12 Things to do for Christmas in Chicago That Feel Straight Out of a Movie
Looking for the best ways to celebrate the festive season of Christmas in Chicago? You’re in the right place. I was born and raised here, and after spending plenty of Decembers exploring the city, I’ve got a go-to list of festive picks that feel like they belong in a holiday movie.
In this guide, I’m sharing 12 of the most magical things to do in Chicago during December. Whether you want to ice skate in the heart of downtown, sip seasonal cocktails at pop-up bars or see classic holiday performances these experiences bring the Christmas spirit to life.
You’ll also find out where to go for festive tea service, which activities need reservations, and how to make the most of Chicago’s holiday magic this winter.
12 Magical Things to Do for Christmas in Chicago
From seasonal cultural experiences to eating, drinking, dining, and seeing the festive lights, here’s 12 activities to ensure Christmas in Chicago is the most wonderful time of the year!
1. Free ice skating at Millennium Park
Though you’ll need to reserve a slot, you can ice skate in downtown Chicago for free in winter. Millennium Park’s pop-up ice rink is open between mid-November and the beginning of February.
They even offer complimentary lessons on Saturdays and Sundays.
If you bring your own skates, you’ll get on the ice for free. Otherwise, you’ll pay $16 or more depending on the day of the week (weekends are a bit more) and any add-ons you may purchase like lockers or skate sharpening.
2. Tree lighting ceremony and Holiday Sing-Along at Millennium Park
A major seasonal event in Chicago during the run-up to Christmas is the annual tree-lighting ceremony. The celebrations include a colorful parade, live musical entertainment and a spectacular fireworks display.
You can also exercise your vocal cords during selected Fridays in December at the Holiday Sing-Along event. Kicking off at 6pm by The Bean, you can join in with all sorts of holiday songs.
3. Christkindlmarket Chicago
Chicago’s Christkindlmarket offers an authentic, German-style festive shopping experience without traveling all the way to Europe.
It’s held in Daley Plaza from late November to 24th December. With the exception of Thanksgiving and Christmas Eve, when it closes at 4pm, it’s open late until 8pm or 9pm every day.
While browsing, you’ll be treated to the scent of warm spices from seasonal food and drinks as well as an appealing array of decorative and gift items. Look no further if you want to find unique gifts for Thanksgiving or Christmas.
4. Frosty’s, the original holiday-themed popup bar
Frosty’s was the first pop-up bar to appear in Chicago during the festive season, and is generally seen as the best. Expect bright lights, jolly music, colorful holiday cocktails, and of course a party atmosphere from November onwards.
You can find Frosty’s Chicago on W Evergreen Ave. With bars in Los Angeles, New York, and Houston in addition to Chicago, the guys behind Frosty’s really do know what they’re doing.
5. Visit the Home Alone house
If you’re a fan of the movie, why not head out to the wealthy Winnetka neighborhood in the North Shore to see the Home Alone house for yourself?
As the house was sold to a private owner in 2024, you cannot go inside. But movie fans often sneak a peek from outside the wrought-iron gates enclosing the symmetrical, Georgian-style property.
6. Holiday tea at The Drake or LondonHouse
Both the Queen and Princess Diana have tucked into a Magnificent Mile afternoon tea at The Drake’s Palm Court. It’s a city institution.
As usual, you can expect finger sandwiches, freshly-baked scones, and pretty cakes with a Christmas twist. Plus carol-singers or other live music on selected dates.
Between mid-November and mid-January, you can also savor a marvelous Christmas afternoon tea in Chicago at LondonHouse. There are plenty of festive delights such as candied orange scones, sugar cookies and gingerbread cake to sample here.
7. See the Joffery Ballet’s The Nutcracker show
It’s a real festive treat to see The Nutcracker choreographed and performed by Joffrey Ballet. Christopher Wheeldon’s 2016 reinvention was revered by the critics, making it even better than the 1987 version that kicked off a much-loved annual event.
The Nutcracker by the Joffrey Ballet is a truly local experience, with the reimagined tale set right here in Chicago over a century ago.
8. Macy’s windows & the original brownie at Palmer House
The Holiday Windows at Macy’s State Street have been wowing locals and visitors alike for over 150 years. Catch the awe-inspiring displays between early November and New Year.
Some of my own earliest memories of Christmas in Chicago revolve around going to see the windows with my parents and sister.
To round off the perfect festive experience, head to Palmer House, a hotel that’s been frequented by leading literary names from the past as well as US presidents.
Brownies were also invented here in 1893, and the rich, walnut-topped confection is still made to the original recipe.
9. Tree Lights at Morton Arboretum
The winter illuminations at Morton Arboretum have been thrilling people for more than a dozen years now. It’s a real feast for the senses, with colorful lights and carefully-matched music.
Enjoy an accessible one-mile trail, s’mores made by the crackling fire, a fairy glade, snack stands, a restaurant and a stunning finale over Meadow lake featuring a laser light show.
10. Dine in a heated igloo
I|O Godfrey at Godfreys Chicago is a rooftop venue open all year round, and you can find heated igloos here in winter for a meal to remember.
There are other options around the city, too, such as LondonHouse, Barcocina in West Town or Lakeview, and The Drake Oak Brook.
You can also dine within heated glasshouses at The Willow Room in Lincoln Park, outdoor bubbles at Fiya in Andersonville, and wooden chalets at Chateau Carbide’s Pendry Rooftop.
There’s something magical about sitting comfortable in a heated, transparent igloo-like dome in the winter and Chicago has no shortage of options if this is on your bucket list.
11. Christmas Around the World and Holidays of Light at MSI
The Museum of Science and Industry hosts a treasured annual event between mid-November and early January each year. Christmas Around the World exhibitions showcase festive traditions from all over the world.
As part of the Holidays of Light event, “snow” falls onto the Christmas trees of North Court every half hour, close to the majestic Grand Tree.
12. Take a festive trip on the CTA holiday train (or bus)
Chicago’s Allstate CTA Holiday Train runs between late November and later December, delighting visitors as well as commuters. There’s also an Allstate CTA Holiday Bus service.
Trains travel on all lines, on different dates. Expect train cars bedecked with seasonal images, lots of fairy lights, and even Santa and his sleigh on the roof, complete with reindeer and Christmas trees. It’s a magical way to brighten up an otherwise ordinary commute.
Is Chicago worth visiting at Christmas?
If you’re wondering whether it’s worth seeing Chicago at Christmas for the holiday season, then the answer cannot be anything other than a resounding yes!
Whether you’d prefer shopping at a German Christmas market, dining in an igloo, ice skating, tucking into afternoon tea, or seeing a spectacular ballet or light show, there are so many top options to keep you busy.
Hit pause on the holiday Hallmark movies for a bit and get out there yourself, instead!
