Summary
Chicago in winter offers plenty for families, from outdoor skating at the Maggie Daley Park Skating Ribbon and Millennium Park to free sledding by Soldier Field. Holiday highlights include Christkindlmarket, ZooLights at Lincoln Park Zoo, and Wintrust Winter WonderFest at Navy Pier, which opens November 27, 2026. For warm-up breaks, downtown museums, the Museum of Science and Industry’s Christmas Around the World exhibit, and Skydeck Chicago are easy indoor picks. Shoreline Sightseeing’s architecture river tours run through the end of 2026, with evening departures that show off the city’s holiday lights from the water. The guide also covers free activities and practical tips like dressing in layers, reserving rinks ahead, and planning around early sunsets.
Table of Contents
- Chicago Winter Activities for Families at a Glance
- Holiday Markets, Festivals, and Light Displays
- See Chicago’s Architecture and Holiday Lights From the Water
- Ice Skating in Chicago
- Sledding in Chicago
- Indoor Things to Do in Chicago in Winter
- Free Winter Activities in Chicago
- Tips for Enjoying Chicago in Winter With Kids
- Make Winter in Chicago a Family Tradition
- Frequently Asked Questions
Popular family-friendly winter activities in Chicago include ice skating on the Maggie Daley Park Skating Ribbon and at Millennium Park, browsing Christkindlmarket, exploring Navy Pier’s indoor Wintrust Winter WonderFest, seeing ZooLights at Lincoln Park Zoo, sledding the hill by Soldier Field, and warming up at top museums like the Shedd Aquarium and Museum of Science and Industry. For a different view of the season, an architecture river tour shows off the city’s holiday lights from the water.
Get ready to bundle up and dive into the frosty fun that Chicago has to offer for families. Don’t let the chilly temps stop you from creating unforgettable memories with your loved ones. This guide from Shoreline Sightseeing covers the best things to do in Chicago in winter, from holiday markets and skating rinks to cozy indoor attractions, so you can plan a trip everyone will enjoy.
Chicago Winter Activities for Families at a Glance
| Activity | Indoor or Outdoor | Typical Season | Good to Know |
|---|---|---|---|
| Christkindlmarket | Outdoor | Mid-November through late December | Free to enter; come hungry |
| Wintrust Winter WonderFest | Indoor | Nov. 27, 2026, into early January 2027 | Ticketed; ice skating included |
| ZooLights at Lincoln Park Zoo | Outdoor | Late November into early January | Check dates and ticketing |
| Maggie Daley Park Skating Ribbon | Outdoor | Mid-November through early March | Reservations required |
| Millennium Park Ice Rink | Outdoor | Late November into early February | Reservations required |
| Sledding Hill by Soldier Field | Outdoor | When temperatures allow | Free; call ahead to check conditions |
| Museums and Skydeck | Indoor | Year-round | CityPASS can bundle admission |
| Architecture River Tour | On the water | Through the end of 2026 | 60-minute tours starting Nov. 2; evening tours show off holiday lights |
Holiday Markets, Festivals, and Light Displays
Visit Christkindlmarket
Step into a winter wonderland, German-style, right in the heart of the Windy City. Christkindlmarket is a festive tradition that pops up every winter, with locations in recent years at Daley Plaza downtown, in Wrigleyville, and in Aurora. Best of all, it’s free to enter.
Make sure you come hungry. There are so many tasty snacks to choose from, including roasted nuts, freshly baked pretzels, sizzling bratwurst, and spiced mulled wine for the adults, so there’s something to satisfy every member of the family. Our favorite is the Raclette sandwich. Not only is it delicious, but it’s so fun to watch them assemble.
After enjoying the treats, check out the shops from vendors around the world. Artisan Christmas ornaments and alpaca sweaters make great holiday gifts. Check the official Christkindlmarket website for this season’s dates and hours before you go.
Explore Wintrust Winter WonderFest at Navy Pier
When the wind picks up, Navy Pier’s Wintrust Winter WonderFest brings the holidays indoors. Running from November 27, 2026, into early January 2027, the event transforms Navy Pier’s Festival Hall into a 170,000-square-foot holiday destination with a sparkling forest of decorated trees, rides like the Cliffhanger and the Arctic Express Train, and an indoor ice rink. Ice skating is included with admission, which makes it an easy choice for families with younger kids.
