15 Best Things To Do in Chicago for a Fun Weekend Getaway

Are you headed to the Windy City for the weekend and need some ideas about what to do? Chicago offers many activities and places to visit. Take advantage of seasonal events like music festivals or sports games. And don’t forget to check out these ideas while you’re there.

1. Lincoln Park Zoo

Lincoln Park Zoo Nature Boardwalk in Chicago
Image Credit: Alan Scott Walker – CC BY-SA 3.0/Wiki Commons.

Stop by the fourth oldest zoo in the country for a day among penguins, gorillas, and polar bears — oh my! The zoo also hosts events (block parties, community runs, and wine nights) throughout spring and summer, so check the calendar before your trip. And the best part? Admission is free!

2. Improv Shows

Image Credit: Victor Grigas, Own Work – CC BY-SA 3.0/Wiki Commons.

For theatre and comedy lovers, Chicago is a great place to take in an improv show. The Second City, iO Theater, and The Annoyance Theater regularly put on shows with up-and-coming talent. They’re also home to well-known alumni like Bill Murray, Tina Fey, and Stephen Colbert.

3. Wrigley Field

Wrigley Field Chicago
Image Credit: CC BY-SA 4.0/Wiki Commons.

Going to Chicago during summer? Grab some tickets for a home game to see the Chicago Cubs play at Wrigley Field. This historic stadium (built in 1914) even offers non-gameday tours for die-hard fans who want a peak behind the scenes.

4. Six Flags Great America

Batman The Ride at Six Flags Great America
Image Credit: Jeremy Thompson – CC BY 2.0/Wiki Commons.

Six Flags Great America is an hour north of Chicago, and the largest theme park in the area. With 17 roller coasters, live entertainment, and tasty food, take the day off and have fun at Six Flags on your next trip to Chicago.

5. Lakefront Trail

Chicago Lake front bike trail
Image Credit: Alan Scott Walker, Own Worker – CC BY-SA 3.0/Wiki Commons.

Interested in some outdoor adventures during your stay? Check out Chicago’s Lakefront Trail, an 18-mile trail on the southside of Chicago along Lake Michigan. Hop on a bike or walk the path as you make your way through surrounding neighborhoods like Hyde Park, Bronzeville, Lincoln Park, and Lakeview.

6. Chicago History Museum

Pioneer, Chicago's first railroad locomotive, Chicago History Museum
Image Credit: Jeremy A., Own Work – CC BY-SA 2.5/Wiki Commons.

If the weather’s a bit cloudy or rainy, spend it indoors at the Chicago History Museum in Lincoln Park, where you can learn all about the city’s history. Tour exhibits and view artifacts covering topics from sports and politics, the Great Chicago Fire, and the Union Stockyards.

7. Wicker Park

Wicker Park, Chicago
Image Credit: Ben Collins-Sussman – CC BY 2.0/Wiki Commons.

No, we’re not talking about the 2004 movie starring Josh Hartnett and Rose Byrne. This is the Wicker Park neighborhood — mecca of the art community in Chicago. Check out indie bands at intimate venues, grab some books at Myopic Books, and find a hidden-in-plain-sight speakeasy that serves up some of the best cocktails at Violet Hour in this art-centric district.

8. Le Piano

Le Piano Rogers Park Chicago
Image Credit: Le Piano Chicago.

The Jazz Age was alive and kicking in Chicago during the 1920s. Le Piano in Rogers Park provides patrons with a cozy atmosphere, antique furniture, and a full bar and food service. You can also catch live entertainment throughout the week.

9. Navy Pier

Navy Pier, Chicago
Image Credit: CC BY-SA 4.0/Wiki Commons.

Located on the shore of Lake Michigan, the Navy Pier is essentially a miniature theme park. There’s a Ferris wheel, Chicago’s Shakespeare Theater, a funhouse, and even a glass-enclosed garden. Spend the day (or night) on Lake Michigan and enjoy the Chicago skyline during your visit.

10. Chicago Botanical Garden

Japanese Garden at the Chicago Botanic Garden.
Image Credit: CC BY-SA 2.5/Wiki Commons.

If you’re looking for something relaxing to do during your trip, stop by the Chicago Botanical Garden. With more than 20 garden displays across 385 acres, the garden is open every day of the year, with extended summer and winter hours.

11. United Center

United Center during a Chicago Bulls game
Image Credit: CC BY-SA 4.0/Wiki Commons.

Ever heard of NBA legend Michael Jordan of the Chicago Bulls? Even though he’s retired, you can still catch a Bulls game at United Center. Hockey fans can also watch the Chicago Blackhawks play in the arena during their season.

12. National Museum of Mexican Art

National Museum of Mexican Art, Chicago
Image Credit: CC BY-SA 4.0/Wiki Commons.

Established in 1982, the National Museum of Mexican Art features Chicano, Latino, and Mexican art and exhibits, celebrating these groups’ cultures and contributions. If you need more convincing to stop by, you can visit the museum for free.

13. Chicago Magic Lounge

Image Credit: Chicago Magic Lounge.

Despite what you may think, magic is cool. The Magic Lounge is both a bar and theater, featuring stage shows and close-up magic performed tableside. They also have delicious food and drinks.

14. Millennium Park

Chicago, Illinois
Image Credit: Shutterstock.

Dying to snap a photo of yourself in front of “The Bean” (officially known as the Cloud Gate statue) you see all over social media? Then you’ll need to make a trip out to Millennium Park. You can also find interactive fountains, music festivals, and green space throughout the public park all year round.

15. The Loop

Chicago 'L' station Adams and Wabash
Image Credit: Daniel Schwen, Own Work – CC BY-SA 4.0/Wiki Commons.

Considered the heart of Chicago, The Loop is a downtown neighborhood that features iconic landmarks, shopping, theaters, and restaurants. The 35-block area is a must-see if you visit the Windy City.

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