities and make your Chicago Itinerary dollars go farther. Find out Chicago Pass options, covering what each includes, the prices, and more. Which Chicago Pass is right for you? Find out before you go.
What to Pack for a Trip to Chicago
When it comes to packing, keep in mind Chicago’s weather during your visit. This city is known for its unpredictable weather changes; hence, it is always safe to pack layers regardless of the season. Summers can be quite warm, so light clothing is advised, but carry a light jacket or cardigan for sudden temperature drops. Winters are very cold, so pack your heavy coat, gloves, and a hat. Always include comfortable shoes, as Chicago is a walking city with many amazing architecture and scenery to enjoy.
Tips for Staying in Chicago
There's a plethora of options when it comes to where to stay in Chicago. If it's your first visit, downtown is a recommended area to base yourself. You'll be in the heart of the city and within walking distance of major attractions like The Art Institute, Navy Pier, and the Magnificent Mile. The Loop, which is part of the downtown area, is known for its stunning architecture. Other vibrant neighborhoods to consider include Lincoln Park, which boasts green spaces and a zoo, or the artistic, hipster-friendly neighborhood of Wicker Park. Chicago has accommodations that suit every taste and budget, ranging from luxurious hotels to cozy guest houses.
For more Chicago Itineraries and tips, visit our blog about things to do in Chicago any time of year.
360 CHICAGO's Sip and View ticket includes an admission ticket to the 94th-floor observation deck and a featured beverage at a special price. Sip and savor the panoramic views at CloudBar - Chicago's bar in the sky, while staying warm and cozy, gazing at the winter wonderland below. The Sip and View ticket is perfect for date night, after a day of shopping, or showing off your city to visitors. CloudBar is open daily from 9 am to 11 pm for all ages, with non-alcoholic beverages and snacks available. Ask us about our holiday cocktails, including Deck the Halls and Holiday Spice specialty cocktails.
For 32 years, the Chicago Transit Authority has been spreading joy with a fully decked-out holiday train and bus. The vehicles are decorated with lights and artwork, and Santa greets riders from his sleigh from an open-air flatcar carrying his reindeer. The CTA holiday train transfers passengers from A to B, and the employees donate their time and money to assemble and deliver 600 food baskets to local food organizations. Now, that's a reason to take public transportation this December!
The Merchandise Mart, also known as the Merch Mart or Mart, is a famous art déco building built in the 1930s. Back then, it was the largest in the world, with 4 million square feet of retail space. Now, it's home to loads of retail stores and businesses. Its confronting presence towering over the Chicago River makes it the perfect backdrop for digital art projections. This year, holiday classics like the Nutcracker are cast on the building in an incredible ensemble of colorful video and music. Art on the Mart is one of the best things to do in Chicago in December, and it's free! The show runs at 7 pm nightly till December 30th.
Another December activity at the Merch Mart is the yearly Holiday Show. You can grab one-of-a-kind gifts from hundreds of artists, makers, and designers who come together to create the perfect shopping destination for those who love original, hand-made work. This fantastic shopping experience is only open from Dec 7 to 10th, so mark your calendars so you don’t miss it!
Warm up indoors and experience Christmas in 50 different countries/cultures at The Christmas Around the World Exhibit at the Museum of Science and Industry in Chicago. See how other countries celebrate the holidays and decorate their Christmas Trees at this event that is now 80 years strong. Take advantage of the four-story Grand Tree that dominates the Museum's Rotunda area. Your ticket includes The Holidays of Light, an exhibit that honors light and enlightenment worldwide. See all this with the museum admission. Open from now until Jan 8, 2023.
Inhale the aroma of roasted chestnuts, sip on mulled wine, tap your feet to the sounds of caroling, and browse through the most traditional outdoor Christmas market you'll find outside of Europe. The Christkindlmarket Chicago boasts hundreds of vendors of gifts, treats, and delicacies that would be worth a shopping trip to Chicago in December! The market is located at Daley Plaza at 50 W. Washington Street and is open on days and evenings till Christmas Eve.
One way to brighten your holiday evenings in Chicago is to visit Lightscape, an exhibit at the Chicago Botanical Garden. Stroll through the outdoor gardens for a display of powerful music, fire, light, and color. It's a holiday showcase for all ages. Tickets sell out fast, so book ahead!
It's the quintessential thing to do during the holidays because it's so darn enjoyable! Strap on some skates and enjoy the scenery at two of Chicago's beloved parks.
