Holiday Festivities in Downtown Chicago
[Last updated in November 2024]
It’s never too early to get festive in Chicago.
From the city’s Official Tree Lighting to checking out dazzling light displays and theatrical shows, it would be hard to miss out on the many holiday traditions Chicago has to offer.
Photo of Millennium Park Christmas Tree by Raymond Boyd via gettyimages.com
Kicking off the official start of the Chicago holiday season, the 111th Annual Christmas Tree lighting ceremony will take place on Friday, November 22nd, 2024, at 6pm. Coming from Logan Square this year, the 53ft Colorado Blue Spruce tree will be near the intersection of Michigan Ave and Washington St. Multiple viewing screens and concessions will be available throughout Millennium Park. Can’t make it to the opening ceremony? Don’t worry- the tree will be lit for your enjoyment until January 8th.
Photo of Magnificent Mile Lights Festival & Parade by Vito Palmisano via wgnradio.com
Following the Christmas Tree Lighting, the next day on Saturday, November 23rd, from 11a-4p, head to Lights Festival Lane at 401 N Michigan Ave. Festive booths and free family activities can be enjoyed, including complimentary photos with Santa Claus at the Wintrust Pavilion.
At 530p, Mickey Mouse and Minnie Mouse will lead the iconic Magnificent Mile Lights Parade, which will start at Oak St and N Michigan Ave, heading South across the Chicago River to Wacker Dr. Along the route, 1 million lights will illuminate on over 200 trees, followed by 40 floats, 385 marching band members and top musical performers.
Be sure to stay until 730pm, when The Wintrust Fireworks Spectacular will go off at the Chicago River.
Photo of The Walnut Room by John W. Iwanski via flickr.com
If you are so lucky to nab a reservation during the holiday season, enjoy a festive meal at this historic restaurant, located inside Macy’s on State Street. The Walnut Room was the first restaurant ever to open in a department store, and during the holidays, you can dine around the Great Tree that towers in the center of it all. While you’re there, don’t forget to also check out the window displays that line the outside of the Macy’s building.
Festive Holiday Displays & Events
Photo of Navy Pier Light Up the Lake by Jaclyn Rivas via timeout.com
With so many different winter events going on in the city, it’s hard to choose which one (or five!) to go to. If you want to brave the cold, check out Lincoln Park Zoo’s Zoo Lights. In its 30th year, you will find many returning light attractions, as well as new amazing displays, like the garden-themed light show on the Zoo’s South lawn. If the Chicago winter is too cold for your liking, another beloved favorite is the Christmas Around the World and Holidays of Lights at the Museum of Science and Industry. Each of their 50+ elaborately decorated trees, represents holiday traditions from across the world. The Holidays of Lights exhibit also honors the traditions of Hanukkah, Kwanzaa, Diwali, Ramadan, Lunar New Year and many more.
Want the best of both indoor and outdoor? Navy Pier will once again be presenting Light Up the Lake, the largest indoor and outdoor holiday experience in Chicago. Stay warm indoors by shopping the local artisan markets, stopping at the free holiday workshops and enjoying the dazzling lights; or you can venture outdoors and cozy up and roast s’mores by the firepits, ice skate on the outdoor rink and ride the Centennial Ferris Wheel.
If you find yourself further up north in Wrigleyville, head over to Winterland at Gallagher Way. There’ll be a Tree Lighting Ceremony on 12/6, a Winter Market 12/6-12/8, and Holiday Movie Nights on 12/12 & 12/19. Then head inside Wrigley Field for lots of rides, games and an ice skating rink.
While you’re downtown, be sure to also walk past the Art Institute of Chicago to see the museum’s beloved lions in their holiday best. And if you’re there in November, you can attend the annual Wreathing of the Lions celebration, a Chicago tradition for more than 30 years.
Holiday Train Rides
Photo of CTA Holiday Train by Visual Acoustics via flickr.com
Sadly, The Polar Express™ train ride will not be back for 2024. If you’re not familiar with it, The Polar Express™ train ride leaves from Chicago Union Station, aboard a magical one-hour trip, where passengers will enjoy caroling and onboard entertainment, while drinking hot chocolate and eating shortbread cookies. Santa and his helpers also board the train to greet each guest and to give out the first gift of Christmas: a silver sleigh bell. So let’s hope it returns in 2025!
Instead, you can keep an out for the CTA holiday train. For more than 30 years, the six-car train is decorated with holiday scenes and thousands of sparkling lights. Santa waves to the riders from his sleigh on an open-air flatcar, which replaces the head car of the train. But what many may not realize, is that one of the holiday train’s main purposes is to deliver food baskets to various charitable agencies throughout the city.
Ice Skating
Photo of Skating Ribbon at Maggie Daley Park by MA1216 via flickr.com
What better way to enjoy the winter outdoors than by ice skating? Probably one of the most picturesque places to ice skate is the Skating Ribbon at Maggie Daley Park. This lengthy rink curves through the tall pine trees of the park, with the Chicago skyscrapers in the background. For another ice rink, close by in Millennium Park is the McCormick Tribune Ice Rink. Locals and visitors alike have been enjoying this rink for more than 20 years, gliding around in the center of downtown Chicago.
