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Fun Things To Do In Chicago During Winter


If you are looking for fun things to do in Chicago this winter, you’re in luck. It turns out the Windy City is a popular destination this time of year for tourists and Chicago suburbanites alike.

Chicago offers things you won’t see anywhere else and less busy tourist attractions like the Art Institute of Chicago and the Museum of Science and Industry. Moreover, the Chicago CityPASS will get you to and from the city’s top attractions at a 50%+ savings (and includes plenty of indoor activities!).

Yes, it will be cold, but freezing temperatures are why brands like Patagonia and North Face exist. So grab your coat and wool stocking cap and mittens, and get ready to enjoy Chicago in the winter.


Millennium Park Campus Holiday Events

family ice-skating in Chicago

People travel from far and near to visit Millennium Park during the holidays. With its collection of sculptures, Tribune Ice Rink, a glittering gigantic Christmas tree, and other amenities it’s always bustling with family and the best part? The Ice-skating Millennium Park is free!

  • See Chicago’s glittering tree set among the city’s sparkling skyline located at Wrigley Square at Michigan Ave. & Randolph St.


  • Grab a photo alongside one of the wreathed lion statues located at the Art Institute of Chicago entrance, 111 S. Michigan Ave.


  • Go ice skating with friends and family at McCormick Tribune Ice Rink located on Michigan Avenue between Washington & Madison St. from November 17 through March 4.


  • The Maggie Daley Park Skating Ribbon is dramatically different from typical civic ice rinks. Enjoy an ice skating experience unlike any other by winding your way through a paved, rolling landscape. Located at: Maggie Daley Park, 337 E. Randolph St.

Ugly Sweater Skate, December 5, 10am–10pm
Skate alongside Santa, FREE! December 15, 10am–noon


Looking for more free winter entertainment?

The Dance-Along Nutcracker® All ages and abilities are invited to dress up as Sugar plum fairies and mouse kings and point their toes to the familiar music of Tchaikovsky’s holiday classic. There’s always something going on at this 1897 neoclassical former library, known as The People’s Palace, which has two spectacular stained-glass domes. Dance-Along Nutcracker® located at the Chicago Cultural Center, 78 E. Washington St.


  • The Gingerbread House Decorating Party gives kids of all ages a fun time decorating gingerbread house complete a hot chocolate bar, candy, and icing treats. Tickets on sale. Sunday, December 16, 10:30am–1pm & 1–4pm at The Park Grill at Millennium Park, 11 N. Michigan Ave.


  • Save the date for the Holly Days, which takes place on December 27–30, 10:30am–3pm.


  • Art Institute of Chicago, Take inspiration from the exhibition Rodin: Sculptor and Storyteller and create a work of art with your family. Located at the Ryan Learning Center, 159 E. Monroe St. Admission to the Art Institute’s Ryan Learning Center is free, and museum admission is always free for kids under 14 and Chicago residents under 18.


Chicago Art Foundation Architectural Walking Tour

woman looking at Chicago skyline during winter

The Chicago Art Foundation is one of the several providers offering tours of Chicago’s famed architectural masterpieces. A visit in December means winter temperatures and wind chill factors can make being outdoors a little chilly. 

For those who don’t want to brave the cold, indoor architectural walking tours are 45 to 60 minutes long. Buildings include the Palmer House Hotel and the famed Chicago Merchandise Mart, which give you the chance to explore Chicago’s architecture while staying warm.


The Art Institute Chicago

wreathed christmas lion at the art institute of Chicago

Founded in 1879 and located in Chicago’s Grant Park, The Art Institute of Chicago is one of the largest art museums in the United States and was voted #1 museum in the world by Tripadvisor in 2017.  

If you are looking for fun things to do in Chicago with your family over the holidays, special events include:

27th Annual Wreathing of the Lions
November 23 at 10:00
Drop-in activity 10:30–3:00

Holiday Choirs  (December 4–8 at 11:30),
$50 adults, $20 children, $75 VIP adults, $45 VIP children
Free for children under two
Registration required

37th Annual Holiday Treasure Hunt and Tea Party
December 9 at 10:45, 12:00, or 1:30

Decorate Your Own Gingerbread House
December 15 at 11:00 or 2:00
Family of four: $55 members, $70 nonmembers
Registration required

Holly Days
December 27–30
Drop in 10:30–3:00


Museum of Science and Industry

mom and child

December is a special time of year for the Museum of Science and Industry, which celebrates by exploring holiday traditions around the globe.

From a four-story, floor-to-dome-ceiling Grand Tree, surrounded by a forest to live holiday performances, MSI offers visitors a one-of-a-kind experience that brings a world of holiday joy under one roof.


Magnificent Mile Lights Festival

magnificent mile christmas paradePhoto Credit: Natasha Jelezkina

The Magnificent Mile Lights Festival is an annual wintertime holiday event. It hosts family-friendly activities like strolling down Lights Festival Lane and a grand tree-lighting parade featuring Mickey and Minnie Mouse. Don’t miss the spectacular fireworks over the Chicago River.


Christkindlmarket Naperville

Naperville christkindl kiosk in Illinois

The cherished German tradition of a holiday night market is held in two Illinois locations annually: Downtown Chicago and the Subrub of Naperville located approximately 35 miles southwest of Chicago.

The main Christkindlmarket in Chicago’s Daley Plaza and the suburb of Naperville. Christkindlmarket Naperville, which runs from November 25 – December 24, 2107.  Special events include wreath making and musical performances in additions to children’s activities.  

A special treat for all is a visit from Christkind—a magical fairy-like being wearing gold and white robes and adorned with a large gold crown. Christkind folklore dates back to the 1500’s.  

Bringing international flair and local charm to Chicago, Christkindlmarket is a holiday favorite.


If you are moving to Chicago this winter, you can count on the friendly storage teams at our self storage locations throughout the Greater Chicago Area.
Download our printable safety checklist for quick tips on moving in the winter. Need storage? As native Chicagoans, we are ready to serve you from the middle of winter to the height of summer every day of the year.
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