1. Catch a Broadway Show in one of Chicago's Iconic Theaters

Year-round
For couples who love live theater, music, or comedy

Forget New York! With Chicago being home to more than 250 theaters, the top comedy scene, and five Tony Award-winning theater companies, there is a venue and performance for any couple looking for entertainment! Watch a Broadway show in the theater district, head to The Second City for a laugh, watch a live music performance, or venture to the neighborhoods for some independent shows. The Chicago Theatre is just one of many Chicago attractions for couples where you'll find something fun to do.

2. Make it A Night Out at CloudBar at 360 Chicago

Year-round
For couples who love good cocktails and amazing views

Elevate date night or girl's night out with a night on the town from 1,000 feet up! For one of the most exciting things for couples to do in Chicago, head over to CloudBar at 360 CHICAGO Observation Deck to order an elevated cocktail (or a beverage from the regular menu) and be prepared to be wowed by the 360-degree views. Head up before dusk for a front-row seat of sunset views and hang out for nighttime grooves and atmosphere while admiring the twinkling lights across the dark Chicago sky.

3. Bike Along the Chicago Waterfront Trail

Seasonal 
For couples who love to explore cities by bike

Get a taste of local life and bike on the Chicago Waterfront Trail. This path, which allows for adequate lanes for runners, bikers, and walkers, spans 18.6 miles from Ardmore Avenue to the north and 71st Street to the south. Enjoy fabulous views of the lake and the city and explore the neighborhoods of Chicago, including Uptown, Lakeview, Lincoln Park, South Loop, Bronzeville, Edgewater, and Hyde Park. Rent a bike at Lakeshore bike rentals in hybrid, road, or carbon bike formats.

4. Dine and Dance on a Chicago Dinner Cruise on Lake Michigan

Year-round
For couples that love to cruise

Plan a romantic night in Chicago on Lake Michigan. Dance, dine, and see some of Chicago's exciting landmarks like the John Hancock Building, Navy Pier, and the Buckingham Fountain. The onboard DJ, fully stocked bar, and giant board games will keep you and your loved one entertained. Available for brunch, lunch, and dinner. Cruises depart from Navy Pier year-round since indoor and outdoor sections are available.

5. Stroll Through the Glorious Chicago Botanic Garden

Year-round
For couples who love the sights and smells of nature

Do you love the sights and smells of nature—the botanical kind? Explore the Chicago Botanic Garden. What could be more romantic than strolling through gardens together? Fortunately, the Botanic Garden is open all year for different experiences depending on the season. See the glorious gardens from spring to fall, then visit the Lightscape show during the winter holiday.

Lightscape is an outdoor show within the gardens of light, fire, music, and color. It's definitely an event that will brighten your evening enjoyment. Check out the monthly calendar of activities even if the flowers aren't blooming.

6. Explore the World Under the Sea at the Shedd Aquarium

Year-round
For couples who love animals

The Shedd Aquarium is one of the best Chicago attractions for couples because it's a place where age doesn't matter and makes for an exciting day out with your partner. Explore the wondrous aquatic animal world at the Shedd Aquarium. Join a guided tour to the must-see sections of the aquarium, sign up for the meet the otters encounter, or use the Shedd App to navigate your way through the aquarium and learn about the animals you want to see. Oh, what a world under the water!

7. Be in Awe at the Field Museum of Natural History

For couples who love to explore the world

The Field Museum of Natural History has something that will amaze any couple, even if they have different interests. 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 that walks through its corridors. The building itself has an incredible history of its own. There's always a new exhibit to explore.

8. Cruise the City from the River

Seasonal 
For couples who love history and architecture

It's a tour through the city for views of Chicago's iconic architecture from the river. Join a tour with exciting narration and details of the legendary people who designed and built Chicago. Sit outdoors or indoors, then relax and enjoy the 90-minute tour. Find more information about a top-rated riverboat architectural tour. 

9. Wet Your Whistle at Chicago's Craft Beer Scene

Year-round
For beer-loving couples

Since Chicago was named the best beer city for its vast number of breweries, brewpubs, and beer bars, checking out the craft beer scene is a must for beer-loving couples. There is even a beer barrel bus tour to hit the top brewpubs (or distilleries and wineries, if you prefer). Choose from public tours or private events. Now that's a city that loves its suds.

10. Go Ice Skating or RollerBlading Hand-in-Hand

Year-round
For couples who love a romantic stroll together

Maggie Daley Ice Skating Ribbon is a lovely spot for skyline views, a fun atmosphere, and fresh air while striding hand in hand on skates. In winter, strap on some skates (rentals available) and glide around one of the coolest skating rink parks. In the summer, it is an excellent spot for rollerblading too. The park offers tons of romantic things to do in Chicago for couples who love spending time outside. Find out all the other things to do at Maggie Daley Park any time of the year.

11. Catch A Jazz Show At An Iconic Club

Year-round
For nostalgia or jazz-loving couples 

It's the iconic jazz club of the city and is 100 years young. The Green Mill Jazz Club is a 1940s-style venue with live music seven days a week starting at 8 pm. It's an experience even if you don't frequent jazz clubs. The history of acts and famous patrons of this place is enough to visit it. Just like in the 1940s, it's a cash-only bar.

12. Scream and Laugh on TILT

Year-round
For couples looking for a thrill

It's the thing to do in Chicago for thrill-loving couples. Take in the enjoyment of the Chicago skyline views, then tilt outward 1,000 feet above the Magnificent Mile. Find the TILT thrill ride at 360 CHICAGO Observation deck. Stay a while and discover the Chicago city views in full panorama. It's definitely a view worth screaming for.

13. Get Your Foodie On with the Tastes of Chicago

Seasonal 
For Foodie lovin' couples

Sure, Chicago is known for Deep Dish Pizza, Italian beef sandwiches, and its infamous BBQ, but there is an endless array of flavors and styles of restaurants, diners, kiosks, and white tablecloth establishments to choose from. An easy way to navigate all these options is to visit Chicago during one of its food events celebrating its eclectic flavors. 

Here are a few of the top events: 

Chicago Restaurant Week is a 17-day festival from Jan 20-Feb 5th, honoring the city's top-billed culinary scene. Three hundred restaurants around the city participate in the event with special menus and offers. This is an excellent opportunity to explore the city and its cuisine. 

Taste of Chicago is a vast outdoor food festival in June and July, held every year with more than 1.4 Million locals and visitors sampling all the delicious bites. The event is a food and music festival at Grant Park.

There are so many more festivals in Chicago dedicated to food. Check out the Chicago Food Festival Guide and plan your visit around an event.

14. Drink and Dine with a View at the London House Rooftop

It's rooftop dining at its finest. Book a table for two and sit outside on the patio with views of the city and the Chicago River. Dine and drink with a modern take on American cuisine. If it's cold out, there are indoor options too. The London Rooftop hosts all kinds of events throughout the year.

There are so many fun things to do in Chicago for couples that you're guaranteed to find activities that fit your interests! For more fun activities over a weekend or vacation, check out the Romantic Things to do in Chicago.

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1. Modern Techniques, Industrial Design

Zen Yoga Garage

Location: Bucktown

Once an old car repair garage, Zen yoga opens its big garage doors to all kinds of classes and students. They focus on postures and share the feeling that comes from dynamic movement. Their classes feature a modern twist like Zen Burn—Yoga with weights or BYO Baby with Yoga, and popular classics like Flow and Vinyasa. Workshops, massage, and aesthetics offerings are available too. Find out more about Zen Yoga Garage Classes here. 

