The best Christmas things to do during the holidays in Chicago

The iconic German-inspired holiday market at Daley Plaza brings just over a month of Christmassy celebrations to the Loop. Browse stalls stocked with handmade gifts, German food and plenty of hot beverages to keep you warm while you wander around and soak in the festive atmosphere. Don't leave without trying spiced glühwein, a German hot wine concoction that's best enjoyed in the market's famous boot mugs.

Every year, Millennium Park is adorned with an epic Christmas tree that remains on display until the beginning of the new year. The larger-than-life attraction is festooned with twinkling lights and crowned with an illuminated star. Spectators can check out the festive tree near Washington Street and Michigan Avenue through early January. Want to see the tree light up for the first time this season? The annual Christmas Tree Lighting Ceremony returns this year on Friday, November 21.

The Cubs may be hibernating for the winter, but Gallagher Way provides some excellent reasons to hang out in Wrigleyville during baseball's offseason. The Wrigley Field-adjacent space hosts a variety of seasonal activities, including photos with Santa, a winter market, carnival rides and holiday movie screenings. Opening on November 23, you'll be able to shop for gifts, sip a hot beverage and enjoy delicious treats through December 31. 

Relive cherished holiday memories—and make plenty of new ones—at Navy Pier's Winter WonderFest. Admire twinkling light displays bedecking Navy Pier's Festive Hall and prepare to be awed by a 42-foot holiday tree. Plus, there's no shortage of activities—for both kids and adults—at Winter WonderFest: Enjoy live music and special performances at the Winter Wonder Stage, lace up for a round of ice skating, enjoy tasty treats and sips and much more.

Satisfy the sweet tooth with a dessert crawl through Lincoln Park. Guests will visit businesses along Clark Street and enjoy a variety of delicious holiday cookies, plus surprises like hot chocolate and photos with Santa. Opt for Boozy Admission to receive three festive alcoholic drinks on the crawl. A ticket includes a map of participating businesses, a Cookie Crawl bag and a medley of pre-packaged holiday cookies.

Looking to support artists during the gift giving season? The One of a Kind Show gathers over 600 artists and artisans on the seventh floor of the Merchandise Mart building for a seasonal bazaar of handcrafted goods and gourmet food. New to the show, One of a Kind will now include hands-on artist demos, fine art gallery tours with artists leading the way and live entertainment. A portion of proceeds from each ticket sold will benefit Ann & Robert H. Lurie Children’s Hospital of Chicago.

The commuter rail system is offering rides on special holiday trains on December 6, 13 and 20. With the Holiday Train expanding onto all Metra routes, you'll have plenty of chances to hop on board one of the decorated railcars, which will be filled with holiday characters. In addition, Millennium Station is also transforming into a North Pole winter wonderland where guests can enjoy treats, festive music, face painting, games and more. Other downtown stations will be decorated as well, and the holiday trains will be used in regular service throughout December. 

Get ready for a festive ride—the CTA Holiday Train and Bus are coming to town! The train is decked out in twinkling holiday lights, with Santa and his reindeer riding outside to wave at families—you can spot the festive locomotive in CTA stations throughout the city from November 29 through December 22. The CTA Holiday Bus, on the other hand, will hit the road on November 28 and make its rounds through December 22. 

The Chicago Botanic Garden hosts this annual (and quick to sell out) display of festive lights, giving guests a host of shimmering reasons to visit the forest preserve during the holiday season. Set along an illuminated path, the after-dark experience features a series of installations to explore, including a 110-foot tunnel made up of 100,000 lights and a group of trees festooned in bulbs that “sing” holiday songs. 

To see one of the largest displays of holiday lights within city limits, you need to head to Lincoln Park Zoo, where the annual ZooLights display strings up millions of LED blubs. While most of the animals will be keeping warm inside, visitors are welcome to wander through the park, snapping photos of the various displays and taking part in a variety of activities throughout the holiday season. New this year, bask in the holiday spirit in the light lounge; as always, guests will also be able to enjoy hot beverages and snacks at stands throughout the park.

