28 Things to Do in Chicago This Winter
Chicago certainly has a reputation for its bitter cold winters, but that doesn’t mean you should spend the next three months hibernating.
We rounded up 28 of our favorite things to do in Chicago this winter. Work your way through our list, and spring will be here before you know it!
Explore world-class museums
1. The Art Institute of Chicago
Located in the heart of downtown Chicago, the Art Institute is considered by many to be one of the best museums in the world. With more than 300,000 works of art, it’s a museum you’ll want to visit again and again.
You may already know that children under 14 get in for free. But now, teens under the age of 18 who are residents of the City of Chicago get in free, too. If you’re a Chicago or Illinois resident, be sure to take advantage of Free Winter Weekdays. You’ll receive free admission on weekdays (Mondays, Thursdays, Fridays) from November 29 to December 17 and January 3 – March 17, 2022. These complimentary tickets must be reserved in advance.
2. The Field Museum
The Field Museum is Chicago’s museum of natural history and is one of the largest in the world. One of the most famous exhibits is SUE the T.Rex, the largest, best-preserved, and most complete Tyrannosaurus rex ever found.
With Free Admission Days, basic admission is free for Illinois residents with valid proof of residency. Keep an eye on their free admission days page for the announcement of any upcoming free days.
3. The Shedd Aquarium
The Shedd is the largest indoor aquarium in the world! With more than 8,000 aquatic animals, it’s a must-see museum in Chicago. Residents of the City of Chicago receive a $3 discount on admission every day, and Illinois residents get free admission on the select dates this winter. Keep an eye on their page to reserve
4. The Adler Planetarium
The Adler opened to the public in 1930 and is the western hemisphere’s first planetarium. Here are four ways to explore Adler this winter. Admission is free to Illinois residents on certain dates throughout the year, so keep an eye on their page for those dates to become available.
5. The Museum of Science and Industry
Chicago’s Museum of Science and Industry brings science to life for kids and adults of all ages. It features a bunch of can’t-miss exhibits including a U-505 submarine. Admission is free to Illinois residents on certain dates, so keep an eye on their page for the announcement of free days.
6. Lincoln Park Zoo
Located just off Lake Shore Drive in Chicago, the Lincoln Park Zoo is open and free every day. Even in the winter, there’s plenty to see, ranging from polar bear training to free flight feeding.
7. Kohl Children’s Museum
The Kohl Children’s Museum is located in Glenview, IL, just north of Chicago. With 17 interactive exhibits, it’s a great way to get kids out of the house this winter. And don’t miss the SpotHero exhibit when you’re there!
Bring the outdoors inside
8. Logan Square Farmers Market
The Logan Square Farmers Market is a summer favorite among Chicagoans, but you can enjoy it in the winter, too! The market runs indoors every Sunday between 10:00 AM – 3:00 PM, from November 21 until March 27. Stop by for local produce and seasonal staples.
9. Rock climbing at Brooklyn Boulders
Get your fill of rock climbing right in the heart of Chicago. This indoor climbing facility has two locations—in West Loop and in Lincoln Park, is ideal for beginners, advanced climbers, and everyone in between.
Brooklyn Boulders: West Loop
Brooklyn Boulders: Lincoln Park
10. Indoor skydiving at iFLY Chicago
Ready to try something new this winter? Indoor skydiving at iFLY gives you the feeling of free fall in a safe environment. No parachute or cliff-jumping is required.
Reserve parking near iFLY here.
Catch the Bulls and Blackhawks
11. and 12. Grab tickets to the Bulls or Blackhawks and head to the United Center for a sure-fire good time this winter. If you’re not picky about who they’re playing, do some digging to find the cheapest tickets.
Have a laugh
13. The Second City
The Second City is a world-famous comedy club, known for its always-entertaining shows as well as its famous alums, including Bill Murray, Tina Fey, Amy Poehler, Steve Carell, and Stephen Colbert. You can’t go wrong with any of the shows–just be sure to reserve your tickets far in advance, as shows regularly sell out.
14. The Comedy Bar
The Comedy Bar, one of Chicago’s top comedy clubs, is located above the Gino’s East in the heart of River North, making it within walking distance of several downtown hotels. But if you’re driving, we’ve got you covered.
15. Laugh Factory
Chicago’s Laugh Factory is an off-shoot of the original Laugh Factory in Hollywood. World-famous comedians have performed here, so if you’re a fan of stand-up, be sure to catch a show here this winter.
Take in some tunes
16. The Green Mill
The famous Green Mill is believed to be the oldest continuously run jazz club in the United States. Check out the calendar of upcoming performances and stop by for live jazz or a poetry slam!
17. Kingston Mines
Kingston Mines is widely considered to be one of Chicago’s best blues clubs. It features a mix of local bands and world-famous blues artists on a regular basis. Kingston Mines is on a busy stretch of Chicago’s Lincoln Park neighborhood, so do yourself a favor and reserve parking in advance.
18. The Vic
The Vic is one of Chicago’s biggest music venues, featuring a beautiful theater with great acoustics. It is located in Chicago’s bustling Lakeview neighborhood. If you don’t want to circle the block a bunch of times, consider reserving parking in advance.
19. The Chicago Theatre
The Chicago Theatre is a landmark theater located in the heart of downtown Chicago that hosts a huge variety of performances. You can view performances and book parking below!
20. Chicago Symphony Orchestra
The Chicago Symphony Orchestra is consistently hailed as one of the best in the world. You can attend one of their many upcoming concerts, or if a traditional orchestral concert is not your speed, try CSO at the movies. Check out the full calendar here.
Try something new on the food & drink front
21. The Chopping Block – Merchandise Mart
Channel your inner Julia Child by taking a cooking class at The Chopping Block. This recreational cooking school offers a range of cooking styles and cuisines, from sushi workshops to simple French food. After you’ve reserved your spot at The Chopping Block, make a reservation for nearby parking.
22. Afternoon Tea at The Drake
Believe it or not, Afternoon Tea at The Drake Hotel has been a tradition for nearly a century. When you arrive at the Palm Court, you’ll choose from 17 selections of tea, plus a tier of finger sandwiches, petit fours, English scones, and mini lemon poppy seed loaf accompanied by preserves, lemon curd, and English Devon Cream.
Chicago Food Halls:
Chicago has seen an explosion of food marketplaces and halls, especially in the last few years.
23. With over 30 vendors, Chicago French Market is a European-style indoor market with fresh food, flowers, and international cuisine. Reserve parking near Chicago French Market here.
24. Eataly is Mario Batali’s sprawling two-story Italian marketplace in the heart of River North. If you find yourself wandering its aisles for hours, you’re not alone. You can reserve Eataly parking here.
25. Revival Food Hall is an all-local outpost in the Loop. Stop by on a weekday and enjoy staples from some of Chicago’s most popular restaurants, including Aloha Poke, Smoque BBQ, Furious Spoon, and many more. You can reserve parking near Revival here.
Solve your way out of an escape room
26. Escape Artistry
Check out The Railcar at Escape Artistry. What begins as a normal commute on the el train soon becomes a race against time. Work with your team to solve puzzles and save the city of Chicago from disaster. You can reserve parking near Escape Artistry here.
27. Fox in a Box
Fox in a Box is another escape room adventure, with four different missions: Zodiac, The Bunker, The Bank, and The Prison. Pair up with a partner or some friends and choose your mission! Then reserve parking in advance.
Take a vacation
28. And if you just can’t take the cold anymore, we wouldn’t blame you for heading out of town. If you’re going to the airport, reserve your parking spot in advance!
Parking near O’Hare Airport
Parking near Midway Airport