Chicago Winter Events
Chicago Winter Activities and Events: A Guide to the 2025–2026 Season
Chicago’s winter season transforms the city into a magical wonderland, brimming with festive events and activities. Across the city there are various winter attractions to enjoy from ice skating to Christmas markets to theater productions. Whether you’re a local or a visitor, there’s something for everyone to enjoy. Here’s an updated guide to the best things to do in Chicago in winter, perfect for the 2025–2026 season. Be sure to check out Your New Year’s Eve Concierge for the top Chicago New Year’s Eve parties in the city with the hottest DJs and the finest amenities.
Navy Pier Holiday Lights
Chicago’s waterfront destination, Navy Pier, plays host to several winter wonderland activities. The main attraction this year is Winter Wonderfest. This spectacle is a holiday experience with rides, music, and performances, running from December 5th to January 4th.
You will be able to experience kid-friendly activities including ice skating, bumper cars, and a holiday train ride. With each ticket, a ride on Navy Pier’s iconic Centennial Wheel is included, giving you amazing panoramic views of Chicago and Lake Michigan.
Jack Frost Pop-Up Chicago
Also making a return this year is Jack Frost’s Winter Pop-Up, one of the most popular winter events in Chicago. Axe throwing, bumper cars, music & lights, seasonal food and drink, and ice skating, make this one of the most special winter events Chicago has to offer in December. This is a romantic setting too, you can get a perfect picture taken or the folks at Jack Frost will even help you make the perfect marriage proposal if you feel ready to pop the big question.
Christmas Markets
At the Daley Plaza in downtown, you can experience a traditional German Christmas market in Chicago for a seasonal sensory experience at the Christkindlmarket festival. Christmas music and colorful lights combine with the smell of freshly baked pretzels and roasted nuts to get you in the mood for the holiday season.
Admission to the markets is free, leaving you to spend your hard-earned dollars at the various vendors selling food, drinks, and gifts. So, whether you want to treat yourself to something or buy a present for that special someone, Christkindlmarket is the perfect Chicago winter event.
New Year Festivities
With 2026 fast approaching, it’s time to make plans for how you’re going to celebrate the new year in Chicago. Hotels across the city are offering glamorous events to welcome in the new year in style. The NYE Soiree at the Palmer House Hilton is billed as the most luxurious event in Chicago this New Year’s Eve with Kiss FM.
The Congress Plaza Hotel is one of Chicago’s most historic landmarks and promises Chicago’s hottest New Year’s Eve party with Chicago’s A-List clientele. Other options include the chance to celebrate NYE on top of Chicago with The Metropolitan at the 66th Floor of the Willis Tower, Alternatively, you could go over to the Magnificent Mile to book a spot at 101 Club Chicago and spend the New Year admiring the city lights & fireworks.
Our other recommendations for a good time on New Year’s Eve include the NYE 2026 celebration at City Hall in Fulton Market, LaSalle Hotel’s 2026 New Year’s Eve Party, and The Great Gatsby New Year’s Eve Gala at the Morgan Manufacturing (MFG). Or, for a truly unforgettable experience, ring in the new year from the water with a one-of-a-kind NYE fireworks cruise that delivers unbeatable skyline views.
Ice Skating in Millenium Park
Ice rinks in winter can be found across the city, but the city’s premier skating destination is in Chicago’s downtown Millennium Park. With a winter wonderland setting guaranteed, ice skating in December makes for a perfect romantic evening for couples or a memorable night for all the family.
Admission is free, but this is a very popular activity in the city, so you need to book a ticket in advance. You can bring your skates or rent a pair for $16. They also offer free skating lessons on weekend mornings but remember to book in advance!
See A Play
Charles Dickens’ A Christmas Carol is back live at the Goodman’s Albert Theatre this year throughout December. The show is appropriate for children 6+ and tells the engrossing story of Ebenezer Scrooge’s discovery of kindness, compassion, and redemption in a theatrical adaptation of the famous novel.
Experience the Top Chicago Winter Activities
Chicago’s 2025–2026 winter season is packed with memorable activities and events for all ages. If you’re wondering what to do in Chicago in the winter, options abound—from ice skating under the stars and exploring festive markets to enjoying world-class theater. You’re sure to create lasting memories in this vibrant city. Plan your visit now and make the most of everything the Windy City has to offer this winter!