2. Yoga With The Best Views of Chicago

Sky Yoga at 360 CHICAGO Observation Deck 

Location: Downtown Chicago

It's the yoga class at the highest location in Chicago at 1000 feet up! Breathe, move, and strengthen your body while gazing at the city's best views and Lake Michigan. Instructor Britta Eumann welcomes all ages and skill levels and takes the intimidation out of yoga, so everyone benefits from a class. Every class ends with a complimentary beverage, including a cup of artisanal Kikwetu coffee or a decadent Hot Toddy to kick-start you into the rest of your day. Yoga class is also an admission ticket to the observation deck, so stay around after class and enjoy the whole 360 observation deck experience. Register for a Sky Yoga class here.

3. Yoga in a Historic House

Sat Nam Yoga

Location: West Loop Downtown

This three-level space, in the historical Abraham Groesbeck House in the West Loop, has a warm and welcoming atmosphere. Enjoy their studio and small boutique spaces, a garden courtyard, and a student lounge. Sat Nam Yoga uses ancient and therapeutic traditions relevant to modern times, including services such as Kundalini Yoga, Reiki, Sound Therapy, and Traditional Thai Massage for all levels. Sat Nam translates to "Truth is My Identity," meaning come to this place to be who you are. Find the weekly list of classes at Sat Nam Yoga. 

4. Up Close with the Origins of Yoga

HTGC

Location: Lemont

Practice yoga in a peaceful and meditative place at the Hindu Temple of Greater Chicago in Lemont, Illinois, 22 miles from downtown. Learn techniques from ancient Indian origins with a Hatha-style class. HTGC's goals are to train the mind, body, and spirit to achieve inner peace and harmony. All ages and levels are welcome, including all cultural or ethnic backgrounds. Classes run every Monday, Wednesday, and Saturday. 

5. Pop-Up Yoga In Unexpected Places

Collective Yoga Co-op

Location: Various

It's a yoga studio for the people, created by the people. The Collective Yoga Co-op's goal is to provide accessible classes for everyone throughout Chicago. They partner with local businesses, groups, or charities to use their space for pop-up yoga and hybrid virtual classes. These unique Chicago yoga studios are in locations such as The Daley Library, The Dovetail Brewery for a Yoga + Happy Hour Session, and the Lululemon Experiential Store. Certified yoga instructors travel around to provide classes such as Vinyasa Lift and Vinyasa Steady varieties. 

6. Yoga Surrounded by Masterpieces

Van Gogh Chicago 

Location: Lighthouse Artspace

Practice yoga surrounded by art and a complete multi-sensory experience at the Van Gogh Immersive art exhibit. This 35-minute class with a certified yoga instructor stimulates the mind and body with a choreographed show of music, sounds, light, and imagery of the works of Van Gogh's prized masterpieces. After the class, receive a sample of Kefir compliments of Lifeway Kefir. Find out more about Van Gogh Chicago classes here. 

7. Yoga While Floating on Lake Michigan

Chicago SUP Yoga

Location: Montrose Beach

It's the yoga class that is only available in the summer. How about combining a yoga class with the peace and tranquility of stand-up paddle boarding (SUP)? That's right; your yoga mat is a paddle board to practice sun salutations on Lake Michigan. SUP yoga is a great way to develop balance, flexibility, and whole-body fitness while connecting with water and nature around you. Meet at Montrose Beach for a class open to all levels. If yoga on the water makes you feel a little queasy, Mary Lou Cerami offers outdoor yoga classes in the park. More about Chicago SUP yoga classes here.

8. Yoga With Furry Friends

Nature's Trail Goat Yoga

Location: Orland Park 

A unique and unconventional yoga space list is only complete with a place that offers Caprine Vinyasa or baby goat yoga. It's the most laid-back (and the funniest) form of yoga class for light exercise and pure entertainment. Take part in yoga poses while baby goats attempt to break your concentration to play with them instead. At Nature's Trail Goat Yoga in Orland Park, classes help with concentration and breaking out of a typical mindset. It's an ideal class for mental health and overall stress relief. After all, it's pretty hard to take yourself seriously when baby goats are involved! Classes run throughout the year indoors and out. The 1.5-hour class includes yoga and playtime with the goats. Find out more about this unique yoga class near Chicago. Nature's Trail Goat Yoga is located on a 5-acre family-owned mini farm. 

Are you looking for more things to do in Chicago? Find out the best spots, haunts, and digs for just about anything in the Windy City on our blog. 

 

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1. Centennial Wheel at the Navy Pier

At the top of the 200-foot Centennial Ferris wheel at the famous Navy Pier, look west to take in the beautiful Chicago city skyline. Perfect at sunset or after dark, especially in the summertime when you can catch a fireworks display on Wednesday and Saturday nights from Memorial Day through Labor Day weekend. It’s also a great place to get cozy with the one you love and snap a few Chicago skyline pictures!

2. Promontory Point

Just south of downtown is the neighborhood of Hyde Park, home to the man-made peninsula jutting into Lake Michigan known as Promontory Point. Despite the park’s distance from the city center, it offers a majestic panoramic view of the whole downtown Chicago skyline.

3. Lincoln Park

Lincoln Park lies along the shores of Lake Michigan and features incredible Chicago skyline views of the city skyline from many vantage points. The park itself is bigger than New York’s Central Park and is home to one of the last free urban zoos in the country. Photograph the skyline through the permanent art installation known as The Honeycomb, or grab a selfie from the Lincoln Park Bridge over South Pond.

4. Chicago River Cruise

The Chicago River runs through downtown Chicago’s canyon of skyscrapers. Book an architectural river tour and learn the history of some of Chicago’s most iconic buildings. 

5. 360 CHICAGO Observation Deck

The 360 CHICAGO Observation Deck 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. If you want to turn up the adrenaline, strap in for TILT, the country’s highest thrill ride.

If you’re interested in getting spectacular views of Chicago at night, then the observation deck is a must visit destination. 360 CHICAGO offers some of the best views of the Chicago skyline at night. It’s a unique opportunity to see the city from a sky view when it’s lit up and glowing.

6. Oak Street Beach

Located near the Gold Coast neighborhood, Oak Street Beach boasts some of the best views in Chicago from ground-level. In the summertime, enjoy biking, watersports, or some relaxing sunbathing with a skyline backdrop.

7. Chicago Riverwalk

For a leisurely tour of Chicago’s towering architecture, take a stroll along the Riverwalk. The Chicago River runs through the middle of the urban canyon with plenty of places to stop and take in the views of historic buildings like the Tribune Tower, Merchandise Mart, and the Wrigley Building.

8. Northerly Island

Northerly Island was designed at the turn of the last century to be a manmade island with breathtaking Chicago skyline views. In 2015, Studio Gang brought that vision to reality by reimagining Northerly Island, formerly Meigs Field Airport, as a 91-acre ecological preserve.

9. The Lakefront Trail

Lace up those sneakers and head out on the trails for some outdoor exercise and epic views of the skyline of Chicago on the Lakefront Trail. This 18 mile stretch of paved trails along the (you guessed it), Chicago lakefront/Lake Michigan shoreline is a favorite amongst runners, walkers, and cyclists. Boom, you get two benefits in one at this location.

10. Palmisano Park

In 2009, the city opened this repurposed natural space as Palmisano Park. Check out the entire panorama of the Chicago skyline from the top of “Mount Bridgeport,” the highest point in this former limestone quarry.

Photo by Eric Allix Rogers

11. Humboldt Park Boathouse

The Humboldt Park Boathouse is a natural oasis and an architectural gem with some of the best views in Chicago of the surrounding natural lagoon. Peeking up over the treeline is the beautiful Chicago skyline that glows orange in the distance at sunset.

