50 Fun Things to Do In Chicago in February from a Local

Is Chicago worth visiting in February? If you like fun things to do without the crowds, then yes! I’ve lived in Chicago for nearly two decades, and I’ve written two books about Chicago. Over the years, I’ve learned that the city never slows down. There are fun things to do in Chicago in the winter and all year long.

February in Chicago features events celebrating Black History Month, Lunar New Year, Valentine’s Day, and more. Whether you’re visiting Chicago in February or you’re lucky enough to live here, here are 50 fun things to do in Chicago in February.

Please note that this post contains affiliate links. I may earn a small commission for my honest recommendations, at no additional cost to you.

Fun Things to Do in Chicago in February

1. Go on a Bronzeville scavenger hunt with Chicago Scavenger

I wrote Chicago Scavenger, a book of 17 Chicago neighborhood tours with a twist—find each location by solving a riddle and photo clue! Black History Month is the perfect time to explore Bronzeville, the historic center of African American culture in Chicago. Discover places like the nation’s first Black art museum and the birthplace of gospel music! Get the book.

2. Learn About Black History at the DuSable Museum

Did you know that Chicago is home to the nation’s oldest African American history museum? Explore the DuSable Museum’s collection in Washington Park to get educated on Black history in the city, from Chicago’s first non-native resident to our first Black mayor to today. Admission is free every Wednesday.

3. International Carnivale at Navy Pier – February 7, 2026

Can’t make it to Carnivale in Brazil, Jamaica, or New Orleans? The free International Carnivale party at Navy Pier brings the Carnivale traditions to the Windy City with an indoor parade through the pier, complete with vibrant music and dancing.

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!

4. Tour Chicago’s African American Heritage

If you prefer a guided tour of Bronzeville, this half-day experience will take you on an African American Heritage Tour of Chicago in a private vehicle. Explore Black history landmarks, the homes of iconic Chicagoans, and soul food dining at a local restaurant.

5. Cuddle with a Furry Friend at a Cat Cafe

Looking for a purrfect way to brighten your day? How about playing and snuggling with feline friends at a cat cafe? Make a reservation to grab a coffee and meet the kitties at the Tree House Humane Society Cat Café in Rogers Park. Play arcade games while cats frolic around you at the Catcade in Lakeview. The cat cafe frequently sells out, so reserve ahead.

6. Fika Fest – February 7-8, 2026

Head to Chicago’s traditionally Swedish neighborhood of Andersonville to indulge in the Swedish tradition of Fika, a “coffee and cake break. Connect with others over a coffee and cocoa crawl or bring a puzzle to swap at the Swedish American Museum during Fika Fest.

7. My Funny Valentine Afternoon Tea – Through February 22, 2026

Feel the love at Alma at Hotel Zachary in Wrigleyville every Sunday in February beginning at 1 p.m. for My Funny Valentine Afternoon Tea. Enjoy teas, chocolate croissants, chocolate-covered strawberries, and heart-shaped Rice Krispies, plus a DIY dried floral bouquet station and a professional photo experience with the ones you love.

8. Indulge in the Chicago Pizza Tour

You can’t drive yourself if you’re in a food coma. Let the Chicago Pizza Tour do the work for you as you eat your way through four historic pizzerias. Devour this slice of Chicago’s culture with a small group, from tavern style to deep dish.

9. Chicago Theatre Week – February 5-15, 2026

There’s no better time to get out and see a show than Chicago Theatre Week. More than 60 shows across the city are deeply discounted to just $15 or $30. Whether you’re all about the drama or improv is more your speed, there’s a show for everyone.

10. Heated Rivalry Drag Brunch – February 7, 2026

The dress code is hockey chic at this drag brunch at Macy’s Walnut Room hosted by Lucy Stoole. Shane and Ilya will heat up the Chicago winter with a Heated Rivalry tribute that you won’t want to miss!

11. Have a Vibrant Day at the Color Factory

Celebrate color through all your senses in the Color Factory’s joyful exhibit. Journey through 14 installations that offer play and sensory exploration, including a giant ball pit! Whether you’re looking for a unique date or a day of family fun, the exhibit includes photo ops, treats, and colorful memories.

