As a lifelong Chicago local, the holiday season is always the most magical time of the year to visit the city. Even when it’s freezing cold, something about it just feels like being in a Hallmark movie! The streets are all lit up, there’s displays in every window, and everyone just feels more merry.
Are you visiting Chicago this winter? Are you a local looking for ways to get in the holiday spirit? Here are 10 cozy things to check out from high energy christmas clubs to classical candlelight concerts.
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1. Glide Around the Skating Ribbon
Starting off with a classic Chicago tradition: ice skating. There are a few places to skate outside in the city (like Millenium Park) but my favorite is the skating ribbon at Maggie Daley Park. Instead of being a typical rink, the ribbon is a winding quarter mile path lined with alpine trees. You’ll have a great view of the skyline as you glide around… or hang on to the wall for support.
In 2022 the ribbon opens November 18th. Going to the skating ribbon has become a December tradition for my family. Bring your own skates (and skate free!) or rent them for $16-22 depending on the date. Make sure you get tickets in advance!
2. Sip Mulled Wine at a Traditional Holiday Market
Christkindlmarket is an authentic German holiday market with food, drinks, live entertainment, and unique handmade gifts. I definitely recommend trying the alpine cheese and mulled wine! If you’re looking for a holiday souvenir, be sure to get a drink in the annual souvenir mug! Many agree that this market is one of the best things to do in Chicago during the holiday season, so be prepared for a crowd.
This year, the market opens November 18th. Admission is FREE and there are three locations: Daley Plaza, Wrigleyville, and Aurora.
3. Do it all at Jack Frost Winterfest
Jack’s is Chicago’s largest Christmas popup and the ultimate holiday experience for the whole family. You can find snow tubing, ice skating, bumper cars, bars, insta-worthy photo ops, axe throwing, fortune tellers, beautiful light displays, and a Christmas tree farm! It’s also affordable with general admission starting at just $10 for adults. Tickets increase in price (or sell out!) as the date gets closer, so make sure you get your tickets in advance!
This year, Jack’s is open December 3rd – December 31st. Jack’s is also 100% cashless!
4. Party all night at Frosty’s Christmas Bar
Have you ever been to a club and wished it looked like Christmas exploded all over it? Frosty’s is the place for you. This 3 level bar is the perfect way to get in the Christmas *spirit* with your friends. Party until 4 AM with festive cocktails, dancing elves, singing Santa, and super fun photo-ops. Admission is 21+ and starts at around $30 when you buy online.
Frosty’s is open November 19th – January 1st. Buy your tickets in advance before they sell out!
5. Watch a Drive-In Christmas Movie
Experience not only a drive-in movie, but a CHRISTMAS drive-in movie at ChiTown Movies this winter. While they show plenty of classic films like Jurassic Park and Back to the Future throughout the year, starting in late November you can catch holiday classics like Home Alone and Elf! You can even get reasonably priced food delivered straight to your car like $1 peanuts, $5 nachos, and a $5 hot dog + fries. Every car gets a free small popcorn!
Tickets are $33/vehicle. Make sure you reserve your spot in advance! This is a dog friendly experience.
6. Immerse Yourself in the Lincoln Park Zoo Lights
The Lincoln Park Zoo Lights are a favorite holiday tradition for Chicagoans of all ages. Watch the city zoo transform into a winter wonderland with thousands of lights. For a couple dollars extra, you can ride the ferris wheel to get a view from above, find your way through the light maze, take a spin on the carousel, and ride the train.
If you want a really memorable experience, you can even flip the switch to turn on the lights (for a couple hundred dollars). The zoo also holds special events on select dates like BrewLights, Adults Night Out, a Sensory Friendly Night, and Zoo Years Eve.
Admission is free on Mondays and $5 on all other regular Zoo Lights dates. All dates require a ticket so purchase in advance before they sell out!
7. Cheer on the Blackhawks at the United Center
What’s more wintery than watching a game of the country’s favorite sport on ice? There are lots of dates to choose from, and starting November 30th the United Center gets decked out in lights and Blackhawks holiday decor! You can also try seasonal holiday beverages. Seats on the first level start at around $150 each, but you can get seats farther back for about $25 each. Get your tickets here.
8. Shop for everyone on your list on Michigan Ave
If you want to feel like the main character of a Christmas movie, walk down Michigan Avenue when all the lights and decorations are up. Holidays on the Magnificent Mile kick off with an annual tree-lighting parade featuring Mickey and Minnie Mouse on November 19th this year. You can find gifts for everyone as you wander Water Tower Place, or just window shop. Pretty much any store you can think of is on the Mag Mile!
9. Relax at a Candlelight Concert
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For those looking for something a little more romantic and intimate, check out the candlelight concert series. Experience live music illuminated by candlelight in some of the most beautiful venues in Chicago. There are a variety of festive concerts to choose from, or you can opt for tributes to Beyonce, Queen, and Taylor Swift. Explore all the options and get your tickets here for around $35.
10. Admire Classics at the Art Institute
Something about wandering around admiring classic works of art is so cozy to me. The Art Institute of Chicago is one of the most renowned art collections in the world and features pieces by Monet, Van Gogh, Picasso, and modern artists such as David Hockney. This is a great way to escape the cold for a few hours and feel inspired!
Regular price adult tickets are $25, but there are several discounts for Chicago residents, teens, seniors, students, and more. Advanced tickets are required, so make sure you pick a time here.