12. Millenium Park

Millenium Park is one of Chicago’s crown jewels, sporting stunning views of the city that surround it from infinite vantage points. The famous Cloud Gate sculpture (aka “The Bean”) reflects a distorted view of the city skyline in its curvaceous chrome. During the summer months, take a stroll through the wildflowers in Lurie Garden at the southern end of the park, a special spot that offers its own views of the skyline.

13. Adler Planetarium

The Adler Planetarium offers more than just breathtaking shoreline views of the Chicago skyline. Inside, you can peer into deep space with its world-class astronomy exhibits and programs.

Photo tips

• Light: Aim for golden hour, just before twilight for warm tones and evening sparkle.

• Weather: After rain, reflections pop on the Riverwalk; in winter, clear cold days provide crisp visibility.

• Crowd Hacks: To minimize crowds, check out North Avenue Beach at sunrise; Museum Campus on weekdays; if shooting from rooftops, inquire about reservations.

• Tripod Rules: Parks and rooftops may limit pro gear — check venue policies.

No matter where you are in the Windy City, you can take in the best views of the Chicago skyline from any number of breathtaking vantage points. Check out the 360 CHICAGO blog for more great visitor tips to get the most out of your time in Chicago!

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NEW! Flash Sale for Ballet 5:8's Imagine Better performance. All tickets are now BUY ONE, GET ONE FREE beginning Wednesday, September 28 through October 3. Guests can use the code FLASH for this limited offer. 

Lakeview

Why you Should Visit

• Looking for a neighborhood with lots of lakeside views? You found it! Lakeview is on the northside of the city, it's the most populated and consists of smaller distinct areas including Wrigleyville, the Southport Corridor and Boystown—one of the most inclusive LGBTQ+ communities. This area is is brimming with fantastic dining, exciting nightlife and many LGBTQ+ owned businesses. Of course, when in Lakeview, you could just hit the beach too.

Fun Things to Do:

• A trip to Chicago is not complete without visiting the home of the Chicago Cubs—Wrigley Field! This is one of the two Chicago baseball fields, and one would argue, it's probably the best looking fields in the roster of National or American league ball parks.
• Take a stroll along The Legacy Walk- a permanent outdoor half-mile stretch of tall rainbow pylons and bronze memorial plaques commemorating the lives and legacies of people who have advanced the rights of LGBTQ+ people all over the world. 
• See a theatre show! Like the Loop Neighborhood, Lakeview is the other significant theatre district boasting 50 theatres that including big name acts, improv and music. Near Wrigley Field is the notable Mercury Theater that opened in 1912, and features lots of fun performances for all ages and interests.

Favorite Eats and Drinks:

• Ready for the best cocktails in ChiTown? Head over to Kit Kat Lounge and Supper Club for over 20 years, this premier martini and cocktail bar and world class entertainment lounge has been serving up food, drinks, and fun with it's "Hollywood-meets-Miami' vibe. The nightly dinner and drag show is a blast and weekend brunch is divine. You can also sample two exclusive cocktails from the Kit Kat Lounge and Supper Club at CLOUDBAR at 360 Chicago.
• Did someone say chocolate? Vosges Chocolate, a luxury chocolate brand and women-owned business in Chicago. Makes delicious delicacies from the owners travels to 7 continents. Visit the Vosges Temple Boutique in Lakeview for the full experience. Vosges chocolate can also be found for purchase at 360 CHICAGO's CLOUDBAR as a chocolate gift or dessert accompaniment to it's cocktail flights.

The Best Views:

•  If you love to walk, run,cycle  or just stroll to check out the city, you'll love the Lakefront Trail. It spans 18miles between the intersections of W Addison Drive, and N. Recreation Drive. From this vantage point, Lake Michigan is very impressive.

Bronzeville

Why you Should Visit

• Bronzeville is the key neighborhood of African-American business and culture located on the Southside of ChiTown from 31st street down to 51st street between LaSalle and Cottage Grove Avenue.

Fun Things to Do:

• For a live venue of music, events, plays, movie screenings and more,  check out the Harold Washington Cultural Center (The HWCC), named after Chicago's first African-American mayor. 
• The Bronzeville Children's Museum is the first of its kind in the country, bringing to life African-American culture for kids through a unique, and memorable guided tour format.
• Gallery Guichard is art that touches the soul. This gallery features modern and contemporary works from artists all over the world, rotating it's showcase every 6 to 8 weeks. This is truly a gallery that exposes every visitor to multicultural arts. One must-do at the here is a stroll through the Great Migration Sculpture Gallery.

Favorite Eats and Drinks:

• For fantastic food and beers, visit  Moody Tongue Brewery—the world's first two start Michelin Brewery that specializes in culinary brewing. The brew master thinks like a chef, blending familiar flavors with quality ingredients to highlight flavors and aromatics in all their beers. Visit the Dining Room or The Bar.  Moody Tongue beers are sold throughout Chicago too.

The Best Views:

• For great views of the lake and south side of the city skyline, check out the Margaret T. Burroughs beach for swimming, running and  lakeside walks. The area is named after the  accomplished artist, art advocate, poet, teacher, civic leader, historian, and founder of the DuSable Museum of African American History.

Old Town

Photo Credit: Bon Appetit

Why you Should Visit

• Get your laugh on in Old Town—the birthplace of comedy and home to the most famous comedy clubs and troupes. 
• This historic neighborhood just north of downtown off of North Wells Street—its main drag, is also the place to find the best preserved Victorian homes, buildings, vintage boutiques, and restaurants. The neighborhood comprises primarily upscale residential dwellings yet becomes more energetic in the Old Town Triangle District to the north, on Division Street on the south side, and on the more populated Wells and Clark Streets. 

Fun Things to Do:

• Catch a show at Second City, the home of the famous improv comedy troupe that started with stars like Bill Murray, Gilda Radner, and Chevy Chase.
• Stroll along the streets or join a walking tour to discover the historic buildings and the few remaining that survived the Great Chicago Fire. Learn how this neighborhood became a hippie hangout in the '60s and '70s. 
• For the lighter side of the city, visit Zanies Comedy Club for a fun night at this decades-old club that features some of the hottest headliners and up-and-coming comedy acts from all across the country. 

Favorite Eats and Drinks:

• Visit the best dive bar in America, a comedy celeb hang out, and Chicago landmark—The Old Town Ale House. 
• Bring your appetite over 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. 

The Best Views:

• For some peace, tranquility, and gorgeous views of the city, head over to the South Pond Lincoln Park—a natural preserve in the city, just adjacent to Old Town.
• While you’re there, make a stop at The Honeycomb along the Lincoln Park Zoo Nature Boardwalk. This is a gorgeous piece of contemporary art that makes a great photograph in all kinds of lighting, both day and night. 

Andersonville

Why you Should Visit

• You know a neighborhood is cool when it literally wins an award for being the #2 coolest neighborhood in the world! 
• Once a small village of Swedish Immigrants, Andersonville's ethnic roots have remained and it is the #2 hub for Swedes in the world outside of Stockholm. This large LGBTQ+ community and home of Pride Month’s Midsommarfest, celebrates both LGBTQ+ and Andersonville's Swedish culture together. 
• Some call this neighborhood the "shop local capital" because if you want to support independent shop owners and entrepreneurs, you've found your place. There isn't a chain store in sight!

Fun Things to Do:

• Head out on the town to the Chicago Magic Lounge, a cross between a speakeasy and magical theater. Enter through a laundromat to be transported into a mysterious, marvelous experience. Besides the surprises and magic, you can satiate your thirst from their craft cocktail menu or order a small plate if you are peckish.  
• For another out-of-this-world evening, visit The Neo-Futurist Theater—a place where interactive performances are considered a blend of sport, poetry, and living newspaper. Their signature show, "Too Much Light Makes the Baby Go Blind,” has been running since 1989.
• Discover 200 years of immigrant history come to life at the Swedish American Museum. 

