Though the shortest month of the year, February can feel like the longest due to its frigid weather. However, it’s a month packed with events. Valentine’s Day, Black History Month, Lunar New Year, and Mardi Gras—with so much going on this month, you’d think it’d be longer than 29 days! Here is a list of the best things to do in Chicago in February to keep your spirits high and souls happy.
1. Explore the CAC Architecture & Design Film Festival
The Chicago Architecture Center (CAC) is excited to host the third edition of its Architecture & Design Film Festival from January 31 to February 4. One of the best things to do in Chicago in February, the festival highlights Chicago’s design legacy through the works of architect Mies van der Rohe while also taking audiences on a journey from Copenhagen to São Paulo and beyond.
It’s an inspiring way to engage with the transformative power of design this winter season.
🗓️ Date: January 31 to February 4
2. Take a trip to the Italian Alps at Eataly’s whimsical pop-up this winter
Escape to the Italian Alps at the ALPINA winter pop-up at Eataly Chicago. Step into a snow-frosted oasis with workshops, delicious food, seasonal drinks, and more! Now through March 2025, try the new ALPINA winter menu, inspired by the rich food and beverage traditions of Northern Italy and neighboring Alpine regions.
Highlights include the Polenta Bar, Fonduta di Formaggio—Italy’s take on Swiss fondue—and cocktails like the Hot Toddy and Bombardino. Don’t miss ALPINA’s special experiences throughout the week, like Après Ski Night every Friday, featuring high-energy DJ sets, incredible cocktail deals, and more. Get a taste of the chic après-ski lifestyle! Secure your spot now. -Melissa Maynard
📍 Location: Eataly Chicago, 43 E. Ohio St., Chicago, IL 60611
🗓️ Date: January 2025 to March 2025
3. Sample Some Sweets at Stan’s Donut Fest
Stan’s Donuts is bringing back its annual Donut Fest, promising one of the best things to do in Chicago in February. This year’s sweet celebration at Moe’s Cantina in River North offers an array of treats for donut enthusiasts. The event features 12 unique donut tastings, including creative confections like the “Cannoli Bombolini” and a red velvet Oreo donut, alongside coffee and alcoholic drink pairings. Guests will also enjoy a live DJ set, giveaways, and plenty of Instagram-worthy photo ops.
📍 Location: Moe’s Cantina in River North
🗓️ Date: February 1st
4. Check out Milk Bar’s Arrival in Chicago
🗓️ Date: February 8, 2025
5. Top Spots to Catch the Super Bowl in Chicago
🗓️ Date: February 9, 2025
6. Watch the Super Bowl at Soldier Field’s Free Fan Fest
Chicago football enthusiasts have a reason to celebrate despite the Bears’ disappointing season. Verizon is hosting a Super Bowl fan fest at Soldier Field on Sunday, February 9, at 3 pm. The event offers an interactive way to watch the game broadcast, featuring meet-and-greets with Bears wide receiver Rome Odunze and other NFL heroes, tailgating games, football challenges, live music, and local food options—definitely one of the best things to do in Chicago in February.
Oh, and tickets are free!
📍 Location: Soldier Field
🗓️ Date: February 9, 2025
7. Get romantic for Valentine’s Day
Of course, two weeks into this month is also the year’s most romantic day. It’s a good idea to lock down plans for the perfect night of romance so the pressure doesn’t build. Luckily, Chicago is teeming with heart-fluttering activities, and there are many ways to celebrate Valentine’s Day in Chicago.
Read our roundup of the best things to do for Valentine’s Day in Chicago.
📍 Location: Various restaurants
🗓️ Date: February 14, 2025
8. Drop your pants for charity at Cupid’s Undie Run
Cupid’s Undie Run is coming back to Chicago! One of the best things to do in Chicago in February is start the day with drinking and dancing, jog about a mile in your undies, and then finish the day with a wild dance party. Join the fun and help raise money to find a cure for neurofibromatosis (NF), a rare genetic disorder that causes tumors to grow on nerve tissue.
