Fun Things to Do in Chicago in Winter: 2026-2027 Activities Guide
Quick Summary: Chicago’s 2026-2027 winter season includes Holidays @ Skydeck (November 13 to January 4), Pie in the Sky dinners on Skydeck’s The Ledge, Lincoln Park ZooLights (November 20 to January 3), Christkindlmarket (opening November 20), Chicago Restaurant Week (January 22 to February 7), and the Chicago Auto Show (February 13 to 21). January is the coldest month, with an average high of 31.6°F, so plan a mix of outdoor highlights and warm indoor attractions like Skydeck, 103 floors above the city.
The best things to do in Chicago in winter include taking in snowy skyline views from Skydeck Chicago, ice skating downtown, walking through Lincoln Park ZooLights, and browsing Christkindlmarket. After the holidays, Chicago Restaurant Week and the Chicago Auto Show keep the calendar full through February. Winter in Chicago splits into two seasons: festive holiday events in November and December, and a stretch of citywide food, culture, and indoor fun in January and February. Here’s how to plan around both.
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What Are the Best Things to Do in Chicago in Winter?
The best things to do in Chicago in winter mix outdoor seasonal traditions with warm indoor attractions, so a cold day never stops the plan. Here are 12 of the top Chicago winter activities and places to visit in Chicago in winter for the 2026-2027 season.
1. See the City From Skydeck Chicago
From 103 floors up in Willis Tower, winter brings crisp skyline views over a snowy city. Step out onto The Ledge, explore the Chicago Museum, and take in the whole city without stepping into the cold.
From November 13, 2026 to January 4, 2027, Holidays @ Skydeck decks out the observation deck and lower-level Chicago Museum with thousands of twinkling lights, festive décor, and holiday photo ops, plus Santa visits and seasonal entertainment. It runs into the new year, so a trip between Christmas and New Year’s can still catch it. To end the night 103 floors up, book a Pie in the Sky dinner on The Ledge after Skydeck closes.
2. Go Ice Skating Downtown
The Maggie Daley Park Skating Ribbon winds through the park with the skyline as a backdrop, and its 2026-2027 season opens in November 2026. Check maggiedaleypark.com for reservations and skate rental pricing. The McCormick Tribune Ice Rink in Millennium Park is another downtown option.
3. Walk through Lincoln Park ZooLights
More than 3 million lights fill Lincoln Park Zoo from November 20, 2026 to January 3, 2027. Plan ahead with the ZooLights 2026 dates, tickets, and free Monday nights.
4. Shop Christkindlmarket
Chicago’s German-style holiday market celebrates its 30th anniversary in 2026. It opens November 20 at Daley Plaza, running through December 24, and at Gallagher Way in Wrigleyville, running through December 31.
5. Take In the Holiday Lights
Lights across downtown and the neighborhoods make an easy evening plan, with plenty of places to see Christmas lights in Chicago.
6. Visit Winter WonderFest at Navy Pier
From November 27, 2026 to January 3, 2027, Wintrust Winter WonderFest fills Navy Pier‘s Festival Hall with rides, festive décor, and indoor ice skating, which is included with every admission. Tickets are $27 when purchased online at least 24 hours ahead.
7. Eat Your Way Through Chicago Restaurant Week
From January 22 to February 7, 2027, restaurants across the city and suburbs offer prix fixe brunch, lunch, and dinner menus for the event’s 20th year.
8. Explore the Chicago Auto Show
The Chicago Auto Show returns to McCormick Place from February 13 to 21, 2027.
9. Catch a Bulls or Blackhawks Game
Winter is the heart of basketball and hockey season, and both the Chicago Bulls and the Chicago Blackhawks play home games at the United Center, an indoor way to experience Chicago’s sports culture on a cold night.
10. Spend a Day at the Museums
Chicago’s museums are a natural fit for cold days, along with plenty of other indoor things to do in Chicago.