Favorite Eats and Drinks:

• Say hello to some incredible Swedish bakery & brunch spots! Check out Lost Larson—a bakery and cafe inspired by owner and chef Bobby Schaffer's Scandanavian roots. 
• You're in little Sweden after all, why not order a Viking breakfast at Svea? This Andersonville diner serves Swedish comfort food specialties perfect for big appetites and hangover cures. The Swedish meatballs are a must.
• Simon’s Tavern is decked out in Scandinavian decor and was once a speakeasy back in the day. If you visit around the holiday season, make sure you try their feature Glögg—warm mulled wine or in the summer, sample their "slushie" version of the same drink. 

The Best Views:

• Feast your eyes on the bounty of colors at this Chicago institution, the Gethsemane Garden Center where you can handpick flowers, herbs, fruits, and vegetables or buy decorative items to dress up your home & backyard for the holidays or the summer months.

West Ridge (Little India)

Why you Should Visit

• Visit the Chicago neighborhood with some serious color and flavor! On the far north side of the city, you'll find West Ridge or Little India. It may have India in the nickname, but it spans beyond East Indian roots into a true melting pot of cultures from Asia, Africa, Eastern Europe, and the Middle East. It's earned the reputation as one of the most diverse neighborhoods in America. 
• Devon Avenue is the heart of West Ridge and an eclectic street of restaurants and shops. One visit will give you a true flavor of this multicultural neighborhood.

Fun Things to Do:

• Make the most of your visit with a Little India Food Tour, that combines tastings of the best South Asian cuisines, with spice store visits, Henna tattoos, and a visit to a temple.
• Shop till you drop at Resham’s for colorful Indian home goods, fabrics, and traditional saris.

Favorite Eats and Drinks:

• Head for a feast of delicious South Indian vegetarian cuisine, including the popular Thalis and Dosas at Udupi Palace. 
• Meat lovers will love Sabri NIhari, an incredible Pakistani cuisine that serves up concoctions with Halal meats.
• Got room for an after-dinner delicacy? Head to the world-famous Tahoora Sweets & Bakery, featuring all kinds of South Asian desserts. Lucky for you, they ship their sweets all over North America if you don't have room in your tummy or your luggage.

The Best Views:

• Stroll through Indian Boundary Park, a 13-acre park that opened in 1922 and is listed on the U.S. national registry of historic places. Brimming with nature all around, the park features a gorgeous lagoon, surrounded by flowerbeds, shrubs, and trees. Here, you are bound to snap a great photo and have some fun at the spray park, playground, and tennis courts.

Wicker Park/Bucktown

Why you Should Visit

• What was once an urban, shabby-chic enclave for artists and musicians has gradually transformed into an upscale, artsy neighborhood buzzing with galleries, nightlife, and living communities. The streets are full of art, murals, and live music which are the beating heart of this vibrant neighborhood.

Fun Things to Do:

• Pay what you can to get a ticket to the Broken Nose Theatre, featuring contemporary plays and musicals for everyone in the community.
• Subterranean is a sprawling live music and comedy venue in a converted century-old warehouse built over Prohibition-era bootlegger tunnels.
• In a city of wonderful farmer’s markets, Wicker Park Farmers’ Market is among the best. It's open most of the year, with indoor markets in the winter and you can even come for yoga and meditation classes, or stay for a storytime for the kids.

Favorite Eats and Drinks:

• Le Bouchon has been a Bucktown staple for nearly 30 years, and is considered one of the country’s best French restaurants.
• Wicker Park/Bucktown is a brunch Mecca, with no shortage of options, but Dove’s Luncheonette is among locals’ top favorites.
• Keep it on the down-low, but speakeasy cocktail pioneer The Violet Hour, serves Chicago’s best craft cocktails. Shhhhh.

The Best Views:

• Get an amazing shot of the Windy City skyline from the rooftop bar at The Up Room at the Robey Hotel. Not only are the views great, but the drinks are top-notch. You’ll need to have a pretty long selfie stick to get the whole Cloud Mural in your shot. It spans the entire side of a four-story building and is sure to make your followers smile.

Logan Square

Why you Should Visit

• Logan Square earns its name from General John A. Logan, a soldier in the Civil War who became a U.S. Senator. The neighborhood has evolved into a hub of the city's culinary and nightlife as well as a beautiful spot to walk through with its classic Greystone buildings accented with charming restaurants, coffee shops, delis, and cocktail bars. 
• Logan Square attracts visitors to it’s main commercial street of North Milwaukee Avenue and attracts locals and visitors alike to its art galleries and music venues.

Fun Things to Do:

• The Logan Theatre anchors North Milwaukee Avenue and is a vintage movie house that opened in 1915. It features a movie theater decked out in sports artifacts and a renovated bar and lounge. The theatre screens indie films, cult classics, and new-and-upcoming pieces. It's no surprise that it's the home of the Chicago Underground Film Festival which showcases experimental, documentary, and independent films. 
• Shop at Chicago's handmade marketplace of local goods from over 300 makers at Wolfbait & B-Girls. Browse for unique jewelry, beauty products, cards, gifts, and so much more.
• For some unique decor, you'll find eclectic gig posters, prints, art, and street art at Galerie F.

Favorite Eats and Drinks:

• Head to the Revolution Brewery - Brewpub and Kitchen, Illinois's largest independent brewery. Get ready for big tastes and variety of options and a fun food menu to accompany your brew. Open for brunch too.
• For the real thing, Parson’s Chicken & Fish – known for its outrageously good fried chicken and the Negroni Slushy, it's easy on the wallet and is always a good time. Parson's has 4 locations throughout Chicago.
• Wet your whistle at The Whistler, a merge of a cocktail bar, with a music venue, and a gallery, while also showcasing independent artists with its record label.

The Best Views:

• Check out the towering Illinois Centennial Monument (featured in the main image above) that  anchors Logan Square, built in 1918 to celebrate Illinois's statehood. If you think it resembles Greek architecture, that's correct, as it emulates a column on the Acropolis in Athens in exact size and proportion.
• For great views of the Centennial Monument, dine at the charming Lula Cafe, which features farm-to-table dining. It's a popular brunch destination featured in Food and Wine, The New York Times, and Bon Appetit.

Humboldt Park

Why you Should Visit

• Located on the west side of Chicago, Humboldt Park has been through profound social and ethnic change, and celebrates its strong Puerto Rican roots since the '70s. There's no mistaking this neighborhood is a strong Puerto Rican community because it will show its pride wherever you go in the area. 
• Locals and visitors love visiting this neighborhood for its numerous cultural events, huge selection of independent and family-owned restaurants, and 70+ street murals made by local artists.

Fun Things to Do:

• Now this is a local walking tour! The Paseo Boricua Neighborhood Tour is led by Eduardo Arocho, a lifelong neighborhood resident who will guide you through the colorful stories and fascinating cultural landmarks that make Humboldt Park truly unique.
• For a local market experience, visit ¡WEPA! Mercado de Pueblo –translated as "the market of the town") which is a Puerto Rican cultural center and a spot for local artisans to sell their goods. This building was once a laundromat but was converted into a center to support small business owners in the area.

Favorite Eats and Drinks:

• When you are in Humboldt, sampling Puerto Rican food is a must!  La Bruquena is a small family-owned cafe that serves up delicious Caribbean classics from the island.
• Another acclaimed locally-owned restaurant is Papa’s Cache Sabroso  which specializes in rotisserie chicken with its acclaimed secret sauce.