See ZooLights at Lincoln Park Zoo
Lincoln Park Zoo’s ZooLights is a longtime Chicago holiday tradition, transforming the zoo into a glowing display of lights each winter. It typically runs from late November into early January, and it’s a great evening outing for families with kids of all ages. Check the zoo’s website for this season’s dates, hours, and ticketing before you go.
Holiday Kickoff Events in Chicago
Chicago’s winter season starts before Thanksgiving. The Magnificent Mile Lights Festival lights up North Michigan Avenue the Saturday before the holiday, and the city’s official Christmas tree lighting in Millennium Park is typically held in late November. Visiting the following week? Plan ahead with these things to do in Chicago over Thanksgiving weekend, including the family-favorite parade on State Street.
See Chicago’s Architecture and Holiday Lights From the Water
No matter the temps, it is hard to argue that Chicago has one of the best skylines in the world. If you bundle up for the weather, you won’t regret hopping on an architecture river tour to see the true magic of Chicago. Shoreline’s architecture tours run through the end of 2026, and starting November 2, each tour is 60 minutes long.
Pro tip: For holiday lights, look for a tour around 4 p.m. or later. Evening tours are especially magical this time of year, as Chicago buildings transform for the holidays and light up the river, including the floodlit facade of the historic Wrigley Building.
If you’re looking for something a little more casual, head to Navy Pier for the Skyline Lake Tour. Starting November 2, the tour is 30 minutes long, the perfect amount of time to enjoy views of the Chicago skyline from Lake Michigan, with hot chocolate on board to keep everyone warm. Lake tours run weather permitting, so check the current schedule before you go.
Ice Skating in Chicago
Some of Chicago’s most popular skating spots are right downtown, with skyline views and holiday lights all around you.
Maggie Daley Park Skating Ribbon
The Maggie Daley Park Skating Ribbon is a winding ice skating path that loops through the park with the skyline in view. It typically opens in mid-November and runs into early March, with a special holiday skating season from December 11, 2026, through January 3, 2027. Reservations are required whether you bring your own skates or rent them, and skate aids are available for beginners.
McCormick Tribune Ice Rink at Millennium Park
Skating at Millennium Park is a classic Chicago experience, with Michigan Avenue, the city’s Christmas tree, and the holiday lights all around you. The rink typically opens in late November and runs into early February, weather permitting. In recent seasons, admission has been free with an online reservation, and skate rentals are available. Both downtown rinks are a short walk from plenty of other things to do near Michigan Avenue.
Indoor Skating at Navy Pier
For a break from the wind, the ice rink inside Wintrust Winter WonderFest lets families skate indoors, with skating included in WonderFest admission.
Sledding in Chicago
In addition to ice skating, families can enjoy sledding at parks throughout the city. One of the coolest spots is the hill by Soldier Field, which offers a 33-foot drop and great skyline views from the top. The Chicago Park District can supplement natural snow when temperatures stay cold enough, but sledding isn’t always available, so check conditions before you head out. It’s free to use.
Indoor Things to Do in Chicago in Winter
Once you’re ready to warm up, you’ll have plenty of cozy indoor options to choose from.
Museums Downtown
Some of the top museums in Chicago are right downtown, including the Shedd Aquarium, Adler Planetarium, Art Institute of Chicago, and Field Museum. You can’t go wrong exploring any or all of them.
Christmas Around the World at the Museum of Science and Industry
If you’re visiting during the holidays, don’t miss the Museum of Science and Industry. Its Christmas Around the World and Holidays of Light exhibit is a longtime family favorite, featuring a towering Grand Tree surrounded by a forest of trees representing holiday traditions from around the globe. Check the museum’s website for this season’s dates.
Skydeck Chicago
If you’re feeling a bit daring, take a trip up to one of the city’s observation decks. Skydeck Chicago at Willis Tower offers an amazing view of snow-covered Chicago. For the thrill-seekers, step out onto The Ledge, a glass balcony that extends 4.3 feet from the building over the city.
Planning to visit several attractions? Bundle up, grab your Chicago CityPASS, and make a day of it.
