55 Fun Things to Do In Chicago in January

While January is typically Chicago’s coldest month, it doesn’t mean that you have to stay inside. After living in Chicago for nearly two decades, I’ve learned that the city is a dynamic destination year round and there’s no shortage of fun things to do in Chicago in the winter. Start the year by exploring Chicago’s cultural attractions, sporting events, concerts, comedy shows, and neighborhood gems. Whether you’re a local or are visiting Chicago in January, here are 55 fun things to do in Chicago in January.

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Fun Things to Do in Chicago in January

1. Discover the City’s Hidden Gems with Secret Chicago

I wrote the book on Chicago’s weird, wonderful, and obscure places. Winter is the perfect time to follow the book to a circus school in a church, have a cocktail in an old train car, or learn how to navigate the underground world of the Pedway! Get the book.

2. Chicago Botanic Garden’s Cocktails Under the Lights – Jan. 3, 2025

Enjoy the wintery magic of illuminated trails at the Chicago Botanic Garden without the family crowds. This 21 and over only evening at the Chicago Botanic Garden features specialty cocktails for purchase.

3. Buddy Guy’s January Residency at Legends – Through Feb. 2, 2025

January is the only month that blues legend Buddy Guy takes the stage at his Legends club. It may be cold outside, but inside the 88-year-old blues icon delivers a scorching show. It’s one of my favorite Chicago traditions! 

4. Bill Murray and His Blood Brothers – Jan. 3-4, 2025

You never know when you might see comedian and Chicago native Bill Murray pop up around town. He’ll join blues musicians Mike Zito and Albert Castiglia, known as Blood Brothers, for a lively show at Thalia Hall. 

5. Skanking Through The Snow: Midwest Ska Fest – Jan. 4, 2025

One surefire way to warm up is skanking in a rock club around fellow ska fans. Cobra Lounge delivers with a Midwest Ska Fest including bands like Beat the Smart Kids, Run and Punch, Space Monkey Mafia, and more.

Download a free printable calendar for January 2025 featuring one of Chicago’s hidden gems.

6. Try Dry January

Not drinking? Drink menus throughout the city have added non-alcoholic cocktails to their offering from Kumiko in the West Loop to Virtue in Hyde Park. If you’re looking for an NA bottle shop and sober community space check out In Good Spirits in West Town and Bendición Bottle Shop online.

7. Recharge at an Indoor Garden

If grey skies are getting you down, get a dose of greenery at one of Chicago’s conservatories. Free for all to visit, they are truly one of Chicago’s treasures. I even got married at one! The Lincoln Park Conservatory features palm, fern, and orchid houses. The larger Garfield Park Conservatory has waterfalls, aroids, and a desert house as well as special exhibits. Reserving a timed entry is recommended.

8. Three Kings Day – Jan. 6, 2025

The holiday season continues on Three Kings Day at the Puerto Rican Cultural Center in Humboldt Park. Take a photo with the Three Wise Men and join the community to celebrate with giveaways and treats.

9. Chill on a Covered Patio

Chicagoans don’t like feeling cooped up all winter, so we bring the outside in. If you’re looking for a covered patio check out the Village Tap in Roscoe Village or Cafe-Ba-Ba-Reeba in Lincoln Park. Château Carbide at the Pendry Hotel has a chic winter rooftop with fireplace tables while the Godfrey Hotel created a rooftop Winter Wonderland.

10. Shedd Aquarium Free Days

The iconic Shedd Aquarium is one of Chicago’s most popular attractions for good reason. See dolphins jump, belugas soar, and penguins play at one of the world’s largest aquariums. Don’t miss the new Wonder of Water exhibit spanning two 28,000-gallon tanks. The Shedd offers free days for Illinois residents January 7-9, 14-21, and 28-30. Reservations are recommended.

11. Shucked at Broadway in Chicago – Jan. 7-19, 2025

A musical about saving a small town’s corn crop? How very Midwestern. Part of the Broadway in Chicago series, Shucked is a Tony-winning musical about an unlikely hero, a lovable con man, and the heart & soil of Cob County.

