Skip the Crowds: Charming Cities to Visit Between Thanksgiving and Christmas

7. Chicago, Illinois

Chicago delivers iconic winter attractions—ice skating at Millennium Park, the Christkindlmarket, and festive window displays—while offering quieter visits in the weeks before the holiday-week surge. As a major city, it still has a steady stream of visitors, but early December and weekdays reduce lines at museums and restaurants. Indoor cultural options are plentiful, so you can alternate brisk outdoor activities with warm museum stops and long lunches. Weather can be wintry, so layer appropriately and plan indoor backups when temperatures drop. Travel + Leisure and Kayak travel analyses note affordability in some winter windows, which can translate to better flight and hotel rates in early December versus the holiday week. For a trip that combines big-city holiday energy with manageable crowds, choose midweek dates and make advance reservations for popular experiences to ensure smoother visits.