The Most Festive Things to Do in Chicago During Christmas

November 15, 2021

The windy city with a history of gangsters and deep-dish pizza may not conjure images of a holiday paradise. However, you’d be hard-pressed to find a city that commits as wholeheartedly to Christmas as Chicago.

Looking for the most festive things to do in Chicago during Christmas?

Already an incredible destination du jour in its own right, thanks to an explosive art scene, world-class museums, stunning architecture, and supreme dining. The merriest season transforms Chi-town into a veritable winter wonderland, complete with illuminating festive light shows, authentic German Christmas markets, and live musical productions.

If you can grin and bear the cold, we think you’ll see there is a world of joy, entertainment, and amazement to discover in Chicago this holiday season. 

Hotels in Chicago

Chicago has endless amounts of historical landmarks, museums, art galleries, and greenery to explore. Make sure to check everything off your Chi-town bucket list this winter by spending a night or two in this metropolis by the Lake. 

Whatever your style or budget, we offer many options for Chicago Hotels, from boutique accommodations to budget inns. Book with confidence, knowing you can stay anywhere from the Magnificent Mile to the loop, with our lowest rate guarantee. 

Holiday Markets, Tours, and Festivals in Chicago

Holiday Hike: Season Sampling Walking & Food Tour

When: End of November-Christmas Eve 2021

Delicious winter eats, an authentic German Christmas market, and the merriest light displays make for a Chicagoan Holiday experience. Foodies, sightseers, and history buffs alike will clamor to sign up for the Holiday Hike: Season Sampling Walking & Food Tour

Don your most festive sweater and comfortable walking shoes as you prepare for this 2.5-hour walking tour. This all-encompassing food-filled adventure features stops and samples at:

  • The lights at Magnificent Mile
  • The Millenium Park ice skating rink and Christmas tree
  • Samples of deep-dish pizza, German bratwurst, and a chocolate brownie
  • A visit to Christkindlmarket and the infamous ‘Bean.’
  • Samples of craft beer & hot apple cider
  • Viewing of the Marshall Field’s Christmas Windows

Related Post: Current Events and Festivals in Chicago, Illinois

Huge Christmas tree with lots of lights and ornaments at Winter Wonderland at Navy Pier in Chicago, Illinois

photo credit: Navy Pier via Facebook

Winter Wonderland Festival at Navy Pier - Chicago, IL

When: TBD

Seeking some frost-bitten family-friendly fun? Head to the Navy Pier to escape city life for an all-expenses-paid trip to the Winter Wonderland Festival! Embrace the snowy season and load up on outdoor activities when you visit this joyous event. 

Kids of all ages will be thrilled to test their skills at their extreme polar obstacle course, ice climbing wall, or skating at the Chicago Blackhawks rink. For more low-key but still memorable yuletide merriment, you can also pay a visit to Santa and decorate your own cookies.

Related Post: Top Attractions in Chicago, Illinois

BYOB Party Bus Holiday Lights Tour ‘Tis The Season - Chicago, IL

When: Select dates November-December 2021

Need a break from that winter chill? Gather your most festive friends for a raucous holiday light tour you’ll never forget. The BYOB Party Bus Holiday Lights Tour Tis’ The Season is the booze-filled party bus Christmas tour of your dreams. 

Brought to you by the Wami Live Inc team, this event combines great tunes, comedy, and the iconic Chicago holiday sights to bring you one epic ride. 

Related Post: A Visitor’s Guide to Getting Around Chicago

Partygoers can expect to soak in the sparkling lights and decor at the Magnificent Mile, Millennium Park Christmas Tree, State Street, Lincoln Park Zoo Lights, and Macy's Holiday Display. Your party bus ticket admission also includes:

  • Souvenir Santa hat
  • Complimentary apps & drink deals
  • Gift card
Light at Lincoln Park Zoo in Chicago, Illinois, USA

Lincoln Park Zoo via Facebook

Seasonal Lights in Chicago

Zoo Lights at Lincoln Park Zoo - Chicago, IL

When: Select dates November 19-January 2nd, 2022

Bright lights + Zoo animals = perfection! Get ready to witness the glow of millions of twinkling lights at one of Chi-town’s most beloved Holiday events. Zoo Lights at the Lincoln Park Zoo is a shining LED fueled extravaganza featuring hundreds of luminous displays, seasonal experiences, and an 18 foot Christmas Tree.

