BEST Things to Do in Chicago in December, 2021 (From a Local!)

December is one of the best months to visit Chicago. Even though the weather is getting colder, it is still comfortable and there are so many fun and festive Christmas and holiday activities and events that take place. Below are the best things to do in Chicago in December.

I suggest bookmarking this blog post as I plan to update it regularly with any new information or updates.

Things to Do in Chicago in December 2021

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Visit an Authentic German-Style Christmas Market

christmas things to do in chicago

Christkindlmarket is an authentic German-style outdoor market.  Visitors can shop for Christmas ornaments and products from around the world and try various German food and drinks such as roasted nuts, fresh pretzels, bratwurst, and hot spiced wine. You can purchase a limited edition souvenir mug to remember your visit.

The market will be in 2 locations in Chicago in 2021: Daley Plaza in downtown Chicago and Gallagher Way in Wrigleyville.

Where: 50 W Washington Street and 3635 N Clark St

When: Until December 24, 2021 (Daley Plaza) and December 31, 2021 (Wrigleyville)

Hours: Hours vary see the website for more details

Cost: Admission is FREE.

See the City of Chicago Christmas Tree

Seeing the City of Chicago Christmas Tree is one of best things to do Chicago in December

The City of Chicago Christmas tree will be at Millennium Park the entire month of December.

The Bean in Chicago's Millennium Park with the Christmas tree in the background

Make sure to stop by Cloud Gate (also called The Bean) for a quick photo. The bucket list worthy attraction is located just a few feet away from the tree and you can even take photos of the Bean with the tree in the background.

Where: Millennium Park (near the intersection of Michigan Avenue & Washington Street).

When: Millennium Park is open daily from 8am to 9pm.

Cost:  Free.

Millennium Park Holiday Sing-Along (previously “Caroling at Cloud Gate”)

The new Millennium Park Holiday Sing-Along (previously “Caroling at Cloud Gate”) will invite Chicagoans and visitors to sing out and celebrate Chicago’s diverse holiday traditions on Friday evenings during the holiday season. This series has been reimagined to be more inclusive of Chicago’s many faith backgrounds, cultures and holiday music traditions. Millennium Park winter programming will also include pop-up performances through the park in  December. A full schedule will be announced soon.

Where: Cloud Gate at Millennium Park

When: 6–7pm on Fridays, December 3, 10, 17, 2021

Cost:  Free.

Go Ice Skating

people ice skating in Chicago in December at Millenium Park
There are several places to go ice skating in Chicago during in December.  One of the best and instaworthy places to go ice skating in downtown Chicago is the McCormick Tribune Ice Rink right in front of the Bean. Another picture perfect spot is the nearby skating ribbon at Maggie Daley Park which has a path twice the length of a lap around a traditional skating rink.

Watch Digital Art at Art on the Mart

Art at the Mart light show during the Christmas holiday season

Art on theMART is the largest permanent digital art projection in the world, projecting contemporary artwork across the 2.5-acre river-façade of theMART. 

Where: The Merchandise Mart, 222 W Merchandise Mart Plaza, Chicago, IL 60654. Spectators can watch the show from the jetty section of the Chicago Riverwalk on Wacker Drive between Wells Street and Franklin Street.

When: 30-minute program of projections are shown two times every evening.

Cost: Free.

Immerse Yourself in the Dr. Seuss Experience

The Dr. Seuss Experience is an imaginative and interactive immersion into the wondrous world of Dr. Seuss is in Chicago for three months. This Seuss-tacular sensory spectacle takes each guest on an awe-inspiring journey through nine different Dr. Seuss books, allowing each visitor a chance to magically step into the pages of each of the books.

Where: Water Tower Place, 835 N. Michigan Avenue, Ste 100, Chicago, IL 60611

Cost:  Prices vary. Tickets prices start from $29.00 for adults and $18.00 for children (1-13 years old) for non-peak hours. Visit their website to purchase tickets in advance.

Immerse Yourself in The Office Experience

The Office Experience pop-up opened October 15 in Chicago for a three month run. Visit Schrute Farms, walk through the Dunder Mifflin set, and relive Jim and Pam’s iconic romance. The world of The Office will come to life with iconic set recreations, original show costumes and props, and opportunities for fans to engage with the show in new ways. Timed tickets are now on sale online.

Where: 540 N Michigan Ave on the Mag Mile.

Cost: General admission is $37.50 plus taxes + fees for off-peak times or $45 plus taxes and fees for peak times. Children 3 and younger are free. Groups can also purchase private access tickets or book the space for a private party.

Watch Classic Holiday Movies at Gallagher Way

Watch classic holiday movies outside as part of the annual Winterland at Gallagher Way festivities. The movie schedule is as follows:

• December 2: National Lampoon’s Christmas Vacation
• December 9: Home Alone
• December 16: Elf
• December 23: A Christmas Story

While you are Gallagher Way, you can also go ice skating and visit the Wrigleyville location of Christkindlmarket.

