Let’s be honest; there’s a lot to do in Chicago. So much so that trying to plan a quick trip to Chi-Town can feel overwhelming. But if you're looking to squeeze the most out of your weekend visit, you've landed in the perfect spot. We've crafted the ultimate itinerary for one spectacular weekend in Chicago, designed to hit all the highlights, sprinkle in some hidden gems, and leave you with incredible memories.
You’ll arrive for your much anticipated weekend in Chicago and check into your hotel. So, what next? No matter whether you arrive by car or plane, you’ll need to stretch your legs and shake off that travel fog. The best place to do that is along the 1.25-mile-long Chicago Riverwalk that runs from Lake Michigan to Lake Street. Stroll past illuminated buildings that are architectural icons, by museums, and popular waterfront bars and restaurants. Plus, this must-do pedestrian path winds past the impossible-to-miss Art on THE MART, which is the world’s largest digital art projection with nightly shows from April through December.
Then it’s time to do dinner right on your first night in Chi-Town. That means diving into a cheesy, saucy, delicious deep-dish pizza. Giordano's offers a stuffed pizza experience that's practically a lasagna in pizza form—layers of cheese and toppings generously sandwiched between two crusts, then topped with their signature tomato sauce. Then there's Lou Malnati's, with its buttery, flaky, almost pie-like crust, a robust tomato sauce, and their special "buttercrust" option that's a game-changer.
Top off your first amazing night in Chicago with a nightcap on the 94th floor of the former John Hancock building. Here, you can kick back at CloudBar in 360 CHICAGO with a handcrafted cocktail (try the Hancock Handshake!) and toast views of the cityscape glowing beneath a blanket of stars.
Get ready for a whirlwind (but in a fun way!) day in downtown Chicago. There’s lots of parking around Millennium Park, which is an excellent central location to begin your exploration. But to truly start your day off right, you need the proper fuel to get you going! Enter Stan’s Donuts & Coffee and Hero Coffee Bar.
If you’d like a more savory breakfast, stop by Hero Coffee Bar on your way to the park. Tucked away in a charming alleyway, this coffee bar offers fantastic coffee and a selection of satisfying bagel sandwiches. If you need a sugar boost to get going, then swing by Stan’s Donuts & Coffee at Millennium Park. From classic glazed to their famous Biscoff pocket and delightful seasonal flavors, you can grab a box of their delicious creations and a coffee to enjoy as you stroll toward the dock for your architecture boat tour.
The CAC River Cruise aboard the First Lady is always a crowd pleaser and has won multiple awards. Pro-tip: Book the 9 a.m. sailing for your architecture boat tour. Early birds get the best views (and beat the crowds, trust us). You'll have unobstructed sightlines for those jaw-dropping skyscrapers, stunning bridges, and the winding river. This early slot means prime photo opportunities without a million other phones in your shot.
The angles you’ll capture from the water are simply epic. Every turn offers a new, dramatic perspective of the city's famous skyline, from historic Art Deco marvels to sleek modern giants. With engaging guides who bring the city's stories to life, you'll learn fascinating facts and entertaining anecdotes about how Chicago became an architectural powerhouse.
After your boat tour, stop by the nearby Wabash Arts Corridor. This isn't your typical stuffy museum; it's a "living urban canvas" where large-scale murals, mind-bending installations, and thought-provoking street art from local and international artists are featured on building facades, alleyways, and unexpected corners.
Ready to refuel after a morning of architectural wonders and artistic marvels? Whether you’re just wanting a snack or are hungry enough to eat a cow, here’s two iconic Chicago eats to add to your must-do list: Garrett Popcorn and Billy Goat Tavern.
Hit up Garrett Popcorn Shop for that irresistible aroma and a snack you can munch on throughout the day. Try their famous Garrett Mix that’s a magical blend of savory CheeseCorn and sweet CaramelCrisp. Then, get a taste of history and a whole lot of character at Billy Goat Tavern. Made famous by "Saturday Night Live" with their "Cheezborger, Cheezborger!" skit, this no-frills spot serves up classic, griddle-smashed cheeseburgers (and yes, it's "cheeps" not "fries," and "Coke" not "Pepsi"). It's a quick, delicious, and wonderfully quirky Chicago institution that promises a satisfying and memorable meal.
Next up is a stop at Navy Pier and a ride on the iconic Centennial Wheel. Perched at the end of the pier, this nearly 200-foot-tall Ferris wheel offers unparalleled lake-meets-sky visuals. Step into a comfortable, climate-controlled gondola to be treated to jaw-dropping, 360-degree panoramic views of Lake Michigan and the city skyline.
After getting the lay of the land on the Ferris wheel, head on over to the waterfront to experience the lakeshore for yourself. Recline on one of Chicago's gorgeous beaches, dip your toes in Lake Michigan, build a sandcastle, or simply relax and enjoy the skyline views.
