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Caroling at the Cloud Gate at the Millennium Park, Chicago

10 Best Things to do in Chicago Over the Holidays

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Chicago, the city which I have called my home for the last 20 years, is a great place to visit year round, but it has a bad rep in the winter months when most travelers try to avoid it. This is unfortunate; with many unique things to see and do, the holiday season in the city of Chicago is quite magical and can make for a very memorable family travel experience.

Here are my top 10 must-do holiday activities in Chicago for families:

1. Magnificent Mile Lights Festival Parade

Taking place every year on the Saturday before Thanksgiving, Magnificent Mile Lights Festival Parade officially kicks off the holiday (and shopping!) season in Chicago with many fun family activities and a Mickey Mouse parade illuminating over one million lights along Chicago’s famous Michigan Avenue (the “Mag Mile”). Immediately following the parade are impressive fireworks on Michigan Avenue where the Mag Mile crosses over the Chicago River.

2. Caroling at the Cloud Gate

This is quickly becoming one of our most cherished Holiday traditions in Chicago. This free-of-charge event takes place every Friday evening between Thanksgiving and Christmas at the famous Cloud Gate sculpture in the Millennium Park (commonly referred to as “the Bean”). The event features a different Chicago choir group each Friday and visitors/spectators are encouraged to join in a holiday sing-along that is guaranteed to make you hum along even if you are not into singing.

3. The McCormick Tribune Ice Rink

Infected with the Holiday spirit from the caroling, you can go ice-skating at the adjoining McCormick Tribune Ice Rink in Millennium Park. Rent a pair of skates and enjoy a cup of hot chocolate as you twirl around one of the most popular winter destinations in the city for Chicagoans and visitors alike.

Ice skating rink at the Millennium Park, Chicago

Ice skating rink at the Millennium Park.

4. Christkindlmarket at the Dailey Plaza

Described as the traditional German American holiday market (and it is – staffed by “real” Germans who fly in specifically to work the market and staff each booth), this event has been taking place at the Chicago’s Dailey Plaza since 1996 when it became an instant success. Sample some delicious and authentic German food (bratwurst, potato pancakes or freshly roasted cinnamon almonds) and drinks (Gluhwein anybody?), shop for toys, ornaments or German candy at various stands, marvel at the miniature train exhibit or enormous Christmas tree set up in the middle of the plaza and certainly don’t forget to have your picture taken with Santa!

Christkindlmarket in Chicago

Christkindlmarket in Chicago is a wonderful place to find unique gifts.

5. Winter WonderFest at the Navy Pier

For a completely different experience, head over to the Winter WonderFest at the Navy Pier, which is basically a giant indoor Christmas themed playhouse. With its unique rides, indoor Ferris wheel, ice-skating rink, and many other amazing attractions (our family’s favorite is the Extreme Ice Trail Ropes Course), it offers a ton of fun for kids of all ages as well as adults.

6. Zoo Lights at Lincoln Park Zoo

For our family, visiting the ZooLights at the Lincoln Park Zoo during the month of December is an annual holiday must! Every year this local gem puts on the most elaborate light display and offers several family-fun activities throughout its grounds such as a musical light show, animal shaped ice carvings, various holiday crafts, a Santa visit and much more.

7. Chicago Trolley Holiday Lights Tour

For those who cannot get enough of lights, there is a Chicago Trolley Holiday Lights Tour, a 2.5 hour circle tour in a trolley or motor coach around downtown Chicago to see a variety of sights and Christmas lights of the city. The tour offers several stops (such as the Christkindlmarket or Lincoln Park Zoo mentioned above). It is a great and easy way to take in the festive atmosphere of the city, especially if the weather is cold.

8. Take a horse-drawn carriage ride

For a more romantic (yet still family friendly) variation, consider taking a horse-drawn carriage ride down Michigan Avenue and the Gold Coast area offered by several local companies. Most of them don’t have set routes and they let you customize your ride. The easiest way to catch them is around the historic Water Tower on Michigan Avenue.

9. Holiday-Themed Museum Exhibits

Many Chicago museums offer special holiday-themed exhibits this time of year. The Shedd Aquarium has a Polar Play Zone where kids can try on a penguin suit and pretend to be a bird, visit belugas in a kid-sized submarine and more. The Museum of Science and Industry is known for their annual Christmas Around the World and Holidays of Light exhibit and the Chicago Children’s Museum guarantees hours of hours of fun with their Snow Much Fun exhibit.

The Museum of Science and Industry Christmas Around the World and Holidays of Lights exhibit, Chicago

Christmas Around the World and Holidays of Light exhibit at the Museum of Science and Industry.

10. Holiday Theater

Finally, the city offers a wide array of excellent holiday-themed theater shows, the most famous one being the Nutcracker by the Joffrey Ballet, which has been performing this impressive production for over 25 years and sells out quickly every year.

Oh, and here is one more bonus idea to consider…known mostly by Chicagoans. Every year the Chicago Transit Authority transforms one of its famous elevated trains (the “L”) into an incredible “Holiday Train.” Decked inside and out with holiday spirit, the train is led by reindeer and Santa on his sleigh. Once onboard, passengers are greeted by cheerful elves, handing out candy canes and singing Christmas carols. Not to be missed! Check the CTA website for exact times and routes.

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A native of Slovenia, Vera moved to the U.S. 20+ years ago after meeting her American husband. Together with their two children they live on the North…

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