More than two million lights cover the trees, fences and structures in the Brookfield Zoo at this annual holiday event, which is now in its fourth decade. Guests can walk through a 300-foot-long tunnel featuring colored lights synchronized to music, spot larger-than-life illuminated animal sculptures, gaze up at a 41-foot-tall lit tree and warm up with concessions such as funnel cakes, pizza, spiced wine and hot cocoa. 

Experience the holiday classic, It's a Wonderful Life, as a 1940s-style live radio play this holiday season at The Athenaeum Center. Set in the venue's Paradiso space, every seat guarantees an intimate experience of George Bailey's renewal of faith in himself, his family and his community. Whether you're returning as part of a cherished holiday tradition or discovering the story's magic for the first time, this production is sure to lift your spirits.

Ready to get into the holiday spirit? The Morton Arboretum's annual holiday light show returns for its 13th anniversary as a mile-long, walk-through spectacle of LED lights and music, featuring a blend of new and returning light displays set amid 50 acres of trees. Back again this year is "Electric Illumination," a series of late-night parties with DJ-curated playlists that will synchronize progressive house and '80s dance beats with the light shows, as well as "IllumiBrew," a special evening where guests can sample beers and ciders from local breweries. 

Every year, the Griffin Museum of Science and Industry puts up its four-story Grand Tree and surrounds the towering pine with more than 50 trees that represent Chicago's various communities and their respective holiday celebrations. Visitors will be able to take in even more seasonal cheer at the accompanying Holidays of Light exhibit, which recognizes the traditions of Chinese New Year, Diwali, Kwanzaa, Ramadan, Hanukkah, Visakha Puja Day and St. Lucia Day. Admission to Christmas Around the World and Holidays of Light is included with a regular Museum of Science and Industry ticket.

Happy’s is back for its farewell season, and they're closing out a holly, jolly run in full holiday spirit. Situated on the ground floor of the Chicago Athletic Association, Happy's transforms the hotel's Tank space into a holly, jolly wood-paneled dive bar serving cocktails and bar bites. Admission is free, and the pop-up is just a short walk from the Millennium Park ice skating rink.

See Christmas lights while staying warm at this pandemic-era innovation that allows visitors to drive through a gleaming tunnel of more than one million LED lights synchronized with holiday music. Plus, the show takes place in Bridgeport at Rate Field, home of the Chicago White Sox.

Wander around with a Bloody Mary in hand at the annual holiday iteration of Randolph Street Market, which always boasts an eclectic smattering of vendors selling vintage furniture, handmade clothing, art, antiques and more treasures guaranteed to make for a memorable gift.

Chicago's only Hanukkah-themed pop-up takes over The Graystone Tavern in Wrigleyville for another year, filling the bar and weatherproof patio with more than 30,000 blue-and-white lights, dreidel ornaments, lighted menorah and a Hanukkah sweater wall (among other festive bits of decor). Dine on Hanukkah classics like latkes and matzo ball soup alongside not-so-classic options like boozy jelly donuts. Pair your meal with a novelty cocktail—we're going with the Hebrew Cold Brew, a caffeinated cocktail crowned with a heavy cream float. Chag Sameach!

Bring a thermos of hot chocolate and a cozy blanket to accompany your ride through Willow Hill Lights, a drive-through holiday light experience in suburban Northbrook. Located at Willow Hill Golf Course, the 2.5-mile display of glittering lights features holiday favorites like Rudolph and Frosty the Snowman—not to mention a 30-foot-tall Christmas tree. Proceeds from the show benefit Misericordia, a not-for-profit that supports more than 600 children and adults with intellectual and developmental disabilities.

Load up the family in the car and head to Geneva for a spectacular drive-thru light show that stretches over a mile in length. Guests will journey through light tunnels and gaze at illuminated dinosaurs, polar bears, reindeers, giant emojis, guitar-playing Santas and more, all of which are synchronized to holiday tunes.