If you’re feeling more adventurous, rent a Divvy bike and hit the 18-mile Lakefront Trail that offers uninterrupted lake views on one side and the cityscape on the other. And if the weather's just right, take your adventure onto the water with a kayak rental.
To close out your day, buy golden-hour tickets at 360 CHICAGO to witness a spectacular sunset. Be sure to reserve your timed entry in advance to snag that perfect golden-hour glow.
After watching the city twinkle to life, enjoy an exhilarating experience on TILT. You'll be securely tilted outwards at a dramatic downward angle, giving you an unparalleled, adrenaline-pumping perspective of the Magnificent Mile far, far below. Lean into the excitement and then unwind at CloudBar with a delicious small-plate dinner. Adults can enjoy local drafts from Chicago's booming craft beer scene, while teens can sip on refreshing mocktails. Don't forget to see the rotating local art exhibits on CloudWalk, located on the outdoor viewing platform.
And while you’re in the area, enjoy a post-deck walk to the Historic Water Tower. It's just a five-minute stroll, and the beautifully lit, gothic tower provides a fantastic opportunity for some stunning night photography.
Savor a leisure Sunday morning with brunch on The Loop. The popular Wildberry Pancakes and Cafe is known for its generous portions and their deep-dish French toast. It's thick, fluffy, and often loaded with decadent toppings. Or, if you're craving a brunch with a side of stunning scenery, Cindy's Rooftop is for you. Located atop the Chicago Athletic Association Hotel, Cindy's serves up views of Millennium Park and Lake Michigan with their brunch menu that features delicious skillet dishes that are perfect for sharing (or not!).
Once your stomach is happily full, feast your eyes on masterpieces at the Art Institute of Chicago.To make the most of your visit at the museum, book your "skip-the-line" tickets online for a Fast Pass experience. Discover one of the world's finest collections of Impressionist art, including iconic works by Monet (don't miss his "Stacks of Wheat" or "Water Lilies"!) and Seurat's mesmerizing "A Sunday on La Grande Jatte" (yes, the one from Ferris Bueller's Day Off!). Then, explore the sleek Modern Wing to see groundbreaking 20th and 21st-century art from giants like Picasso, Chagall, Dalí, Warhol, and more.
Touring Chicago’s art scene wouldn’t be complete without a stop at Millennium Park. Here, you can visit the iconic Bean, officially known as Cloud Gate. This giant, reflective sculpture mirrors the city skyline and distorts your reflection in the most wonderfully warped ways. It's endlessly fun to walk around, under, and through for a new perspective every time. The Crown Fountain is another truly unique art piece that features two 50-foot glass block towers that project ever-changing faces of Chicagoans. Watch as water spouts from their mouths (especially delightful on a warm day!), creating a playful splash pad that's a hit with kids and adults alike.
Pro-tip for those perfect, crowd-free photos: Set your alarm! Arrive early in the morning, right as the sun is coming up. You'll have these magnificent masterpieces almost entirely to yourself, allowing for serene, unobstructed shots of "The Bean" and the whimsical "Crown Fountain" before the crowds descend. For the motivated photographers, you can stop here first before you head to The Loop for brunch.
Wicker Park & Bucktown is one of those effortlessly cool neighborhoods that’s perfect for digging into Chicago’s local culture. Get ready for some seriously fun vintage thrifting, where you can unearth everything from retro band tees and classic denim to one-of-a-kind dresses and quirky accessories. The neighborhood is also a vinyl lover's paradise with established giants like Reckless Records (a Chicago institution!) to smaller, curated spots offering everything from rare jazz pressings to indie rock and punk.
A visit to Original Mindy's Hot Chocolate is an absolute must before you leave Chicago! While it's now Mindy's Bakery with a focus on pastries, you can still find those incredible, rich hot chocolates that put James Beard award-winning chef Mindy Segal on the map. Or if you lean toward ice cream over pastries, then Jeni's Splendid Ice Creams is the place to be. With unique, intensely flavored scoops like Brambleberry Crisp, Salty Caramel, or Gooey Butter Cake, Jeni's offers a truly "splendid" experience. And if you’re visiting during baseball season and are a sports fan, you absolutely have to tour Wrigley Field. Go behind the scenes, check out the dugouts, press box, and even step onto the hallowed field (on non-game days). Or, for a shot of pure basketball greatness, make your way to the United Center atrium and pose with "The Spirit," the legendary Michael Jordan statue that’s a tribute to one of the greatest athletes of all time.
From dazzling river cruises and heart-pounding tilts at 360 CHICAGO to indulging in iconic deep-dish pizza and discovering unique treasures in Wicker Park, this will be one spectacular weekend in Chicago. You’ll see the city from the sparkling lakefront to its towering rooftops, and even up close with masterpieces of art and architecture. Chicago truly delivers on every front: culture, cuisine, thrills, and charm. Now comes the fun part, coming to town and experiencing this itinerary for yourself!
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