Winter in Chicago is far from dormant. Even as temperatures drop, Chicago still has plenty of hot events and things to do. As a January baby, I love this month—it signifies fresh opportunities to experience new things and revisit old favorites.
Whether you’re a local looking to experience your favorite annual affordable, food-driven event or a visitor, seeking to take Chicago in at a much slower, yet exciting pace, January delivers countless opportunities to embrace Chicago’s year-round charm.
Whatever your reason for braving the cold, these are the best January events to check out this month in Chicago, that offer something for every kind of winter adventure this month.
The Best 2025 Events to Checkout this January in Chicago
Use the navigation below to dive into top events, recurring favorites, and my handpicked recommendations for what to do this month. Keep an eye out—events might change, and I might sneak in a few extra surprises along the way, just because!
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, affordable food-driven event in Chicago.
Chicago Bulls: Derrick Rose Night
January 4th | United Center
Derrick Rose, the 16-year NBA veteran and 2008 No. 1 overall pick by his hometown will honor Rose with a special, retirement night, “Derrick Rose Night”. This event will take place during the Bulls game against the New York Knicks, whose coach Tom Thibodeau also coached Rose in Chicago, Minnesota, and New York.
No I.D. Alcohol-Free Cocktail Competition & Tasting Event 2025
January 16th | Artifact Events
This Dry January, sip on creative non-alcoholic cocktails from local and national brands. Sample, vote for your favorite, and support Ben’s Friends charity with every ticket purchase.
Martin Luther King Jr. Day Chicago Events
January 15th | Various Locations
Celebrate MLK Day with free museum days, community gatherings, and volunteer opportunities across Chicago. Discover enriching ways to honor Dr. King’s legacy.
Tomorrow Never Knows Festival
January 15th–19th | Various Venues
Brave the Chicago cold for this five-day winter music and comedy festival featuring rising indie artists and national acts. Taking place at venues like Lincoln Hall and Schubas, this event is a must for music lovers.
Cubs Convention
January 17th–19th | Sheraton Grand Chicago
Spend a winter weekend with fellow Cubs fans at the 38th annual Cubs Convention. Meet players and legends, join panel discussions, and enjoy fan-favorite activities like Cubs Bingo.
Chicago Restaurant Week
January 24th – February 9th | Various Locations
Food lovers, rejoice! Chicago Restaurant Week is back, featuring over 470 restaurants, including 71 first-time participants and 50 suburban spots. Enjoy specially curated prix fixe menus priced at $30 for brunch or lunch and $45/$60 for dinner. It’s the perfect time to revisit your favorites or discover new culinary gems.
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? Explore something different this month with these ongoing activities in Chicago—challenge yourself, learn a new skill, and make the most of your time with these indoor events.
- 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.
- Chicago Crime & Mob Bus Tour: Step into the city’s darker history and discover infamous crime spots.
- The Escape Game Chicago: Solve puzzles in immersive escape rooms in downtown Chicago.
- Frank Lloyd Wright Robie House Admission: Admire the innovative design of this UNESCO World Heritage Site.
- Visit downtown Chicago and West Town Neighborhood: Explore two Chicago neighborhoods great for cold weather hangouts and cozy dinners.
- All-Season Patio Hangouts: Sip cocktails and savor seasonal menus on Chicago’s best-heated patios.
- Skydeck Chicago & Navy Pier Ferris Wheel: Marvel at the city’s skyline from these landmarks at wallet-friendly prices.
- Interactive Museums: Dive into vibrant creativity at the Museum of Ice Cream or the colorful Color Factory.
- Museum Free Days: Take advantage of free or discounted admission at museums.
The Curated List of Chicago Events this Month
Here is my handpicked selection of the city’s best events, activities, and hidden gems to enjoy this month in Chicago.
PurseSoul Presents: Quincy Jones Celebration
What: Celebrate the legacy of Quincy Jones with an incredible tribute covering his iconic work across jazz, R&B, and pop.
When: January 2, 2025
Link for more information: Quincy Jones Celebration
Kevin Hart at the Chicago Theater: Acting My Age
What: Kevin Hart brings the Acting My Age tour to The Chicago Theatre. This is a device-free show.
When: January 3-5, 2025
Link for more information: Kevin Hart Tickets
Indigo Sessions: A Night of Jazz, Poetry & Expression
What: A soulful showcase celebrating the artistry of Black women and femmes with jazz, poetry, and community vibes.