The Ice Skating Ribbon at Maggie Daley Park in the Chicago Loop is a lovely, leisurely skate through a winding path around the park, with fantastic views of the Chicago Skyline. Skating here is popular, so participants need to buy timed tickets. Book ahead! Alternatively, Ice skating at Millenium Park at the McCormick Tribune Plaza is also a popular favorite. Skate on one of the two public ice rinks with views of "The Bean" while you glide and twirl. Skate rentals are available at both parks if you don't have your own (and you probably didn't bring any in your luggage).
Chicago in December is only complete with a visit to the Morton Arboretum for a gorgeous display of color, light, and sound in the trees at Illumination. Explore the 50 acres of forested area to see (and hear) nature from a different perspective. Electric Illumination was a success last year; this adults-only (18+) event features trance and house music synchronized to light displays. This event runs four evenings in December. If you love to get out into nature, this is the place for you!
It's the most epic spectacle of color and light casting over the city—The fireworks display from Navy Pier. Get the best views from 94 floors up at 360 CHICAGO. There's a fireworks display every night until Dec 31 at 9 pm.
Then, Enjoy New Year's from the Highest Cocktail Lounge. Watch the NYE fireworks display and attend the best party —2024 New Year's Eve in the Sky. Tickets include live music featuring DJ Dre Martin, a glass of sparkling wine, unlimited rides on TILT—Chicago's highest thrill ride and more served up at Cloudbar, Chicago's highest cocktail lounge. Get NYE tickets early to get the best price before they sell out!
A Candlelight Concert is always dreamy, but it becomes more magical in December in Chicago. With a handful of holiday concerts, you can embrace the season or pick whichever concert piques your interest! Either way, it’s impossible to go wrong with melodic music by candlelight.
Welcome to Jack Frost, a holiday pop-up shop that offers an unforgettable outdoor, interactive Christmas event in the heart of Chicago. The festivities pop up at Fulton Market and feature various activities, from a captivating nighttime light display to a full-sized ice skating rink. Regardless of what you seek this festive season, Jack's offers an unforgettable multi-sensory experience for everyone. Jack Frost's festive experiences are suitable for all ages, and ideal for a corporate holiday party or a seasonal gathering.
Every year around this time, The Godfrey Hotel transforms its rooftop into a festive, heated igloo experience where you can sip on seasonal drinks and eat dinner while escaping the cold. The transparent igloos allow you to wonder at the city’s skyline, giving you the perfect opportunity to enjoy the outdoors while staying warm this December!
The annual ZooLights display is back! While you enjoy a hot beverage and snack from one of the stands throughout the park, you can stroll through their many displays of lights, see the cold weather animals, enjoy interactive activities, and more! They will also host an Adults Night Out and tribute to “A Charlie Brown Christmas” if you are looking for extra holiday cheer!
This interactive exhibit is full of activities to help you embrace the season! From their Pinkmas tree forest to a speakeasy, larger-than-life snow globe, and festive crafts, many memorable moments are here. And, of course, don’t forget to jump into their famous pink sprinkle pool!
The home of the Chicago Dogs baseball team turns into the home of holiday lights, train rides, ice skating, a two-story ice slide, and more during December. Their Sparkle Light Festival houses five different displays of lights, all with a separate theme, for you to walk through. To enjoy the festival to the max, you can purchase the River’s Stadium Club tickets for unlimited tubing, buffet access, and drinks!
Celebrate everybody’s favorite elf this December in Chicago at the Elf pop-up inside the Stretch Bar & Grill. With hundreds of decorative elves scattered throughout the bar, Christmas trees, festive lights, and Buddy’s favorite snacks, it’s like stepping into the world of Elf! You can embrace his favorite food groups (spaghetti with maple syrup, anyone?!) or ramp it up with a 36-ounce beer served in an elf boot. Buddy himself is known to show up between Thursday and Sunday, so keep an eye out!
Take advantage of the thriving theater scene in Chicago in one of many neighborhoods in the city. The most famous is the downtown Loop. Check out the iconic Chicago Theater, or choose a theater slightly off the beaten path. The Chicago Magic Lounge, located in the Andersonville neighborhood, offers a unique blend of a speakeasy, magic show, and theatrical production that you won't find anywhere else. Enter through the secret door to a laundromat and be transported into a mysterious location. Find a list of the top Chicago theaters here.
The 360 CHICAGO Observation Deck, located at the top of the former John Hancock building, boasts awe-inspiring 360-degree views of Lake Shore Drive and the rest of downtown Chicago from nearly 1,000 feet up. Marvel at the magnificent vistas of the Windy City during the day, at sunset, or under the illuminated night sky. Check 360 Chicago ticket availability.
Embark on an adventure in the world of digital entertainment with Redline VR. This virtual reality experience provides an exhilarating ride for children and adults, allowing them to explore everything from outer space to underwater realms. Utilizing top-of-the-line technology and offering interactive gameplay, Redline VR ensures an unforgettable and thrilling activity, ideal for a Chicago rainy day.