But for a truly unique ice skating experience, visit the Sky Rink at The Peninsula Chicago, located on the fourth floor terrace that overlooks Michigan Ave.
Holiday Markets
Photo of Christkindlmarket by Lucas via flickr.com
The vast amount of holiday markets in Chicago do not disappoint. The most traditional of them being the Christkindlmarkets. These authentic outdoor German-inspired Christmas markets have lots of booths to shop with nutcrackers, cuckoo clocks, beer steins, collectible holiday mugs and glass ornaments. The whole family can also enjoy German street food-favorites like schnitzel, potato pancakes, German sausages and goulash. Gluhwein (a mulled wine) is also a must when you visit the market—there are both alcoholic and non-alcoholic versions to choose from! Chicago offers 2 different locations for Christkindlmarkets: Downtown at Daley Plaza and at RiverEdge Park in Aurora.
For a more local artisan market, check out the One of a Kind Holiday Show at the Mart, which features over 500+ booths, selling creative collectibles such as hand-painted pottery, sustainably made jewelry, artisanal bitters and many other unique gifts. This pop-up market also has live music and delicious food to enjoy. Or maybe you want to head over to Morgan Manufacturing for the Renegade Craft Fair, that has been a part of Chicago for 20 years. Selling independent artisan gifts, you can find anything from clothing to jewelry and other accessories, handmade ceramics and stained glass ornaments.
But the list of markets would not be complete, without mentioning the Pre-Kwanzaa Holiday Marketplace held at the Harriet Harris Park District located at 6200 S Drexel. Prepare yourself for a 2-day festive celebration that honors African culture through art and entrepreneurship. Don’t miss out on experiencing the cultural festivities and amazing vendors throughout the market.
Festive Hotel Stays
Photo of Swissotel Santa Suite by Kelly via kellyinthecity.com
One of our favorite things to do downtown with our kids during the holiday season, is to spend a night (or two!) at a hotel—and with the many festive options to choose from, why wouldn’t you! Our go-to stay is at Loews Hotel, where they have offered a GingerBed + Breakfast package, that includes a Gingerbread Cookie Decorating Kit, a tent set up in your room for the kids, an in-room seasonal movie, delicious hot cocoa and a book(s) from the Holiday Bedtime Story Cart. However, I am unsure if they are offering this same package this year, but they do have many other winter offers that are worth checking out!
But probably the most popular festive downtown Chicago hotel would have to be the Swissotel. Families can book the Santa Suite where guests can stay in the whimsically decorated room surrounded by 17 Christmas trees, a sweets & treats bar that includes hot chocolate, holiday crafts and cookie decorating and of course a visit from Santa!
Other holiday-themed hotels worth visiting are the Fairmont Chicago, with their indoor “fire pits” and Breakfast with Santa, the Hotel Zachary that has specials for Winterland at Gallagher Way located across the street, along with a Teddy Bear Tea and Breakfast with Santa, the Radisson Blu Aqua Hotel and the Waldorf Astoria with their beautiful festive decorations, or book the Holly Jolly Family Holiday Package at the Peninsula.
For more ideas on festive hotels to stay at, check out my blog post on Decked Out Chicago Hotels.
Theater Entertainment
Photo of The Joffrey Ballet’s The Nutcracker by Cheryl Mann via chicagoreader.com
Chicago holiday theater performances are not to be missed. A family favorite of my daughter’s and mine is ‘Twas the Night Before… by Cirque du Soleil. Based on the classic poem, “A Visit from Saint Nicolas” by Clement Clarke Moore, this entertaining show features thrilling acrobatics and a festive soundtrack. Unfortunately, it looks like the show will not be in Chicago this year, but it is in Milwaukee- worth the drive in my opinion!
Another fan favorite and classic is A Christmas Carol at the Goodman Theater. It made its debut in 1978, and many Chicagoans have long made it their annual tradition. And yet another classic tale to add to your list is It’s a Wonderful Life at the American Blues Theater.
What about watching a new twist on a classic ballet performance, where contemporary hip hop dance converges with the elegant holiday score of Tchaikovsky at The Hip Hop Nutcracker? Or would you rather stay more traditional with The Joffrey Ballet’s The Nutcracker, which has been wowing a Chicago audience since 1987.
And for those that grew up with or are wanting to know more about Will Hershel, be sure to catch Hershel and the Hanukkah Goblins, playing at the Chicago Loop Synagogue. This one is the story of how a traveling troupe of actors comes to a town to find no one celebrating Hanukkah; so they must put on a show and tell the tale of how Hershel of Ostropol outsmarts the goblins who haunt the old synagogue, thus saving the spirit of Hanukkah! Info hasn’t been published yet for 2024, so be sure to check their website often for updates!
[Updated November 2024]
What Holiday traditions does your family like to do? Let me know in the comments!
‘Tis the season for holiday markets and festive decor! But even better if you pair that with a local farm that sells fresh produce, baked goods or Christmas trees, or has a petting and feeding zoo.