🗓️ Date: Saturday, February 22
9. Watch the ‘The Terminator’ Live in Concert
The Auditorium and the Chicago Philharmonic are excited to kick off the second season of the Auditorium Philms Concert Series with The Terminator in concert. This multimedia experience showcases iconic films brought to life with live orchestral performances of their scores.
The beloved sci-fi film will be screened while an all-electric chamber orchestra performs the dynamic score composed by Brad Fiedel. The performance will include in-sync dialogue and sound effects from the original film. This one-night-only presentation is scheduled for Saturday, February 22, at 7:30 PM at The Auditorium.
📍 Location: Chicago Auditorium
🗓️ Date: Saturday, February 22
10. Ice skating at Maggie Daley Park
There’s no better way to combat the doom and gloom of winter than with some iconic ice skating experiences. Though Chicagoland has a wide range of ice rinks offering wonderful skating experiences during the winter months, there are none quite like the Maggie Daley Park ice rink.
One of the best things to do in Chicago in February, Maggie Daley ice rink offers an “alpine in the city” experience, skating down a quarter-mile rink in the heart of Chicago. The winding ribbon of ice curves up and down around a 40-foot climbing wall with the city’s stunning skyline in the backdrop.
11. Experience Chicago’s Unique Hot Tub Boats This Winter
Chicago Electric Boat Company’s Hot Tub Boats are back for another season, offering a one-of-a-kind winter experience on the city’s waterways. These unique vessels combine the comfort of a hot tub with the excitement of a boat ride, allowing you to cruise through Chicago’s iconic cityscape while staying warm and cozy. Equipped with underwater lights, Bluetooth speakers, and a BYOB policy, these boats provide an unforgettable adventure for up to six passengers. Prices range from $350 to $425 for a 90-minute cruise, depending on the day of the week.
12. Score big at this epic Bingo Loco party
An epic bingo party with confetti showers, lip-sync battles, dance-offs, and CO2 cannons is coming to Chicago for two nights only, on February 7 and 28. One thing is certain…this isn’t your grandma’s bingo night! You could win incredible prizes like a cruise package, a piano, a giant inflatable flamingo, a microwave, a lawnmower, a trip to Vegas, and so much more! Grab your tickets now!
13. Be captivated by a Candlelight Concert
Candlelight concerts offer another incredible spectacle that can be enjoyed this month. Step into Chicago’s most exquisite spaces to experience some unforgettable performances. The beloved Candlelight series has organized an array of talented musicians performing at the city’s best venues illuminated with hundreds of candles, and extra dates have been added due to popular demand.
See the full list of candlelight concerts in Chicago.
14. Enjoy a day at the Shedd Aquarium for free
It is no secret that Chicago has a remarkable range of world-class museums and attractions, but visiting them all can become costly. Luckily for us, winter is often a time when they love to announce free admission for Illinois residents.
Chicago’s beloved aquarium is one such attraction that has announced it will offer a plethora of free days throughout winter before kicking off spring with weekly free evenings through to summer.
15. Get free entry to the Field Museum on a Wednesday
Field Museum is another one of Chicago’s incredible museums offering free admission this month, but unlike the others who are offering sporadic dates over the next few weeks, the Field Museum has announced that it will now be free every Wednesday in 2025 for Illinois residents
16. Gaze at the stars at the Adler Planetarium for free
Another place you’ll find a fantastic free experience on a Wednesday is at Chicago’s Adler Planetarium. Illinois residents can enter for free every Wednesday evening from 4-10 pm provided they bring proof of residency and enjoy access to the largest public telescope in the Midwest as well as a range of exciting astronomy events and activities.
17. Send your senses soaring with a Dining-in-the-dark sushi experience
If you’re looking to take your date nights to new levels this year or embark on a memorable adventure with friends, a blindfolded meal could be the perfect new experience. Dining in the Dark invites guests to engage their taste buds to their maximum in circumstances you’ve never done before, and now, for the first time, they’ve released a new sushi version of the iconic experience.
