Shop My Looks

Hi, I'm Jess

Come along as I share everything from Chicago life, events, and experiences to sales, restaurants, motherhood, style, travel and more.


shop ltk

Grab my
Discount Codes!

Here are 9 things to do in Chicago this winter

Feb 20, 2023

Okay, I won’t lie— winter in Chicago isn’t my favoriteee season. While I would definitely prefer Chicago in the spring or autumn, the city still has plenty of fun activities to offer during the winter season. Here are a few ideas if you’re looking for something to do during these chilly times:

1. Ice Skating

There’s still a few more weeks left to try out one of the most popular activities in Chicago during the winter— ice skating! There are many places to go ice skating in the city, including Millennium Park and the Maggie Daley Park Skating Ribbon, which are open until March 5!

2. Visit the Museums

Chicago has some of the best museums in the country, and they are a great way to escape the cold. The Art Institute of Chicago, the Field Museum, and the Museum of Science and Industry are all great options. There are also lots of FREE admission days for Chicago residents for you to take advantage of this winter.

3. Go to a Blackhawks game

The Chicago Blackhawks are the city’s NHL team, and going to a game at the United Center is a great way to experience the excitement of Chicago sports while getting to stay warm indoors!

4. Watch a movie:

What says winter better than cuddling up for a movie! There are so many theaters throughout the city to go and enjoy movies, both new and classic! One of my favorites is on the Southport Corridor, one of my favorite areas of the city. The historic Music Box Theatre is a great place to watch a movie during the winter season. They shows classic films and hosts special events throughout the year!

5. Walk through the Lincoln Park Zoo:

Lincoln Park Zoo is one of my favorite places in the city. It is one of the U.S.’s oldest FREE zoos. It’s the perfect place to take the fam on those not-too-chilly days. And if you go early enough in the season, you can catch the LPZ Lights festival— a magical experience for people of all ages that features over two million lights and hundreds of displays spread throughout the zoo.

6. Visit Navy Pier

Navy Pier is a popular destination year-round, from its famous Centennial Wheel to the Shakespeare Theater, amazing restaurants, and Chicago’s Children’s Museum, there is always something to do on the pier!

7. Go to a comedy show

Chicago is known for its comedy scene, and going to a show at one of the city’s many comedy clubs is a great way to have a laugh and stay warm. Second City and The Laugh Factory are two popular options, but I highly recommend checking out the city’s hidden gem’s like the Den Theatre or the Raven Room which host comedy events regularly, too!

8. Check out the skyline views

What’s more iconic than the Chicago skyline? The Willis Tower Skydeck (featuring The LEDGE) and the 360 Chicago Observation Deck (featuring The TILT) are both great places to take in the city’s stunning skyline views during the winter season.

Taken at 360 Chicago

9. Try the local cuisine

Chicago is, of course, famous for its PIZZA, and trying this local specialty is a must-do during any trip to the city. Pro-tip: Don’t go for the traditional deep dish pizza. Chicago is also known for its amazing tavern-style, thin-crust pizza! A few of my favorites are D’Agostino’s in Wrigleyville or Pequod’s in Lincoln Park (they have deep dish, too!)

+ view comments


More to Love:

Here are 9 things to do in Chicago this winter

Join the Crew