It’s finally time to say goodbye to 2024 and welcome in 2025. Despite the arrival of the Midwest’s merciless winter, Chicago is alive and kicking, and there is plenty of time to find the best things to do in Chicago in January this year.
From immersive exhibitions and captivating concerts to new restaurants and spectacular speakeasy experiences, here’s a roundup of everything you should be excited about, whether you’re a long-time local or an enthusiastic tourist. Three hundred sixty-five days, 365 new chances!
1. Experience “alpine in the city” at Maggie Daley Park
There’s no better way to glide into 2025 than with some winter skating. One of the best things to do in Chicago in January is skating on an ice rinks during the winter months; there are none quite like the Maggie Daley Park ice rink.
One of Chicago’s best winter-time activities, the 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.
2. Cruise down the Chicago River in a hot tub boat
For over a decade, The Chicago Electric Boat Company has offered a unique, environmentally friendly way to see the city of Chicago thanks to their fleet of rentable 100% electric boats, but now a winter addition will join the Chicago Electric Boat Company fleet, this time in the form of Hot Tub Boat Cruises.
Yes, you read that correctly. Launching out of the docks at Marina City, the new zero-emissions vessels will take up to six people at a time floating along the main branch of the Chicago River in a boat equipped with a fully functioning hot tub—and it’s one of the best things to do in Chicago in January.
3. 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 be 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.
4. Secure your spot for this wild Bingo Loco party
This isn’t your grandma’s bingo night! This high-energy bingo party is coming to Chicago on February 7 and 28 with confetti showers, lip-sync battles, dance-offs, and CO2 cannons with hilarious comedian MCs leading the way. Get the chance to win epic prizes like a cruise package, a piano, a giant inflatable flamingo, a microwave, a lawnmower, a trip to Vegas, and so much more! It’s only in town for two upcoming dates. Snag your tickets now!
5. Check out the best of Chicago’s vegan-friendly restaurants
Of course, the beginning of the new year marks pastures for many. New Year’s resolutions and lifestyle changes see people approach the first month of the year differently from others. While some harbor intentions of changing their ways for the entire year, many go into it looking to complete ‘Dry January’ or ‘Veganuary.’
If the latter applies to you, we’ve compiled a list of the best vegan restaurants in Chicago for brunches, snacking, and dining out. So you can cut to the chase and enjoy the best vegan options for one of our favorite things to do in Chicago in January.
6-8. Discover Chicago’s Top Fitness Destinations for 2025
Kick-off 2025 with a commitment to fitness at one of Chicago’s premier gyms. From luxury athletic resorts to boutique studios, the Windy City offers diverse options to suit every fitness enthusiast. Whether you’re into HIIT workouts, luxurious amenities, or affordable spaces with essential equipment, Chicago has a gym for you. Explore top-notch facilities like Midtown Athletic Club, Equinox, and LifeTime, or try specialized venues such as CrossTown Fitness and Rumble Boxing for unique workout experiences—it’s one of the best things to do in January if you want to start the year on a healthy note.
📍 Location: Various locations across Chicago
9-12. 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.
13. Discover Chicago’s Top Mocktail Destinations for Dry January
14. Get free entry to the Field Museum on a Wednesday
Field Museum is another one of Chicago’s incredible museums offering free admission this January.
Illinois residents will be able to enter the popular natural history museum completely free of charge between 9:00 a.m. and 5:00 p.m. on Wednesdays, provided they bring proof of residency.
That means this month, five different dates will be free beginning Wednesday, January 3rd, until the last day of the month, Wednesday, January 31st.
Read more about Field Museum’s free days.
15. Gaze at the stars at the Adler Planetarium for free
Another place you’ll find a fantastic free experience is at Chicago’s Adler Planetarium on a Wednesday. 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.
16. Drink in a personal snow globe
As winter gripped hold of Chicago in recent years and pandemic mitigation measures simultaneously restricted indoor dining, we saw rooftops go the extra mile, reinventing themselves with igloos, fire pits, and much more.
Of all the memorable moments rooftops began offering up among the Chicago skyline, it was at the Godfrey Hotel in River North which offered one of the most magical setups. 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 January.
17. Enjoy curling and cocktails at Gwen Hotel
One of the best things to do in Chicago in January can be found on 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.
18. Check out Chicago’s extravagant mini golf cocktail bar
If those kinds of competitive leisurely activities are up your alley, you might want to check out Chicago’s quirky mini-golf concept bar, Puttery, which fuses high-tech gameplay with craft cocktails and curated cuisine!
The exciting mini-golf and cocktail experience transports guests to wholly unexpected locations while motivating competitive socializing.
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.”
19. Sip a Guinness at the new Guinness Taproom
For anybody who loves Chicago beer and has a thirst for that smooth, creamy, world-famous Irish dry stout, you’re in luck! The Ireland-based brewer finally opened the 15,000-square-foot Guinness Open Gate Brewery Chicago in West Loop, providing a unique new experience and resulting in one of the best things to do in Chicago in January.
Read more about the Guinness Open Gate Brewery Chicago.
20. Kick back at a revered 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.
21. 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, or enjoying drinks out at one of Chicago’s many bars and restaurants, you can be sure a finely-crafted cocktail is only seconds away.
From top-notch margaritas to more innovative cocktail concoctions and everything in between, the Windy City and its abundance of revered mixologists have the answers to whatever it is you’re after.
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.
22-23. Revel in one of Chicago’s best speakeasies
A 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—guaranteed one of the best things to do in Chicago in January this year.
24. 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.
25. 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.
26. Get a Free Pet Portrait For Your Furry Friend
West Loop pet owners have a reason to celebrate this month with the opening of Lovet, a new veterinary clinic focused on affordable pet care. The clinic is celebrating its grand open on Wednesday, January 15 with an open house event.
Chicagoans and their furry friends are invited to stop by for a tour of the space, plus animal care information, treats for humans and pets, giveaways, and free professional pet portraits!