Chicago: the city of deep-dish pizza, wind that might just sweep you off your feet (literally), and skyscrapers that tickle the clouds. Whether you’re a culture vulture, a history buff, or just in it for some good old-fashioned fun, there’s plenty to keep you entertained. Here’s your go-to guide for the top 19 things to do in Chicago, each peppered with a dash of humor to add to your itinerary’s flavor.
1. Get Sky-High at Willis Tower
- Where: 233 S. Wacker Drive
- Best Time to Visit: Just before sunset
- Insider Tip: Skip the long lines by buying tickets online.
Formerly known as the Sears Tower, Willis Tower offers a view so vast you might just see into tomorrow. Step onto the Skydeck and dare to stand on the glass boxes—guaranteed to make your knees feel like jelly. Perfect for Instagram, or making your friends back home instantly jealous.
2. Take a Time Machine to The Art Institute of Chicago
- Where: 111 S. Michigan Avenue
- Best Time to Visit: Weekday afternoons for fewer crowds
- Insider Tip: Don’t miss the miniatures room—tiny art at its finest!
Ranked as one of the best art museums globally, it houses works that span thousands of years. Spend a day with the likes of Van Gogh and Monet and play “spot the security guard” — they blend better than a chameleon.
3. Navy Pier Shenanigans
- Where: 600 E. Grand Avenue
- Best Time to Visit: Summer evenings for fireworks
- Insider Tip: Ride the Centennial Wheel for breathtaking skyline views.
Ah, Navy Pier, where you can eat, shop, ride, and repeat. Whether you’re there for the iconic Ferris wheel or to catch a wave on a boat tour, it’s where adulthood meets childhood nostalgia with a side of spectacular lake views.
4. Play Ball at Wrigley Field
- Where: 1060 W. Addison Street
- Best Time to Visit: During a Cubs game, obviously!
- Insider Tip: Grab a pre-game drink at one of the rooftop bars across the street.
Even if you’re not a sports fan, the vibe is infectious. The crowd’s energy could probably power the city for a day. And who knows? You might just become a Cubs fan by the end of the ninth inning.
5. Laugh Out Loud at The Second City
- Where: 1616 N. Wells Street
- Best Time to Visit: Catch a late show on Saturday
- Insider Tip: Book in advance, shows sell out fast!
Ever wondered where many SNL stars started? It’s right here. Get your dose of belly laughs and possibly witness the birth of the next big star in comedy. Who needs abdominal workouts when you’ve got this?
6. Lincoln Park Zoo
- Where: 2001 N. Clark Street
- Best Time to Visit: Early morning to beat the crowds
- Insider Tip: Visit during the holiday season for the beautiful ZooLights.
One of the oldest zoos in North America, and guess what? It’s free! Lions, tigers, and bears – oh my, without spending a dime!
7. A Slice of Pizza Paradise
- Where: Lou Malnati’s Pizzeria (among others)
- Best Time to Visit: Lunchtime to beat the dinner rush
- Insider Tip: Go deep or go home – try the classic Chicago deep dish.
No trip to Chicago is complete without wrestling with a slice of deep-dish pizza. It’s less of a meal and more of an event. Remember, it’s a marathon, not a sprint.
8. The Magnificent Mile
- Where: Michigan Avenue
- Best Time to Visit: Weekday mornings
- Insider Tip: Look out for hidden gems like the tucked-away gardens and historical landmarks.
Shop till you drop, and then shop some more. High-end brands, towering malls, and chic boutiques—it’s the Disneyland for shopaholics.
9. Millennium Park & The Bean
- Where: 201 E. Randolph Street
- Best Time to Visit: Early morning for fewer photo bombers
- Insider Tip: Find the perfect angle for your Bean selfie from the east side.
Cloud Gate, a.k.a The Bean, is perfect for bizarre, distorted selfies. It’s also surrounded by enough art and architecture to keep you busy all day. And yes, touching the Bean is a must. It’s like Chicago’s version of rubbing the Blarney Stone.
