5 things to do in Chicago during the holidays

Christmas in Chicago is a magical time of year. With seasonal markets and festive activities around every corner, the city knows how to do the holidays right. Add a fresh blanket of snow, and Chicago is transformed into a veritable winter wonderland every December. If you’ll be spending some time here this holiday season, add these Christmas events in Chicago to your itinerary.

1. See a production of A Christmas Carol

Two actors of A Christmas Carol in Chicago.
Credit: University of the Fraser Valley on Flickr

No “bah humbugs” here! Held at the iconic Goodman Theatre, this timeless Chicago holiday tradition will be celebrating its 40th anniversary this year. Settle in for a special adaptation of Charles Dickens’ beloved holiday classic. Jubilant music, mesmerizing dancing, and Scrooge’s rediscovery of the holiday spirit will set a merry tone to kick off your Christmas season in Chicago. Tickets to A Christmas Carol are on sale through December 29.

2. Set off on the Chicago Winter Tour

Holiday window displays are one of our favorite things to do during Christmas in Chicago.
Credit: anokarina on Flickr

Christmas in Chicago has a lot to offer. What better way to see it than on a winter tour that explores the unique personalities (and of course the Chicago holiday lights and displays) of some of the city’s most popular neighborhoods?

A local tour guide will offer an authentic take on some of Chicago’s most popular Christmas activities. On the agenda: the Loop, Chinatown, and Wrigleyville. You’ll have the chance to explore the legendary german Christmas Marketing in Chicago: the Christkindlmarket, Chicago’s underground pedway system, and the historic holiday windows and decorations at Marshalls Fields (now a Macy’s). Grab tickets to the Chicago Winter Tour now to secure your spot.

Book top Chicago holiday activities with PlacePass

3. Ride the Chicago Union Station Polar Express

The iconic Polar Express in Chicago's Union Station.
Credit: David Wilson on Wikipedia

All aboard! Hop on the Polar Express for a magical one-hour ride to meet Santa. Set to the soundtrack of the The Polar Express™, your journey will start as your hosts make their way through the train to punch your golden ticket. Dancing chefs will treat you to hot chocolate and cookies as you read along to the classic children’s book. Santa and his elves will make an appearance, and each guest receives a keepsake sleigh bell to take home.

Trains depart Chicago Union Station. Tickets to the Polar Express are available for select dates between November 23 – December 29. Standard ticket costs are $60 for adults; $50 for children ages 2-11.

4. Explore Chicago’s Christkindlmarket

The famous German Christmas market in Chicago, Christkindlmarket, is a must-see in Chicago during the holiday season.
Credit: Emily Mathews on Flickr

Inspired by Nurmeburg’s famous German Christmas market, Chicago will host this cherished seasonal tradition for the 24th year in a row in 2019. The open-air Christkindlmarket offers unique holiday finds, including hand-blown ornaments, cuckoo clocks, nutcrackers, and handicrafts from local and international artists. Knock out some Christmas and Hanukkah shopping as you sample some of Chicago’s best savory and sweet treats. While you’re here, be sure to check out the vendor demonstrations on a variety of crafts and take in the performances by local dance troupes, magicians, school choirs, comedians, and more.

Festivities will run from November 15-December 24, 2019. Check the Christkindlmarket Chicago 2019 Facebook page for vendor updates and a full schedule of events and entertainment.

5. Go ice skating at Millennium Park

Ice skater at Chicago's Millennium Park.
Credit: Andrew E. Larsen on Flickr

No holiday season is complete without spin on the ice in Millennium Park surrounded by Chicago’s Christmas lights. The city will celebrate its 18th season of this quintessential Christmas tradition, and skating is free and open to the public all winter long (weather permitting, of course).

Skate rentals are available for a small fee and free skating lessons are available for all ages and skill levels on select days throughout the season. The rink is open daily dependent on the weather, and severe weather closures are posted on Millennium Park’s Facebook and Twitter pages. For a full list regular and holiday hours, rules and regulations, and private events, visit Skate Millennium Park.

With beloved local traditions, a city full of twinkling Christmas lights, and over-the-top displays, the holidays in Chicago are a magical time of year. As you plan your stay, PlacePass can help you find the best seasonal activities and experiences to help you make the most of your time in the Windy City.

Traveling to another city this holiday season? Check out our holiday activity guides in Los Angeles, New York City, Boston, and Philadelphia.

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