12. Taste of Ravenswood – February 6, 2026

Taste your way through the neighborhood’s food and beverages all inside the gorgeous Ravenswood Event Center. This year’s Taste of Ravenswood features businesses like Spacca Napoli, Half Acre, XOChimilco, Dovetail Brewery, and more.

13. Black History Concert Series:  Voices of Àṣẹ – February 24, 2026

Celebrate Africana music and its impact on Chicago at this free concert series at the Auditorium Theatre. Uniting Voices brings school program singers from all over the city together to perform this year’s theme, Voices of Àṣẹ.

14. Get Sweet at Margie’s Candies

Chicago’s most beloved sweet spot, Margie’s Candies, has been in business for more than a century! The nostalgic candy store and ice cream parlor has served generations of Chicagoans, and the Beatles even stopped by in the 1960s! If you want to eat like the Fab Four, order an atomic sundae.

15. Black History Month Celebration: Rooted in Resilience – February 4, 2026

Explore the connection between food, art, and culture at this free Black History Month celebration. Rooted in Resilience brings a film screening, panel discussion, a cookbook signing by chef Bryant Terry, and light bites for sampling to the Logan Center for the Arts in Hyde Park.

16. Crafting Character: The Costumes of Paul Tazewell – Through September 7, 2026

Admire the award-winning work of fashion and costume designer Paul Tazewell, the first Black man to win an Oscar in best costume design. From the Wicked movie to Broadway’s Hamilton, Tazewell’s talent is on display at the Museum of Science and Industry in Hyde Park.

17. Admire Chicago from its Highest Point at the Skydeck

Step beyond your comfort zone and into the glass box at Skydeck, located on the 103rd floor of the Willis Tower (Sears Tower if you’re a real one). Be the envy of Instagram with your glass balcony photos and admire skyline views from the highest point you can visit in Chicago.

18. Vintage House Valentine’s Market – January 31-February 1, 2026

Need a thoughtful gift for your Valentine or yourself? Shop 120 vendors at Vintage House Chicago’s free Valentine’s Market at Rockwell on the River in Avondale from 12-5 p.m.

19. Crying at the Shed – February 12-14, 2026

Spend Valentine’s Day watching messy romantic tearjerkers at the Salt Shed’s Crying at the Shed film fest. Ten films from Lost in Translation to Lady and the Tramp will have you reaching for your tissues.

20. Chicago Black Restaurant Week – February 8-22, 2026

You’ve been to Chicago Restaurant Week, but Chicago Black Restaurant Week celebrates its eleventh anniversary in 2026. Support Black-owned restaurants around town, enjoy special deals, and get a taste of traditional African American dishes.

21. Orchid Show at the Chicago Botanic Garden – February 7-March 22, 2026

Transport to the beauty of India with the Chicago Botanic Garden’s annual Orchid Show. The stunning show features a floor-to-ceiling peacock crafted from orchids, a banyan tree, and a tribute to groovy ’60s and ’70s.

22. Hit the Ice and Try Curling

Chicago loves a patio, even in the winter. Why not challenge your pals to a curling competition this month? The Gwen in River North boasts a rooftop bar with spiked hot chocolate and an iceless curling rink. Or hit the curling rink at Kaiser Tiger in the West Loop to try sweeping the ice.

23. Chicago Auto Show – February 7-16, 2026

Gearheads unite at the largest auto show in the country. Running since 1901, the Chicago Auto Show features vehicles from more than 20 manufacturers over more than one million square feet of exhibit space.

24. Warm Up at a Hidden Coffee Shop

If you need a caffeine boost or just something warm to hold while you’re exploring Chicago’s Loop, why not find a hidden coffee shop? Hero Coffee Bar is tucked into a historic alley off Jackson Boulevard. The tiny space is a charming bit of old Chicago.

25. Lunar New Year Parade on Argyle – February 21, 2026

Welcome the Year of the Snake in Uptown with a Lunar New Year parade! The fun steps off at Argyle and Sheridan around 10:30 am and features community groups, dancers, and performers.

26. Black Makers Market – February 7, 14, 21, 28

Stop by Navy Pier every Saturday in February for the Black Makers Market. Support local entrepreneurs, artisans, and creatives from across Chicago selling fashion, jewelry, and more.

