Family. Friends. Shopping. Eating. Drinking. Merriment.
Once upon a time, Frozen used to be my favorite movie. Some may even say I moved to Chicago to emulate my dreams of building an ice castle with my bare hands in under 3 minutes. I fear this wasn’t the reality I met, but to be honest, Chicago is best at embracing the cold.
From dazzling holiday light displays and Christmas markets to festive pop-up bars, ice skating, and enough hot cocoa to keep us warm until spring, the city is really showing off. Whether you're looking to get some holiday shopping done, catch a classic Christmas show, or just find an excuse to leave your apartment despite the freezing temperatures, we've rounded up the best ways to make the most of the season. So bundle up, and prepare to romanticize the Chicago winter like your life depends on it.
To be close, but not quite Elsa, “Let’s Go!”
Looking for more seasonal inspiration? Explore our other picks:
photo via chicago botanic garden
Nov. 13 – Jan. 3
1000 Lake Cook Rd, Glencoe, IL 60022
Ever dreamt of falling through a rabbit hole and getting lost in a winter wonderland? I’ve got great news for you. Chicago’s Botanic Garden’s Lightscape is back with glowing tunnels, dazzling installations, no dizziness, and enough holiday magic to make the windy walk worth it.
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photo via brookfield zoo
Nov. 21 – Jan. 3
3300 Golf Rd, Brookfield
In the mythical land of Chi-town, all Chicagoans have fur to keep warm against frost. Join us at the Brookfield Zoo to soak up the festive vibes. Crawl around with other creatures, man and beast alike.
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photo via garfield park conservatory
Nov. 25 – Jan. 3
300 N Central Park Ave
This winter, I’ve been craving the tropics. Join me at Garfield Park Conservatory for a tropical escape filled with festive flowers, seasonal greenery, and the coziest holiday vibes. Let's ignore the freezing temperature.
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photo via santa baby bar
Santa Baby Christmas BarNov. 20 – Jan. 3
3505 N Clark St
Christmas cheer, but make it extra. Santa Baby is decking the halls with over-the-top decorations, festive cocktails, and enough holiday photo ops to fill your camera roll. Ugly sweaters are terribly encouraged.
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photo via one of a kind
Dec. 3–6
222 W Merchandise Mart Plaza, 7th Floor
I got sick of receiving Santa-smeared cards years ago. Skip the same-old gifts this year! The One of a Kind Holiday Show brings hundreds of independent artists and makers together for a shopping experience packed with handmade treasures, unique finds, and serious gifting inspiration.
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photo via chicago shakespeare theater
Nov. 11 – Jan. 3
Chicago Shakespeare Theater, 800 E Grand Ave
“Lord, what fools these mortals be!” Chicago Shakespeare Theater is bringing Shakespeare's beloved comedy to life with a snowy twist, an enchanted forest, and plenty of romance, mischief, and holiday-season wonder.
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photo navy pier
Saturdays, Nov. 28 – Dec. 26, 8 PM
600 E Grand Ave
Baby, it’s cold outside, but Navy Pier is bringing the heat! Bundle up, bring your favorite people for extra warmth, and catch the fireworks lighting up the lakefront on Saturday nights throughout the holiday season. Guess what? It costs nothing.
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photo via celestia
Nov. 20 – Jan. 31
St. Vincent de Paul Church, 1010 W Webster Ave
Looking for something a little different this holiday season? CELESTIA transforms a historic Lincoln Park church into a dreamy world of lights, music, and larger-than-life projections. Trust us, your camera roll will thank you.
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photo via Griffin MSI
Dec. 10, 6–10 PM
5700 S DuSable Lake Shore Dr
Science meets holiday shenanigans at Griffin MSI! Whether you're bringing the whole family or heading out for an adults-only evening, these after-hours celebrations serve up festive fun with a side of museum magic.
Photo via Facebook.com/Christkindlmarket
Nov. 20 - Dec. 24
50 W Washington St
Sipping hot mulled wine out of a boot-shaped mug is a Chicago tradition if there ever was one. This German-inspired open-air market has been bringing holiday joy to locals since 1996. Its flagship location sets up shop in Daley Plaza every winter and runs through December 24th.
Even if you've already wrapped up your holiday shopping for the season, Christkindlmarket's food and drink options still make it a fun place to wander with someone you're sweet on.
Walk The Magnificent Mile & Check Out The Macy's Window Displays
Nov. 21; parade 5:30 PM
Michigan Ave, from Oak St to Wacker Dr
Chicago's Magnificent Mile, the stretch of Michigan Avenue between Oak Street and the Chicago River, always looks especially stunning during the holidays, with tons of lights, store window displays, and carriages lining the streets. It makes for a beautiful nighttime stroll.
Keep heading south past the river and pop over to State Street for more of the city's longest-running holiday traditions. The Macy's window displays are always extravagant and always dazzling. Once you're done posting to Instagram, you can snag more double-tap-worthy pics inside the department store's restaurant. The Great Tree, a 100+ year tradition, towers 45 feet above the dining room and is on display through early January.