Skate under the Chicago skyline and within eyeshot of the Chicago Christmas Tree at the McCormick Tribune Ice Rink in Millennium Park. Plus, take advantage of free skating lessons on most Saturdays and Sundays, where you can learn both beginner- and intermediate-level skills. Note that you'll need to make a free online reservation for both regular skating and lessons, and if it seems too warm to skate, call ahead—this rink is open through early February 2026, weather permitting.

Situated in the heart of downtown Chicago with the city's sweeping skyline as a backdrop, the Skating Ribbon at Maggie Daley Park is a winter attraction unlike any other. Skaters can lace up and wind around a winding ice-covered path that's twice the length of a lap around a traditional rink. Reservations for the popular ice rink should be made in advance, as they tend to fill up quickly.

Pinkmas at the Museum of Ice Cream is more than your run-of-the-mill holiday outing—it's a dazzling, immersive holiday experience. Visitors can share their wildest dreams with a Wishing Tree, walk through a life-size snowglobe, and feast on festive treats and ice cream creations, all while taking advantage of countless photo opportunities.

Ravinia, a North Shore arts and culture staple, is celebrating the holiday season with an eclectic Winter Weekend, which offers a little something for everyone: a cappella, klezmer music, a piano cabaret and a kids' classic. The Ravinia Café will be slinging hot cocoa and holiday treats, and the Festival Shop will be selling cozy winter goods. Guests are welcome to walk the park grounds before each day's shows.

Don't forget to hit the ice during your next visit to Winterland at Gallagher Way! Until February 15, 2026, visitors can rent ice skates for $16 or bring their own, ride ice bumper cars and more. Check out the Gallagher Way website to stay updated on skate nights, skating lessons and curling matches—all beginning January 2026.

All aboard! For the first time ever, the Chicagoland Independent Bookstore Alliance is bringing together 43 indie bookstores throughout Chicagoland for a special holiday shopping experience tailormade for all the book worms out there. With 10 routes to choose from, each trolley ride will include special holiday swag and stops at four to five participating bookstores.

Having retired cofounder Robert Joffrey's production of The Nutcracker after nearly 30 years, the Joffrey Ballet debuted a brand-new version in 2016, set in Chicago against the backdrop of the 1893 World's Columbian Exposition. This year's production will be staged in the Civic Opera House (where the Lyric Opera also resides), featuring music performed by the Lyric Opera Orchestra and the stunning choreography of Tony Award winner Christopher Wheeldon. The Chicago-inspired iteration of the classic Christmas ballet will have you humming “Dance of the Sugar Plum Fairy” for days after you leave the theater.

Slide past an indoor skydiving center and Fogo de Chão on the Chicago Wolves Ice Rink at Rosemont's Parkway Bank Park, where you can hit the ice on most days through the end of January. Check the official website for hours. Admission is free, and skate rentals are $8 per pair.

For the 42nd year, Southport Corridor’s favorite historic theater brings three weekends of Christmas singing followed by a double feature of classic holiday films to Chicago’s North Side.  Sit back in plush theater seats with snacks and drinks as you belt “Rudolph the Rednosed Reindeer” and “It's Beginning to Look a Lot Like Christmas,” and just when you’ve worn yourself down, stay for a showing of White Christmas and It’s a Wonderful Life.

Located on the terrace of The Peninsula Chicago, the 2,100-square-foot Sky Rink offers ice skating in the shadows of the city's tallest buildings, all while overlooking Michigan Avenue. Show off your skills in a winter wonderland featuring snowflake lighting and festive music, and when you need to warm up, grab a hot drink and snack at the Chalet.

There’s no better place in Chicago for holiday cheer than under Millennium Park’s Cloud Gate (a.k.a. “The Bean”), where like-minded songbirds delight in shared songs amidst the twinkling lights of the city Christmas tree and the sounds of laughter from nearby ice skaters. With some hot cocoa in your hand, join local choirs and bands as they lead attendees in a powerful sing-along of joyful holiday carols. This year, the series takes place Fridays at 6pm from December 5–19, with a different choral group highlighted each week.