12. Scandal: Salacious Stories of Chicago’s Past – Jan. 7-Mar. 25, 2025

Nerd out with Chicago for Chicagoans as experts dig into some of the city’s juiciest, most controversial history. Get the tea on scandalous stories from Chicago’s first murder to “Unforgivable Frank Lloyd Wright.”

13. Soar over the City at Flyover Chicago

Chicagoans and visitors alike will enjoy this thrilling ride over the city from never-before-seen views. Flyover Chicago flies you over the city to admire it from all new perspectives. Marvel at Chicago’s iconic architecture and lakefront from a unique perspective with this 30-minute immersive ride.

14. Dovetail Beer Hall Week – Jan. 10-12, 2025

Explore a different type of beer hall culture on each day of Beer Hall Week at Dovetail Brewery. Friday will feature Czech-style beer service, Saturday serves up 19th century Austria, and Sunday offers a German match of Altbier versus Kölsch.

15. Improvised Twilight Zone  – Jan. 10-31, 2025

Enter the Improvised Twilight Zone through the doors of the Annoyance Theatre in Lakeview. The improv show will explore a dimension as vast as space and as timeless as infinity, the middle ground between light and shadow, between science and superstition. 

16. Visit an Independent Bookstore

Chicago boasts an incredible community of independent bookstores throughout the city. As an author, I’ve had the pleasure of getting to know many of Chicago’s fantastic booksellers. A few of my favorite Chicago bookshops include the Book Cellar, Volumes Bookcafe, City Lit, and 57th Street Books.

17. Root for the Windy City Rollers – Jan. 11, 2025

This isn’t roller skating, it’s roller derby! Root for Chicago’s Windy City Rollers in their third home game of the season and be amazed by the ferocity of these female athletes.

18. Too Hot to Handel: The Jazz-Gospel Messiah – Jan. 11-12, 2025

This isn’t your grandparents’ Handel. The iconic “Messiah” piece is reimagined for Too Hot to Handel with an R&B, jazz, and gospel spin. Jump to your feet at the Auditorium Theatre for this uplifting reinterpretation.

19. 007 Science: Inventing the World of James Bond

If you’ve ever wanted a peek into Q’s lab in the James Bond movies, the 007 Science exhibit at the Museum of Science and Industry takes you behind the scenes. See cars and gadgets from the films as well as real espionage equipment. Don’t miss your chance to admire the 1965 Aston Martin DB5 from Skyfall and the jetpack from Thunderball.

20. Sample Chicago Spirits at a Distillery

Chicago is the nation’s brewery capital, but if you’re more into spirits we’ve got you covered. January is a great time of year to meet up with friends in a distillery tasting room and sample Chicago spirits. Koval was the first Chicago distillery to open after Prohibition, and it boasts a sunny, inviting tasting room in Ravenswood. In West Town, Rhine Hall focuses on fruit brandy while in the West Loop CH distillery’s line includes the cult favorite Malort. Marz is best known for their beer, but they’ve gotten into the spirits game with a bourbon, gin, and vodka in their design-forward Bridgeport taproom.

21. The Moth Chicago StorySLAM – Jan. 13, 2025

Bring your best stories to this open-mic storytelling competition at the Den Theatre in Wicker Park or just sit back and listen. The Moth StorySLAM features five-minute stories from anyone who enters, and this month’s theme is “Reset.”

22. Jaja’s African Hair Braiding – Jan. 14-Feb. 2, 2025

Enter a Harlem hair salon via the Chicago Shakespeare Theatre for this Broadway show. Jaja’s African Hair Braiding West African immigrant braiders share their dreams and secrets as they work their magic on the locals’ locks.

23. Warm Up at Afternoon Tea

Feel fancy, eat snacks, and enjoy a warm cuppa. What’s not to love about afternoon tea? Our favorite places in Chicago for afternoon tea include the majestic Palm Court at the Drake Hotel, iconic Palmer House Hotel lobby (birthplace of the brownie!), and the Lobby at Peninsula Chicago for a contemporary tea. For an authentic Eastern European tea experience visit Russian Tea Time just steps from the Art Institute. Before you go, don’t forget to review your afternoon tea etiquette.

