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Chicago Winter Events

After a quiet 2020, Chicago’s winter wonderland is set to return with a bang this year. Having only been a virtual spectacle last year, the Chicago Christmas Tree in Millennium Park is already shining brightly near the intersection of Michigan Ave. and Washington St. this year. And across the city there are various winter wonderland attractions to enjoy from ice skating to Christmas markets to theater productions. Be sure to check out Your New Year’s Eve Concierge for the top Chicago New Year’s Eve 2022 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 Light Up The Lake. This spectacle is an indoor, temperature-controlled holiday lights experience with more than 600,000 lights that runs from late November through to January 2nd. 

Inside, you will be able to experience kid-friendly activities including ice skating, kiddie train rides, and Santa’s Merry Main Street. For the adults, there’s the Alpine Pub complete with a beer garden serving beer and festive cocktails. Tickets range from $26 for adults to $21 for children (3-12 years old). There are notable discounts available on Mondays, Tuesdays, and Wednesdays and every ticket includes a complimentary ride on Navy Pier’s iconic Centennial Wheel 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 Pop-Up Winter Walk and Christmas Tree Farm on Goose Island. Axe throwing, bumper cars, music & lights, seasonal food and drink, ice skating, and a huge range of farm-fresh Christmas trees for sale 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 Wrigleyville is an alternative location for the perfect Christmassy time. 

New Year Festivities

With 2022 fast approaching, it’s time to make plans for how you’re going to celebrate 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  Hilton Chicago Michigan Avenue is billed as the number one event in Chicago this New Year’s Eve. Meanwhile, Chicago’s newest luxury hotel, JW Marriott Chicago, boasts the most exclusive event for NYE in the city. 

​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 at Swissotel Chicago, Chicago’s most luxurious hotel on the river. Alternatively, you could book a spot at  W Chicago City Center, the trendiest hotel in the city center. 

Our other recommendations for a good time on New Year’s Eve include the Rock Around The Clock party at Hard Rock Cafe and The Great Gatsby New Year’s Eve Gala at the Morgan Manufacturing (MFG). 

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 $10. They also offer free skating lessons on weekend mornings but remember to book in advance!

See A Play

Having had to become an online audio event in 2020, 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. Tickets are available for $25 on some days, although at peak times it is upwards of $50. 

As you can see, there’s something for everyone in Chicago in winter. Be sure to check out local listings throughout the month for more information and pop-up festivities. Lastly, make sure you wrap up warm! 


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