Free Winter Activities in Chicago
A Chicago winter doesn’t have to be expensive. Several family favorites are free or low-cost:
- Christkindlmarket. Entry is free, so you can browse the stalls and soak up the atmosphere before deciding what to eat or buy.
- Sledding by Soldier Field. The hill is free to use when conditions allow.
- Millennium Park Ice Rink. In recent seasons, admission has been free with a reservation. You pay only if you rent skates.
- Holiday kickoff events. The Magnificent Mile Lights Festival parade, the Thanksgiving parade, and the Millennium Park tree lighting are free to attend.
- Holiday window displays and lights. A walk down Michigan Avenue or along the Riverwalk after dark costs nothing and shows off the season.
Tips for Enjoying Chicago in Winter With Kids
- Dress in layers. Chicago winters are cold, and wind off the lake and river makes it feel colder. Hats, gloves, scarves, and waterproof boots make outdoor activities much more fun.
- Reserve ahead. The Maggie Daley Skating Ribbon and Millennium Park rink require reservations, and holiday weekends fill up fast.
- Mix indoor and outdoor plans. Pair a skating session or market visit with a museum or Winter WonderFest so everyone has a chance to warm up.
- Plan around early sunsets. It gets dark in the late afternoon, which is perfect for holiday lights but means outdoor daytime activities should start early.
- Check dates before you go. Seasonal events, rinks, and exhibits change year to year, so confirm hours on official websites.
- Warm up with a meal. Browse options for dining with a view in Chicago for a cozy break between activities.
Make Winter in Chicago a Family Tradition
As you can see, there’s a whole winter wonderland of fun waiting for you in the Windy City. From gliding around on ice skates to discovering cozy indoor play spots, there’s a flurry of family fun to be had. Add a river tour with Shoreline Sightseeing to see the city’s holiday lights from the water, and you’ll have a trip the whole family will remember. Trust us, it’s going to be snow much fun.
Frequently Asked Questions
Popular family-friendly winter activities in Chicago include ice skating at Maggie Daley Park and Millennium Park, visiting Christkindlmarket, exploring Wintrust Winter WonderFest at Navy Pier, seeing ZooLights at Lincoln Park Zoo, and sledding the hill by Soldier Field. Families can also take an architecture river tour to see the city’s holiday lights from the water. For indoor breaks, museums like the Shedd Aquarium and Museum of Science and Industry are easy picks.
Chicago in winter offers holiday markets, outdoor ice skating, sledding, indoor festivals, world-class museums, observation decks, and holiday light displays, including evening river tours that show off the lights from the water. Many seasonal events run from mid-November through early January, while skating often continues into February or March.
Yes. Chicago has plenty of winter activities for kids, with outdoor fun like skating and sledding, indoor options like museums and Winter WonderFest, and boat tours like the 30-minute Skyline Lake Tour, which serves hot chocolate on board, weather permitting. Dressing in layers and planning indoor breaks makes the cold much easier to enjoy.
Downtown favorites include the Maggie Daley Park Skating Ribbon, the McCormick Tribune Ice Rink at Millennium Park, and the indoor rink at Navy Pier’s Wintrust Winter WonderFest. Reservations are required at Maggie Daley Park and Millennium Park.
The hill by Soldier Field is a popular downtown option, with a 33-foot drop and skyline views. The Chicago Park District can supplement natural snow when it’s cold enough, but check conditions before you go, since sledding isn’t always available.
Wintrust Winter WonderFest at Navy Pier opens November 27, 2026, and runs into early January 2027. Ice skating is included with admission. Check Navy Pier’s website for daily hours.
Shoreline Sightseeing’s architecture river tours run through the end of 2026, including evening tours that show off the city’s holiday lights. Starting November 2, architecture tours run 60 minutes and the Skyline Lake Tour runs 30 minutes, with hot chocolate on board. Check the current schedule for dates and departure times.
Top indoor options include the Shedd Aquarium, Field Museum, Adler Planetarium, Art Institute of Chicago, Museum of Science and Industry, Skydeck Chicago, and Wintrust Winter WonderFest at Navy Pier.
Free winter activities in Chicago include browsing Christkindlmarket, sledding the hill by Soldier Field, skating at the Millennium Park rink with a reservation, attending holiday kickoff events like the Magnificent Mile Lights Festival, and walking Michigan Avenue to see the holiday lights.