The Best Views:

• The Humboldt Park Boathouse (circa 1907) and lagoon, is one of the city's nature oasis sites that boast fantastic views of the wetlands area and equally great views of the city's skyline.
• Another greenspace project in the city is The Bloomingdale Trail at the 606, a community-supported rail trail that runs east-west through the neighborhoods of Humboldt Park, Logan Square, Wicker Park, and Bucktown. This urban trail resulted in a true partnership between government departments and communities working together (and it's a great place to snap photos of the city!)

Ukrainian Village

Why you Should Visit

• Spanning Western and Division Avenues, The Ukrainian Village is a quiet residential neighborhood of brick row houses and townhomes amongst four elaborate cathedrals. It's home to over 54,000 Ukrainian and Ukrainian-American residents so, it's pulsing with folk music, dance, and the best cultural eateries in the city.
• The Ukrainian National Museum of Chicago is home to over 10,000 folk and fine arts pieces that are prized by the community. Despite its Ukrainian roots, you'll be sure to also find trendy cafes and interesting cocktail bars.

Fun Things to Do:

• For a contemporary flare, visit the Ukrainian Institute of Modern Art which includes famous and undiscovered pieces from the best Eastern European and Ukrainian-American artists.
• Alternative music can be found in the village at The Empty Bottle, a popular spot for music and drinks for almost thirty years.

Favorite Eats and Drinks:

• For Ukrainian food with a modern twist, Tryzub Ukrainian Kitchen creates popular favorites such as borscht, pierogies, and potato pancakes but also offers a new take on dishes like charcuterie boards.
• The village would not be complete without Ukrainian Bakeries. The Shokolad Bakery & Cafe creates custom desserts, pastries, chocolates, and even traditional main course plates for when you know you haven't got your fill of pierogies yet.

The Best Views:

• For the best views in the neighborhood, take a load off at Homestead on the Roof, an authentic farm-to-table restaurant, a 3,000-square-foot organic garden, and an open-air patio. Now, this is a place for fresh food!

Little Italy/University Village

Why you Should Visit

• Located on the northwest side of Chicago on its main artery of Taylor Street, Little Italy is the historic epicenter of Italian immigrants, and has evolved into a diverse ethnic and socio-economic enclave that is home to the University of Illinois at Chicago. No doubt, you will find some of the best Italian restaurants, bakeries, and delis on these streets.

Fun Things to Do:

• Who doesn't love a good market? The Maxwell Street Market is open every Sunday. This street market dates back to the 1900s when immigrant families would sell goods out of pushcarts. Today, the market is in a different location and is a fun place to bargain for thousands of different goods.
• The Jane Addams Hull House Museum pays homage to the settlement homes that served as a community center, food kitchen, and orphanage for Chicago immigrant residents. This historic site was created by social reformer and Nobel Peace Prize Laureate, Jane Addams.

Favorite Eats and Drinks:

• Craving a steak or some of your favorite Italian staples? Head to The Rosebud, one of the most famous steakhouses in Chicago that dishes out all the Italian classics. This place always reserved a regular table for its most famous customer—Frank Sinatra. 
• A visit to Little Italy would not be complete without a shaved ice treat from Mario’s Italian Lemonade. Mario’s has been creating shaved ice masterpieces from its seasonal stand including flavors such as blue raspberry, cantaloupe, pineapple, and more since 1954.
• Once a wooden stand on Laflin and Harrison, Al’s Italian Beef opened in 1938 and still continues to serve its famous Italian beef sandwich. Check out their story on the website (it's amazing), then head there for a bun piled 6 inches high of thinly sliced beef! This establishment even won top honors as "The Top Food to Eat in Chicago Before You Die" designation!

The Best Views:

• The streets of Little Italy/University Village are an architecture lover’s dream. Two notable buildings are The Shrine of Our Lady of Pompeii and the Notre Dame de Chicago. 
• Walk off all that good Italian food on Lexington Street for a history lesson in Italian architecture, including a stop at the John Coughlan House built in 1871. The neighborhood is also known for its many historic churches including Saint Basil and Holy Family.

Hyde Park

Why you Should Visit

• Located seven miles south of the Chicago Loop and nestled on the shores of Lake Michigan, this beautiful neighborhood is the home of the University of Chicago, former President Barack Obama, and has been a breeding ground for Nobel Prize winners. This area is also a great place to find fabulous restaurants, bookstores, and cafes.

Fun Things to Do:

• The exciting Museum of Science and Industry, located in Jackson Park is definitely worth visiting, and contains more than 2,000 exhibits from the largest display of Lego art in the world, to space and tornado exhibits. The architecture of the building is fascinating and still includes one of the last standing buildings from the Chicago World’s Fair of 1893.
• In Washington Park, you can find the DuSable Museum with displays dedicated to African American history and culture. While visiting, check out the bird and butterfly sanctuary and the photogenic Fountain of Time.

Favorite Eats and Drinks:

• For a hearty breakfast, head over to the 100-year-old Valois Restaurant frequented by former president Barak Obama.
• A trip to Chicago's top deli may be in order, and it's located in Hyde Park! Morry’s Deli has been serving Chicagoans for over 50 years with mouth-watering subs, triple-decker sandwiches, and breakfast plates.

The Best Views:

• For an architectural wonder, visit Frank Lloyd Wright’s Robie House to see his incredibly restored home which is a designated UNESCO World Heritage Site.
• For a beautiful view of one of Chicago's greatest parks, The Midway Plaisance Park should be on your list. This park is tastefully landscaped with long avenues of trees and accented with architectural beauties like the University of Chicago campus.

Streeterville

Why you Should Visit

• Streeterville is brimming with local attractions on the bucket list for visitors to the city. It's the home of the 360 CHICAGO Observation Deck, Navy Pier, Museum of Contemporary Art, access to the beaches of Lake Michigan, and so much more!

Fun Things to Do:

• Head to Navy Pier for family and couples fun including amusement rides, games, and the 200ft Centennial Ferris Wheel. Check out their weekend events, eateries, gift shops, and the Chicago Shakespeare Theatre 
• For a more avant-garde experience, pop over to the Museum of Contemporary Art for a peek at the latest experimental exhibit.
• Shop till you drop on the Magnificent Mile, for uber luxury boutiques including Gucci, at 900 shops, and department stores like Bloomingdales.

Favorite Eats and Drinks:

• While at the Museum of Contemporary Art, stop for a cup of Kikwetu coffee at the Tuesday morning Farmer's Market.
• Looking for some international flavors to tantalize your tastebuds after a day of walking the Mag Mile? Head to Sayat Nova a Streeterville staple serving authentic Armenian cuisine since 1970.
• For a healthy and delicious option, celebrity chef Matthew Kenny serves up organic, thoughtfully sourced, and plant-based masterpieces at Althea restaurant.

The Best Views:

• If you haven't visited 360 CHICAGO at the former John Hancock building yet, the panoramic views of the Chicago skyline and Lake Michigan are a must-see!
• Get easy access to the beach via Oak street for views of Lake Michigan and many Chicagoans catching some rays.

River North

Why you Should Visit

• Located along the Chicago River, River North is known as the Gallery District. You’re never too far away from an amazing meal, a beautiful walk along the Riverwalk, or a stimulating tour through the country’s best contemporary fine art.

Fun Things to Do:

• Known as the River North Gallery District for a reason, go on a Gallery Walk starting at the intersection of Superior and Wells and head west for a deep dive into the country’s best contemporary fine art. Stop and start at any gallery you choose. You will also catch some of the best views of the city.
• Hop aboard a Chicago Water Taxi from the Riverwalk for a fun time on the river for the whole family.
• Step back in time to Chicago’s gilded age at the Driehaus Museum, also known as Chicago’s Marble Palace. The museum presents some of the most luxurious designs of the late 19th and early 20th centuries.

