Festive Things to do in Chicago

There are certain places that shine extra bright during the holidays–both figuratively and literally–and Chicago is one of them. Christmas is the most wonderful time of the year in the windy city. There are countless ways to celebrate and enjoy the holiday festivities, despite the frigid weather. There are also plenty of things to do, no matter your age. 

Here is a round up of the best, festive things to do in Chicago during the holiday season. 

Festive Things to do in Chicago

21 Festive Things To Do In Chicago

ZooLights At Lincoln Park Zoo

Nothing screams Christmas like mesmerizing light displays, but none are quite as impressive as the one at the Lincoln Park Zoo. 

The whole family can come together for ZooLights at Lincoln Park Zoo, where you’ll see the entire zoo illuminated by more than 2.5 million Christmas lights, including moving displays set to music. To make this event even more fun, there are special events and theme nights to keep an eye out for. 

ZooLights at Lincoln Park Zoo runs from November 19 to January 1, from 4:30 PM to 10 PM. General admission is $5 Tuesday through Sundays and free on Mondays.

Click here to learn more and to check out the calendar of special events. Click here for directions.


To get a taste of what Christmas is like in Germany, check out Christkindlmarket in Daley Plaza. This is a free, annual event that features vendors selling traditional German crafts and treats like ornaments, cuckoo clocks, hand-knit gloves, hot-mulled wine, and more. It’s a holiday market unlike any other.

Christkindlmart runs Sundays through Thursday from 11 AM to 8 PM and Fridays and Saturdays from 11 AM to 9 PM. On Christmas Eve (December 24), the market will be open from 11 AM to 4 PM.

Click here to learn more about Christkindlmarket. Click here for directions.

Ice Skating At Millenium Park

Ice skating at Millenium Park is another great way to spend some time during winter in Chicago. Skating at the McCormick Tribune Ice Rink in Millennium Park runs from November 18 through March 5. Admission is free, but you’ll need to reserve a ticket online ahead of time. 

Slip on your ice skates and skate for a full 90-minute session and enjoy snacks and hot drinks from Momentum Coffee and Millenium Hall. If you need a little help on your skates, there are free skating lessons (reservations required) from 9-10 AM on most Saturdays and Sundays. 

The ice rink is open daily depending on weather. You’ll need to reserve a skating session before you go. Reservable Ice Skating sessions are 90 minutes, beginning at 11 AM, 1 PM, 3 PM, 5 PM, 7 PM, and 9 PM Monday through Sunday.

Click here to learn more and purchase tickets to Ice Skating at Millenium Park. Click here for directions.

Ice Skating At Maggie Daley Park

Ice skating rinks are popular attractions in Chicago during the holidays, but the one at Maggie Daley Park is one of the more popular ones, and for good reason. Unlike the more traditional ice skating venues, skaters glide across and around a ribbon of ice, rather than a standard rink. 

You’ll need to reserve tickets in advance, even if you plan on bringing your own skates. With so many opportunities to hit the ice, you can easily make ice skating one of your new holiday traditions. 

Click here to learn more and purchase tickets. Click here for directions. 

Christmas Around The World And Holidays Of Light At The Museum Of Science And Industry

Even the museums in Chicago like to participate in the holiday festivities. The Museum of Science and Industry hosts their annual Christmas Around the World and Holidays of Light. There are 50 trees elaborately decorated to represent different holiday traditions from all around the world. 

Click here to learn more and purchase tickets to Christmas Around the World and Holidays of Light at the Museum of Science and Industry. Click here for directions. 

Visit The Walnut Room

Visiting the Walnut Room in Macy’s for a holiday meal is one of the most festive things to do in Chicago during the holiday season. Before the world-famous Walnut Room, there weren’t any restaurants in department stores. 

The 17,000 square foot dining room is every bit as elegant as it is grand. Take a break from shopping and sit down for a holiday meal you won’t soon forget. The opening of holiday dining at the Walnut Room coincides with the reveal of the 55th annual holiday windows and State Street signature trumpets.

Click here for more information and to make a reservation. Click here for directions. 

Watch A Holiday Movie At The Drive-In

ChiTown Movies is an old-fashioned drive-in movie theater that gives you the chance to watch some of your favorite holiday movies from the comfort of your own car. Plan accordingly and you’ll be able to watch favorites like Elf, Love Actually, The Polar Express, and more.

Click here for more information about the movies playing at the drive-in. Click here for directions.

Catch The Holiday Train And Bus

The Allstate CTA Holiday Fleet is one of Chicago’s most unique and beloved holiday traditions. Celebrating its 31st year of operation, the Holiday Train and Holiday Bus will be traveling through the neighborhoods of Chicago, spreading holiday cheer all along the way. The train and bus are decked out in lights and other festive decor to really put you in the holiday spirit.

Click here to learn more about The Holiday Train and Bus and to take a closer look at their schedules.  

Winterland At Gallagher Way

This year, the annual holiday experience, Winterland at Gallagher Way, is moving many of its holiday festivities from beside the iconic Wrigley Field, to inside the ballpark for a truly unique wintry attraction. 

The 12,000-square-foot Gallagher Ice Rink is easily the star attraction, but don’t forget to check out other on-field games, carnival rides, a miniature train, an ice slide, and even ice bumper cars. You don’t want to miss out as Wrigley Field is transformed into a winter wonderland!

Click here to learn more and to purchase tickets. Click here for directions. 

See The Iconic City Of Chicago Christmas Tree

The City of Chicago Christmas Tree is so epic, it’s definitely worth seeing in person. A larger-than-life Christmas tree is put up in Millennium Park every year and stays there until the beginning of the year. The tree is adorned with twinkling lights and topped with a glowing star and is a beautiful sight to see in person. 