24. Chicago Crime and Mob Bus Tour

Chicago’s notorious crime history isn’t its finest moment, but its stories still attract attention a century later. Dig in with the Chicago Crime and Mob Bus Tour and learn the stories behind the Al Capone and John Dillinger. Enjoy it all from the comfort of a coach bus no matter the weather.

25. Tomorrow Never Knows Festival – Jan. 15-19, 2025

Tomorrow Never Knows is a five-day music festival stretches across indie music venues across the city to spotlight up-and-coming artists and national acts. Don’t miss acts like Half Waif at Sleeping Village, Maps & Atlases at Metro, and Lutalo at Schuba’s.

26. See Jaw-Dropping Views at 360 Chicago

360 Chicago boasts one of the best views of Chicago hands down. Visit the 94th floor observatory for iconic views of Chicago and Lake Michigan. TILT over the city if you dare and order a drink at the CloudBar while you soak in the scenery. 

27. Chicago International Puppet Theater Festival – Jan. 15-26, 2025

Puppets take center stage during the Chicago Puppet Fest. The festival spans 12 days and dozens of Chicago venues, featuring more than 100 puppetry activities. From children’s productions to adults-only cabarets, there’s a puppet event for everyone.

28. Run Through LGBTQ+ History – Jan. 16, 2025

Read & Run Chicago is a book club that takes runs based on books about Chicago. I’ve even led runs based on both of my books! Hit the streets of Lakeview for this 3-mile run based on Rebecca Makkai’s award-winning novel, The Great Believers.

29. Cozy Up at a Bar with a Fireplace

Cold outside? Just add a fireplace. Sipping a cocktail by a roaring fire is one of the most pleasurable things to do in Chicago in the winter. Stop by Wilde Bar in Lakeview, Frontier in Noble Square, Moody’s in Edgewater, and Scofflaw in Logan Square.

30. Cheer on the Chicago Blackhawks

If you’d rather leave ice skating to the professionals this winter, head to the United Center to watch the Blackhawks take the ice. We may not be leading the NHL standings, but at least tickets are more affordable than when they were Stanley Cup champs.

31. Sip on a Hot Chocolate

Indulge in a comforting sweet treat with a warm cup of hot chocolate around Chicago. Chef Mindy Segal may have closed her Hot Chocolate restaurant, but you can still purchase her hot chocolate blends at Mindy’s Bakery in Wicker Park. For European-style sipping chocolate visit Katherine Anne Confections in Logan Square. Prefer Mexican hot chocolate? Hit up Xoco, Cafe Jumping Bean in Pilsen, or Back of the Yards Coffee. 

32. Chicago Cubs Convention – Jan.17-19, 205

If you can’t wait until spring, get your baseball on at the annual Chicago Cubs Convention. Meet Cubs greats like Kerry Wood and current players like Michael Busch. With autographs, memorabilia, and meet and greets, you won’t even think about last season’s record.

33. Cruise the Chicago River in a Hot Tub

Why wait until summer to get out on the water when you can float from the comfort of a hot tub boat? Chicago Boat Company offers 90-minute hot tub boat cruises for up to six passengers. Pack your swimsuit and matching earmuffs!

34. Go Sledding

Despite our flat prairie landscape, Chicago does have a few hills. Grab a sled and go for a ride in Humboldt Park, Palmisano Park in Bridgeport, Cricket Hill in Lincoln Park, and the tallest hills in the Dan Ryan Woods near Beverly. In Soldier Field’s south parking lot, they even provide man-made snow! You can also find places to snowshoe in the Chicago Park District and get started ice fishing.

35. Peek Inside Chicago’s Iconic Architecture

Have you ever wondered what’s inside all the skyscrapers you walk past downtown? Chicago’s Secret Interiors Architectural Walking Tour takes you inside stunning architectural marvels that you might not know about from the Gilded Age to the Jazz Age. Plenty of the tour is spent inside so you can enjoy it no matter the weather.

