Our Favorite Ways to Spend the Holiday Season Around Chicago, IL

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Chicago. This vibrant and bustling Midwestern Metropolis is the scene for the arts among literature, film, theatre, comedy, gastronomy, music- all between its renowned skyline and storied neighborhoods. Today, Chicago continues to draw millions of tourists from over the world, and with so much occurring at every part of the year, it’s easy to understand why. Whether a visitor drafting travel plans, returning home to visit friends and family, or a local looking for something to do near home, Chicago has something for everyone. Read on for some of our favorite holiday season festivals and events here around the Windy City.


The Christkindlmarket is a festive and beautiful attraction of Chicago’s holiday season, an outdoor market and fair celebrating the Holidays and the Chicago area’s strong German-American heritage. At Christkindlmarket, visitors can experience Christmas and the holiday season in a way that reflects Central European tradition, including Christmas trees, live choirs, dance groups, live music, Santa encounters, as well as a wide range of crafts and delicious food such as wines, beers, cookies, kolachkes, strudels, sausages, toys, and handmade souvenirs. The Christkindlmarket is a great opportunity to take photos and enjoy Chicago’s holiday spirit for parties of all sizes and ages.

Ice Skating at Millennium Park

Ice Skating is a timeless wintertime tradition, and Chicago is no exception to this- also subject to frosty temperatures here on the Great Lakes so lace up your skates and enjoy ice skating with the whole party just next to the iconic Cloud Gate at Millennium Park!

Every day from mid-November through late February, travelers can reserve a free spot for ice skating on one of the city’s many free skating rinks. This is a great way to enjoy this holiday season tradition while in some of Chicago’s most memorable locations, on the ice with friends, family, and neighbors alike. Bring everyone to the ice at Millennium Park, and enjoy skating a little while.

Navy Pier’s Light up the Lake

To add to the fun and action at Chicago’s bustling Navy Pier, every holiday season, the pier dives deep into the holiday spirit with the ‘Light up the Lake’ series! From late November to January, lights adorn the pier, interior, and exterior, light sculptures are brought to tower over visitors, an ice rink is installed, a holiday beer garden joins the fun and Santa comes with his own gift marketplace. This is a great option for groups of varying interests and ages, with the sheer variety of activities to explore! In addition to all of these great holiday events, there is also the Ferris wheel that operates year-round providing pleasant views over the Chicago waterfront, other thrilling rides, a kiddie train, and a number of delicious eateries! (We recommend the giant, soft pretzels!) Bring the whole group to Navy Pier and enjoy one of Chicago’s favorite spots during the holiday season.

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