The Haute Seeker

The Best Festive Holiday Events in Chicago(That Even Locals Love)

There’s nothing quite like Christmas in Chicago. The city shines bright with merriment as visitors and locals celebrate the holidays with cheer. There are plenty of activities, but we’ve curated a few of our favorite things to do just for you. From holiday shopping in charming neighborhoods to traditional holiday activities that are fun to enjoy year after year.

Checkout the best festive holiday events in Chicago, that yes, even the locals love.

Holiday Events and Activities in Chicago

Spot the Holiday Train or Bus On the Way to Your Next Destination

November 11th – December 19th

All aboard for a magical ride through the city of Chicago! The beloved Chicago tradition of The Allstate CTA Holiday Train. The holiday train serves two very important purposes: to deliver joy and the holiday spirit to thousands of riders and also to deliver food baskets to various charitable agencies throughout the city. Today, 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. It’s an annual holiday tradition that you have to see to believe.

Musicians performing during Candlelight Concert
Musicians performing during Candlelight Concert // Image via Facebook

Listen to cheerful holiday music during a Candlelight Concert

Date ane Time Varies

Enjoy a multi-sensory musical experience during Candlelight: Holiday Special featuring “Silent Night, “Jingle Bells,” and More performed by Metropolis String Quartet. The awe-inspiring locations are like never seen before in Chicago. Get your tickets now to discover Holiday inspired music at Stan Mansion under the gentle glow of candlelight.

Watch a Live Holiday Themed Play or Musical

Catch holiday classics on the big stage at a popular Chicago theater or watch a show put on by the local community:

Discounted tickets to A Christmas Carol at The Goodman

Cheap tickets to The Joffrey Ballet: The Nutcracker

The Steadfast Solider at the Lookingglass Theater

Alternative holiday night out The Buttcracker: A Nutcracker Burlesque

Christmas Bingo: It’s a Ho-Ho-Holy Night! A holiday comedy show in Lincoln Park

For more Chicagoland plays or musicals, visit our events calendar

Spot Your Favorite Animals and More During Lincoln Park Zoo Lights

November 19th – January 1st

The most wonderful time of the year deserves the most wonderful event of the year! Celebrate the holidays with ZooLights Presented by ComEd and Invesco QQQ. This festive, one-of-a-kind holiday experience offers a merry, family-oriented tradition in the heart of the city. Book your spot for this holiday activity online and spend quality time with your favorite animals and a host of dazzling lights this holiday season in Lincoln Park. 

Haute Tip: Attend Zoo Lights for free on Mondays during the holiday season. Tickets will be released the Tuesday prior at 11 a.m. each week.

Beverage from Santa Baby Bar // Image via Facebook

Enjoy Festive Drinks at a Holiday Themed Pop-up Bar

Pop-out to holiday pop-up bars as they transform into holiday-themed experiences. Here are a few noteworthy ones to check out this season:

A Chicago Holiday Cocktail Party in River North

Santa Baby Bar in Wriglyville

Jack Frost Winterfest

JoJo’s Winter Wonderland in various Chicagoland neighborhoods and Detroit

See the Millennium Park Christmas Tree Light up Downtown Chicago

November 18th – January 8th

Chicago’s “official” Christmas tree in Millennium Park will shine brightly near the intersection of Michigan Ave. and Washington St. The 109th City of Chicago Christmas Tree is a 55-foot Colorado Blue Spruce, donated by the Glisovic family of Morton Grove. Find all of the details of this annual Chicago tradition by visiting the City of Chicago.

Slide across the best ice skating rinks in Chicago

November 18th – February 20th

Have fun and stay active outdoors this winter season by skating at various ice rinks across the city of Chicago. In addition to open skate sessions, most rinks offer programming and some events throughout the season. All outdoor skating through the Chicago Park District is free(does not include skate rental). Grab friends and family and get your skate on around Chicago.

Haute Tip: Pre-registration is required for all programs at the outdoor rinks, including OPEN SKATE sessions. 

Awe at synchronized lights at the Illumination: Tree Light at The Morton Arboretum

Saturday, November 19th – Saturday, January 7th

Join in celebrating the tenth annual Illumination: Tree Lights at The Morton Arboretum during the Arboretum’s 100th anniversary year. Explore 50 acres of the Arboretum’s majestic trees during this one-of-a-kind spectacle of color, light, and sound featuring six dazzling new displays as well as returning favorites. You will be awed and delighted by the first Illumination display in The Gerard T. Donnelly Grand Garden, leading to a spectacular laser-light finale. And as a bonus, this year, Morton Arboretum will host Electric Illumination, a late-night experience for adults 18 and older with a curated mix of trance and progressive house music, synchronized to the breathtaking light displays.

Haute Tip:Advance purchase is recommended, as many nights will sell out.

Sip on Holiday Tea at a Fancy Chicago Hotel

Delight in afternoon tea during the festive holiday season at one of Chicago’s high-end hotels. Luxury destinations like The Peninsula ChicagoThe Drake Hotel, and The Langham offer their own unique experiences. Most often, these holiday traditions consist of lavish holiday décor, live entertainment, specialty dishes, and sweet treats to pair with an array of delicious tea options. Book your seating and make this experience part of your holiday tradition.

Find Holiday Gifts at Chicago Small Businesses

Support local businesses in Chicago while checking everyone off your holiday shopping list. Thanks to Chicago’s diverse neighborhoods, discovering new shops with great deals during the holiday season is simple. Check out our guide to The Best Neighborhoods to Shop Small this Holiday Season and accomplish your holiday shopping with ease.