Related Post: Chicago for Kids: The Ultimate Parent’s Guide

This year the Zoo is ramping up the Christmas spirit with even more special activities and ticketed experiences such as:

  • Photos with Santa
  • Snowy’s Spirits & S’more pop-up holiday bar
  • Light Maze Presented by Invesco QQQ (ticketed experience)
  • Enchanted Forest (ticketed experience)
  • AT&T Endangered Species Carousel (ticketed experience)

Pro Tip: Zoolights is a special ticketed event, Wednesday-Sunday evenings tickets are $5, but Monday & Tuesday nights are free. 

To enjoy all of the animals and exotic species at the Lincoln Park Zoo during the day, we highly recommend combining the Zoo with any one of our other unique Chicago attractions featured on the Chicago Explorer Pass.

interior view of the Chicago Museum of Industry Christmas Around the World and Holidays of Light in Chicago, Illinois, USA

Christmas Around the World and Holidays of Light, Museum of Science and Industry - Chicago, IL

When: November 17-January 9th, 2022

A stunning celebration of multiculturalism and holiday joy, the Christmas Around the World and Holidays of Light event has brought smiles to people’s faces since 1942. This year’s theme, the ‘Golden Age of Travel,’ promises to whisk you away to destinations unknown.

Watch as visitors young and old gasp in awe at the four-story, floor-to-dome Grand Tree, surrounded by a forest of over 50 smaller trees. 

Related Post: The 10 Most Romantic Things to Do in Chicago for Couples

The painstakingly decorated displays showcasing holiday traditions worldwide remind us that while our heritages may vary, we all appreciate the love and magic of this special season.

Pro Tip: Don’t miss out on getting your fridge-worthy snapshot with Santa, who will be waiting in the festive photo studio inside the Holiday store.

Tickets for Christmas Around the World are included in general admission, so why not stick around and soak in the best of the Museum of Science and Industry post-Santa photo op?

Illumination at the Morton Arboretum - Chicago, IL

When: November 20-January 2nd, 2022

Fantasizing of an enchanted forest filled with magic, color, and light? Fulfill your fantasy with a visit to Illumination at the Morton Arboretum this winter. 

This truly immersive, one-of-a-kind experience allows visitors to leisurely meander through a one-mile path containing light installations, projections, and special technology, all designed to illuminate and change the appearance of trees and other plant life. 

Related Post: A Weekend in Chicago: How to Make the Most of 2 Days

Visitors are encouraged to interact with their wintery environment by hugging a tree and watching as the lights respond. 

Be sure to warm up with a cup of steaming hot chocolate or an ooey gooey roasted marshmallow s’more post-walk!

Performers in T'was the Night Before by Cirque Du Soleil bowing in Chicago, Illinois, USA

photo credit: The Chicago Theatre via Facebook

Shows & Spectacles in Chicago

Twas’ The Night Before… by Cirque du Soleil - Chicago, IL

When: November 26-December 5th, 2021

Twas’ The Night Before Christmas and all through the house, not a creature was stirring, not even an acrobatic mouse!

Introduce children to the magic of Cirque du Soleil through their thrilling retelling of this classic Christmas tale. 

Twas’ The Night Before... needs to be at the top of your things to do in Chicago during Christmas. This splashy acrobatic spectacle includes colorful artistry and a sleigh full’s worth of good old-fashioned holiday cheer.

Theatergoers of all ages will be entranced by the visual display of athleticism, talent, and creativity displayed in Cirque’s first-ever Christmas show.

Related Post: How to Vacation in Chicago on a Budget

Polar Express Train Ride, Chicago Union Station - Chicago, IL

When: December 3-January 1st, 2022

All aboard, next stop, the North Pole! For all of those who still believe and those who have never stopped, now is your time to recreate the spellbinding enchantment of the Polar Express.