10. Chicago Riverwalk
- Where: Along the Chicago River from Lake Shore Drive to Franklin Street
- Best Time to Visit: Sunset for magical views
- Insider Tip: Try the architecture boat tour—it’s a floating history lesson.
Stroll, dine, drink, and repeat. The Riverwalk offers a serene escape from the city hustle, with the added benefit of feeling like you’re on a movie set.
11. See a Show at the Chicago Theatre
- Where: 175 N. State Street
- Best Time to Visit: Evening performances
- Insider Tip: Look up! The ceiling architecture is as breathtaking as the performances.
It’s not just a theatre; it’s a piece of Chicago’s soul. From dazzling marquee lights to shows that might just make you a theatre convert, this place is all about razzle-dazzle.
12. Field Museum
- Where: 1400 S. Lake Shore Drive
- Best Time to Visit: Late afternoon for fewer school trips
- Insider Tip: Don’t miss Sue the T. rex; she’s a star in her own right.
Dinosaurs, mummies, gems—oh my! It’s like walking through a treasure chest of Earth’s history. Perfect for a date…with science.
13. Kayak on the Chicago River
- Where: Various rental locations along the river
- Best Time to Visit: Morning or late afternoon for cooler temperatures
- Insider Tip: Prepare for a workout; those skyscrapers don’t look tall by themselves.
Why walk when you can kayak? See the city from a duck’s perspective, and yes, you’re allowed to quack if you want to.
14. Jazz it Up at the Green Mill
- Where: 4802 N. Broadway Street
- Best Time to Visit: Late evenings, especially during a jazz set
- Insider Tip: Check out the Al Capone booth for a brush with history.
Step into the 1920s with a night of smooth jazz and maybe a cocktail or two. It’s like a time machine, only with better music and less prohibition.
15. The Museum of Science and Industry
- Where: 5700 S. Lake Shore Drive
- Best Time to Visit: Weekday mornings
- Insider Tip: Get hands-on with the interactive displays; be a kid again!
It’s huge, it’s informative, and it’s fun. From submarines to simulated tornadoes, it’s where you come to realize science is way cooler than you remembered from school.
16. Explore Historic Pullman
- Where: Pullman National Monument, 11141 S. Cottage Grove Ave.
- Best Time to Visit: Daytime for the best historical tours
- Insider Tip: Don’t miss the factory tour; it’s like stepping into a time warp.
Travel back in time to America’s industrial age with a visit to the Pullman Historic District. It’s part museum, part neighborhood, and all fascinating.
17. Hit the Beach
- Where: North Avenue Beach
- Best Time to Visit: Summer, when it’s actually warm
- Insider Tip: Try beach volleyball, or just people-watch; both are sports in their own right.
Yes, Chicago has beaches! And yes, they are worth a visit—if only to say you’ve swum in Lake Michigan without turning into an icicle.
18. Take the Kids to the Chicago Children’s Museum
- Where: Navy Pier, 700 E. Grand Avenue
- Best Time to Visit: Weekday mornings
- Insider Tip: Check out the climbing schooner—it’s a pirate ship in disguise.
Who says museums can’t be fun? Packed with interactive exhibits and educational play areas, it’s where kids (and adults) can let their imaginations run wild.
19. Savor the Flavors at a Food Festival
- Where: Various locations, depending on the festival
- Best Time to Visit: Whenever your stomach says it’s time
- Insider Tip: Taste of Chicago in July is a must for foodies.
Chicago is a melting pot of cuisines, and what better way to sample its offerings than at a food festival? Stretchy pants highly recommended.
So there you have it, 19 fantastic, somewhat quirky, and entirely enjoyable things to do in Chicago. Whether you’re hanging out with a T. rex or kayaking down the river, Chicago’s charm is sure to sweep you off your feet—just hold onto your pizza.