Favorite Eats and Drinks:

• Celebrity chef and Chicagoan Rick Bayless, opened Frontera Grill back in 1987, but it continues to serve some of the most innovative and delicious Mexican cuisines in the country. Try its fine dining sister restaurant, Topolobampo which is right next door.
• The best deep-dish is in River North at Lou Malnati’s Pizzeria, an iconic name in Chicago pizza since the 1940s.

The Best Views:

• Some of the best cityscape views and celebrity stargazing can be found at the London House Rooftop. This is also a fantastic choice for Sunday brunch.

Gold Coast

Why you Should Visit

• The Gold Coast area was originally referred to as the Astor Street District, named for John Jacob Astor, who wasn't a resident of Chicago but rather a name that was used to attract wealthy developers.
• The Gothic Chicago Water Tower on Michigan Ave. is the second oldest water tower in the US and was the only public building to survive the Great Chicago Fire of 1871.
• Rush Street is one of Chicago’s oldest streets, dating back to the city’s incorporation in 1837. Today, it’s home to luxury hotels and amazing restaurants, and if you are in the market for buying a Bentley or Lamborghini, you can find their showrooms in this neighborhood.

Fun Things to Do:

• Located in Water Tower Place, the Broadway Playhouse was restored and reopened in 2010, and hosts hit productions of America’s favorite plays and musicals.
• Housed in the historic Nickerson Mansion just steps from the Magnificent Mile, The Driehaus Museum exhibits art, architecture, and design of the late 19th century to the present day.

Favorite Eats and Drinks:

• A celebration of French-colonial Vietnamese culture and cuisine—Le Colonial is a Gold Coast institution. Located on Rush Street, you will enjoy their Southeast Asian fare with French bistro flare.
• Dine al fresco (even in the winter) in the light and airy courtyard within the historic building that houses the 3 Arts Club Café.

The Best Views:

• Capture Chicago’s iconic skyline on the shores of Lake Michigan at Oak Street Beach on N. Lake Shore Drive. This area also extends into the Streeterville neighborhood.
• Take in the amazing views of Chi-town’s iconic skyline from Devereaux, the swanky rooftop bar at the Viceroy Chicago.

Loop

Why you Should Visit

• The Loop 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.
• One of the visitor favorites is the sprawling 24.5-acre Millennium Park to wander around its year-round flower displays with its iconic Cloud Gate sculpture (a.k.a the Bean), which illuminates the faces of passers-by.

Fun Things to Do:

• Welcome to Chicago's theater district boasting 11 of the best theaters in the city, including the 5,000-seat Chicago Theater (circa 1921), which is home to popular events and its famous illuminated marquee sign.
• 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.

Favorite Eats and Drinks:

• For an amazing cup of coffee, look out for Kikwetu coffee- family-owned Kenyan coffee purveyors. Their coffees can be found at the Green City Market on Saturday mornings in the West Loop and also in Lincoln Park.  
• Satisfy your hunger at Revival Food Hall, which brings all of Chicago's local culinary flavors under one roof. It's perfect for groups looking for different options.
• Former food truck chefs bring together Asian-Latin flavors at Saucy Porka or take your dining up a notch with Italian flavors at Acanto restaurant and wine bar steps from Millennium Park.

The Best Views:

• Soak in the views of the windy city's famous architecture on a Chicago Riverwalk along Wacker Drive from Franklin Street to Lake Shore Drive. You can also hop on a river cruise for another vantage point for some stellar vacation photos.

Explore the neighborhoods of Chicago! This is where all the fun happens, and every neighborhood is different. For more information about things to do in Chicago, check out our Chicago blog for more tips, news, and suggestions.

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CloudWalk

Guests will have another reason to hold their breath when looking down as they experience 360 CHICAGO’s new 3D mural by artist Nate Baranowski. This is the first commission Baranowski will complete for an observation deck, and its optical illusion tempts visitors to step into the artwork, onto a crane platform in the clouds for a thrilling experience beginning Friday, July 15.

 

Baranowski, a street painter, muralist, and fine artist who earned his BFA from the University of Illinois-Champaign, says lots of preparation and design goes into every project. The 360 CHICAGO installation will take Baranowski and project partner, artist Chris Carlson, approximately 50 hours over three days to complete the 10’ x 30’ 3D mural. Originally inspired to pursue 3D mural work after discovering the art at chalk festivals in Florida, he was very interested to see people stepping into the artwork. 

“3D pieces are designed to view from one exact vantage point to get the full 3D effects. We’ll put a sign or footprints in place to illustrate where to capture the perfect viewpoint and the optical illusion,” says Baranowski who has completed over 200 3D works of art in a combination of permanent, semi-permanent and temporary works.

“We continually seek imaginative ways to showcase our spectacular views, and Nate’s incredible talent really captured a thrilling new way to enhance our guests’ experience while providing an entirely new and artistic attraction for visitors,” says Nichole Benolken, managing director for 360 CHICAGO.

360 CHICAGO also features an ongoing and rotating art series that spotlights local Chicago talents who capture the importance of social change, positive movement forward and the beauty of Chicago.

Located at 875 N. Michigan Avenue, 360 CHICAGO is open daily at 9 a.m. General admission and TILT ride tickets and timed-entry ticket packages are available at 360chicago.com.

Romantic Date Ideas & Things To Do In Chicago

1. The Art Institute of Chicago

This world-renowned museum has one of the country’s most celebrated collections of historic and contemporary fine art, including famous works like Edward Hopper’s “Nighthawks,” Seurat’s “A Sunday Afternoon…” and about 300,000 more.

Why this is a romantic thing to do: When the weather is too hot, too cold, too rainy or windy, spend your romantic day among the masters and hold your significant other close while exploring stunning art.

Go to the Art Institute’s website to learn about special exhibitions and to buy tickets or memberships.

2. The Chicago Symphony Orchestra

Often hailed as one of the best symphony orchestras in the world, the Chicago Symphony performs nearly 100 concerts annually. During the year, they perform downtown at the Symphony Center, but in the summer season they move to the North Shore for the Ravinia Festival.

Why this is a romantic thing to do: There’s nothing more romantic than listening to some of the greatest music ever composed with your boo, but it’s not all Beethoven and Brahms – they often feature live performances of movie scores like Star Wars, The Princess Bride, and Harry Potter. 

Check their calendar for upcoming events and to get your tickets.

3. The Magnificent Mile

The most famous stretch of road in Chicago, the Magnificent Mile is 13 blocks on North Michigan Avenue, filled with world-class shopping, dining, museums, and entertainment venues.

Why this is a romantic thing to do: Even if you’re just out for a walk, you and your squeeze will be treated to the city’s most stunning historic architecture. Even if you live in Chicago, the Mile is home to a cadre of luxury hotels, perfect for a romantic staycation.

4. CloudBar at 360 CHICAGO

If Chicago at street level isn’t romantic enough for you, try elevating your expectations with a visit to the new CloudBar at 360 CHICAGO Observation Deck. This is the coolest new bar in town, with views from 1,000 feet up. Enjoy a cocktail, a cold drink and small plates that are inspired by Chicago's vibrant neighborhood flavors. 

Why this is a romantic thing to do: Panoramic sunset and evening views, and one great cocktail will be the date that you and you partner remember for a lifetime. Stay a while, walk around the deck, or for that more adventurous couple, try out TILT - The highest thrill ride in the world! 

Access the Cloudbar with a 360 CHICAGO general admission ticket here. 