The Chicago Union Station Polar Express Train Ride is an interactive theatrical experience that guarantees unforgettable festive memories. 

Train passengers will imagine themselves the heroes of the titular movie as they get to live out this live retelling of the beloved Christmas tale. 

Your one hour train ride of make-believe and magic features:

  • Thematic music from the motion picture soundtrack
  • Delicious hot chocolate and Walkers Shortbread cookies
  • Dancing chefs and carolers
  • Fun, festive activities
  • A passenger read-along of the original book
  • A keepsake silver sleigh bell
Ariel view of Ribbon Rink in Daley Park Chicago, Illinois, USA

photo credit: Maggie Daley Park via Facebook

Ice Skating in Chicago

Skating Ribbon at Maggie Daley Park - Chicago, IL

When: Opens November 19th, 2021

Nothing says ‘white Christmas’ more than a snow-filled ice skating session at one of Chi-town’s best ice skating rinks. The Skating Ribbon at Maggie Daley Park is unique in that its curved serpentine structure makes it twice the length of a traditional ice skating rink.

close up of hot chocolate mug with marshmellow at XO Marshmallow in Chicago, Illinois, USA

photo credit: XO Marshmallow Facebook Page

Cheery Treats in Chicago

A full day of sledding, building snowmen, and sightseeing around the Second City can build up quite the appetite. 

Reward (and warm) yourself with any number of mouth-watering treats and soothing beverages from our favorite Chicago cafes and bakeries:

XO Marshmallow Cafe - Chicago, IL

Looking for an Instagram-worthy cup of cocoa that’s (almost) too pretty to drink? XO Marshmallow Cafe’s multi-colored chocolates are seriously stunning and tasty to boot. Spice up your feed with the luscious lavender, white chocolate cocoa with matching lavender honey marshmallows. 

Pro Tip: For all of the Harry Potter fans out there, don’t forget to stock up on their gourmet Butterbeer White Hot Chocolate so you can recreate this tasty treat at home!

Katherine Anne Confections - Chicago, IL

Consistently named one of the ‘best hot chocolates in America’ by Fodor Travel, Katherine Anne Confections has built up one stellar reputation.

Luckily, their velvety thick, and rich hot chocolate lives up to the hype. Enjoy up to 10 varieties of this indulgent beverage with flavors like chai, peanut butter, salted caramel, and more. Each cozy cup can be topped with homemade marshmallows, Kilgus Farm whipped cream or both!

Stan’s Donuts and Coffee - Chicago, IL

Think pink! Take a walk on the wild side when you stop for a sip (or two) of pink hot chocolate at Stan’s Donuts and Coffee. This photogenic cup of cocoa pairs perfectly with a fresh donut (might we suggest a festive red velvet). 

We are also partial to their delectable hot chocolate malt, which features real chocolate malt balls!

The Midwest’s largest city is a magnificent mess of lakefront beaches, iconic architecture, and an impressive art collection. But, for a city so thoroughly urban, it’s shocking to discover the holiday spirit alive and well in everything from decorated CTA trains to the sparkling lights at Millenium Park.

Every year visitors from all over the world flock to the White City to enjoy first-class entertainment, live shows, festive illumination, and delicious eats.

From memories under the mistletoe to a real live train ride aboard the Polar Express, a holiday in Chicago is something you’ll never forget!

What Festive Things to Do in Chicago During Christmas Did We Miss?

Do you know of other festive events in Chicago that we need to cover? Share them with us!

  1. Holliday says:

    Hello,
    I was just their on Saturday. I got re-directed due to the closing of the streets for the parade. I wish we had left earlier so the kids would have more time.
    Besides Winter Wonderland at Navy Pier, what else can we do (coming from as far as Indianapolis, IN) and what are some of the best hotels that are kid friendly. I spend most Christmas at the Renaissance and we had booked the Royal Sonata. We really want a hotel on the river with river view from our room.

    Thank you,
    Holliday

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