One of our favorite holiday traditions in Chicago, the Christkindlmarket is a festive market inspired by the traditional Christmas markets of Germany. Located in the heart of the loop, it features charming wooden stalls filled with handcrafted gifts, ornaments, and seasonal treats, along with classic German fare and warm mulled wine. It’s the perfect place to soak in the holiday spirit while exploring the city, and we highly recommend visiting during your stay!
Take a walk down the Magnificent Mile to enjoy the sparkling lights along Michigan Avenue, festive storefronts, and holiday shopping. The tree-lined stretch feels especially magical in December, with luxury stores and seasonal décor all along the avenue. For even more holiday charm, nearby Macy’s on State Street is famous for its holiday windows and the historic Walnut Room!
A classic Chicago winter activity, the Skating Ribbon at Maggie Daley Park is a beautiful outdoor ice trail with stunning views of the city skyline. It’s a fun and festive way to enjoy the city in the winter!