5. The Lincoln Park Zoo

Home to more than 200 species of animals, the Lincoln Park Zoo is 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.

Why this is a romantic thing to do: Escape the hustle and bustle of everyday life and connect with your significant other while exploring the wildlife and share your love for animals.

Check out the site to see what’s happening for you and your loved one to enjoy together.

6. The Navy Pier

It wouldn’t be a romantic day in Chicago without a walk out on the famous Navy Pier. Boasting some of the best views of the Chicago Skyline.

Why this is a romantic thing to do: Some outdoor couples fun. There are always fun things to do at the Pier like free concerts, dinner cruises on Lake Michigan, or an evening at the Chicago Shakespeare Theatre. And you and your boo definitely don’t want to miss the fireworks all summer long! 

Check out their calendar to see what’s happening.

7. Chicago Food Tours

One thing is for sure – Chicagoans know how to eat well. The best way to experience a local’s knowledge of the city’s best cuisine is to sign up you and your partner up for a food tour. There are a bunch to choose from, including a great food tour of the trendy West Loop restaurant row and any number of great Chicago pizza tours.

Why this is a romantic thing to do: You and your ride-or-die can experience an amazing introduction to Chicago's incredible cuisine and explore the city from a culinary perspective.

8. ChiTown Drive-In

Movie lovers! Featuring modern classics like The Breakfast Club, Spider-Man: No Way Home, and Nightmare on Elm Street, a drive-in movie is a great way to spend a romantic evening together with your significant other. It's a fun, affordable way to enjoy a movie, and it can be a lot more intimate than going to a traditional movie theater.

Why this is a romantic thing to do: there’s nothing more romantic than parking with your significant other and taking in a great movie. And if you’ve already seen it, it’s a good excuse to steam up the windows a little – in a PG kinda way, of course. 

Check their site for showtimes!

9. Morton Arboretum

Take a walk with your sweetheart through this stunning nature preserve in suburban Lisle where you’ll encounter more than 4,000 cataloged species of plantlife. Until March 2023, wander among the towering sculptures of the popular outdoor Human + Nature art exhibition.

Why this is a romantic thing to do: The Arboretum also hosts romantic events like special dinners, Aerial Tree Yoga, and more.

Reserve your tickets here for timed admission or special exhibits and events.

Photo Credit: Alanscottwalker

10. Maggie Daley Park Skating Ribbon

In the winter months, the gradually sloping quarter-mile Ribbon is home to the city’s coolest ice skating rink, complete with skate rentals. In the summer, strap on your rollerblades and enjoy the nice weather.

Why this is a romantic thing to do: Alone time, holding hands, and a fun atmosphere to take in the skyline as you go around the winding path.

If you want to hit the ice this winter, you’ll have to make reservations ahead of time.

11. Promontory Point

This man-made lakeside peninsula in Hyde Park’s Burnham Park is a lovely spot to take a scenic walk with your sweetie. If things are serious between you two, the stunning skyline is a perfect backdrop to pop the question!

Why this is a romantic thing to do: this gem features an intimate view of the city's skyline with seating to relax and enjoy the lakefront.

Photo Credit: Michael Christensen

12. Garden of the Phoenix in Jackson Park

This Japanese walking garden in Jackson Park’s Wooded Island is a beautiful place to take a stroll with the one you love, especially in the spring when the cherry blossoms are blooming.

Why this is a romantic thing to do: Surprising that special flower lover with a wander through heaven. The flowers are at their peak in late April and May, and you can check on their bloom status here. The Japanese even have a name for the act of enjoying the flowers: hanami.

13. A Romantic Dinner In The City

A list of romantic things to do in Chicago wouldn't be complete without first mentioning all the intimate dining options this great city has to offer. From cozy bistros to elegant fine dining establishments, Chicago has a vibrant culinary scene with excellent restaurants for couples interested in a romantic dining experience. No matter what your taste, you're sure to find something to your liking in Chicago.

Why this is a romantic thing to do: an intimate dinner in a beautiful setting is a classic date night idea that you can always fall back on. Plus, with Chicago's incredibly diverse cuisines and world-class restaurants, you're sure to find something you'll both love.

14. The Garfield Park Conservatory

Great for a romantic day together all year round, this 4.5 acre botanical garden is often referred to as “landscape art under glass.” Home to thousands of plant species from all over the world, showcased in eight unique display gardens, the conservancy also features regular special events like art classes, guided walks, and concerts. Reservations are free and required for entry.  

Don’t wait, lovebirds! Now’s the time to get out into the city and kindle that flame between you. If you’re looking for more romantic things to do in Chicago, have a look at how we recommend you spend a day on the Magnificent Mile. If the summertime weather is calling your names, check out our comprehensive Guide to Chicago Summer Events. But whatever you do, make sure you do it with the one you love!

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Morning

Stan’s Donuts and Coffee

The north side of the Mag Mile is where we’re going to start because that’s where we’ll find Stan's Donuts and Coffee at 535 N Michigan Ave (they have multiple locations in the area). Their freshly made donuts and breakfast treats will make your mouth water and their coffee is sure to put some pep in your step.

While munching on your donut and sipping your coffee, make sure to purchase your tickets for your activities later in the day. We are going to take an awesome architectural tour with Shoreline Sightseeing, browse the Art Institute of Chicago, dine at The Purple Pig, and check out the Chicago skyline views at 360 Chicago, so make sure to book reservations and buy tickets for the smoothest transition from each activity to the next.

The Shops at North Shore Bridge

Right down the road from the Stan’s location, you will stumble on The Shops at North Shore Bridge, the perfect jumping off point to the best Magnificent Mile shopping. With over 50 well-known and established brands, it will be easy to wander for hours. Arriving around 10 AM, when they open Monday - Saturday, will help you beat the crowds and browse through your favorite stores without any competition.

Afternoon

Lou Malnati’s Pizzeria

With so many dining options within the shopping center, it won’t take long for those delicious scents to make you hungry for lunch. Of course, you can always dine at the shopping center, but we want to see and experience as much as we can on the Magnificent Mile, so we are going to head to Lou Malnati's Pizzeria! At Lou’s, they serve the kind of deep-dish pizza that both locals and tourists dream about. But don’t worry, they don’t leave out those who aren’t deep-dish fans as they also have an amazing thin crust pizza and other lower carb options. You’ll find this location on the ground floor of The Wrigley Building.

Shoreline Sightseeing Tour

After lunch, it’s time to hop across the street to your Shoreline Sightseeing Architecture River tour! This 60-minute tour is a top contender for the most interesting Mag Mile thing to do. It’s the perfect length to see Chicago’s brilliant architecture while learning about hidden gems and long-standing landmarks. Their Michigan Avenue dock will make it super easy to catch your reserved tour right after lunch.

The World’s Largest Starbucks

After seeing Chicago from a new perspective, a pick-me-up is a must, and there is no better place for that than the World’s Largest Starbucks. So, grab a coffee, tea, refresher, frappuccino, or anything else that might be calling your name, and then get ready to continue exploring because we’ve still got so many things to do on Michigan Avenue.

The Art Institute of Chicago

Off we go to the Art Institute of Chicago, one of the oldest and largest museums to date, located at 111 S Michigan Ave. This is the place for inspiration and contemplation as you look at perfectly curated new and old works of art. After walking away from the art on the walls, take advantage of that inspiration and find the art that lives in many of the magnificent Mile’s stores– luxury stores to be exact.

900 Shops

With over 70 luxe shops on the Magnificent Mile, 900 Shops has art in many forms, and it’s our natural next stop. Go into stores like Gucci's Chicago Flagship store, MaxMara, Montblanc, Bloomingdales, and more. This will also bring us a little further north where we will be for the rest of the evening.