The city boasts a thriving and dynamic bar and club scene that caters to a diverse range of preferences, and it's one of the best indoor activities in Chicago for adults. With an array of options from historic dive bars to sophisticated lounges, there is something for everyone seeking indoor nightlife activities.
For a unique and unforgettable experience, the CloudBar at 360 CHICAGO is a must-visit destination. This lounge, located on the 94th floor, is the highest bar in Chicago and offers unparalleled panoramic views of the city and Lake Michigan. Its modern and sleek setting provides an ideal backdrop for a date or a night out with friends, and visitors can enjoy elevated cocktails, specialty coffees, mocktails, and snacks.
Get ready for a night of wildly fun interactive games. Game Night Out is a fully hosted game night (or game day) experience. It's one of the coolest Chicago indoor activities and it’s held in spacious, private living rooms that feel like one of your friend's homes. The competition will be fierce, and the memories will last a lifetime.
Chicago is renowned for its comedy scene and is home to the birthplace of some of America's greatest comedians. For a chance to witness legends and future stars, visit the various locations offering improv and sketch comedy, such as Zanies Comedy Club, known for special appearances from iconic comedians such as Joan Rivers, Jerry Seinfeld, and Ellen DeGeneres. Zanies hosts both local and national acts. However, the most famous of Chicago's comedy clubs is Second City, where legendary comedians from John Belushi to Tina Fey and Steve Carell have trained. Laughter is the best medicine, so why not spend your rainy day in Chicago indoors at one of these top clubs and get ready to laugh until it hurts?
Experience the thrill of indulging in boundless desserts and unrestricted playtime within a dynamic wonderland of immersive installations at the Museum of Ice Cream, one of the most whimsical things to do on rainy days in Chicago. Rekindle your inner child as you embark on an adventure featuring delectable ice cream hot dogs, a miniature golf course with dessert-inspired obstacles, and a plunge into the world-renowned sprinkle pool. The Museum of Ice Cream offers the most delightful venue in Chicago for an unforgettable frosty excursion!
Opening its doors in 1894, The Field Museum has a collection of over 40 million specimens and artifacts from all over the world that are bound to amaze anyone who walks through its corridors. The building itself has an incredible history of its own. Visit this Chicago indoor attraction again and again, as there is always a new exhibit to explore.
It's one of the highest thrill rides in the world, and it's indoors! TILT at 360 CHICAGO Located on the 94th floor of the former John Hancock Building, TILT provides a unique and thrilling view of the city. Visitors can lean outwards on a glass window that tilts forward to a 30-degree angle, offering an exciting perspective of the Windy City. It's an exciting ride not to miss and ideal for a rainy day.
The Shedd Aquarium is the perfect indoor activity in Chicago on a rainy day. This exhilarating indoor public aquarium, with a diverse collection of over 32,000 marine animals and creatures worldwide, offers a rare and fascinating opportunity to discover marine life and its preservation. From the thrill of touching stingrays to witnessing impressive dolphin shows and engaging exhibits, the Shedd Aquarium promises an unforgettable experience. Whether on a rainy day or otherwise, visiting this aquatic wonderland in Chicago is highly recommended.
Step back and explore the historic Logan Theatre, an iconic vintage movie house that opened in 1915. This landmark establishment is a cornerstone of North Milwaukee Avenue and is known for its unique blend of cinematic experiences, including indie films, cult classics, and exciting new releases. Adorned with an impressive collection of sports artifacts and boasting a beautifully renovated bar and lounge, the Logan Theatre provides a memorable atmosphere with endless indoor things to do in Chicago for moviegoers of all kinds.
Shop to your heart's content at Macy's, on State Street's discount department store zone, or at an array of eclectic boutique shops. For luxury shopping, visit 900 North Michigan Shops, a 450,000-square-foot retail space with over 70 luxe retailers like Gucci, MaxMara, Montblanc, Bloomingdales, and Aster Hall Food Hall. Learn about more things to do on the Mag Mile.
Experience a day of exhilarating entertainment with your loved ones indoors at WhirlyBall in Bucktown. The entire family can participate in various activities, including laser tag, bumper car racing, and the timeless game of WhirlyBall. With an array of exhilarating things to do inside in Chicago, children and adults can relish a day filled with excitement.
Make your rainy day afternoon a little fancy. Visit the Drake Hotel at Palm Court for Afternoon Tea. This century-old tradition has had royals grace its halls, from the Queen to Princess Diana. Peruse the menu of 17 unique tea blends of classic choices or teas with a modern twist. Tea is served in individual tea pots accompanied by the traditional three-tiered tea tray filled with finger sandwiches, scones, and petit fours with house-made preserves.
