During this time of year, the city shines exceptionally bright, with lights illuminating every corner you turn. From sipping cocktails on one of Chicago’s many winterized rooftops to basking in the spectacle of one of Chicago’s exhilarating light shows. Here are the most festive things to do for Christmas this holiday season in Chicago!
Of all Chicago’s holiday season shenanigans, there are few as iconic as ice skating in Chicago’s many amazing ice rinks, and there are few as unique at the Maggie Daley Park Ice Rink.
Offering an “alpine in the city” experience skating down Maggie Daley Park’s quarter-mile rink in the heart of Chicago has to be one of the activities we most associate with the festive season.
The winding ribbon of ice curves up and down around a 40-foot climbing wall with the city’s stunning skyline in the backdrop. It’s a must for your Christmas checklist.
It’s also free with your own pair of skates all the time, Monday through Thursday!
🗓️ Dates: November 17 – March 10
Chicago’s German-inspired annual Christmas market is also one of the more notable Chicago Christmas events. The famed German-style outdoor market returns to Daley Plaza, Wrigleyville, and Aurora on Friday, November 17, for its 27th year in Chicago.
Enjoy the smell of roasted nuts, fresh pretzels, bratwurst, hot spiced wine, and the magic of festive music, all in the coziest of atmospheres!
🗓️ Dates: November 17 – December 24 (Loop & Aurora), November 17 – December 31 (Wrigleyville)
Now running on select dates until January 7, 2024, Lightscape at the Chicago Botanic Garden dazzles with brand-new installations and beloved favorites, offering guests the chance to immerse themselves in a world of light, color, and sound.
After debuting in 2019, the trail of twinkling lights has been a complete sell-out in its first four seasons. The electrifying experience offers visitors the chance to embrace the season’s beauty with a must-do holiday activity in Chicago.
🗓️ Dates: November 10 – January 7
Last year voted as the best light display in the Midwest, Chicago’s beloved Illumination: Tree Lights at The Morton Arboretum is another one of Chicago’s fantastic light shows that you’ll want to secure tickets for.
Returning for its eleventh edition, one of the famous Chicago Christmas events experiences features 19 unique displays accompanied by music soundtracks that together highlight the beauty of trees in winter.
Situated across 50 acres of the nonprofit public garden and outdoor museum, Illumination: Tree Lights will take guests snaking through the Arboretum’s majestic landscape along an enchanting one-mile tree-lined walking trail.
🗓️ Dates: November 18 – January 6
Making up Chicago’s top trio of light shows, Lincoln Park Zoo’s ZooLights is the third light show to have on your calendar.
The much-loved annual event at Chicago’s beloved zoo features hundreds of larger-than-life 3D LED displays as well as a one-of-a-kind light maze and an enchanted forest offering guests the chance to “meander among butterflies, flowers, mushrooms, and dripping lights with whimsical music and a magical ambiance.”
With many $5 nights and free Mondays, it is one of Chicago’s most affordable and enjoyable holiday experiences.
🗓️ Dates: November 10 – January 7
Santa’s holiday train trip around Chicago is always one of the most eagerly anticipated activities, providing affordable fun for people all over the city.
The Chicago Transit Authority’s train and bus are decorated inside and out with festive decorations and thousands of lights to make them glow as they glide and glimmer around Chicago.
Now in its 32nd year of operation, the Allstate CTA Holiday Train and the Allstate CTA Holiday Bus began lighting up Chicago on Friday, November 24th, and will be whizzing around all eight lines through Monday, December 19th.
Read more about the CTA Holiday Train and Holiday Bus.
While Chicagoans await the chance to jump aboard the CTA Holiday Train every year, it isn’t the only train Santa rides as Christmas approaches Chicagoland.
Having returned last year for the first time in 2 years, the Canadian Pacific Holiday Train will again be returning to the Chicago ahead of Christmas bringing glowing lights, holiday decorations, and musicians to several stops close to the City of Chicago.