11. Warm Up at the City’s Conservatories
The Garfield Park Conservatory and the Lincoln Park Conservatory, just steps from Lincoln Park Zoo, fill their glass houses with lush indoor gardens that feel worlds away from the cold. Reservations are recommended, so check each conservatory’s website for hours and admission before you go.
12. Plan a Winter Date Night
Skyline views, skating, and cozy dinners are just a few winter date ideas in Chicago.
Chicago Winter Events 2026-2027
Chicago’s winter events run from mid-November through February, starting with holiday celebrations and continuing with citywide food and auto events after the new year.
| Event | Dates | Ubicación |
|---|---|---|
| Holidays @ Skydeck | November 13, 2026 to January 4, 2027 | Skydeck Chicago, Willis Tower |
| Maggie Daley Park Skating Ribbon | Opens November 2026 | Maggie Daley Park |
| Christkindlmarket Chicago | November 20 to December 24, 2026 | Daley Plaza |
| Christkindlmarket Wrigleyville | November 20 to December 31, 2026 | Gallagher Way |
| Lincoln Park ZooLights | November 20, 2026 to January 3, 2027 | Lincoln Park Zoo |
| Winter WonderFest | November 27, 2026 to January 3, 2027 | Navy Pier |
| New Year’s Eve Fireworks | December 31, 2026, at 11:59 p.m. | Navy Pier |
| Chicago Restaurant Week | January 22 to February 7, 2027 | Restaurants citywide and in the suburbs |
| Chicago Auto Show | February 13 to 21, 2027 | McCormick Place |
Visiting during the holidays? Get more on December events and weather for visiting Chicago in December, and find fireworks, countdowns, and more for New Year’s Eve in Chicago.
What to Do in Chicago in January and February
January and February are a great time for food, culture, and indoor fun in Chicago. Chicago Restaurant Week runs from January 22 to February 7, 2027, the Chicago Auto Show takes over McCormick Place from February 13 to 21, and outdoor skating continues downtown. Skydeck stays open daily from 9 a.m. to 8 p.m. through February 28, and until 9 p.m. on Saturdays, so a skyline visit fits easily into a short winter trip. Visiting for Valentine’s Day? Pair a sunset skyline visit with a cozy dinner for a classic winter date.
Is February a Good Time to Visit Chicago?
February is a good time to visit Chicago if you’re coming for events like the Chicago Auto Show and the final days of Restaurant Week and don’t mind the cold. February averages a high of 35.7°F and a low of 21.8°F, slightly warmer than January, so pack for winter weather and plan a mix of indoor and outdoor stops.
What to Do in Chicago When It’s Cold
When it’s too cold to stay outside, Chicago’s indoor attractions keep the day going. Start at Skydeck, where you can see the city from 103 floors up without stepping into the wind, then grab a bite at Catalog, the dining and shopping destination inside Willis Tower. Museums, theaters, and other indoor things to do in Chicago round out a warm day.
Free and Cheap Things to Do in Chicago in Winter
Chicago has several free and low-cost winter activities worth planning around:
- Lincoln Park Zoo: Daytime admission is free and the zoo is open 365 days a year.
- ZooLights free Mondays: ZooLights is free on November 23 and 30 and December 7 and 14, 2026, with a ticket reserved in advance.
- Low-cost ZooLights nights: On other nights, Fixed Date ZooLights tickets start at $7 when purchased in advance.
- Holiday lights: Walking past the city’s Christmas light displays costs nothing.
Winter Activities for Families, Couples, and Adults
Chicago Winter Activities for Kids and Families
Families can pair ZooLights and skating with indoor stops that keep kids warm and curious. At Skydeck, the interactive Chicago Museum and The Ledge give kids a whole new way to see the city. During Holidays @ Skydeck, kids can also catch Santa visits and holiday photo ops through January 4. Explore more of what Skydeck offers for kids and families.
Winter Ideas for Couples
Winter is a cozy season for date nights, from sunset skyline views to skating under city lights. At Skydeck, you can pair the views with a private Pie in the Sky dinner on The Ledge for a memorable night out. There are plenty more Chicago winter date ideas to fill a weekend.
