Chicago leans into winter. From late November through the new year, the city fills with holiday markets, light displays and traditions that have run for decades. Here are the ones worth planning a trip around.
1. Christkindlmarket
Modeled on the Christmas markets of Germany, Christkindlmarket has been held at Daley Plaza in the Loop since 1996. Wooden stalls sell ornaments, crafts and gifts, alongside bratwurst, pretzels and mulled wine (Glühwein) in a collectible mug. Admission is free.
For 2026, the market opens Friday, November 20 at three locations:
- Daley Plaza (50 W. Washington St.): daily through December 24
- Gallagher Way in Wrigleyville, next to Wrigley Field: through December 31
- RiverEdge Park in Aurora, the largest of the three: select days through December 24
Check christkindlmarket.com for hours. Weekday afternoons are the least crowded.
2. ZooLights at Lincoln Park Zoo
Each winter, Lincoln Park Zoo lights up with millions of LEDs along paths through the grounds, with hot drinks and snacks along the way. Lincoln Park Zoo is free to enter year-round; see lpzoo.org for ZooLights dates and any ticketed nights.
3. Ice skating in Millennium Park
The McCormick Tribune Ice Rink in Millennium Park sits beneath the downtown skyline, a short walk from Cloud Gate. Admission is free, with skate rental available. The City of Chicago's Christmas tree goes up in Millennium Park each year; in 2026 the tree lighting is the same night Christkindlmarket opens. Check the Millennium Park site for rink hours and conditions.
4. The Music Box Christmas Sing-A-Long
The Music Box Theatre, a 1929 movie palace on Southport Avenue, has held its Christmas show since 1983. Santa leads the audience in carols with the theater's organist before screenings of White Christmas and It's a Wonderful Life, and plenty of people stay for both. Shows usually run through most of December; see musicboxtheatre.com for this year's dates.
Flying privately to Chicago in winter
Private flights into Chicago commonly use:
- Chicago Executive (PWK): in Wheeling, northwest of the city, a dedicated general aviation airport
- Chicago Midway (MDW): closest to the Loop, with private terminals
- O'Hare International (ORD): closest for the northwest suburbs, with private terminals
Winter storms can affect any Chicago trip, so allow some flexibility in your schedule. Read more about how weather affects private jet flights. From the Southeast, a midsize jet usually suits the trip. Our advisors can also arrange ground transportation. Learn how on-demand charter works, or contact our team to plan a trip.
