Chicago is one of the few major American cities where the holiday season truly looks like winter. The city pairs a near-guaranteed snow season with a defining mid-century retail history and one of the country's longest-running open-air German markets, with most landmarks clustered around the Loop and the Magnificent Mile.

• Christkindlmarket Daley Plaza: Modeled on Nuremberg's original, this open-air market is among the largest authentic German Christmas markets in the United States.
• Macy's Walnut Room: The seventh floor of the former Marshall Field's building is the originating home of the in-store Christmas tree tradition, dating to the late 19th century.
• State Street Windows: The animated holiday windows at the State Street store continue a department-store tradition that predates most others in the country.
• Berghoff and Chicago Eating: The German-American Berghoff on Adams Street, in business since 1898, anchors the city's downtown holiday dining alongside Garrett Popcorn's Chicago Mix and Italian beef from the West Side stands.