36. Dim Sum & Drag – Jan. 18, 2025

You’ve had dim sum, but have you had dim sum brunch accompanied by Asian drag performers? Dim Sum & Drag is back to celebrate the New Year with some glamour gods & goddesses for a sickening drag brunch at Furama in Uptown.

37. West Loop Beer and Pizza Fest – Jan. 18, 2025

It doesn’t get better than beer and pizza. The West Loop Beer and Pizza Fest invites you to spend the afternoon sampling 15-20 beers and 5 different pizzas.

38. Reggeton Rave – Jan. 18, 2025

Latinx and Electronic music collide for an epic dance party at Reggaeton Rave. Lose yourself in pulsating rhythms and unmatched energy at Concord Music Hall in Logan Square.

39. Empty Bottle Free Mondays

When was the last time you listened to new music? Legendary indie rock club the Empty Bottle makes it easy with its Free Mondays series. Head to Ukrainian Village this month for headliners like Man-Eaters, Facing, and Dogcatcher.

40. Hear the Chicago Symphony Orchestra for Free – Jan. 19, 2025

The Chicago Symphony Orchestra heads to the South Shore Cultural Center for a free show. Listen to Sergei Rachmaninov’s Second Symphony featuring flutist Valerie Coleman and violinist Jessie Montgomery.

41. Chicago Sinfonietta’s “Black Being” MLK Tribute Concert – Jan. 19-20, 2025

The annual Chicago Sinfonietta concert honors Martin Luther King. This year features “Black Being” a composition by Flutronix blends flute, voice, and electronics with orchestra.

42. Dig into a Bowl of Ramen

What’s better than a hot bowl of ramen on a cold day? Akahoshi Ramen is all the rage, with reservations booking out weeks in advance. Wasabi has been slurping up ramen in Logan Square since 2010. For more noodle goodness try Strings where noodles are made fresh daily in Chinatown or the hidden, subterranean High Five Ramen in the West Loop. 

43. Lunar New Year Celebration at the Old Town School of Folk – Jan. 22, 2025

Enjoy a performance of Asian arts presented by the Chinese Fine Arts Society and Old Town School of Folk Music. Celebrate Lunar New Year with traditional Chinese and Thai dance, Asian music, and Chinese yo-yo. The event is free to attend with a recommended donation.

44. Disney on Ice: Let’s Dance – Jan. 23-26, 2025

Allstate Arena is transformed into a wintery Disneyland for Chicagoland’s kids and Disney adults for Disney on Ice. Sing along to your favorite Disney tunes while Mickey, Minnie, Donald, and Goofy DJ and skaters wow you with their stunts.

45. Be Amazed at the Chicago Magic Lounge

Did you know that Chicago has its own style of magic? The Chicago Magic Lounge will school you in the style and then amaze you with close-up and on-stage magic acts. But first, you have to find the entrance.

46. Meet Siberian Huskies at Polar Adventure Days – Jan. 25, 2025

The Chicago Park District brings winter fun to the city with Polar Adventure Days. Don’t miss the chance to see Siberian husky sled dog demonstrations by the Free Spirit Siberian Sled Team and Free Spirit Siberian Rescue. 

47. Brave the Polar Plunge – January 25, 2025

What’s crazier than jumping into Lake Michigan in January? Doing it with hundreds of other people! The cold is worth it for a good cause, as the Chicago Polar Bear Club’s annual Polar Plunge raises money for Chicago families in need.

48. Chicago Winter Whiskey Tasting Festival – Jan. 25, 2025

There’s nothing warmer than a whiskey festival in the dead of winter. Taste 20+ whiskies at the Chicago Winter Whiskey Tasting Festival. Chat with industry pros, win prizes, and dance to a DJ (after a few drinks, of course).

49. The 32nd “Annual” St. Timothy’s Day Dance – Jan. 25, 2025

The Hideout in West Town presents a celebration of at least 15 people named Tim at the St. Timothy’s Day Dance. Bring your favorite Tim and groove to (T)Imperial Sound, a swinging pop band with soul.

