December 2025

• You can ride CTA trains and buses for free today and tomorrow!
• This is the only Christkindlmarket in Chicago still open for the season
• Young Playwrights Festival
• Chicago in winter: Our ultimate guide
• Chicago Polar Plunge
• Chicago Boat Show
• Polar Adventure Day
• The Kitty & Kellie Show
• No I.D. Alcohol-Free Cocktail Competition & Tasting Event
• The best bookstores in Chicago
• Chicago has a new No. 1 bookstore, according to Time Out
• Chicago Christmas tree recycling 2026: Dates, locations and map
• See inside The Radicle, the highly anticipated new bar from the Daisies team
• Why is everyone talking about this "Chicago-style" hot chocolate at Soldier Field?
• The 17 best ski and snowboard resorts near Chicago
• After all that cold, Chicago is set to have one of the warmest Christmas Days ever
• Everything we know about Hello Kitty Night for the Chicago Bulls
• 10 art exhibitions in Chicago to look forward to in 2026
• The best gyms in Chicago
• 11 things to look forward to in Chicago in 2026
• The Chicago Hip Hop Heritage Museum will officially close
• If Emmett Till Lived: Freedom on American Ground
• MoCP at Fifty: Collecting Through the Decades
• A Tale of Today Presents Brendan Fernandes: In the Round
• Korean National Treasures: 2,000 Years of Art
• I AM WILD: A Charley Harper Exhibit
• Crafting Character: The Costumes of Paul Tazewell
• Yoonshin Park: Prompt and Prompted
• Dancing the Revolution
• Pokémon Fossil Museum
• This national park is just a one-hour train ride from Chicago—and it’s perfect for a winter day trip
• North Pond
• The best books of 2025, according to Chicago’s independent bookstores
• Giordano’s limited-edition pizza celebrates a big football anniversary
• The 26 best steakhouses in Chicago
• Beloved hot dog chain Portillo's is reportedly opening on Michigan Avenue
• The best places to watch New Year's Eve fireworks in Chicago
• A Savannah Bananas–style baseball team is coming to Chicago—and they’re holding tryouts next month
• Illinoisans: It’s your final year to visit the viral Taylor Swift–themed Christmas house.
• Is Drag Race: The Experience worth it? Our full review of the massive ‘RuPaul’s Drag Race’-themed installation.
• STS9 NYE 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
• Amadeus at Steppenwolf
• True story: feel-like temperature to dip to -12 degrees in Chicago this weekend
• The best New Year’s Eve events and parties in Chicago to ring in 2026
• 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
• Dovetail Holiday Market
• House Calls NYE
• Beyond Fest
• Christmas in Chinatown
• 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
• 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
• 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
• 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