December 2025

• The 2026 Chicago Restaurant Week lineup is here, with a record number of participants
• Miller High Life's Free Rides program is back for New Year’s Eve in Chicago
• The 23 best spas in Chicago
• The best January 2026 events in Chicago
• Drag Race: The Experience
• Is Drag Race: The Experience worth it? Our full review of the massive ‘RuPaul’s Drag Race’-themed installation.
• Amadeus at Steppenwolf
• True story: feel-like temperature to dip to -12 degrees in Chicago this weekend
• The best December 2025 events in Chicago
• The best New Year’s Eve events and parties in Chicago to ring in 2026
• The best things to do in Chicago this weekend
• The best free museum days in Chicago
• Paris in Black
• Prince Street Pizza is turning into Little Nero's from 'Home Alone' for a weeklong pop-up tomorrow
• Catalyst: Im/migration and Self-Taught Art in Chicago
• PAWS Chicago Holiday Adopt-a-Thon
• The Phantom of the Opera
• Dovetail Holiday Market
• House Calls NYE
• Beyond Fest
• Christmas in Chinatown
• STS9 NYE 2025
• Bridgeport Art Center Holiday Market
• These five Chicago restaurants were just ranked as some of the best in the world
• Bruce Goff: Material Worlds
• Matisse’s Jazz: Rhythms in Color
• A free pop-up rage room is opening in Chicago for one day only
• The best clubs in Chicago for dancing the night away
• This former quarry is the most stunning park to visit in Chicago this winter
• The best things to do in Chicago this week
• New Year's Eve Festa
• New Year’s Eve at Lottie’s Pub
• New Year’s Eve at aliveOne
• New Year's Eve Party at The Metropolitan
• New Year's Eve at the Owl
• State/Lake CTA is closing for repairs in 2026. Here is what to expect.
• New Year’s Eve at The Bassment
• City of Chicago's New Year's Eve Celebration
• Gimme Gimme Disco
• New Year's Eve at Pizzeria Portofino
• New Year's Eve at Raised Rooftop Bar
• New Year's Eve 2026 Fireworks River Cruise
• Heat Sync: New Year’s Eve at The Whistler
• New Year’s Eve at The Godfrey Hotel Chicago
• New Year's Eve Party at Palmer House
• Eve of the Eve
• Christmas Dance Party at The Owl
• A massive Fulton Market hotspot is hosting Chicago’s most epic New Year’s Eve party
• A number of 'Letters to Santa' stations were just set up at both Chicago airports
• The best literary and poetry readings in Chicago
• Chicago’s first-ever cookie market is coming to Wrigleyville—and it’s benefitting a great cause
• The 15 best karaoke bars in Chicago
• Chicago was just named one of the top 10 best festive waterfront destinations in the country, beating out Los Angeles and Boston
• Chance the Rapper wants Chicagoans to enjoy the ride
• The best Christmas bars and holiday pop-ups in Chicago
• Chicago’s newest Christmas bar is taking over this West Loop rooftop
• Chicago was just voted one of the best cities in the world
• Christkindlmarket Chicago 2025: Everything you need to know
• The Chicago Bears’ 1985 rap classic “The Super Bowl Shuffle” (rightfully) gets the documentary treatment from HBO
• Simone Mitchell-Peterson is proving that joy doesn’t age
• Dennis Scott is the man who makes the Music Box sing
• For Maya-Camille Broussard, a humble pie can create more change than you might think
• Best of the City: The nine best things Time Out Chicago editors saw, ate and visited in 2025
• Yippee Ki Yay: A ‘Die Hard’ Christmas Pop-up Bar
• Change Machine
• Introducing Little Ripper Skateboarding, Chicago's best skate school-turned-community resource
• How to snag a free cookie at the Harry Potter Shop Chicago this week
• The 15 best vegan and vegetarian restaurants in Chicago
• Renegade Craft Fair
• Chicago Auto Show
• Christmas in Chicago 2025: Guide to celebrating the holidays
• The best cheap things to do in Chicago for fun on a budget
• Chicago’s top bartenders will compete in an epic West Loop cocktail competition
• The Chicago Public Library just released its list of top books in 2025
• The 10 best fine-dining restaurants in Chicago
• The best free things to do in Chicago this month
• Navy Pier Fireworks
• This perennial Chicago favorite was just crowned the best restaurant in the U.S. in the 21st century
• Family Storybook Yoga
• This viral Chicago chicken shop is giving away free sandwiches this week
• 360 Sky Yoga
• The 50 best things to do in Chicago right now
• The 24 best restaurants in Chicago right now—the official ranking