27. Raise Your Glass at a Chicago Winery

Don’t be surprised that Chicagoans are making wine in the city. The city’s first winery actually makes mead! Wild Blossom Meadery in Beverly has been creating mead from honey harvested around the city for more than two decades. Looking to pair your wine with a concert? Check out City Winery’s lineup in the West Loop. Bronzeville Winery is a Black-owned and woman-owned business founded by Eric Williams of The Silver Room and Cecilia Cuff of The Nascent Group.

28. Watch the Super Bowl at a Sports Bar – February 8, 2026

Even if your team didn’t make it to the big game, who doesn’t love the Super Bowl for its halftime show and bar food? In a sports town like Chicago, there’s no shortage of spots to catch the game. In Logan Square, try the Moonlighter’s burger and crunchy tacos or cozy up by the fire at Park & Field. Murphy’s Bleachers in Wrigleyville is great for more than baseball, as is Cork & Kerry in Bridgeport.

29. Valentine’s Day with Rapt In Plastic at IMSS – February 14, 2026

Not a fan of traditional Valentine’s Day plans? Spend the evening at the International Museum of Surgical Science surrounded by sculptures of scientists to a David Lynch-like soundtrack. Rapt in Plastic will play mysterious dream-pop music while you bask in the museum’s Hall of Immortals.

30. Stock up on Chocolate at Mr. Kite’s

My favorite place to buy sweets in Chicago is Mr. Kite’s in Wicker Park. The small shop is bursting with every chocolate creation you can imagine, from turtles to s’mores and fudge to chocolate-covered strawberries. Dominick Gusmanos has delighted Chicagoans with his old-fashioned confectionery shop experience since 1987!

31. The Hustle: 70’s Disco Party – February 121, 2026

Dust off your jumpsuit and strap on your platforms, it’s time to disco, baby. Subterranean in Wicker Park presents The Hustle, a night of classic disco inspired by Donna Summer, ABBA, Chic, and more.

32. Valentine’s Day Fireworks – February 14, 2026

Sparks are flying, literally, at Navy Pier on Valentine’s Day with this free fireworks display. Spend the evening admiring the colorful show over Lake Michigan, starting at 9 p.m.

33. Find a New Hobby at Lillstreet Art Center

Lillstreet Art Center is a community of artists, students, and enthusiasts in Ravenswood. If you’re looking to learn a new skill, try one of their 800 art classes and workshops each year, from printmaking to metalsmithing and ceramics to jewelry.

34. Interview Show at the Hideout – February 20, 2026

The Interview Show is basically like watching a podcast in person. For this edition of the long-running program at the Hideout, host Mark Bazer chats with Stephen Malkmus of Pavement and Claire Pollard, Northwestern’s Women’s Tennis Coach.

35. Chow Down at an International Food Hall

Can’t decide what to eat? Taste your way through a food hall. Chicago has a food hall for every appetite, from pan-Asian delights at Gangnam Market in River West to Italian ingredients and restaurants at Eataly in River North to French flavors at the Chicago French Market in the West Loop.

36. Hamnet at Chicago Shakespeare Theater – February 10-March 8, 2026

See the U.S. premiere of the Royal Shakespeare Company’s stage adaptation of Hamnet. Explore love and grief through the relationship of Shakespeare himself and natural healer Agnes Hathaway.

37. Celebrate Black History Month at the Chicago History Museum – February 28, 2026

Celebrate Black art and its impact on social change in Chicago during this Black History Month commemorative day at the Chicago History Museum. Bring the family and enjoy music, speakers, art, and other activities together.

38. Polar Adventure Day – February 21, 2026

Bundle up and celebrate the wonder of winter in Chicago with the Chicago Park District. Polar Adventure Day at Big Marsh Park offers sled dog demonstrations, ice carvings, hot cocoa, and live music for free.

39. Music Frozen Dancing – February 21, 2026

An outdoor music festival in the winter? Chicago isn’t scared. The Empty Bottle’s annual Music Frozen Dancing music festival heats up Western Ave. and Cortez St. in West Town for a block party featuring live music by Los Thuthanaka, Good Flying Birds, and Lip Critic.

40. Chicago Bacon Fest – February 28, 2026

Bacon, beer, and live music. What more do you need? Chicago Bacon Fest sizzles at Old Crow Smokehouse in Wrigleyville, offering bacon-back shots, bacon cocktails (and mocktails), and bacon dishes.

