Weather in Chicago this time of year can be fickle. Fortunately, there are plenty of fun and cozy things to do in Chicago to keep you entertained indoors. From sampling fresh sushi in a curated environment to visiting your favorite works of art at a well-known museum. Whether you’re looking to stay warm and dry or want to try something new, these activities will brighten up any dreary day. Here are 15 fun activities to enjoy on a cold or rainy day in Chicago.
1. Catch a movie at a landmark theater
Movie theater’s like Davis Theater, The Music Box, and Logan Theater have operated for over a century. Cinema buffs and avid movie goers can appreciate modern amenities at affordable prices at these landmark, neighborhood theaters. Plus, an offering of diverse films—from newly released films to independent flicks, there is something for every one at these historic theaters.
2. Listen to your favorite acts at City Winery
From folk acts and jazz quartets to legendary singer-songwriters and buzz-worthy indie rock bands, this innovative venue is serving up some of the best music Chicago has to offer — along with some of its finest vintage wines. See what’s coming up at this Chicago music venue.
3. Catch up on reading in a beautiful Chicago library
Spend a few hours exploring, touring, and enjoying Chicago’s free public libraries. This is a fun and easy activity that can be done with the entire family or solo. Browse the pages of thousands of publications at facilities like Harold Washington Library Center or Chicago Public Library, Chinatown Branch while embracing astonishing surroundings and leaning something new.
4. Race go-karts at top speed at an indoor track in the Chicago Suburbs
Have a need for speed? Jump into the driver’s seat of high-performance racing at Accelerate Speed Indoor Speedway & Events. This is a fun and easy indoor activity to try when it’s especially cold and dreadful in Chicago. Buckle up, and enjoy the drive!
5. Savor a delicious meal at an all-season patio
Sometimes you want the appeal of dining outdoors without actually dining outside. Get the best of both worlds when you enjoy a meal at one of Chicago’s fully enclosed rooftop bars and patios. Find a few of my favorites here.
6. Visit a new or familiar exhibition at the Art Institute of Chicago
his world-famous museum, located in the Chicago Loop is home to a vast collection of art, including works by well-known American artists such as Kerry James Marshall, Georgia’ O Keffe, and Andy Warhol. Take a guided tour or have fun exploring the galleries on your own. Save a few bucks and check out thismuseum for free on select days of the week!

7. Peek behind the doors of a Wicker Park record shop
It may look like a regular record shop from the outside, but The Dorian Record Shop doubles as a speakeasy for those brave enough to seek out the hidden gem. Discover a new sound and sip delicious cocktails at this hidden bar in Chicago.
8. Plan a secret mission to a spy-themed bar
Explore authentic spy artifacts, interactive gadgets, and delicious eats and cocktails at the SafeHouse, a secret Chicago bar hidden in plain sight. This is a fun and easy experience for all ages—plan your mission today.
9. Nibble fresh omakase at a high-end hotel
Tucked away in several of Chicago’s luxury hotels (like The Emily or Hotel Lincoln) are guided sushi dining experiences. Guests can enjoy an extensive selection of Japanese spirits, craft cocktails, and of course fresh and high-quality sushi in a fun atmosphere that is perfect for any occasion.
10. Practice your golf swing indoors
From simulators to mini-golf, Chicago has plenty of fun and easy indoor golfing options. These golf options are great activities perfect for fun date nights or large group outings.

11. Take a walk and smell the roses (and other plants) at a conservatory
Chicagoland is home to many indoor gardens with a variety of exotic plants to admire, making a visit to a conservatory in Lincoln or Garfield Park are the perfect escape to a cold or rainy day in the city.
12. Shop for vintage pieces along 18th Street
Locals love 18th Street, the commercial district in the popular neighborhood of Pilsen. On this block find cool thrifts and unique finds from a selection of locally owned and operated shops.
13. Visit a black-owned coffee shop
Chicago is home to an independent and unique coffee shops. Support black-owned ventures like Overflow in the South Loop, plus more incredible shops across Chicago. Sip on a warm drink and unwind in a cozy environment.
14. Relax and release at a local spa
Treat yourself to a relaxing spa day in Chicago. Take a dip in the pool, retreat to a sauna, or enjoy a massage at area spas across Chicago. Plus spas make excellent winter hangouts.
15. Take a dance class
Learn a new dance style at a local dance studio at M.A.D.D. Rhythms in Bronzeville.
These fun and easy activities are the perfect way to experience a cold or rainy day in Chicago. Have favorites from the list? Share them below.
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