16 Best Things to Do in Chicago On a Weekend Getaway

Steve Cummings


If you’ve never been to Chicago, get ready for a fantastic time! Chicago is an incredible city, from the iconic buildings to the delicious eats. It’s a city so full of life that you’re bound to find something new every time you visit. 

With such a mix of things to do, it can be pretty overwhelming for visitors. Don’t worry! We’ve collected a list of the 16 best things to do in Chicago on a weekend getaway. With this list, you shouldn’t miss out on any key things to do in Chicago! 

1. Wander the Art Institute of Chicago

Art Institute of Chicago
Credit: Jkirsch13/Depositphotos

The Art Institute of Chicago is a can’t-miss activity, even if you’re not the biggest art fan. This Chicago staple has been open for over 140 years and has a fantastic collection. There is something for every style, from Picasso and Seurat to Warhol and traveling exhibitions! Wander the different wings, which stretch from Modern Art to Ancient & Byzantine Art with everything in between. Plus, it’s right in the loop, so it puts you near other key things to do in Chicago.

2. Laugh All Night With Second City 

Chicago is known for its comedy clubs, but none more than Second City Comedy. This comedy club has been laughing since 1959 and has several notable alums, including Tina Fey, Steve Carrell, and Chris Farley. The club has several stages so that you can pick the right show for your group. Whatever you do, be prepared to laugh all night long. 

3. Float Down the River on an Architecture Tour 

An architecture tour is undoubtedly one of the best things to do in Chicago! In a city famous for architecture, it’s simply a must. Chicago is renowned for its Neoclassical style and unique buildings, concentrated downtown. On a boat tour, you’ll sail past all the best sights, such as the Wrigley Building, Tribune Tower, and more. The tour guides also tend to bring their sense of humor, so it’s a unique experience every time.  

4. See a Game at Wrigley Field 

Wrigley Field
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If you’re a sports fan, when you think of Chicago, you might think of Wrigley Field! Home to the Chicago Cubs, Wrigley Field is one of the oldest baseball stadiums in the country. It has a magical old-world feel with all the excitement of modern-day baseball. Seeing a game here is one of the quintessential things to do in Chicago. If you can’t catch a game, you can still schedule a behind-the-scenes tour of the stadium to learn about this iconic spot! 

5. Explore Millenium Park & Take the Famed “Bean” Selfie 

Credit: Depositphotos

In the Loop, you’ll find Millenium Park in the heart of the city! This park is a center of activity, especially around the holidays, with ice skating and decorations galore. At any time of year, it’s a beautiful green space. You’ll have to visit and snap the classic Chicago “Bean” selfie. Known as the Bean for its shape, Cloud Gate is the city’s best-known sculpture, reflecting the city around it. It’s basically a mandatory thing to do in Chicago, so stop by and take a reflective selfie with this Chicago classic! 

6. Spend an Afternoon at Navy Pier 

Navy Pier
credit: depositphotos

This is one of the best things to do in Chicago on a nice day. You can ride the Ferris wheel and the carousel or see the Children’s Museum and Botanical Gardens. It has the feel of a carnival, with all the great snacks and sights to match. Plus, if you’re there on a Saturday evening, you can catch the free fireworks show (between Memorial and Labor Day). 

7. Enjoy a Slice of Chicago Pizza 

Chicago pizza
credits:Manvi Mathur/unsplash

This is an obligatory thing to do in Chicago, so grab a slice! Chicago is famous for its deep-dish pizza, baked in a tall pan with layers of delicious cheese, sauce, and fillings. Visitors tend to try Giordano’s and Lou Malnati’s for a taste, but you can get a more local flavor by trying Pequod’s or Beatrix Market instead. (Don’t worry which one you pick, though. They’re all terrific!)

8. Walk (or Bike) Along the Lakefront Trail

Lakefront Trail
Credit: MaciejBledowsk/Depositphotos

The lake is one of the most beautiful parts of Chicago, and it is best enjoyed when walking along the lakefront trail. You can walk a short portion of the way or rent a bike to see everything. If you make it at least to the Museum Campus, you will have fantastic views back towards the city. No matter how you do it, wandering the lakefront trail should be on your list of things to do in Chicago! 

9. Go Museum Hopping at Museum Campus 

Museum Campus has several excellent museums, so it would be criminal to pick just one for a list of things to do in Chicago! This area is half a mile south of Millenium Park and has three notable museums: the Field Museum of Natural History, the Shedd Aquarium, and the Adler Planetarium. Each museum has something different to offer, but the Field Museum is a local favorite (and also home to the famous Sue the Dinosaur)! 

10. Grab Brunch in Boystown

Spend some time outside of downtown and eat a delicious brunch in Boystown! Whether you’re looking for a diner-style meal or bottomless mimosas with your avocado toast, you can find it in Boystown. Boystown is also packed with coffee shops, cute parks, bars, and restaurants, so consider wandering once you’re there. 

11. Take in the Views from Skydeck

Skydeck Chicago, located in the John Hancock building, takes you 1000 feet above the Chicago streets for incredible views! From up there, you get panoramic views of the entire city. If you have a daredevil among you, you can also experience the TILT, which is a thrill ride that tilts you out over the streets with only a pane of glass beneath you! For extra fun, you can also explore the Magnificent Mile and do some shopping since it’s very close by. 

12. Catch a Show! 

Undeniably an arts city, Chicago has plenty of fun shows to choose from! From free concerts in Millenium Park (spring & summer) and jazz spots like Green Mill Jazz Club to the Chicago Theatre and Shakespeare Club, you should never be without something to do at night. Chicago has a rich history of jazz, blues, and theater, so at least one of them should be on your list of things to do in Chicago. 

13. Grab a Drink on the Chicago Riverwalk

Woman drinking in Cruise
Image Credit: Shutterstock.

The Chicago River rolls through the center of downtown Chicago, with beautiful bridges crossing it at several points. There is a pedestrian section below, full of little restaurants and bars. During pleasant evenings (or afternoons), it is one of the best spots in the city to enjoy a drink and watch the river go by. Some places need reservations, but others are more drop-in friendly, so see what you can find! 

14. Chow Down on Michelin-Starred Food

If you’re a foodie, put some of Chicago's Michelin-starred restaurants on your list of things to do in Chicago! Chicago is an amazing destination for foodies, with over 20 restaurants earning Michelin stars. They’re spread around the city, but you’ll find many assembled in the West Loop and Lincoln Park. Start calling early for your reservation, as tables at these restaurants are difficult to snag. 

15. Go Back to School with the University of Chicago 

University of Chicago
credit: Shutterstock

If you want a real collegiate feel, hop down to the University of Chicago campus. It is a stunning area, especially in the spring and fall. The classic brick buildings, complemented by the greenery, make for great photos and a relaxing walk. The campus is also dotted with plenty of great coffee shops, perfect for reading a book or enjoying an afternoon. 

16. Check Out a Music Festival

One of the best things about Chicago is its events throughout the year. Whether you’d like to dance all day at Lollapalooza, bump to reggaeton at Sueños Music Festival, or hear some jazz greats at the Chicago Jazz Festival, there’s no denying Chicago has top-rate music festivals. Plan in advance if you want to enjoy one of these shows, as tickets can be hard to come by. 

Best Things to Do in Chicago on a Weekend Trip

As you can see, there are plenty of great things to do in Chicago! There are so many, and you may find it hard to fit them all into one weekend. However, this list should give you a good place to start so you don’t miss any of the true classics! Like any city, Chicago is best when just explored for the adventure. So make sure that you’re reserving some time to wander around and see what catches your attention. No matter what you do, we guarantee you won’t be bored! 

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