When: January 5, 2025
Link for more information: Indigo Sessions Tickets
Too Hot to Handel: The Jazz-Gospel Messiah
What: Experience a re-imagining of Handel’s Messiah with R&B, jazz, and gospel influences in this dynamic musical extravaganza.
When: January 11 & 12, 2025
Link for more information: Too Hot to Handel Tickets
Meet IRL x Rebuilding Exchange: Singles Crafting Night
What: Craft with reclaimed materials, enjoy drinks, and meet new people in this instructor-led workshop for singles aged 25–34.
When: January 16, 2025
Link for more information: SIngles Crafting Night
Black Panther In Concert
What: Relive the iconic story of T’Challa while Ludwig Göransson’s Oscar®-winning score is performed live by one of Chicago’s finest symphonic orchestras, featuring Senegalese tama drummer Massamba Diop.
When: January 18, 2025
Link for more information: Black Panther in Concert
Reggaetón Rave at Concord Music Hall
Dance the night away at Reggaetón Rave! This electrifying event blends Latinx and electronic music for an unforgettable celebration of rhythm and energy. Ages 18+, doors open at 9:00 PM.
When: January 18, 2025
Link for more information: Grab your tickets here
Glow in the Dark Pickleball Tournament
What: Play pickleball illuminated by blacklights, enjoy a 3-hour drink package, and compete for prizes in this fun-filled night.
When: January 18, 2025
Link for more information: Register to play
Hyde Park Handmade Market
What: Explore the best artisan food, art, and design at this free neighborhood market at The Promontory.
When: January 19, 2025
Link for more information: Hyde Park Handmade Market
Community Soup Event
What: Enjoy endless bowls of soup from Chicago’s best chefs while supporting charity, with music and a lively atmosphere.
When: January 22, 2025
Link for more information: Community Soup Event
Sox Fest at Ramova Theatre
What: Join White Sox fans for interactive experiences, player meet-and-greets, and entertainment in this re-imagined fan convention.
When: January 24–25, 2025
Link for more information: Sox Fest Tickets
Mac & Cheese Crawl
What: Get ready for the ultimate comfort food event! Enjoy seven servings of mac and cheese, drink specials, fun giveaways, and more at this cheesy bar crawl. Bring your appetite and join the party!
When: January 25, 2025
Link for more information: Get tickets here
2025 Chicago Winter Whiskey Tasting Festival
What: Discover a variety of whiskey flavors at this annual tasting event perfect for connoisseurs and enthusiasts.
When: January 25, 2025
Link for more information: Whiskey Tasting Festival
Chinese New Year Dumpling Making Dinner
What: Celebrate the Year of the Snake with a traditional dumpling-making dinner, storytelling, authentic cuisine, and a lion dance in Chinatown.
When: January 25, 2025
Link for more information: Dumpling Dinner Tickets
Repair Fair with the Chicago Tool Library
What: Give your beloved or broken items a second chance at the free, community Repair Fair.
When: January 25, 2025
Link for more information: Visit the website
January in Chicago
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.
Is January a good time to go to Chicago?
Is January a good time to go to Chicago?
Yes, January is a great time to visit Chicago if you want to experience the city at a slower pace and with fewer crowds. While the temperatures are chilly, you’ll find a more relaxed atmosphere at popular attractions, shorter wait times at restaurants, and discounted hotel rates. It’s also a fantastic time to enjoy seasonal activities like ice skating, cozy indoor experiences, and winter-themed events.
What to do in Chicago in January for free?
What to do in Chicago in January for free?
In January, even in the colder weather, Chicago offers plenty of free things to do. Head downtown to Millennium Park to marvel at iconic landmarks like “The Bean” (Cloud Gate) or go ice skating at the park’s rink if you have your own skates. Many museums, like the Art Institute of Chicago and the Museum of Science and Industry, offer free admission days for Illinois residents during this month—check their schedules in advance. For outdoor enthusiasts, explore the Lakefront Trail or the city’s snow-dusted parks for scenic winter walks.
What to Look Forward to in January
As we kick off 2025, January in Chicago proves that winter is no excuse to hibernate. From world-class cultural events to intimate neighborhood gatherings, this month sets the tone for what promises to be an extraordinary year in the Windy City. Bundle up, step out, and discover why Chicago’s January calendar is worth celebrating.