The Goodman Theatre’s annual holiday production of the Charles Dickens classic returns to the stage, with Christopher Donahue and Austin Tichenor taking on the role of Ebenezer Scrooge. The play has been a staple of the Goodman's calendar for more than 40 years, allowing returning attendees and new generations to see the quintessential Christmas story unfold before their eyes. Prepare to be visited by three spirits—and don't be suprised if A Christmas Carol's touching tale of redemption makes you shed a few tears.

Who's Holiday!, Theater Wit's holiday hit, returns for the fifth year running. The 65-minute show finds a 40-year-old Cindy Lou Who holding court in her mobile home at the base of Mount Crumpet, retelling the story of the sordid events that transpired after meeting the Grinch. Oh, and one more thing: The entire story is told in R-rated Seussian rhymes...

Pinkies up! Little ones and their families are invited to ring in the holiday season in style during The Beatrix Potter Holiday Party, an annual trunk and puppet show at the Chicago Children's Theatre that brings Potter's beloved stories to life with whimsy and humor. The play's young viewers get to interact with characters like Tom Kitten, Jeremy Fisher and Peter Rabbit throughout the 60-minute production, which features live music alongside narration and puppetry. Afterwards, audience members can meet the cast while enjoying juice, chocolate milk and holiday treats courtesy of Eli's Cheesecake for a proper tea party celebration.

The Loop’s National Historic Landmark Orchestra Hall is ornate enough to dazzle year-round, but shines extra bright for the Chicago Symphony Orchestra’s Merry, Merry Chicago! holiday concert conducted by Alastair Willis. On a stage decked with—literally—boughs of holly, larger-than-life red bows and wreaths, the acclaimed instrumentalists play tunes ranging from beloved holiday favorites to Christmas in Chicago, a local treasure. Before the show and during intermissions, you’ll even hear pop-up performances from Chicago school choirs and community ensembles throughout the halls.

Gezelligheid is a Dutch word that loosely translates to “cozy,” and as the darkest days approach, any Chicagoan knows we need all the comfort we can get. Award-winning singer-songwriter Andrew Bird conjures the sentiment in his 15th annual Gezelligheid concerts at Fourth Presbyterian Church, a holiday concert tradition aiming to bring us together with cheerful, moving music. This year, Bird celebrates the 20th anniversary of his acclaimed record The Mysterious Production of Eggs, performing the record for the first time in its entirety alongside a full orchestra.

If your motto is the more saxophone the better, soak up the smooth sounds of Tim Warfield’s Jazzy Christmas show. Joined by a talented band of piano, trumpet, vocalists and more, the American saxophonist embraces the holiday classics you love with new interpretations. Sip a warming cocktail and enjoy the atmosphere at Jazz Showcase, one of Chicago’s most historic clubs. 

A lot of song and a little dance: Experience upbeat jazz and exhilarating tap dance performances at the Chicago Human Rhythm Project (CHRP)’s annual Holiday Rhythms concerts. Groove to invigorating holiday beats from artists Jumaane Taylor, Brinae Ali, Marty Bronson and Keyana Latimer and the Eric Hochberg Trio. The show is filled with music, dance and joy—and even a complimentary drink and dessert bar so get ready for a holiday celebration (and accompanying treats) like no other. 

Holidays, but make it gay: That’s what Chicago Gay Men’s Chorus’s annual concert does best. This year, the 200-person choir will be decking the halls with rhinestones for Holly Dolly Christmas: A very twangy celebration of the one and only Dolly Parton. Whether you’re craving heart-pumping holiday cheer or can’t get enough of country vibes, you’ll be tapping along to tunes—and maybe even singing along yourself. 

This immersive, multi-level Christmas pop-up bar boasting wall-to-wall holiday decor returns to Wrigleyville, taking over Stolen Saddle during the most festive time of the year. You'll find photo ops galore as well as drinks decked out with decorative garnishes and garlands, including large-format cocktails. Feeling hungry? Feast upon festive options like Santa's Smash Burger, Festive Fry Flight and Grinch Shake. 

