Celebrate the Season with Chicago Holiday Events!

Join the holiday fun with the City of Chicago’s annual tree lighting ceremony, ice rink, holiday art market, free art exhibitions, live music and more! An insider gives us all the festive details.

It’s Christmastime in the city! Get ready to enjoy the holiday spirit with a roster of free Chicago holiday events hosted by the Chicago Department of Cultural Affairs and Special Events (DCASE).

With the help of DCASE’s Deputy Commissioner of Programming Nancy Villafranca, we’ve put together a list of holiday highlights you won’t want to miss. Bring the whole family downtown to experience the magic of the holiday season in the city!

Note: All times listed below are subject to change. Be sure to stay updated on the DCASE website: Chicago.gov/Holiday. 

Annual Tree Lighting Ceremony

The official Chicago holiday events season begins with the lighting of the 110th Annual City of Chicago Christmas tree in Millennium Park. This year’s tree is an impressive 45-foot Colorado blue spruce donated by the De La Cruz family of Darien. Irika Sargent and Joe Donlon from CBS2 Chicago will be emceeing the event.

You’ll enjoy an exciting lineup of live holiday performances including DJ TREW, Meagan McNeal, cast members from “BOOP! The Betty Boop Musical,” Chicago Dance Crash and more. Plus, enjoy Puerto Rican guest artists as part of the Puerto Rican Arts Alliance’s 2023 National Cuatro Festival. 

You’ll also find fabulous food, ice skating and holiday shopping featuring local vendors and artists. 

And, of course, Santa and Mrs. Laura Lynn Claus will be on hand to wish everyone a Merry Christmas and a Happy Holiday!

Where: Millennium Park

When: Nov. 17

Schedule of events:

5-6 p.m. Pre-show

6-6:30 p.m. Tree lighting ceremony & fireworks

6:25 p.m.    Christmas tree is illuminated

6:30-7 p.m. Post show 

New this year: Due to construction on Cloud Gate Plaza, the event mainstage is located on Washington Street next to the Chicago Cultural Center and directly across Michigan Avenue. 

Other highlights: Millennium Park provides multiple viewing stations with large screens so that you won’t miss a minute of the mainstage action. You’ll also find delicious treats located throughout the park, including hot drinks and cocktails. 

Tip: “Bundle up,” says Villafranca. “We have a lot of fun but as you know, it can get cold downtown. I suggest layering up against the weather and then you can stay here having a good time for as long as you want!”

A couple walks into the Millennium Park Art Market during Chicago Holiday Events.
Photo courtesy of the City of Chicago Department of Cultural Affairs and Special Events (DCASE)

Holiday Art Market

When: Nov. 17-19

Hours: Friday, Nov. 17 from 12-8 p.m.

Saturday, Nov. 18 from 12-8 p.m.

Sunday, Nov. 19 from 12-5 p.m.

Where: Millennium Park, Chase Promenade North tent

Feel like doing a little holiday shopping? Join more than 30 diverse artists displaying their creations including jewelry, drawings, painting, pottery and more.

“When you shop here, you’re supporting local Chicago artists and giving them opportunities,” says Villafranca.

Tip: After you find the perfect holiday gift, enjoy live music, good food and festive cocktails in the Holiday Art Market Lounge! 

Millennium Park ice rink in Chicago with Christmas trees and skyline
Photo courtesy of the Chicago Department of Cultural Affairs and Special Events (DCASE)

McCormick Tribune Ice Rink

Where: Millennium Park

When: Beginning Nov. 17, 2023, through March 3, 2024 (Weather permitting)

Highlights: Admission is always free! Families will enjoy free beginner to intermediate skating and hockey skills lessons every Saturday and Sunday from 9-10 a.m. Check out the ice rink website to find the full lesson schedule and book your skating reservations.

Tip: “Skating times must be reserved online and skating lessons require reservations. Be sure to plan your trip in advance,” says Villafranca.  Go to the Millennium Park website to plan your visit.

Extra tip: Discounted parking is available for pre-purchase at Millennium Garages.

A choir sings at the annual Chicago Holiday Sing-a-Long in Millennium Park
Photo courtesy of the City of Chicago Department of Cultural Affairs and Special Events (DCASE)

Holiday Sing-Along Series

Where: Wrigley Square in Millennium Park

When: Dec. 1, 8 and 15 from 6-7 p.m.

Highlights: Guests are led in holiday songs by a local choral group. The schedule includes:

Dec. 1: Northeastern Illinois University Choir

Dec. 8: Windy City Gay Chorus

Dec. 15: League of Chicago Theaters

Tip: Get there early so you don’t miss a note, dress warmly and bring the whole family to this festive city tradition!  

A view of the gift shop, Buddy, at the Chicago Cultural Center.
Photo courtesy of the City of Chicago Department of Cultural Affairs and Special Events (DCASE)

Chicago Cultural Center Holiday Open House

Where: Chicago Cultural Center, 78 E. Washington St. 

When: Saturday, Dec. 9 from 1-6 p.m.

Highlights: “December 9 is all about families. All entertainment this day will be family friendly,” says Villafranca. “Kids will love the Sloomoo Slime Activation, holiday films and live holiday and bilingual performances from Uniting Voices Chicago (formerly the Chicago Children’s Choir), along with Son Monarcas, the Chicago Inclusive Dance Festival, Changing Worlds and more.”

The gift shop called “Buddy” features more than 300 artists and includes an amazing array of items including children’s books, prints, functional art, textiles, jewelry and more.

Tip: You’ll find free art exhibitions, architecture tours and programming every day. “The Chicago Cultural Center is open year-round and is a great place to come inside and warm up during your trip to Chicago,” says Villafranca. 

Villafranca encourages families to make the most of what Chicago has to offer at the most wonderful time of the year. “Our holiday activities are a fun way to wrap up the year, relax and enjoy some holiday cheer. This is a time to make family memories. Come downtown and join us!”

Jennifer Kales
Jennifer Kales
Content editor Jennifer Kales has been in the business of writing for more than 20 years creating advertising copy, blogs, books and everything in between. She loves helping Chicago Parent clients tell their stories in a way that resonates with audiences.


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