Looking for a weekend planned with fun, food, and exciting events? Chicago is always ready to give surprises for both a first-time traveller and a seasoned local visitor. And for a weekend, the city certainly has unending ways of surprising you. The Windy City always has something exciting, from world-renowned attractions to hidden charms. If you’re thinking about what to do while you’re off, we have got you covered: Grab this excellent list of 16 best things to do in Chicago this coming weekend.
Let’s dive in!
Things to Do in Chicago
1. Walk Through Millennium Park and Take a Selfie at “The Bean.”
Begin your weekend in Chicago by visiting Millennium Park, which holds the chocolate-covered Cloudgate (“the bean”). It is perfect for people-watching, gorgeous pictures, and impromptu performances. If temperatures increase, stroll through the peaceful Lurie Garden or cool off in the Crown Fountain.
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2. Take in the Skyline Views from Skydeck Chicago
This is the place with the most jaw-dropping views, as Skydeck boasts a panoramic viewpoint on the 103rd floor of Willis Tower. The glass ledge allows you to stand above the city—talk about a thrill-worthy moment on Instagram! The golden hour experience is best enjoyed around sunset.
3. Indulge in a Chicago-Style Deep Dish Pizza
Your Chicago trip would be incomplete without munching on the famous deep-dish pizza. Visit Lou Malnati’s, Giordano’s, or Pequod’s to have that thick, cheesy, saucey slice of heaven. To top it all off, drink it with local craft beer or soda to experience the whole Windy City flavour.
4. Visit the Art Institute of Chicago
No matter whether you’re an art lover or just inquisitive, you must visit the Art Institute of Chicago. From Grant Wood’s American Gothic to Monet’s water lilies, you could spend hours soaking in the beauty and inspiration therein. Don’t forget to explore the stunning modern wing or the grand staircase.
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read more: Top Attractions in Chicago
5. Cruise the Chicago River on an Architecture Boat Tour
As you drift through the city’s heart, you’ll learn the most interesting stories connected to that skyline of towering buildings. For many, the Chicago Architecture Center’s River Cruise is one of the best city tours in the world. This is an educational and scenic must-see for first-timers or anyone living here.
6. Enjoy a Night of Live Comedy at The Second City
If you’re in the mood to laugh, Chicago is the place to be: the birth city of improv, and The Second City is where legends like Tina Fey and Steve Carell started it all. Get tickets to an evening show and prepare for intense belly laughs. With its small venue size and quick-witted performers, it ensured that you left with the memory of a great night.
7. Check Out the Immersive Art Experience at the WNDR Museum
This isn’t your regular museum. Interactivity, Instagram-worthy exposure, and being one of the remarkable things to do in Chicago this weekend with your friends or kids is what WNDR Museum is. Prepare for mind-blowing installations that will challenge your perception of space and creativity.
8. Stroll Along the Lakefront Trail
These eighteen miles of Chicago’s Lakefront Trail offer premier views of Lake Michigan, sandy beaches, parks, and neighborhoods. Walk, bike, or jog along to assimilate nature’s beauty in silence. On the way, do not forget to stop by North Avenue Beach or the Museum Campus.
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9. Shop (or Window Shop) on the Magnificent Mile
Need some retail therapy? The Magnificent Mile is Chicago’s premier shopping avenue, full of flagship stores and luxury boutiques with top dining establishments. Even if you do not spend a dime, strolling through is worth it just for the architecture and atmosphere. Street performers and seasonal displays add a layer of charm throughout the year.
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10. Experience a Local Street Festival or Farmers’ Market
During the warmer months in Chicago, a weekend street fest full of live music, food trucks, and good vibes really shines. Head out to the Logan Square Farmers Market or events in Wicker Park and Pilsen this weekend – flavor is guaranteed. Various markets also feature handmade crafts, fresh flowers, and yummy baked goods.
11. Visit the Museum of Science and Industry
Great for families and anyone with an inquisitive mind, the Museum of Science and Industry contains hands-on exhibits, a U-505 submarine, and the immersive Coal Mine experience. It is one of the most fun and educational places to be. The interactive exhibits will engage you so much that you won’t even realize you are picking up something.
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13. Indulge in Chicago’s Best Hot Dogs at Portillo’s
No ketchup, please! A faithful Chicago-style hot dog is slathered with mustard, onions, relish, tomato, pickle, pepper, and celery salt on a poppy-seed bun. Portillo’s is one of the best places for the real thing. If you’re still hungry, get their Italian beef sandwich, the other local favourite.
13. Chill at Navy Pier with Food, Fun, and Fireworks
Food, fun, and fireworks await at a Navy Pier outing—family attractions, shows, lake cruises, and fireworks. Do not miss the Centennial Wheel for aerial views of the city and the lakefront. Plenty of restaurants and bars offer respite to enjoy a meal or drink.
14. Step into the Past at the Chicago History Museum
If you’re into gangster stories, jazz, and political drama, the Chicago History Museum is crawling with fascinating exhibits about the city’s colorful history and cultural legacy. You’ll meet the characters who forged the town, from Abraham Lincoln to Al Capone.
Book Hotels Near the Chicago History Museum
read more: Romantic Hotels in Chicago
15. Have Cocktails with a View at the Rooftop Bar
Cap off your day at one of Chicago’s places-to-be rooftops while sipping drinks and enjoying skyline views. Cindy’s Rooftop, LondonHouse, and The J. Parker are killer sunset or night cityscape spots. These locales also serve imaginative cocktails and small plates to keep things fresh.
16. Catch a Game or Concert at Wrigley Field or United Centre
For the sports nut or the person who just loves the excitement of live events, Wrigley Field (home of the Cubs) and the United Centre (home of the Bulls, Blackhawks, and significant concerts) are delivering a tremendous lineup this weekend. Fun pre-game festivities and bars right outside make the entire experience that much more exciting.
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Bonus: Seasonal Events You Shouldn’t Miss
Chicago has the sort of weekend magic that comes as a bonus and is popularly active during festivals, celebrations, and traditions that bring together tourists and locals. If you happen to be one of the lucky ones in town, here are some can’t-miss events that will elevate the energy of the city to the next level:
- Chicago Air and Water Show
- Christkindlmarket (Winter)
- Chicago Blues Festival
- Open House Chicago (Architecture Weekend)
Pro Tips for Navigating the City This Weekend
- Using the “L” Train: It is budget-friendly, speedy, and connects to most prominent neighborhoods.
- Grab a CityPASS: Save money if you intend to visit several mainstream attractions.
- Bundle Up or Dress Light: Weather changes swiftly here; it’s all about layering.
- Stay Central: A hotel in The Loop or River North will keep you close to most of the action.
Final Thoughts
There are many interesting things to do in Chicago, from exciting events to art, food, architecture, sports, or just soaking up the city’s aura. Whether world-class locations or hidden local gems, this city promises memory-making experiences every season.
So, what are you waiting for? Put on some comfy shoes, grab your camera, and walk through the best of Chicago this weekend. You will live with incredible memories- and most likely an appetite for more deep-dish pizza.
Check out more city guides, hotel deals, and travel tips on Tripinn. Your perfect weekend in Chicago starts here!
