Five Things To Do in Chicago: Jan. 23 to 25, 2026

Don't let the cold hold you back — these weekend events are worth layering up for. See what's happening near you.

Sip your way through the Winter Whiskey Tasting Festival.
Chicago's winter whiskey scene heats up with this seasonal tasting festival bringing together more than 20 whiskies from craft, small-batch, and international distillers. Sample a wide range of styles while chatting with whiskey ambassadors on hand to guide each pour. The festival also supports Bear Necessities, with additional tasting cups benefiting pediatric cancer research.

Date: Jan. 24
Time: 2:30 p.m.–5 p.m.
Cost: $13+
Location: King's, 1500 N. Clybourn Ave.
More Info: eventbrite.com

Head to The Banchet Awards After Party.
Following the annual Jean Banchet Awards, the celebration continues with the official after party spread across the 9th and 10th floors. The evening features bites from top chefs, craft cocktails from leading bartenders, and music that carries the festivities late into the night.

Date: Jan. 25
Time: 8:30–11 p.m.
Cost: $155
Location: SIX10, 610 S. Michigan Ave.
More Info: exploretock.com

Sing along at Cash for Kids.
Chicago's only Johnny Cash–inspired music festival returns for its 21st year, featuring nine bands performing across three stages in one venue. The lineup spans bluegrass, country, rockabilly, and folk, with each act drawing from Cash's catalog or his lasting influence. Performers include The Waco Brothers, Iron Horse, Alaina Stacey, and The John Allen Green Band, making this a full-day tribute to the Man in Black and the local artists he continues to inspire.

Date: Jan. 24
Time: 5 p.m.–12 a.m.
Cost: $25
Location: Irish American Heritage Center, 4626 N. Knox Ave.
More Info: fundraise.givesmart.com 

Bring your appetite to Mac & Cheese Fest.
Mac & Cheese Fest turns Wrigleyville into a neighborhood-wide tasting crawl, with participating bars serving their own spins on the comfort-food classic. From buffalo chicken and jalapeño popper mac to four-cheese and mac-and-cheese pizza, the event offers a wide range of styles within walking distance of one another. Along the way, attendees can enjoy drink specials, and giveaways.

Date: Jan. 24
Time: 11 a.m.–7 p.m.
Cost: $16+
Location: Various Locations, Wrigleyville
More Info: eventbrite.com 

Vote live at Art Battle.
Live painting meets friendly competition at Art Battle, where artists face off in timed rounds to create original works in front of a live audience. Each round lasts 20 minutes, with spectators voting to determine who advances and ultimately wins the night. All completed pieces are available through a silent auction, offering attendees the chance to take home artwork created in real time during the event.

Date: Jan. 23
Time: 7–10 p.m.
Cost: $26
Location: SPIN Chicago, 344 N. State St.
More Info: artbattle.com