Looking for the best things to do in Chicago in winter?
It may be a chilly time, but there is lots of magic in the windy (snowy) city!
There are tons of indoor and outdoor activities to enjoy in Chicago any time of year, but winter features some particularly fabulous holiday activities.
The best winter things to do in Chicago include visiting the Skydeck, and Color Factory, seeing an evening show, going to the seasonal Christkindl Market, exploring holiday pop-ups, dining at the Walnut Room, and more.
From indoor activities to ice skating and winter festivals, you’re sure to enjoy a Chicago trip even in the winter.
1. Skydeck
Skydeck provides one of the most iconic views of Chicago, all from the warmth of the 103rd floor of the Sears Tower! (Now it’s known as the Willis Tower).
Skydeck is unique because it’s a fully immersive experience.
The newest addition is an interactive museum on the way to your viewpoint at the Skydeck.
This features taking a “ride” on city transportation, “performing” at Second City, and small architectural layouts of the entire city.
I spent a full hour exploring before I even took the elevator to the top!
There are long lines to view the Skydeck, which of course makes sense. You are unfortunately limited to 3 minutes in the Skydeck itself in order to accommodate all guests.
It kind of makes sense, because you could easily be enjoying the city from one of those sky boxes all day! The good news is that you can get back in line as many times as you want.
The better news is that the entire top floor of the Skydeck has the same, amazing views. You can stay on the top floor as long as you want! (The line is for stepping on the ledge of the Skydeck itself).
Cost: Varies. Approximately $35 for general admission tickets. Reservations here
2. Color Factory
Color Factory is also located in the Sears Tower. If you’re feeling cold, you won’t even need to leave one of Chicago’s tallest skyscrapers to keep having fun!
I recommend the Color Factory most for splashing up your Instagram or photo collection. It’s also one of my Chicago girls’ trip recommendations.
Every room features an immersive exhibit with tons of colors. We’re talking colorful ball pit, confetti room, munching on macaroons- I won’t give it all away!
Cost: $45/person
Midwest Vacation Planning
3. Candlelight Show
There’s nothing to warm up to like a cozy, shique candlelight show.
The best part of the candlelight series is that they are featured in small venues across Chicago, which gives you an opportunity to experience smaller neighborhoods and hidden gems. The show I saw was in Wicker Park which is a super fun neighborhood.
They have holiday shows for winter. Other themed shows are Taylor Swift, classic rock artists, and more.
Tip: Fever features tons of candlelight shows across the United States, so catch one in another city if it doesn’t line up during your winter in Chicago trip!
Cost: Varies. Booking here
4. Laugh Factory
Laugh Factory is literally laugh-out-loud hilarious. I think this is one of the best comedy clubs in Chicago!
They have shows throughout the evening, with start times ranging from 7:00pm to 11:30pm. Show themes include: Open Mic, Fresh Faces of Chicago, Chicago’s Best Stand Up, and more.
I recommend booking tickets at least a day in advance because tickets can sell out at the door.
Keep in mind that they require a two-drink minimum purchase. This is in addition to the entrance tickets. They do not keep the drink prices on the menu, so be sure to ask before ordering a drink so there are no hidden surprises when you get the bill!
Bottles of water are included with drink purchase options- it does not need to be alcohol.
Cost: Varies. Booking here
Other Winter Shows in Chicago:
- The Nutcracker Ballet
- Cirque du Soleil
- More at the Chicago Theatre
5. Christkindl Market
This is, by far, one of my favorite winter activities in Chicago! It’s a local and tourist favorite.
There are two Christkindl markets: one is located on Daley Plaza in Downtown Chicago.
The second Christkindl Market is located outside of the Winter Wonderland Festival in the Wrigleyville neighborhood. The market opens in November so it’s also a good Midwest Thanksgiving vacation activity!
A bonus to going to the Wrigleyville location would be seeing all of the lights and festivities of Winter Wonderland inside of Wrigley Field, home of the Chicago Cubs! However, this festival comes with an entrance ticket cost.
Another bonus to the Wrigleyville location is checking out the holiday-themed pop-up bars throughout the Wrigleyville neighborhood.
Cost: Free
Read Next: Chicago 4 Day Itinerary, Chicago Girls Weekend, Best Places to Hike Near Chicago
6. Holiday Pop-Ups
Several bars in Chicago, primarily the Wrigleyville neighborhood, transform into full-out holiday-themed bars for the Christmas season. We’re talking totally decked out with decorations from floor to ceiling.
Some of the most famous ones are Frosty’s and Santa Baby- but these come with a price tag to get in.
Jack Frost Winterfest is another popular Chicago pop-up. This one is not a bar but a full-out festival. It is located on the same grounds it uses for its “Pumpkin” pop-up fall festival each fall. I haven’t made my way here yet due to the price tag, but I bet it’s worth the hype!
Cost: Varies
7. Walnut Room
The Walnut Room in Macy’s on State Street is known as one of the most iconic, quintessential holiday activities in Chicago.
Reservations begin filling months in advance, so I recommend planning ahead of time if you are planning to eat a meal in the room!
Tip: You can still experience the magic of the Walnut Room without a reservation.
Several visitors take photos of the ginormous Christmas Tree from outside of the room. It’s a pretty crowded standing area, but worth it if you’re in the area anyway!
Cost: Free to visit. Reservations here
8. Macy’s Holiday Windows
Macy’s on State Street in Chicago is famous for changing their holiday window displays each year. It is a favorite for Chicago locals and tourists in the winter.
It is convenient because it’s free, located in the same building as the Walnut room, and only a 5-minute walk from the Downtown Christkindl Market.
Cost: Free
9. Ice Skating at Millennium Park
Ice skating pop-ups have gotten popular across Chicago over the past couple of years.
Some of the best places to go ice skating in Chicago are Millennium Park and Maggie Daley Plaza. Other ice skating pop-ups can be found at Navy Pier’s Winter Wonderland and Maggie Daley Park.
Tip: Book ice skating reservations online in advance. These fill up quickly during the holiday season. Bring your own skates to save money on rental costs.
Cost: Free to skate, but cost for rentals. Reservations required here
10. Hot Tub Boats
This new Chicago winter activity as of 2024 is all the rage. I only wish I had experienced this one myself, but for now, it remains high on the list!
Cost: Reservations here
11. Lincoln Park Conservatory
Check out the Lincoln Park Conservatory for a free, nature experience to beat the cold!
Built in the late 1800s, the historic conservatory features 4 glass display houses with plant species from over 60 countries around the world.
Timed entry reservations are required.
Cost: Free. Reservations here
Chicago Winter Weather
The winter weather is no joke. Beginning in mid-January, temperatures have gotten as low as zero degrees.
That is almost dangerously cold. I recommend the indoor activities on this list if you are visiting during temperatures like this!
Through December, the weather has stayed between 20 – 40 degrees Fahrenheit. I know this is a pretty broad range, but Chicago weather is known to be unpredictable!
💼I recommend packing the following items:
Conclusion
There are plenty of wonderful things to do in the winter in Chicago each year. From indoor activities like Lincoln Park Conservatory to outdoor activities like Christkindl Market, there are plenty of winter wonderland activities throughout the windy city.
If you plan a Chicago winter trip, please let me know your favorite things to do- would love to hear from you!