41. Cupid’s Undie Run – February 28, 2026

Strip down to your skivvies and jog for a mile through Wrigleyville before ending in a dance party. It’s probably not the first time. Cupid’s Undie Run raises money to support those affected with neurofibromatosis (NF). 

42. Field Museum Free Days – Through March 25, 2026

There’s 1.2 million square feet of natural history waiting for you at the Field Museum. From SUE, the most complete T-rex ever found to Maximo the Titanosaur—the biggest dinosaur ever discovered. Explore Inside Ancient Egypt or be dazzled by the Halls of Gems and Jades. Basic admission is free to Illinois residents every Wednesday through March.

43. Chicago Beer Festival – February 28, 2026

Need another reason to visit the Field Museum? The Chicago Beer Festival brings more than 65 breweries to the museum, including specialty pours. Where else can you sip a beer surrounded by dinosaurs?

44. Get Crafty and Learn to Knit

Cozy up to mountains of yarn while you make yourself something warm to wear this winter. Learn your knit from your purl at a knitting class in Chicago. Sister Arts Studio offers classes in Lincoln Park. Knit 1 will teach you how to knit or crochet in North Center, as will yarnify! in Printers Row. Firefly Fiber Arts Studio offers workshops in Logan Square, and Nina Chicago teaches you how to knit in West Town.

45. Architecture & Design Film Festival – February 19-22, 2026

The Chicago Architecture Center presents design-focused cinema for the Architecture & Design Film Festival. The 10 films explore topics from designing for NASA to Antarctica and are shown at the Gene Siskel Film Center and the Chicago Cultural Center.

46. See a Flick at an Old School Movie Theater

What’s more charming than digging into popcorn at a historic movie theater? The Music Box in Lakeview has been showing art-house films complete with a live organist since 1929. Originally opened in 1915, the Logan Theatre features indie films and events like movie trivia. The Davis Theater in Lincoln Square features first-run films in a building from 1918. In Hyde Park, the Harper Theater first opened in 1915 and the Doc Films Theater at the University of Chicago has been running for more than 80 years.

47. UChicago Folk Festival – February 20-21, 2026

Since 1961, folk music fans have gathered in Hyde Park for the UChicago Folk Festival. This year’s fest features six acts performing at Mandel Hall. You can stream the concerts online for free.

48. Chicago Irish Film Festival – February 26-March 8, 2026

The Chicago Irish Film Festival has been sharing the work of Irish filmmakers since 1999. This year’s edition features films and documentaries in both English and the Irish language.

49. Ball Out at a Professional Basketball Game

Chicago is a legendary basketball town for a reason. Gear up in your jersey and watch the Chicago Sky dunk at Wintrust Arena in the South Loop or the Chicago Bulls hit the court at the United Center in the West Loop. Just don’t get showered in popcorn by Benny the Bull.

50. Get Your Shuffleboard On at Royal Palms

Pretend you’re on a cruise in the middle of Chicago winter by playing shuffleboard and sipping a tropical cocktail at Royal Palms in Wicker Park. Walk in or reserve ahead to challenge your friends on the shuffleboard court.

Visiting Chicago in February FAQ

Is February a good time to visit Chicago?

February is a great time to visit Chicago if you want to avoid the winter holiday crowds and the madness of St. Patrick’s Day. Sandwiched in between is February, a colder but less crowded time of year. Visiting Chicago in the winter means that you can find great cheaper flights and hotel deals in February. With less visitors in February, it’s a great time to snag a hot restaurant reservation or visit one of Chicago’s top attractions like the Field Museum, 360 Chicago Observation Deck, or the Art Institute, without a wait.

How cold is Chicago in February?

February tends to be just slightly warmer than January in Chicago, although spring-like days tend to surprise us sometimes. According to the National Weather Service, the average temperatures in Chicago in February range from a high of 36 degrees to a low of 22 degrees. Snow is always a possibility. Winter in Chicago is still fun if you know what to wear. Check the forecast before you visit Chicago in the winter, so you can pack accordingly.

What should I wear to Chicago in February?

Be sure to check the weather forecast before you visit Chicago in January so you can pack accordingly. It’s safe to assume you should wear layers so that you can bundle up while you’re outside (especially near the lake) and be comfortable indoors.

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 February

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 this gave you some fun ideas for visiting Chicago in February!

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 January
• 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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