Omakase, as defined by Michelin Guide, is a form of Japanese dining in which guests leave themselves in the hands of a chef and receive a seasonal, elegant, artistic meal that uses the finest ingredients available.
This special 12-course menu will surprise you with its burst of flavors encompassing the highest standard of Japanese cuisine while focusing on taste and smell alone.
18. Drink in a personal snow globe
Talking of gazing up at the stars, there are some wonderful winterized rooftops around Chicago offering cozy winter hideouts this month.
Of all the rooftops going the extra mile to reinvent themselves with igloos, fire pits, and much more, the Godfrey Hotel in River North is one of the most unique. Boasting Chicago’s largest indoor-outdoor rooftop with a retractable roof, the hotel’s annual whimsical winter wonderland is the perfect place to frequent during the doom and gloom of winter.
Signature heated igloos cover the rooftop’s portico and offer the perfect place to shelter from the winter elements in style, cozying up with a cocktail, s’mores, and sweeping skyline views—it remains one of the best things to do in Chicago in February.
19. Enjoy curling and cocktails at Gwen Hotel
Another unique thing to do in Chicago in February is to visit The Gwen Hotel’s luxury rooftop. While you won’t find lavish igloos here, you’ll instead be able to enjoy the hotel’s annual Curling and Cocktails experience. The hotel kits out its rooftop each winter with no igloos or ice skating but an outdoor curling rink high in the sky.
Curling sessions come with small bites and a complimentary round of cocktails, meaning you can sip away on your favorite tipple while battling your buddies on the state-of-the-art curling rink.
20. Play pickleball at Chicago’s indoor pickleball courts
If those kinds of competitive leisurely activities are up your alley, you might want to drop into Chicago’s largest indoor pickleball center, which just opened towards the end of last month. Set up by four friends from Lincoln Park, Social Pickleball Fun now offers a 40,000-square-foot facility with an indoor turf field, a restaurant, a coffee shop, nine indoor pickleball courts, and luxurious locker rooms complete with saunas and showers.
21. Check out Chicago’s extravagant mini golf cocktail bar
Another indoor experience for those looking to shelter from the winter elements while enjoying some competitive socializing can be found at Chicago’s quirky mini-golf concept bar, Pottery. The exciting mini-golf and cocktail experience transports guests to wholly unexpected locations, fusing high-tech gameplay with craft cocktails and curated cuisine!
The 23,000-square-foot venue in the heart of Fulton Market District features “uniquely themed putting courses, stunning bars, and swanky lounge spaces within a lively atmosphere to provide an unmatched immersive experience.”
22. Kick back at a brewery
Talking of which, frequently recognized as one of the best beer cities in the country, our seasoned and inventive beer scene has produced so many fantastic breweries and taprooms in Chicago that we’re spoilt for choice. There are now over 200 breweries, big and small, across Chicagoland, meaning there are plenty of opportunities to enjoy a finely crafted beer in a range of different environments, whatever the weather.
To make sure you’re checking out the best of the best, we’ve here rounded up the best breweries, brewpubs, and taprooms in Chicago to make the most of February in Chicago!
23. Stay warm with a glass of wine at an incredible Chicago wine spot
If beer isn’t your drink of choice, there are also many amazing spaces around the city where you can grab a glass of wine with friends—it’s one of the best things to do in Chicago in February.
From All Together in West Town to Chicago Winery in River North, Chicago, is home to some brilliant wineries and well-stocked bars.
24. Sample the best cocktails in Chicago
If a fruity cocktail is more up your street than craft beer, worry not, for Chicago has an abundance of acclaimed watering holes making sensational cocktails. Whether you’re treating yourself to brunch in Chicago, kicking back on a Chicago patio, you can be sure a finely-crafted cocktail is only seconds away. We’ve recently filtered through the noise to round up the best cocktail bars in Chicago based on our experiences at Secret Chicago, our reader’s most popular choices, and a scrupulous assessment of settings and drink quality.