Each year, various bars and restaurants across Chicago transform their spaces and decorate themselves head to toe in an exorbitant amount of holiday decor.
While the boozy milkshakes and Christmas-themed cocktails can sometimes border on the obscene, if there is one time of the year to indulge yourself, we all know it is Christmas time in Chicago.
One of our top picks from the array of Christmas pop-ups in Chicagoland is the immersive Santa Baby Pop-Up that comes to Wrigleyville every year.
Here, you’ll find a selection of decadently garnished drinks, mouth-watering cocktails, and a food menu from ‘Santa’s Snack Shack’ offering more than twenty different Christmas-themed bites.
Read more about the Santa Baby Pop-Up.
🗓️ Dates: November 24 – January 7
Recently named one of the best hotels on the planet, LondonHouse Chicago and its elegant tri-level rooftop bar requires no rhapsody.
Renowned for having some of the best views in Chicago, the luxury hotel frequently festoons its rooftop for varying seasonal soirees. Its elevated winter experience, however, has proven most popular since its launch in 2020.
Now back for its fourth year, the festive “Rudolph’s Rooftop” is one of the more unforgettable Chicago Christmas events. The magic is high in the sky this holiday season, featuring “heated igloos, picture-perfect whimsical décor, sparkling lights, and breathtaking Chicago skyline views.”
Another place you’ll find cocktails, cozy blankets, and igloos is at Godfrey Hotel’s winter wonderland.
Boasting Chicago’s largest indoor-outdoor rooftop with a retractable roof, Godfrey Hotel will again host various exciting experiences, including frequent fire dancing, live DJs, and unique seasonal snacks all beneath the city lights.
Thanks to the heated, clear-domed igloos covering the rooftop’s portico and several firepits stationed beneath gazebos, guests can cozy up with a cocktail, s’mores, and sweeping skyline views this winter.
Another unique winter experience can be had on The Gwen Hotel’s luxury rooftop. While you won’t find lavish igloos here, you’ll instead be able to enjoy the hotel’s annual Curling and cocktails experiences. The hotel kits out its rooftop with no igloos, no ice skating, but an outdoor curling rink high in the sky.
Curling sessions come with a complimentary round of cocktails, meaning you can sip away on your favorite tipple while going toe to toe with your friends on the state-of-the-art curling rink.
Rivalling Gwen Hotel for the coolest active rooftop experience is Peninsula Hotel’s SkyRink.
Located on the 4th floor of the award-winning hotel, guests can this winter once again enjoy a one-of-a-kind hybrid rink perched high above Magnificent Mile.
Returning for its 11th season, the Peninsula Sky Rink provides an elevated winter wonderland for 20+ select days through to the end of the year. In addition to a rooftop bedecked in pine trees and Christmas lights, a chalet provides hot beverages and seasonal snacks to ensure skaters are kept well-fueled and well-fed while enjoying the iconic rink.
🗓️ Dates: November 18 – December 31
Described on the Museum of Ice Cream website as “a Willy Wonka factory come to life that you won’t want to leave,” the Michigan Avenue location opened in 2022 with an array of magical and interactive installations across over 13,500 square feet.
Adding to the experience for Chicago Christmas events, the museum has been decked out in pink decor, including an enormous snow globe and various areas for festive crafts.
Guests can expect “a pink wonderland of interactive, limited-time activations like a Pinkmas tree forest, life-sized snow globe and a take-home gingerbread craft activity as well as guest favorites like the iconic sprinkle pool,” according to the release.
Meanwhile, guests can stay warm with seasonal sips and treats from the cafe, including over-the-top ice cream sundaes or holiday cocktails for those 21+.
🗓️ Dates: November 17 – January 15
Of all Chicago’s public art pieces, Art on the MART is certainly one of the most spectacular. We’ve been treated to many months of stunning art spectacles on the facade of the Merchandise Mart since they returned earlier in the year.