Where: Gallagher Way, 3635 N Clark St, Chicago, IL 60613

When: Thursdays from December 2-23 starting at 6 p.m.

Cost:  Free.

Go Holiday Shopping (or Window Shopping)

Chicago is a great city for shopping with every type of store you can imagine.  Many shopping centers and departments stores have holiday decorations and attractions to put you in a festive mood.  Make sure not to miss Macy’s State Street (formerly Marshall Fields) – the building is a National Historic Landmark and it is known for its holiday window displays.

The major shopping areas in downtown Chicago include State Street (where you can find Macy’s, Target and many smaller stores) and The Magnificent Mile (where you can find three shopping centers, luxury designers and labels, several departments stores and popular brands).

If you are looking for something more unique, check out the One of a Kind Show and Sale (December 2-5, 2021) for handmade items.

Spot the CTA Holiday Train and Bus


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The CTA Holiday Train is a holiday tradition unique to Chicago. As the train pulls into each station, Santa waves to riders from his sleigh on an open-air flatcar carrying his reindeer and decorated holiday trees. Each car of the train is wrapped with holiday and seasonal images. Thousands of twinkling lights outline the shape of the train and windows, with even more lights running across the tops of the cars.

The CTA Holiday Bus is 60-foot bus turned into a winter wonderland with holiday music playing and Santa waving and from the roof-hatch of the bus. The exterior of the bus features Chicago’s skyline one snowy evening with “Ralphie the Reindeer” leading the way, his nose aglow and Santa’s sleigh in tow. Festive strings of lights outline the bus and its windows, along with sparkling snowflakes that light-up at night.

When: The CTA Holiday Train and CTA Holiday Bus typically runs until Christmas Eve. See https://www.transitchicago.com/holidayfleet/ for full details on routes and times. 

Cost: Regular CTA fare to enter the platform and see the train. See transitchicago.com for prices. You can see the bus for free from the street.

ZooLights at Lincoln Park Zoo

ZooLights Presented by ComEd and Invesco QQQ at Lincoln Park Zoo is a cheerful, family-friendly holiday event in the heart of the city. Zoolights features hundreds of luminous LED displays and seasonal experiences, all under the glow of millions of lights.

Where: Lincoln Park Zoo, 2400 N. Cannon Drive, Chicago, IL

When: 4–10 p.m. on select dates in December. Reservations are required and tickets to the general public will be available October 28.

Cost: Monday and Tuesday nights are free and Wednesday-Sunday tickets are $5.

Christmas Around the World and Holidays of Light


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The Christmas Around the World and Holidays of Light at the Museum of Science and Industry annual celebration began in 1942 and features a four-story, floor-to-dome Grand Tree, surrounded by a forest of more than 40 trees and displays which represent the holiday traditions from cultures around the globe.

Where: Museum of Science and Industry (5700 S Lake Shore Drive).

Cost: Included in regular museum admission. Here is a link to the official website for more information.

Light Up the Lake at Navy Pier

Light Up the Lake at Navy Pier is Chicago’s newest holiday adventure. The indoor, temperature-controlled experience features a sprawling light garden of large-scale sculptures comprising more than 600,000 twinkling lights; a massive Alpine ice rink; authentic holiday beer garden; kiddie train rides; Santa’s Merry Main Street and gift market; and other family-friendly and date-night activities. Public ticket sales begin October 25, 2021.

Where: Festival Hall at Navy Pier, 600 E Grand Ave, Chicago, IL 60611

Cost: Tickets start at just $13.50, including a ride on the iconic Centennial Wheel, offering inspiring views of the city all decked out for the holidays.

Take a Holiday Tour

If your time in Chicago is short, there are a few tours that focus on Chicago’s holiday attractions.  For some history with your holiday tour, check out this walking tour or this Segway tour.


See a Holiday Show

There are many holiday shows you can see in Chicago this December, including:

This is a great list of all the holiday shows in Chicago.

See Christmas and Holiday Lights Around Chicago

There are many places to see Christmas and holiday light shows in Chicago and the suburbs. There are several drive thru holiday lights shows in the Chicago area or you can also drive through neighborhoods known for their holiday lights. Here are the best places to see Christmas and holiday lights in and around Chicago.

December 2021 Events

In addition to the activities mentioned above, other December 2021 events include: One of a Kind Show and Sale (December 2-5, 2021), Santa Hustle 5K (December 4, 2021), 8th Night 8th Light (December 5, 2021), C2E2: Chicago Comic & Entertainment Expo (December 10-12, 2021), Adults Night Out: Holidaze! (December 16, 2021) and Zoo Year’s Eve (December 31, 2021).

As you can see there are many fun things to do in Chicago this December.

Planning a trip to Chicago? Check out my Chicago guides and itineraries:



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