Discover clues, solve puzzles, and accomplish tasks with a group of friends or family on a rainy day! Move throughout the puzzle room to find the fastest way out. Some of the most highly rated Chicago indoor activities include The Escape Game and Fox in a Box, with escape rooms that have different themes.
Indulge in a journey to another world at the Lincoln Park Conservatory. Nestled in the heart of Lincoln Park, this renowned landmark encourages visitors to immerse themselves in its four breathtaking display houses - the Palm House, Fern Room, Orchid House, and Show House. As you stroll through the lush greenery, you'll feel transported to a tropical paradise, no matter how wet or cold the weather is outside!
Bowling, a classic indoor activity, is a favored pastime in Chicago. With various venues to choose from, such as Seven Ten Social, Diversity River Bowl, and Lucky Strike, each provides its unique approach to the beloved game.
Explore your musical side at The Music Box Theatre, Chicago’s go-to venue for independent, foreign, cult, and classic films since 1929. For some added fun, visit during a sing-along movie screening throughout the year, like The Sound of Music, Mary Poppins, or a seasonal Christmas movie.
Chicago's rich musical legacy dates back decades. Experience the electrifying energy of live performances at the city's eclectic music venues, such as The Hideout. This venue showcases various music genres, ranging from country to punk, and offers unique events like poetry readings and open mic nights. For jazz aficionados, The Green Mill, a century-old institution, is the ultimate hotspot to catch local and national jazz acts any day of the week. This venue offers an elegant and nostalgic atmosphere.
The Museum of Science and Industry is globally recognized for its 400,000-square-foot expanse of interactive exhibits and offers tons of things to do indoors in Chicago for visitors of all ages. It seeks to stimulate scientific curiosity and ignite the flame of creativity in its visitors. What sets it apart is not just its collection but also its unique architecture, including the building from the Chicago World’s Fair of 1893.
After touring Chicago, a pick-me-up is essential! There is no better place than a visit to the World’s Largest Starbucks, located on the Magnificent Mile. Indulge in a coffee, tea, refresher, frappuccino, or anything else calling your name. In no time, you'll be energized to continue your exploration because there is so much to experience in Chicago, even on a rainy day.
Chicago loves a good food hall. There are several food halls where you can sip, eat, shop, and sample plates from some of the top restaurants in the city, all under one roof. Check out Time Out Chicago, a 50,000-square-foot market featuring 18 eateries. Or visit Revival Food Hall in the heart of the Chicago Loop, specializing in local food. For a comprehensive Italian-focused food hall experience, head over to Eataly for al dente pasta plates, wine pairings, Neapolitan pizza, and more.
Immerse yourself in the wonders of the cosmos at America's first planetarium. Engage with interactive exhibits and delve into mesmerizing cosmic truths. Discover two impressive domed theaters covering an expansive 60,000 square feet, and explore the renowned Doane Observatory, which houses the most extensive publicly available telescope in the Chicagoland area. Prepare for an unforgettable indoor activity in Chicago that truly takes you beyond the realm of Earth.
The Chicago Transit Authority (CTA) Map is the ideal guide to help you easily get around the city by train or bus. It provides detailed information about buses, trains (known as the "L") stations, and timetables, with a comprehensive system-wide map to simplify the journey. Before you know it, you'll be a pro at getting around Chicago public transport.
For an alternate method of sightseeing, make sure to take a look at the city's extensive bikeways featuring bike lanes, neighborhood greenways, and off-street trails. Courtesy of Chicago Transportation, these maps will have you on two wheels exploring the city with the bonus of getting some great outdoor exercise.
For the best insight into the 77 neighborhoods of Chicago, including what festivals, entertainment, food, and culture the Windy City has to offer, download the Chicago neighborhoods map that displays the intersections with major streets and discover hidden gems in places not always listed on tourist maps.
Visiting the city and want an overview of the most popular attractions? Look no further than the tourist map of downtown Chicago, outlining the 26 top attractions in downtown Chicago, including 360 CHICAGO Observation Deck (formerly John Hancock Observatory).
Take your Chicago sightseeing a step further and create a customized plan with this map of Chicago attractions. Select and plan your destinations according to your own personal interests and get a map to ensure that you don’t miss a single exciting experience. Download the Chicago Attractions Map to get where you want to go below.
Before departing, utilize the airport map for the four Chicago O'Hare International Airport terminals. This map covers everything from airline locations to food and shopping to provide a complete airport orientation before takeoff.
Now you are ready to explore Chicago! For more tips and things to do in Chicago, visit our blog.
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