Click here for directions.

Illumination: Tree Lights At The Morton Arboretum

The Morton Arboretum’s annual holiday light show is back for the 10th year. People come from all over to see the mile-long, walk-through attraction featuring LED lights and music. The light displays are set up amid 50 acres of trees. 

You will need to purchase a timed entry ticket for Illumination, which runs from November 19 through January 7. You can usually get 20 percent off deals on select Tuesdays, Wednesdays and Thursdays.

Click here to learn more and to purchase tickets. Click here for directions. 

Lightscape At Chicago Botanic Garden

Few holiday festivities sell out as quickly as Lightscape at The Chicago Botanic Garden. The annual display of festive lights brings hundreds of guests to the forest preserve during the holiday season. 

Once the sun goes down, the lights come on. There are several installations to see, including a 110-foot tunnel made up of 100,000 lights, a group of trees that appear to sing holiday songs, and a 130-foot-long tunnel lit by more than 700 handmade acrylic stars. 

Click here to learn more and purchase tickets. Click here for directions.

Amaze Light Festival

The Amaze Light Festival is another opportunity to view holiday lights while you can. It will be held in Tinley Park this year, with five themed light-up exhibits as well as a Christmas market, photo ops, and more. 

With a general admission ticket, you get access to the light shows, food and beverage areas, and shops. There are also some exciting add-ons to consider for even more fun at the Amaze Light Festival.

Click here to learn more and purchase tickets. Click here for directions.

Light Up The Lake

If you want to enjoy holiday festivities but aren’t a fan of frigid winter temperatures, head to Light Up the Lake at the Navy Pier. This indoor attraction takes place in the huge 170,000-square-foot Festival Hall. You can enjoy ice skating, kiddie train rides, and a lit-up maze. There’s also a 600,000-bulb light show and a reflection pond. Each ticket includes a ride on the Navy Pier’s 200-foot Centennial Wheel. The gondolas are fully enclosed and heated so it’s just as enjoyable during the winter as it is in the summer!

Click here to learn more and purchase tickets. Click here for directions.

Listen To Classical Music At A Candlelight Concert

For a more unique holiday activity, consider attending one of Chicago’s Candlelight Concerts. The Candlelight Concerts is a series of classical music concerts that take place by candlelight. Chicago’s Candlelight Concerts in December feature holiday-inspired music, making for a memorable holiday experience.

Click here to learn more and purchase tickets. Click here for directions.

Watch Art On TheMart

Art on theMart is the largest permanent digital art projection in the world. Contemporary artwork is projected across the 2.5-acre river-facade of theMart, and during the winter the program takes on a holiday theme.

The winter program features Joffrey Ballet’s “The Nutcracker”. The program of projections runs for 30 minutes and is shown twice per night. You can watch the show from the jetty section of the Chicago Riverwalk on Wacker Drive between Wells Street and Franklin Street.

Click here to learn more. Click here for directions. 

Millennium Park Holiday Sing-Along

What used to be known as “Caroling at Cloud Gate” is now Millennium Park Holiday Sing-Along and it’s back for four Fridays during the 2022 holiday season. Local singers and choruses come together to joyfully sing out in celebration of the season. 

This year’s sing-alongs will take place on November 25, December 2, 9, and 16. Admission is free.

Click here to learn more. Click here for directions.

Immersive Nutcracker: A Winter Miracle

The Immersive Nutcracker: A Winter Miracle is an exciting holiday experience unlike any other, and it’s one the whole family can enjoy. The Immersive Nutcracker brings the timeless classic to life on a ginormous scale. As the music of Peter Ilyich Tchaikovsky’s iconic music fills your ears, you’ll be completely immersed in Christmas magic. It’s an attraction you just have to experience for yourself. 

Click here to learn more and purchase tickets. Click here for directions. 

Drink Glogg At Simon’s Tavern

This is one festive activity that Chicagoans know and love. Drinking the signature mulled wine, or glogg, at Simon’s Tavern is a regular holiday tradition. Simon’s Tavern is a dive bar in Andersonville that has been in business for decades. It’s always packed, but even more so during the holiday season when people flock to the bar for their own serving of glogg. 

Click here to learn more. Click here for directions.

Sip On Specialty Hot Chocolate

Spending the holiday season in Chicago wouldn’t be complete without indulging in some of the incredible hot chocolate drinks available in restaurants across the city. Buyer beware: these aren’t your normal hot cocoas. They’re some of the most unique, decadent, and extravagant hot chocolates you’ll ever encounter. 

Some of the more noteworthy options include the epic, monstrous hot chocolates at Bombobar, the decadent South Asian-inspired cocoa at Chocolat Uzma, and the drinking chocolate from Cocoa & Co. that was named one of the best hot chocolates in the country on FoodNetwork.com.

Holiday Shopping On The Magnificent Mile

The Magnificent Mile is the most popular street in Chicago for shopping. You can take in all the sights and wonders of the holidays in Chicago while taking care of your Christmas shopping at the same time. 

The Magnificent Mile offers enough unique boutiques, department stores, and high-end shops to let you finish your holiday shopping all in one place.

Click here to learn more. Click here for directions.

Holiday Events in Chicago

Holiday Events In Chicago

what to do during the holidays in chicago
Nothing can compare to spending the holidays in Chicago!

I might be slightly biased, but I really do think Chicago is the best place to be during the holidays. If you prefer to spend the holiday season somewhere else, I’d love to hear about it! Or if you also enjoy Chicago during the holiday season, tell me about your favorite festivities! 

To read more about my favorite places to go and things to do, check out my blog.