Winter Activities for Adults
Adults can plan around Chicago Restaurant Week, the 21+ Adults Night Out at ZooLights on December 10, 2026, and evening visits to Skydeck, which stays open until 8 p.m., or 9 p.m. on Saturdays, through February. For a later night, Pie in the Sky dinners on The Ledge begin at 9:30 p.m. after Skydeck closes.
Is Chicago Worth Visiting in Winter?
Yes. Chicago is worth visiting in winter for travelers who want holiday traditions, citywide events like Restaurant Week and the Auto Show, and iconic views from indoor attractions like Skydeck. The tradeoff is the cold, so the best winter trips balance a few outdoor highlights with warm indoor plans.
What Is the Weather Like in Chicago in Winter?
Chicago winters are cold and snowy. Based on National Weather Service climate normals, January is the coldest month, averaging a high of 31.6°F and a low of 18.8°F, while February averages a high of 35.7°F and a low of 21.8°F. January and February each average more than 10 inches of snow. Snow can arrive as early as November, and how much it snows in Chicago varies from year to year. December brings its own mix of cold and holiday cheer when visiting Chicago in December.
Plan Your Winter Visit to Skydeck
Skydeck Chicago is open 365 days a year, so it’s an easy winter plan in any weather. From October 1 through February 28, hours are 9 a.m. to 8 p.m. daily and until 9 p.m. on Saturdays, with last entry 30 minutes before close. Visit during Holidays @ Skydeck through January 4 for seasonal décor and photo ops, or plan a team outing with Skydeck’s corporate events options.
Dine on The Ledge With Pie in the Sky
For a winter night to remember, Pie in the Sky is a private dining experience after Skydeck closes to the public. Enjoy a customizable Chicago-style pizza dinner from Giordano’s, with salad, soft drinks, and dessert, served on The Ledge 1,353 feet above the city. From October through February, Ledge seatings begin at 9:30 p.m., and reservations are required. It’s a natural fit for date nights, birthdays, and anniversaries.
Buy your Skydeck tickets in advance to start your winter day 103 floors up.
Frequently Asked Questions About Things to Do in Chicago in Winter
What are the most popular events in Chicago during winter?
Popular winter events in Chicago include Holidays @ Skydeck, Lincoln Park ZooLights, Christkindlmarket, Chicago Restaurant Week, and the Chicago Auto Show. Holiday events run from mid-November into early January, followed by Restaurant Week and the Auto Show in January and February.
How cold does Chicago get in January?
January is Chicago’s coldest month, with an average high of 31.6°F and an average low of 18.8°F, based on National Weather Service climate normals.
Are there things to do in Chicago when it’s too cold to go outside?
Yes. Indoor attractions like Skydeck Chicago, the city’s museums, and Catalog at Willis Tower let you explore Chicago without braving the cold.
What can you do in Chicago in winter for free?
Free winter activities in Chicago include visiting Lincoln Park Zoo, which has free daytime admission year-round, walking the city’s holiday light displays, and attending ZooLights on its free Monday nights with a reserved ticket.
When does the Maggie Daley Skating Ribbon open?
The Maggie Daley Park Skating Ribbon’s 2026-2027 season opens in November 2026. Check maggiedaleypark.com for the exact opening date, reservations, and skate rental pricing.
Can you have dinner at Skydeck in the winter?
Yes. Pie in the Sky offers a private Chicago-style pizza dinner on The Ledge after Skydeck closes, with seatings at 9:30 p.m. from October through February. Reservations are required.
What is there to do in Chicago in February?
In February, you can visit the Chicago Auto Show (February 13 to 21, 2027), enjoy the final days of Chicago Restaurant Week, go ice skating downtown, and see the winter skyline from Skydeck.
Image sources:
christkindlmarket.com
maggiedaleypark.com
lpzoo.org
navypier.org