Photo via Facebook.com/Goodmantheatre
Nov. 13 - Dec. 31
170 N Dearborn St
The story of A Christmas Carol is a classic in any city, but the Goodman's production is a longstanding favorite and 40+ years into its annual run.
Image via Facebook.com/Lincolnparkzoo
Nov. 20 - Jan. 3
2400 N Cannon Dr
We're always down to hit up Lincoln Park Zoo and hang with snow monkeys and sloths and penguins, but what about when they're illuminated by 2.5 million holiday lights?! It's even better. Plus, there are family-friendly activities scheduled throughout the month (and adult beverages for sale, too).
Image via Facebook.com/Mortonarboretum
Nov. 14 - Jan. 2
4100 Illinois Route 53
The Morton Arboretum's annual tree lighting display, "Illumination," projects beautiful hues onto the mile-long walking stretch through January 3rd. Wintry activities like marshmallow roasting also abound here.
Image via Facebook.com/Maggiedaleypark
Go Ice Skating In The Loop
McCormick Tribune | Nov. 20 - Feb.
McCormick Tribune | 55 N Michigan Ave
Maggie Daley | Nov. 13 - Mar. 7
Maggie Daley | 337 E Randolph St
The McCormick Tribune Ice Rink is one of the most picturesque rinks in the city, surrounded by twinkling skyscrapers and nestled under The Bean. Don't forget: admission is also free! (However, skate rentals do cost between $17 and $23.) Thanks to the Maggie Daley Park Skating Ribbon, you now have another ice skating option nearby if your tradition needs a slight change-up.
Image via Facebook.com/Thejoffreyballet
Dec. 4 - 27
Lyric Opera House
We've come to expect a fresh take on old classics from The Joffrey Ballet and they continue to prove us right with the company's production of The Nutcracker, retold with a Chicago twist.
image via malcolm x college
Celebrate The Spirit Of Kwanzaa
Dec. 26 - Jan. 1
DuSable Black History Museum
Come on down to Malcolm X College to celebrate this year’s flagship multi-day Kwanzaa marketplace, featuring local artisans, apparel, art, and food vendors. If you’re following a program, they’ve got a children’s reading circle and a myriad of performances and history lessons. It’s also (my favorite four-letter word) FREE. How about filling up on Jollof rice before heading over to the DuSable Black History Museum, or even Bronzeville Children’s Museum next? Yeah, I thought so. I’ll see you there.
Photo via Cityofchicago.org
Dec. 4, 11, and 18
Millennium Park
Does anything scream "so Chicago" as much as bundling up in the middle of December and singing holiday songs in front of The Bean? I mean, come on! It's so cute it's almost annoying.
image via the music box theater
Dec. 5 - 24
3733 N Southport Ave
It's exactly what you think it is. The Music Box's annual holiday extravaganza features White Christmas and It's A Wonderful Life. Each screening starts with Santa Claus himself, along with the theater's organist, leading the audience in renditions of beloved carols before the film begins.
Image via Transitchicago.com
Catch The Holiday CTA Train & Bus
Expected late Nov.
Various CTA stations and bus routes citywide
It's the only time of year you'll race to catch a certain train for reasons other than running late to work. The Chicago Transit Authority's holiday train and bus are back and more decked out than ever. Follow along with the schedule (aka Santa tracker) here.
image via graystone tavern
Celebrate Hanukkah On The North Side
Dec. 4 - 12
Daley Plaza
For the best Hanukkah activities, I’d recommend attending the Chanukah Bazaar – a goliath shopping event on November 15th, along with the Mishkan Chicago Hanukkah Market on the 13th. What better place to wear your new jewelry than the Festival of Lights Chanukah Soiree on Dec 6th?
Photo via NavyPier.org
Nov. 27 - Jan 3
Festival Hall
Navy Pier's Festival Hall gets decked out in holiday spirit again this year. Hundreds of trees, thousands of ornaments, giant nutcrackers, and plenty more wintery whimsy. Complete the day with hot cocoa and hot apple cider. Who knows? You might even spot Santa!
Nov. 7 - Jan. 3
5700 S DuSable Lake Shore Dr
The Museum of Science and Industry's yearly holiday celebrations "Christmas Around The World" and "Holiday Of Lights" are back through January 6th. More than 50 holiday displays representing cultures and traditions from around the globe are on display now, with special performances happening every weekend!
Photo via Facebook/Gallagher Way
Winterland at Gallagher Way
Nov. 20 - Dec. 31
Gallagher Way
Wrigleyville is bursting with holiday joy, events, and cheer this holiday season. Stop by the neighborhood that's home to 25+ holiday-themed bars, a Christkindlmarket, and more! It's your one-stop shop for holiday joy and perfect for visits anytime.
Updated october 2026
Happy holidays, Chicago! Make this season count. Did we miss your favorite thing to do? Let us know!