Join the Wicker Park Bucktown Chamber of Commerce to celebrate the holiday season with a full day of family-friendly festivities. One of Chicago's most eclectic neighborhoods will be hosting live holiday music, outdoor s'mores stations, a Grinch-themed scavenger hunt and more. A grand tree lighting will take place at the Wicker Park Field House in the evening. 

If you're jonesing for an outdoor Christmas adventure this year, the folks behind Jack's Pumpkin Pop-Up are bringing back its winter sibling in Fulton Market. The sprawling two-acre attraction boasts a Christmas market, photo opportunities and a variety of activties like ice skating, bumper cars, axe throwing, curling and more. You'll also have the opportunity to sip on boozy hot cocoa and other holiday cocktails while wandering through a light-filled Christmas tree walk.

The 2003 holiday movie Elf takes center stage at this Wrigleyville pop-up located inside of Stretch Bar & Grill, which gets dressed up with more than 1,000 decorative elves, Christmas trees and plenty of festive Christmas lights. Take a seat at tables stocked with the four main food groups (candy, candy canes, candy corn and syrup) and treat yourself to a plate of Buddy's breakfast pasta (spaghetti loaded with maple syrup, chocolate fudge and syrup, mini marshmallows and strawberry frosted pop tarts) or a beer served in a 36-ounce elf boot. 

Celebrate the holiday season at Navy Pier's annual winter fundraiser. Proceeds from ticket sales directly support Navy Pier’s accessible programming efforts, which afford local schools and community groups the opportunity to visit the Pier free of charge. Admission includes access to all rides and attractions, ice skating with minimal lines and a photo opp with Santa.

Immerse yourself in a picture-perfect whimsical décor, sparkling lights and breathtaking Chicago skyline views from the 22nd floor and indulge in a delightful selection of holiday-themed cocktails, including steaming spiced mulled wine and chilled festive drinks. 

Frosty's Christmas Bar near Goose Island brings three levels of festive fun, four bars, two dance floors, life-size toy soldiers and a themed soundtrack that keeps the crowd bumping well past midnight every night of the week. Don your favorite holiday attire and enjoy a glass of something boozy and marshmallow-topped while eating Christmas cookies amidst the twinkling lights, tinsel and over-the-top decorations.

The weather outside might be frightful, but you'll be plenty cozy inside JoJo's Shake Bar, which has transformed every inch of its outdoor patio into a Winter Wonderland decorated with an eight-foot tall nutcracker, giant ornaments and thousands of string lights. Treat yourself to over-the-top shakes—such as the Winter Wonderland Shake, which is peppermint flavored and topped with cookies, marshmallows, a candy cane and a snowman made of donut holes—and fanciful seasonal cocktails like Santa's Sangria, and be sure to grab a table close to the pop-up's Christmas tree. 

The Music Institute of Chicago celebrates the holidays with Duke It Out! Nutcracker, its annual music and dance program for families. The Music Institute’s ensemble-in-residence Quintet Attacca and members of Braeburn Brass team up with Dance Chicago for a one-hour rendition of The Nutcracker that alternates between Tchaikovsky's original score and the jazz version by Duke Ellington and Billy Strayhorn. 

The Godfrey’s rooftop becomes a winter wonderland when the temperatures plunge, featuring clear heated igloos decorated with festive lights that can be booked for groups of up to 10 people indulging in bottle service. Even if you’re not going all out, you can hang out at a booth under the retractable roof or gather around an outdoor fire pit for s’mores and a hot cocktail.

River Grove tiki bar Hala Kahiki has transformed into Sippin’ Santa, a famed holiday pop-up with locations across the country. The tropical experience features over-the-top, kitschy decor and a themed cocktail menu, including new and returning drinks like Jingle Bird, Frost Bite and Designated Sledder.