Chicago events in January are anything but frigid.
I may be slightly biased since it’s my birthday month, but even with the cool temperatures, Chicago shows up with a packed calendar of events, food festivals, and cultural experiences worth leaving the house for.
From major citywide festivals to cozy, culture-forward happenings, these are the best things to do in Chicago in January 2026 for every winter adventure.
The Best Events and Things to Do in Chicago in January 2026
Use the navigation jump links below to dive into top events, recurring favorites, and my handpicked recommendations for what to do this month.
Top Events: Must-attend highlights of the month
Recurring Activities: Regular events worth adding to your calendar
The Curated List: Personal recommendations for unique Chicago experiences
Top Events in Chicago in January
Experience the most popular Chicago events this January in Chicago. From an alcohol-free cocktail competition with a purpose to the biggest, most affordable food-driven event in Chicago.
Tomorrow Never Knows Festival (20th Anniversary Edition)
January 8-31, 2026 | Multiple Chicago Venues
Chicago’s premier multi-venue winter music festival returns for its 20th anniversary. Spanning four weekends, Tomorrow Never Knows showcases indie music, comedy, and emerging artists across some of the city’s best music and entertainment venues.
South Loop Farmers Market Winter Indoor Market
January 10–March 28, 2026 | Roosevelt Collection Shops, Chicago
January 11–March 29, 2026 | Water Tower Place, Chicago
Shop for one-of-a-kind treats, fresh produce, and unique goods at the South Loop Winter Farmers Market. This is a great family-friendly winter activity in Chicago. Enjoy a lineup of local farms, food vendors, ready-to-eat eats, and one-of-a-kind artisans and makers at two different locations from January through March. Both markets will feature live DJs, music, and fun activities for kids and pets.
Haute Tip: Enjoy 2-hour free validated parking at the Roosevelt Collection Shops and Water Tower Place
Cubs Convention
January 16–18, 2026 | Sheraton Grand Chicago
An action-packed weekend where fans can mingle with Cubs players, prospects, and icons. While attending the Cubs Convention at the Sheraton Grand Chicago, expect autograph sessions, exclusive panels and podcasts, prizes, and the latest Cubs gear. A classic January event that officially kicks off the baseball season.
No I.D. Alcohol-Free Cocktail Competition & Tasting Event 2026
January 18, 2026 | Artifact Events
Celebrate Dry January at this alcohol-free cocktail competition and tasting. This is a popular, sober-friendly winter event in the Ravenswood neighborhood that always sells out! Sample zero-proof drinks from local and national brands, vote for your favorites, and support Ben’s Friends charity
Martin Luther King Jr. Day Chicago Events
January 19, 2026 | Various Locations
Celebrate MLK Day with free museum days, community gatherings, and volunteer opportunities across Chicago. During this holiday, I especially like to support local Black-owned businesses in solidarity with Dr. King’s Dream.
Chicago Restaurant Week
January 23 – February 8, 2026 | Citywide
This is one of the most highly anticipated Chicago food and drink events of the year! Chicago Restaurant Week features hundreds of restaurants offering prix-fixe menus across dozens of neighborhoods. Brunch and lunch start at $30, with dinner menus priced at $45–$60. I try to knock out at least one restaurant from my list during this event, and I find it’s one of the best ways to explore Chicago’s dining scene in winter.
Chicago Winter Whiskey Tasting Festival
January 24, 2026 | Chicago
Warm up your winter with a Chicago festival this January. The Chicago Winter Whiskey Tasting Festival features a wide selection of whiskeys to sample, plus opportunities to discover new brands and styles. A must-attend January event in Chicago for whiskey lovers.
Sox Fest Live at Ramova Theatre
January 24–25, 2026 | Ramova Theatre
Sox Fest returns with a re-imagined fan experience celebrating White Sox baseball. Expect interactive activations, player appearances, panels, and entertainment all under one roof on the South Side of Chicago.
Repair Fair with the Chicago Tool Library
January 25, 2026 | 4015 W Carroll Ave
Give your broken or beloved items a second life at this free, community-focused Repair Fair hosted by the Chicago Tool Library. Volunteer fixers help repair clothing, small appliances, bikes, and household items while promoting sustainability and reuse. One of the best free things to do in Chicago in January is for eco-minded locals.
Wrigleyville Mac & Cheese Crawl
January 25, 2026 | Multiple Chicago Bars
This comfort-food-focused bar crawl is a winter favorite. Enjoy seven servings of mac and cheese, drink specials, giveaways, and festive vibes as you hop between participating venues. A fun, casual Chicago food event perfect for January.
Looking for Chicago events and things to do in Chicago this weekend? Check out the events calendar.
Recurring Activities to Experience in January
Need a reason to step out of the house this winter in Chicago? Explore something different this month with these ongoing Chicago winter activities and indoor experiences. Challenge yourself, learn a new skill, and make the most of your time with these unique indoor things to do in Chicago.
- All-Season Patio Hangouts: Sip cocktails and savor seasonal menus on Chicago’s best-heated patios.
- Candle-Making Class on the Magnificent Mile: Design your custom candle while enjoying a chic atmosphere.