25. Drink cocktails at a winter rooftop bar
One of the best things to do in Chicago in February is lounging on a winter rooftop, of course! One of our favorites is Chateau Carbide; the indoor-outdoor lounge features luxurious private chalets scattered across the rooftop. Each chalet will be adorned with relaxing fireplaces, and the winter-inspired menu includes small bites and seasonal cocktails that are perfect for starting or ending your night.
26. Revel in one of Chicago’s best speakeasies
Another sky-high retreat can be found perched high above the Magnificent Mile at the Four Seasons Hotel. This exclusive cocktail destination is one to remember, filled with vibrancy, style, and immersive drinks. The experience starts before you even take off.
When you check-in you’ll be given a glass of champagne and a room key to the hidden speakeasy lounge on the 46th floor. There, you’ll embark on a gilded journey through inventive cocktails inspired by the most exquisite and spectacular sunsets from around the globe.
Read more about Chicago’s best speakeasies.
27. Try an escape room in Chicago
While at speakeasies the challenge can be getting in, at Chicago’s escape rooms the challenge is getting out. A great plan for families, friends, or work events, escape rooms put your problem-solving skills to the test with puzzles, clues, and tasks designed for groups of all ages to enjoy. Luckily, Chicago has an array of exciting escape rooms from which to choose!
28. Buckel up for a Drunk Shakespeare show
Another brilliant Chicago experience comes in the form of a live Drunk Shakespeare show.
On a stage in a hidden speakeasy behind the Chicago Theater, guests will find a glam cocktail bar and library with over 10,000 books. Five classically-trained actors meet as members of “The Drunk Shakespeare Society.” One of them has had at least five shots of a strong spirit, and then they (quite over-confidently) attempt to perform a major role in a Shakespearean play!
Hilarity and mayhem ensue while the four sober actors try to keep the script on track. Every show is different depending on who is drinking… and what they’re drinking!
Grab tickets to a Drunk Shakespeare show.
29. Chuckle away at Chicago comedy show
If you’re looking for more laughs, there’s no place better for that than at a Chicago comedy show. Famous for its production of funny guys and girls, Chicago has some of the best places to see a comedy show in the country.
At Laugh Factory Chicago, some of today’s biggest names and local comedians are delivering something for every taste and style throughout the year.
Grab tickets to a show at Laugh Factory Chicago.
30. Taste one of the best burgers in the world
With an array of acclaimed hotels, bars, and restaurants across the city, Chicago’s hospitality scene is no far friend from flattering accolades. Already boasting a pizzeria ranked one the best in the world, a Windy City diner has now been awarded one of the best burgers in the world.
In the inaugural World’s 25 Best Burgers list by Burger Dudes, Chicago’s Au Cheval was ranked inside the top 5, being named the fourth-best burger on the planet!
31. Warm-up and revitalize at Chicago’s most unique spas
One of the best things to do in Chicago in February is having a spa day. There is simply no better place in Chicago for some rest than AIRE’s Ancient Baths located inside a restored historic River West factory. Inspired by the traditional Roman, Greek, and Ottoman bathing experience, this preserved structure has been restored to its original splendor. You can now find optimum relaxation within the building’s exposed brick, wooden beams, and industrial columns.
There are, however, an array of idyllic spas and bathhouses in Chicago all offering medicine for mind, body, and soul.
32. Head out of the city and see Illinois’ natural spectacles
We know this one isn’t strictly in Chicago, but with so much going on in the city, it can be nice to escape to the quiet of Illinois’ natural beauty.
Though our state may not boast wonders with the universal magnitude of the Grand Canyon nor the grandiose reputation of Niagra Falls, Illinois is teeming with diverse ecological landscapes that transform into incredible winter wonderlands this time of the year.
From monolithic marvels covered in snow to cascading waterfalls frozen in time, we’ve selected seven natural wonders of Illinois that you can visit while they’re a different beast in winter.