Now, the “largest permanent digital art projection in the world” has begun showing some sensational new shows for its winter program titled ‘Season of Light‘.
The new winter program celebrates “the emerging and established talent coming from the School of the Art Institute of Chicago (SAIC), a beloved Chicago institution internationally regarded as one of the top art and design schools in the world.”
The 30-minute shows will run nightly on the 2.5-acre river façade of the Merchandise Mart starting at 7:30 pm and 8 pm. The best places to view the projections are from the jetty section of the Chicago Riverwalk between Wells and Franklin Streets.
🗓️ Dates: November 16 – December 30
🗓️ Dates: Various dates
Step into Chicago’s most exquisite spaces to experience some of the most treasured holiday classics if you’re looking for Chicago Christmas events. From Christmas concerts to tribute performances, the beloved Candlelight series is bringing talented musicians to perform at venues illuminated with hundreds of candles this season.
Here are some of our favorite festive concerts taking place this holiday season:
- Candlelight: Holiday Pop Classics and Modern Favorites at Arts Center of Oak Park on December 15
- Candlelight: Holiday Carols on Strings at Wicker Park Lutheran Church on December 16
- Candlelight: Holiday Special featuring “Silent Night, “Jingle Bells,” and More at St Luke’s Episcopal Church on December 22
The magic of the holiday season comes alive with a visit to Santa’s winter wonderland. One of the best things to do for Christmas in Chicago is a visit to the Jolly Man. Santa will be there until December 24th at the Chicago Fashion Outlets, located in Center Court, near the Food Court. A visit with Santa is always free, and photo packages are available for purchase.
Macy’s Walnut Room has become synonymous with the holidays with a towering 45-foot Great Christmas Tree over the years. The holiday setup changes every year but is always a bright spot during the season. The historic restaurant brings all the holiday cheer with an incredible setup, infusing the entire space with unbeatable magic.
The Joffrey Ballet’s critically acclaimed reimagined classic, The Nutcracker, by Tony Award®-winning choreographer Christopher Wheeldon, returns to celebrate the magic of the holiday season. One of the most coveted Chicago Christmas shows, Wheeldon’s American Tale relocates Marie and her immigrant family to the Chicago World’s Fair in 1893, where Marie embarks on a whirlwind adventure with the Nutcracker Prince.
There are a ton of places that seasonally deck their halls. Whether you’re visiting Chicago for the weekend or want to find a festive place to find drinks, there are holiday bars in Chicago that go all-out with Christmas decorations. And we guarantee it will make it to your camera roll.
Though not necessarily Christmas-themed, the wildly popular Dining in the Dark event series has just returned to Chicago, offering a restaurant experience like nothing you’ve encountered before.
Using just taste and smell alone, you’ll elevate your meal to a whole new level, making it the perfect date night or a Christmas meal out with friends or colleagues this December.
Grab tickets to a Blindfolded Dining Experience at Fulton Market Kitchen or a Dining in the Dark: Sushi “Omakase” Edition now!
Venture to Disney100: The Exhibition to see the ‘Crown Jewels’ of the Walt Disney Archives during the most enchanting season of the year! Disney enthusiasts can now rejoice as the highly anticipated exhibit has arrived in Chicago just in time to be enjoyed during the holiday season.
It has taken over an impressive 20,000 square feet of space, showcasing original costumes, props, and mesmerizing visuals that even the most devoted Disney fans haven’t encountered before, all while celebrating 100 years of The Walt Disney Company. Leading up to Christmas, kids can write to Santa and send their letters off in a special ‘mailbox.’
Don’t miss out on the holiday fun! Grab tickets!
22. Hit the slopes
Get away with your loved ones this holiday season! One of our favorite things to do for Christmas in Chicago is letting loose on a holiday getaway. Boyne Falls is the ultimate playground and one of the must-visit ski resorts.. So head there with the family for an outdoorsy activity.
[Featured image from Shutterstock]