5Chicago, Illinois

Chicago brings big-city holiday excitement with a touch of Midwestern charm. The city’s Magnificent Mile lights up with millions of twinkling lights, and the annual Chicago Christmas Tree in Millennium Park is a sight to behold.

Visitors can enjoy ice skating with the skyline as their backdrop or explore one of the many holiday markets around town.

One of Chicago’s must-see events is the Christkindlmarket, inspired by the traditional German markets. Located in Daley Plaza, it’s filled with holiday treats, handcrafted ornaments, and gifts from around the world. After warming up with a cup of hot spiced wine, visitors can head to Navy Pier, which transforms into Winter WonderFest, featuring carnival rides, ice skating, and holiday entertainment.

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