55 Fun Things to Do In Chicago in January From a Local

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 and writing two books about Chicago, I’ve learned that the city is a dynamic destination year-round. 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 Lightscape 21 and Over – Jan. 2, 2026

Enjoy the wintery magic of illuminated trails at the Chicago Botanic Garden’s Lightscape 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 – Jan. 3-30, 2026

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. 9-10, 2026

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: Ska Fest – Jan. 3, 2026

One surefire way to warm up is skanking in a rock club around fellow ska fans. Cobra Lounge delivers a ska fest called Skanking Through the Snow, including bands like Something To Do, Runaway Ricochet, Rude Echoes, and more.

Need more information on what to do while you’re in Chicago? Check out all of my Chicago articles and don’t miss my Chicago books Secret Chicago: A Guide to the Weird, Wonderful, and Obscure and Chicago Scavenger!

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.

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 Celebration – Jan. 7, 2026

The holiday season continues on Three Kings Day at Vintage Bar in Little Italy. Join Windy City Salsa Studio for salsa energy, delicious food, music, dancing, and community spirit.

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 6-8, 13-20, 27-29. Reservations are recommended.

11. The Phantom of the Opera – Through Feb. 1, 2026

The Cadillac Palace Theatre transforms into the Paris Opera House for The Phantom of the Opera. Enjoy the music and mystery of this classic love triangle from Broadway in Chicago.

12. Chicago Misconceptions : Criminally Overrated – Jan. 6, 2026

Nerd out with Chicago for Chicagoans as experts dig into some of the city’s juiciest, most controversial history. Dive into misconceptions about Chicago, exploring the unfair stereotypes, urban legends, and assumptions of the city’s history.

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 Month – Jan. 10-31, 2026

Explore a different type of beer hall culture on each day of Beer Hall Week at Dovetail Brewery. Visit the brewery in North Center across three Saturdays to experience beer hall culture from Prague, Köln, and Vienna.

15. “This Too Shall Slap” at the Second City

If you’re looking for laughs, you can’t go wrong with the legendary Second City in Old Town. Its current Mainstage Revue, “This Too Shall Slap,” is a sketch comedy show filled with chaos and charm that will make you question your reality.

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 in Lincoln Square, City Lit in Logan Square, and 57th Street Books in Hyde Park.

17. Root for the Windy City Rollers – Jan. 17, 2026

This isn’t roller skating, it’s roller derby! Don’t miss the action-packed Windy City Rollers as the top two teams face off for the Juanna Rumbel Championship, and be amazed by the ferocity of these female athletes.

18. Open Heart: An MLK Tribute Concert – Jan. 19, 2026

Honor Dr. Martin Luther King, Jr. at the Chicago Sinfonietta’s annual concert. This performance at the Auditorium Theatre in the Loop pays tribute to Dr. Daniel Hale Williams, a Black Chicago surgeon who performed the first successful open-heart surgery.

19. Marvel’s Spider-Man: Beyond Amazing – Through Feb. 8, 2026

Get your Spidey senses tingling with the Spider-Man exhibit at the Museum of Science and Industry in Hyde Park. Explore the beloved character’s evolution from comic books to TV, movies, and more and enjoy hands-on activities for kids.

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. 12, 2026

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 “New Leaf.”

22. Suzy Eddie Izzard at the Chicago Shakespeare Theatre – Jan. 16-17, 2026

The legendary Suzy Eddie Izzard returns to Chicago Shakespeare Theater, the site of her acclaimed solo performance of Hamlet, for a two-night benefit. Izzard will talk Shakespeare, marathons, acting, performing in different languages, and answer questions from the audience.

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. 8-31, 2026

Tomorrow Never Knows is a music festival that stretches across four weeks at indie music venues across the city to spotlight up-and-coming artists and national acts. Don’t miss acts like Perfume Genius, DIIV, Swamp Dogg, and Real Estate.

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. 21-Feb. 1, 2026

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. Three Girls From Bronzeville Book Club Run – Jan. 24, 2026

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! Join this three-mile run on a route through Bronzeville inspired by journalist Dawn Turner’s award-winning memoir, Three Girls From Bronzeville, then meet the author.