50. Take Your Ice Skates for a Spin

Is there anything more picturesque than skating side by side in the city? Ice skate in front of the iconic Bean at the McCormick Tribune skating rink or wind around the Skating Ribbon in Maggie Daley Park. Both offer skate rentals and require reservations.

51. Blues for the Soul – Jan. 25, 2025

Celebrate southern soul at the University of Chicago’s Logan Center for the Arts with Blues for the Soul. Jam out with Mississippi native Nellie “Tiger” Travis, Chicago pianist and vocalist Joe Barr, and soul singer Theo Huff and The Platinum Band.

52. Chicago Restaurant Week – Jan. 24-Feb. 9, 2025

If you’ve had some restaurants on your list to visit, now is the time. Chicago Restaurant Week is actually 17 days of discounted dining at nearly 500 local restaurants around town. Book your reservations in advance!

53. Take a Class at the Old Town School of Folk Music

Can’t hold a tune? The pros at the Old Town School of Folk Music have been schooling Chicagoans in music since 1957. Opt for guitar or banjo or branch out with lessons in mandolin or harmonica. If music isn’t your thing they also offer dance classes.

54. Cats: Predators to Pets

They’ve stolen our hearts, and the internet. Now you can learn about cats big and small in science, history, and pop culture in the Field Museum’s interactive Cats exhibit. You can even submit your own cat for competitions throughout the run of the exhibit!

55. Have Dinner at the Circus with Teatro Zizzani

You’ve heard of dinner and a show, but not like this. Teatro Zizzani combines the circus with comedy, cabaret, and spectacle. How could you resist a show called “Love, Dinner, and Chaos?”

Visiting Chicago in January FAQ

Is January a good time to visit Chicago?

You never know what kind of weather you’re going to get when you visit Chicago in the winter, but January will probably be cold. Yet there are many good reasons to visit Chicago in January. You are likely to find the best deals of the year on cheaper flights and hotels in January. I like to plan a staycation in Chicago in January to experience great hotels at a cheaper rate than usual. Fewer crowds around Chicago in winter mean that popular attractions like the Shedd Aquarium and Art Institute are easier to get into and more enjoyable.

How cold is Chicago in January?

January is the typically the coldest month in Chicago. According to the National Weather Service the average temperatures in January range from a high of 31 degrees to a low of 18 degrees. There is potential for ice and snow in January, and wind can feel even colder downtown near the lake. Check the forecast before you visit Chicago in the winter, so you know what to expect and pack accordingly. Winter in Chicago is still fun as long as you dress for the weather.

What should I wear to Chicago in January?

It’s essential to check the weather forecast before you visit Chicago in January so you can pack for the weather. Pack layers so that you can bundle up while you’re outside and stay comfortable when you’re enjoying indoor activities.

After nearly two decades of living in Chicago, here are my recommendations for what to wear in Chicago in the winter.

• Comfortable shoes for walking. A lug boot will keep women’s feet warm. If it’s snowing, consider a duck boot for men and for women.
• Wool socks for men and women.
• Thermals to wear under your jeans for men and women.
• Dress in layers so you can adjust to the different temperatures indoors and outdoors. Merino wool makes a great base layer for men and women. Women may want to layer with a flannel shirt or sweater.
• A long jacket, preferably made with down.
• A winter hat and my favorite merino wool gloves. Don’t forget a scarf!

Where to Stay in Chicago in January

Wondering where to stay overnight in Chicago in the winter? I love the views of Grant Park from the Blackstone Hotel and the iconic pool at the InterContinental. The Chicago Athletic Association has great views of Millenium Park and a rooftop fire pit while the LondonHouse looks at the Chicago River and boasts rooftop igloos.

Click here for a full list of Chicago hotels!

If you want to research hotels and vacation rentals for your Chicago visit, this map can help you compare the available options. It’s set to show hotels and rentals in downtown Chicago, but you can view any neighborhood where you’d like to stay.

I hope that you have fun in Chicago this January!