20 Fantastically Festive Things To Do In Chicago This Holiday Season

Elliot McGowan Elliot McGowan

20 Fantastically Festive Things To Do In Chicago This Holiday Season

The holiday season is in full swing in Chicago!

During this time of year, the city shines particularly bright with lights illuminating every corner you turn. From sipping cocktails in a rooftop igloo to seeing the epic light shows taking place across Chicago—here are 20 of the most festive things happening this holiday season in Chicago!

1. Go ice skating at Maggie Daley Park

Of all Chicago’s holiday season shenanigans, there are few as iconic as skating 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 Monday-Thursday if you bring your own skates!

More information can be found here.

3-5. Be captivated by a Christmas Candlelight Concert

Step into Chicago’s most exquisite spaces to experience some of the most treasured holiday classics. From Stevie Wonder to Tchaikovsky, the beloved Candlelight series is bringing talented musicians to perform at venues, illuminated with hundreds of candles this December. Here are some of our favorite festive concerts taking place this month:

See the full list of candlelight concerts taking place in Chicago here.

6. Hit up Hubbard Inn’s 3-floor holiday pop up

The holiday season is alive and kicking and Hubbard Inn has fully transformed into The Christmas Inn to make your holidays on Hubbard Street merry and bright! Experience 3 levels of holiday bliss with festive cocktails, Instagrammable moments and live entertainment at this limited-time holiday pop-up!

Each floor has its own Christmas theme, with the classic magical Christmas on the first floor, 60’s ‘Kitchmas’ vibes on the second floor, and the third floor Christmas apocalypse.

From brunches and mixology classes to holiday trivia nights and paint and sip classes, there is entertainment scheduled throughout each week at Hubbard Inn this holiday season!

You can grab tickets to Holidays on Hubbard Pop Up here.

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7. Cozy up in an igloo

Cocktails, cozy blankets, and igloos? Yes, please! It’s officially cozy season, so what better way to celebrate the colder weather than by running away from it and sheltering under one of Chicago’s enchanting igloos? Many of Chicago’s rooftops and patios have erected igloos for the holiday season so you can enjoy cocktails in your own personal snowglobes beneath the stars. Here are a few of our tops picks:

8. Embrace Christmas in all its colors at Sleigh Bells

Sleigh Bells: A Kaleidoscopic Christmas” is not your average Christmas pop-up—it’s a trippy, humorous, non-traditional take on the holidays full of color, sound and Christmas spirit in Chicago!

Explore immersive and interactive art installations transporting you to places like an infinity mirror ice cave, Santa’s workshop, and even Santa’s… ‘armory’, all brought to life with LED lights, projection mapping and more mesmerizing tech. To top it all off, you’ll also find a holiday vendor to get some unique Christmas swag and plenty of food & beverage to go around.

You can grab tickets to Sleigh Bells: A Kaleidoscopic Christmas here.

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9. Sip Glühwein at Christkindlmarket

Chicago’s German-inspired annual Christmas market is another extremely popular Christmas event. After taking to the internet last year, the 25th edition of the beloved Christmas market returned on Friday, November 19th, and will run through to Christmas.

This year both The Christkindlmarket Daley Plaza and The Christkindlmarket Wrigleyville are welcoming guests into villages to peruse handmade gifts whilst enjoying German food and beverages beneath the snowflakes and glistening lights. Enjoy the smell of roasted nuts, fresh pretzels, bratwurst, hot spiced wine, and the magic of festive music all in the coziest of atmospheres!

More information can be found here.

10. Jump on board the BYOB Party Bus Holiday Lights Tour

Come on down to Chicago’s only BYOB party bus and take a grand tour of the holiday lights. What better way to get into the holiday spirit than with sights such as Millennium Park Christmas Tree, State Street, Macy’s Holiday Display, and more! ‘Tis the season to be happy and merry as you party from place to place with the help from DJ Tecknique! BYOB and get ready for some festive fun with your friends!

You can grab tickets for the Party Bus Holiday Lights Tourhere.

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11-15. Check out a light show or three

Photography by Alex Hewitt

Chicago’s many light shows are some of our most treasured winter traditions. In 2020 all light show experiences turned to drive-thru events or were heavily adapted hindering the real light show experience but this year they’ve returned to their true formats and in some cases expanded and evolved.

Gorgeous natural backdrops, cutting-edge light art installations, and festive cheer all combine providing some of Chicago’s most magical multi-sensory events and we’ve rounded up the best of them all.

16. Ride the holiday train

One of Chicago’s most cherished Christmas events is back and has returned to its original format! Santa’s holiday train trip around Chicago is always one of the most eagerly anticipated activities providing affordable fun for all Chicago families. 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.

After the inevitable changes last year this year the CTA Holiday Train and CTA Holiday Bus have returned to normalcy bringing even more Christmas cheer to Chicago and Santa, accompanied by his new helper Ella the Elf, is now rolling through Chicagoland neighborhoods for the 30th year.

The CTA Holiday Train and Holiday Bus schedules plus more information can be found here.

17. Shop and sip at Blitzen’s Holiday Pop Up

Grab the reins and let Blitzen take you to a holiday pop-up like no other in Chicago! At this event, you’ll find fun for all: enjoy a winter market with local vendors selling unique items, a festive bar with holiday-themed drinks, and plenty of picture-perfect photo ops (including one with Hipster Santa!).

Think Christmas lights and joyful bites. Candy cane swings and endless seasonal things. Kisses under an enormous mistletoe and maybe even a bit of snow. Come one, come all, and experience the magic of the holidays in a beautiful venue decked to the halls in holiday decor at Blitzen’s Holiday Experience.

Get your tickets here.

18. Go Christmas shopping in Rosemont

Talking of shopping, despite the jubilance of the holiday season it can also be a stressful time with all the gifts that need buying. Luckily, Rosemont has the answer in the form of the award-winning Fashion Outlets of Chicago.

The 530,000 square-foot shopping center is home to over 130 designer outlets and a kids wing that makes it as efficient as it is plentiful. Cutting-edge amenities, concierge services, and unbeatable savings make for a shopping trip that checks all the boxes.

The best part, however, is that a stone’s throw from the Fashion Outlets of Chicago, you’ll find Rosemont’s entertainment district Parkway Bank Park with over 40 amazing restaurants, 17 luxury hotels, and the climate-controlled Chicago Wolves Ice Rink where guests can skate free with their own skates and just $8 with a rented pair!

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19. Check out Chicagoland’s all-new AMAZE Light Festival

There’s yet another reason to head out to Rosemont this year and that’s for the debut of Rosemont’s very own light festival. Taking place inside Rosemont’s Impact Field stadium this season, AMAZE Light Festival offers pure holiday magic featuring train rides, a holiday market, a candy shop, a Santa’s Workshop, and a “Thrill Hill” where friends and family can race down icy slopes on single and double tubes.

Seven theme-based illuminated worlds where guests can enjoy a variety of different adventures ranging from the company of elves in the North Pole to the smell of fresh pine at the Tree Farm.

You can find out more about AMAZE Light Festival and grab tickets while they last here.

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20. Go on a New Year’s Eve bar crawl in Chicago

From dance parties, DJs, live bands & the must-have midnight champagne cheers… the Chicago New Year’s Eve Bar Crawl is the perfect place to wrap up 2021 and celebrate the kick-off of 2022 with those you care for the most. Now the real question is… which venue, midnight kiss, and cocktail will you ring 2022 with? Live music and food/drink specials await you throughout your crawl, where you can even participate in a scavenger hunt.

Grab tickets to the Chicago New Year’s Eve Bar Crawl here.

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