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4 Chicago Winter Activities to Make the Most Out of the Holidays

The Windy City has a lot to offer - even when the temperatures drop. Don’t let the changing weather scare you into staying inside all winter! Here are four local activities for families that embrace the season and celebrate the holidays.

4 Winter Activities to Do in Chicago




Photo courtesy of Ben Miller

Visit Christkindlmarket


From November 15 through December 24, residents and tourists head to 50 W. Washington Street to visit Christkindlemarket at Daley Plaza. The original Christkindlemarket began in 1545 in Nuremberg, Germany, and the first Chicago version took place in 1996. Today, the mostly open-air event is free to attend and includes vendors selling beautiful holiday ornaments, crafts, clothes and jewelry. Watch vendors creating their stunning creations like wood toys while eating strudel and sipping on mulled wine in a seasonal collector’s ceramic boot mug. Dress warmly but expect heaters and heated enclosures where you can warm up in between browsing charming holiday wares.


Photo courtesy of K Tao

Skate the Ribbon at Maggie Daley Park


Ice skating in downtown Chicago is an experience your family will never forget. Instead of skating around in circles on a rink, head to Maggie Daley Park at 337 East Randolph Street to glide along on the Skating Ribbon. This unique experience opened November 15 and is twice the length of a lap on a classic skating rink and offers a stunning view of the city. Skate rentals range from $13 to $15, depending on the day. Try your hand at twirls and swirls in figure skates or speed across the ribbon on hockey skates. Admission is free, so bring your own appropriate footwear and you won’t pay a penny to make memories on this beautiful rink.


Photo courtesy of Marit & Toomas Hinnosaar

Walk Through Zoo Lights at the Lincoln Park Zoo


Lincoln Park Zoo at 2001 North Clark Street pulls out all the stops each year with the Zoo Lights display. During the winter, the already beautiful zoo transforms into a magical wonderland with colorful lights and illuminated 3D displays that are timed to go off in time with seasonal music. Some nights, you can even walk the pathways under the twinkling lights while listening to live carolers. You can still view many of the animals during this fun seasonal experience, so it’s a great mix of exciting wildlife and holiday cheer. Zoo Lights runs from November 29 through January 5 and is open every weekend with additional hours, including daily shows during Christmas week. Admission costs $3 per ticket, but packages are available for groups and families looking to bring out-of-town visitors.

Peruse the Macy’s Holiday Display


Photo courtesy of Dan Perry
Many Chicagoans love ringing in the holiday season by browsing the Macy’s displays at 111 North State Street. Each year, the retailer unveils a theme and builds realistic and fantastical window exhibits that match. The 2019 window theme “Believe in the Wonder” was revealed on November 2. From whimsical glimpses into Santa’s workshop to peeks behind the scenes at the North Pole mailroom, your family will love adding this tradition to their seasonal schedule. Visit the Macy’s website to learn about upcoming holiday events in the store, like meeting Santa. Be sure to stop inside to view the Great Tree, a 45-foot-tall Christmas tree that is a sight to behold. The displays and tree will be visible through January 5.

If you’re ready to spend this winter enjoying a Chicago-area home, contact the KlopasStratton team to start viewing properties today. Whether you’re looking to rent a Lakeview two-flat or purchase a Ukranian Village condo, they’ll help find the perfect home to decorate for the holidays.


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4 Chicago Winter Activities to Make the Most Out of the Holidays