- Deep Dish Cooking Class at Pizzeria UNO: Learn to craft Chicago’s iconic deep-dish pizza.
- Escape Game Chicago: Solve puzzles in immersive escape rooms in downtown Chicago.
- Downtown Chicago and West Town Neighborhood: Explore two Chicago neighborhoods great for cold-weather hangouts and cozy dinners.
- Interactive Chicago Museums: Dive into vibrant creativity at the Museum of Ice Cream or the colorful Color Factory.
- Free Chicago Museum Days: Take advantage of free or discounted admission at museums.
The Curated List of Chicago Events this Month
Here is my handpicked choice of the city’s best events, activities, and hidden gems to enjoy this month in Chicago.
Mavis Staples with Special Guest Nathaniel Rateliff
What: Legendary vocalist and civil rights icon Mavis Staples brings her Sad and Beautiful World tour to Chicago, performing alongside special guest Nathaniel Rateliff. Expect gospel-rooted soul, powerful storytelling, and music that spans generations at the Chicago Theatre.
When: Saturday, January 10, 2026 | Doors 6:30 PM | Show 7:30 PM
Where: The Chicago Theatre
Link for more information:Buy Tickets
Crafting Character: The Costumes of Paul Tazewell
What: Step inside the creative world of award-winning costume designer Paul Tazewell, featuring iconic costumes from Wicked, Hamilton, West Side Story, and more. An immersive look at the artistry behind some of stage and film’s most recognizable looks at the Museum of Science and Industry.
When: Opens January 19, 2026
Where: Griffin Museum of Science and Industry
Link for more information: Explore the Exhibition
Chicago International Puppet Theater Festival (8th Edition)
What: North America’s largest puppetry festival returns with performances, workshops, artist intensives, symposia, and free neighborhood events. A citywide celebration of innovation, storytelling, and global puppetry traditions.
When: January 21–February 1, 2026
Where: Various Chicago venues
Link for more information: Festival Details & Tickets
MoCP at Fifty: Collecting Through the Decades
What: Celebrating its 50th anniversary, the Museum of Contemporary Photography presents a rare look at its evolving collection. The exhibition explores how photography, representation, and institutional values have shifted across decades.
When: January 22–May 16, 2026
Where: Museum of Contemporary Photography
Link for more information: View Exhibition Details
Chicago Bulls: Derrick Rose Jersey Retirement Night
What: The Chicago Bulls officially retire Derrick Rose’s iconic #1 jersey, honoring his legacy and impact on the franchise and the city. One of the most historic Chicago sports moments of 2026 at the United Center.
When: January 24, 2026
Where: United Center
Link for more information: Buy Tickets
The Sunday Issue: Champagne & Furs Edition
What: A grown and stylish rooftop day party curated for Chicago’s fashion-forward crowd. Expect elevated vibes, good music, and a beautifully dressed room. Fur attire encouraged. This is a curated Sunday experience, not a brunch or a club night.
When: January 25, 2026 | 4:00 PM–9:00 PM CST
Where: Time Out Market Chicago
Link for more information: Learn More
Chicago in January: What You Actually Need to Know
What’s the weather like in Chicago during January?
January in Chicago is the heart of winter, bringing cold temperatures and a good chance of snow. The average high temperature during the month hovers around 31°F (-1°C), while lows can drop to 17°F (-8°C).
Snowfall is common, with the city typically receiving 10-12 inches (25-30 cm) of snow throughout the month. Be sure to bundle up and wear layers, as wind chills can make it feel even colder.
If you’re thinking, “Cool, now what should I pack for Chicago during January?” Check out this guide on how to dress and what to wear.
Is January a good time to go to Chicago?
Yes! While it is a freezing time of the year, January is a great time to visit the city of Chicago, especially if you want to experience the city at a slower pace and with fewer crowds.
This is the time of year to experience the city just like a local would. For me, that means getting out of the house and, at a minimum, hanging out somewhere cool and different, which is not hard to find in a city like Chicago.
What is there to do in Chicago in January for free?
Even in the chilly January weather, Chicago is full of free things to do! Here are my favorite winter activities to try this month in Chicago. Start by heading downtown to Millennium Park to admire iconic landmarks like The Bean (Cloud Gate) or lace up your skates for some winter fun on the park’s ice rink.
Museums are also a great winter escape. Many, including the Art Institute of Chicago and the Museum of Science and Industry, offer free admission days for Illinois residents (be sure to check their schedules ahead of time).
For outdoor enthusiasts, the Lakefront Trail and Chicago’s snow-dusted parks make for scenic winter walks, offering a peaceful way to enjoy the city while it’s dressed in its January finest.
Things to Look Forward to in Chicago for January 2026
January in Chicago proves that winter isn’t a pause, it’s a shift in pace. With fewer crowds, standout food events, and a calendar full of culture-driven experiences, the city feels more accessible, more local, and more intentional this time of year.
Whether you’re planning a winter visit, easing into the new year, or simply looking for reasons to leave the house, January 2026 offers some of the best opportunities to experience Chicago beyond the surface. Bundle up, lean into the season, and start the year by seeing the city a little differently.
Which of these events are you most excited to check out?