Evening

The Purple Pig

It’s time to take a load off and feel pampered by the wonderful food at The Purple Pig. This chic restaurant is known for its delicious pork (hence the pig in The Purple Pig) and wine. It is sure to feed your stomach, eyes, and soul– yeah, it’s that good.

360 CHICAGO

Since you need to experience as much of the Mag Mile as possible, after dinner, we are going off to watch the sunset from 94 floors up at 360 CHICAGO. This observation deck is very intentionally named as it offers a 360-degree view of Chicago from its very own floor of the John Hancock Building. It’s hard to beat a sunset over this skyline.

The Gage

Relaxed after watching a stunning sunset, we are heading to our last destination, a lively Irish pub called The Gage. This pub isn’t just known for its expansive list of beers, but its great view of Millennium Park. So, sit back and relax, because you just spent a full and exciting day in one of the most revered neighborhoods in the world– the Magnificent Mile.

Common Questions About The Mag Mile

What exactly is the Magnificent Mile?

The Magnificent Mile is the famous, 13-block stretch of North Michigan Avenue. It's not a separate street, but rather the nickname for the section of Michigan Avenue that runs from the Chicago River on the south to Oak Street on the north. It's known globally as one of the premier destinations for luxury shopping, fine dining, and iconic architecture.

What is there to do on the Magnificent Mile?

The Magnificent Mile is packed with activities. The main draw is shopping, with everything from major department stores to international luxury boutiques. Beyond shopping, you can explore architectural landmarks like the Tribune Tower and the Historic Water Tower, visit art galleries, dine at world-class restaurants, or see the city from above at 360 CHICAGO.

What are the main stores on the Magnificent Mile?

You'll find hundreds of retailers, but the anchor stores and major flagships include the 900 North Michigan Shops (home to Bloomingdale's), Water Tower Place, Nordstrom, Neiman Marcus, Saks Fifth Avenue, and flagships for brands like Apple, Burberry, and Gucci.

Is the Magnificent Mile safe to walk?

Yes, the Magnificent Mile is considered one of the safest and most heavily trafficked areas in Chicago for tourists and locals. It is well-lit, constantly busy with shoppers and visitors, and has a significant police and private security presence. As in any major urban area, it's always wise to be aware of your surroundings, especially at night.

How far is the Magnificent Mile from Navy Pier or Millennium Park?

The Magnificent Mile is very close to other major attractions. From the southern end of the Mile (the Michigan Avenue Bridge), it's about a 15-minute walk (0.8 miles) to Navy Pier to the east, and less than a 5-minute walk (0.3 miles) to Millennium Park to the south.

How far is O'Hare Airport (ORD) from the Magnificent Mile?

O'Hare is approximately 18 miles northwest of the Magnificent Mile. By car, the drive can take anywhere from 45 minutes to 2 hours, depending heavily on traffic. For a more predictable travel time, you can take the CTA Blue Line train from the airport to downtown; it runs 24/7 and typically takes about 45-50 minutes.

How far is Midway Airport (MDW) from the Magnificent Mile?

Midway is about 12 miles southwest of the Magnificent Mile. The drive by car usually takes between 30 minutes and 1.5 hours, depending on traffic conditions. The CTA Orange Line train is a great alternative, connecting Midway to downtown in about 30-35 minutes.

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The View: Lakefront Panorama vs. Western Grid

360 CHICAGO Views

360 CHICAGO is located on the 94th floor of 875 N Michigan Avenue, formerly known as the John Hancock Building. Situated in the heart of the city 1,000 feet above the Magnificent Mile, 360 CHICAGO offers you sweeping views of Lake Michigan and our neighboring states of Wisconsin, Indiana, and Michigan. 

Reddit comments from past guests mention "Iconic lakefront views and city skyline" and "better lake and city views, hands down!" "a must see!"

This Chicago observation deck is very convenient if you’re staying north of the river around Michigan Avenue, near the Navy Pier, or along Magnificent Mile. Another plus is that you don’t need a car to reach 360 CHICAGO because the former John Hancock Center is ideally situated close to public transit. Numerous shops and restaurants abound, so you can make a day of it—hang out on the 94th floor at 360 CHICAGO, then go shopping and savor delicious local cuisine at a nearby restaurant.

Skydeck Willis Tower Views

Skydeck is located on the 103rd floor of the Willis Tower, which is the tallest building in Chicago at 1,353 feet high. Located on Wacker Avenue, Skydeck does offer a different perspective than 360 CHICAGO with predominantly views from the west as well as the Chicago River, Wacker Drive and parts of Lake Michigan. On a clear day, you can see as far as the surrounding states of Illinois, Indiana, Wisconsin, and Michigan.

Located on the South Loop, this observation deck is an ideal location if you’re staying on or near Wacker Drive. This area also has easy transit access and is near shops and restaurants.

Some of our guests that have visited both towers have commented that "once you are at the top of any Chicago Observation deck, it's just high! The difference in feet isn't noticeable.”

Hannah R visited both the 360 CHICAGO Observation Deck and the Willis Tower Skydeck and said, 

"It was great to see the city from two different angles", and I liked the 360 tower because it was on the outside edge of the skyscrapers, so you could see almost all of them on the other side."

360 CHICAGO offers stadium seating for sunset viewing on the west side.

What are the best tower views in Chicago?

There is no doubt that 360 CHICAGO and Skydeck are the best observation decks in Chicago. Both offer fantastic views of the city from different perspectives. If you are going to choose one based on just the views, perhaps it depends on where you are staying in Chicago. North of the river, near Michigan Avenue is closer to 360 CHICAGO and south downtown near Wacker Drive is closer to the Willis Tower Skydeck. 

Wait times 360 CHICAGO vs. Skydeck

360 CHICAGO has timed access to elevators to ensure that during busy tourist days, wait times are reduced for visitors. There’s also a skip-the-ticket desk line to further reduce wait times. We do our best to manage wait times and keep them to a minimum. 

Skydeck has timed elevator access during busy days and seasons and premium tickets to expedite entry as well.  Willis Tower earns the status of tallest building in Chicago, so naturally, travelers want to see it. Perhaps the lines are longer than 360 CHICAGO, but wait times can vary by day, time, and season.   

The wait time difference between these observation decks? Our answer is: It depends! We all do our best to ensure visitors get more time enjoying the views.

The Rides: TILT at 360 CHICAGO vs. The Ledge at Skydeck

360 CHICAGO TILT

TILT is Chicago’s highest thrill! Guests grab the handlebars, lean forward, and hold their breath as the glass tilts forward, moving eight people 1,030 feet over Michigan Avenue. Guests actively participate in experiencing the movement and views from the glass. 

"I'd highly recommend TILT. You lay against the glass windows and they tilt you over the edge of the building for a couple minutes. It's pretty wild." -Court

Skydeck The Ledge

The Ledge is a glass box that extends out 4.3 feet from Willis Tower. Guests step into the glass box, look down to experience what 1,353 feet above feels like. There is a  timed 60 (or 90 seconds for groups) to walk on the Ledge and take some fantastic pictures.

Visitors on Reddit said:
"It's a glass cube sticking out from the building, so you can look straight down to the street" 
Another says  "It's good for a photo, you don't do much there."

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Photos courtesy of The Office Experience

Created by Superfly X and Universal Live Entertainment, in consultation with The Office’s U.S. creator Greg Daniels, The Office Experience has been lauded as “easily enough to make any The Office fan’s heart sing,” by the Chicago Tribune. Ticketed and non-ticketed guests are also welcome to check out the on-site warehouse-themed retail store featuring exclusive products never before offered for sale.