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. 16-18, 2026

If you can’t wait until spring, get your baseball on at the annual Chicago Cubs Convention. Meet the 2016 World Series champs and current players. 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 Dazzling Interiors Architectural Walking Tour takes you inside stunning architectural marvels stunning interiors downtown. Plenty of the tour is spent inside, so you can enjoy it no matter the weather.

36. Dim Sum & Drag – Jan. 10, 2026

You’ve had dim sum, but have you had dim sum brunch accompanied by Asian drag performers? Dim Sum & Drag is back with a Pokémon drag brunch your favorite performers bring Pokémon characters to life at Furama in Uptown.

37. West Loop Beer and Pizza Fest – Jan. 24, 2026

It doesn’t get better than beer and pizza. The West Loop Beer and Pizza Fest invites you to spend the afternoon sampling 10 beers and 5 different pizzas.

38. Reggeton Rave – Jan. 24, 2026

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 Strapped and ABOLISHVICTORY! 

40. Hear the Chicago Symphony Orchestra for Free – Jan. 25, 2026

The Chicago Symphony Orchestra heads to the Epiphany Center for the Arts in West Town for a free show. Let’s Think About This… combines music, speech and movement, while the Civic Fellows collaborate with members of the International Contemporary Ensemble.

41. MLK Day at the Chicago History Museum – Jan. 19, 2026

Celebrate the legacy of Martin Luther King Jr. with the entire family at the Chicago History Museum in Lincoln Park. Learn about Dr. King’s fight for civil rights, enjoy hands-on activities, and find out how to become more civically engaged in your community. Admission will be free for Illinois residents.

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. Cider Summit Chicago – Jan. 31, 2026

No gluten? No problem. Cider Summit Chicago is back for the 12th annual festival. Sample more than 125 ciders from 40 producers, watch the Spanish pour competition, and get your snack on at Navy Pier.

44. Disney on Ice: Jump In! – Jan. 22 – Feb. 8, 2026

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. 24, 2026

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 and drink hot cocoa by a bonfire at Northerly Island Park.

47. Brave the Polar Plunge – January 24, 2026

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. 24, 2026

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. Amadeus at Steppenwolf – Through Jan. 25, 2026

Wolfgang Amadeus Mozart and Antonio Salieri go head-to-head in a thrilling rivalry for musical dominance in the 18th-century Viennese court. See the Tony and Academy Award-winning performance of Amadeus at the Steppenwolf Theatre in Lincoln Park.

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. Julia Keefe Indigenous Jazz Ensemble – Jan. 30, 2026

Hear the work of Native jazz pioneers and Indigenous musical traditions with the Julia Keefe Indigenous Jazz Ensemble at the Logan Center for the Arts in Hyde Park. The ensemble of Indigenous musicians features a lineup spanning North and South America.

52. Chicago Restaurant Week – Jan. 23 – Feb. 8, 2026

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. Drag Race: The Experience

Are you ready for your moment in the spotlight? Get your wig ready, because this interactive experience brings the world of RuPaul’s Drag Race to life. Drag Race: The Experience lets you choose your favorite costume, sashay down the main stage, and film a confessional without leaving Logan Square.

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, Chaos, & Dinner?”

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 Field Museum, 360 Chicago Observation Deck, and the Art Institute are easier to get into and more enjoyable.

How cold is Chicago in January?

January is 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 Millennium 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!

Need more information on what to do while you’re in Chicago? Check out all of my Chicago articles and don’t miss my Chicago books Secret Chicago: A Guide to the Weird, Wonderful, and Obscure and Chicago Scavenger!

Find out what to do in Chicago throughout the year:

• Fun Things to Do in Chicago in February
• What to Do in Chicago in March
• Fun Things to Do in Chicago in April
• Fun Things to Do in Chicago in May
• What to Do in Chicago in June
• Fun Things to Do in Chicago in July
• What to Do in Chicago in August
• Fun Things to Do in Chicago in September
• What to Do in Chicago in October
• Fun Things to Do in Chicago in November
• What to do in Chicago in December

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