Chicago
Saturday December 6 ☁️ -6℃ — -1℃
- Saturday December 6 08:30 17th Annual CASA Christmas Express New Lenox station
- Saturday December 6 11:00 Shop Jarvis Square R Public House
- Saturday December 6 12:00 Howliday Wag N' Shop Dog-Friendly Market Fundraiser 4011 N Ravenswood Ave, Chicago, IL 60613-2409, United States
- Saturday December 6 12:00 An Afternoon with America's Anchorman Bill Kurtis & WGN-TV's Larry Potash 440 W Randolph Street, 60606
- Saturday December 6 15:00 Heavenly Cynt Youth Pop Up Fun Activities Video Games, Life Skills ) Hub 401 N Trumbull Ave
- Saturday December 6 17:00 Chicago's Byob Party Bus Holiday Lights Tour 'Tis The Season | Navy Pier Santa's Workshop at Old Crow Smokehouse
- Saturday December 6 18:00 Cookies & Carols 2025 Cross of Christ Fellowship
- Saturday December 6 18:30 Book Launch Celebration 3850 S Indiana Ave
- Saturday December 6 21:00 Bollywood Glam Night with Mallika Sherawat The Matrix Club
Sunday December 7 🌨️ -6℃ — -3℃
- Sunday December 7 12:00 Brunch Like A Diva at The Piggery The Piggery
- Sunday December 7 12:00 Holiday Market and Exchange National Public Housing Museum
- Sunday December 7 14:00 Holiday Market Five Year Anniversary Stan Mansion
- Sunday December 7 18:00 Chicago Bulls vs. Golden State Warriors United Center
Thursday December 11 ☁️ -7℃ — -2℃
- Thursday December 11 18:00 Ornament Painting at Café Con Leche Cafe Con Leche
- Thursday December 11 19:30 OnlyWrestlers Frozen Fury Logan Square Auditorium
Friday December 12 ☁️ -9℃ — -5℃
- Friday December 12 19:00 Frequency Leak: Drone Read Elastic Arts
Saturday December 13 ☁️ -10℃ — -5℃
- Saturday December 13 08:30 Breakfast with Santa Chicago Neiman Marcus Saturday, December 13, 8:30am 737 N Michigan Ave
- Saturday December 13 10:00 EDUCATOR EVENT: Honoring Belief and Heritage in the Classroom 1400 S. Jean Baptiste Pointe DuSable Lake Shore Drive , Chicago, IL, United States, Illinois 60605
- Saturday December 13 10:00 Vjosa Holiday Market Vjosa Cafe & Events
- Saturday December 13 11:00 Holly Jolly Trolley - HOLS, NCNA, and DANK HAUS Giddings Plaza
- Saturday December 13 14:30 Christmas in Chicago Concert The Moody Church
- Saturday December 13 15:00 Yu-Gi-Oh! Winter 3v3 OTS Tourney! 835 N Michigan Ave, Chicago, IL, United States, Illinois 60611
- Saturday December 13 17:30 St. Al’s Christmas Ball 1429 W Wellington Ave, Chicago, IL
- Saturday December 13 22:00 CHICAGO'S HAAYE SARDI BOLLYWOOD PARTY@LORE NIGHTCLUB Lore Chicago
Thursday December 18 ☁️ -6℃ — 0℃
- Thursday December 18 17:00 Palenque LSNA Margaritas for a Mission After Party SABA Italian Bar + Kitchen
Saturday December 20 🌦️ -1℃ — 6℃
- Saturday December 20 10:00 Chicago holiday market 6100 S Blackstone Ave
- Saturday December 20 11:00 Renegade Chicago Morgan Manufacturing
- Saturday December 20 12:00 Chicago Bears vs. Green Bay Packers Soldier Field
- Saturday December 20 13:00 Chicago SantaCon 2025 PB&J: Pizza Beer and Jukebox
- Saturday December 20 14:00 🎄 The Elfed Up Christmas Crawl 🎅🏻 60610
- Saturday December 20 16:00 The Official Christmas Bar Crawl - Chicago SPIN
Friday December 26
- Friday December 26 19:00 Christian Singles Speed Dating Chicago (In-Person) Chicago
Saturday December 27
- Saturday December 27 17:00 Chicago's BYOB Party Bus Holiday Lights Tour | Navy Pier Old Crow Smokehouse - Wrigleyville
Wednesday December 31
- Wednesday December 31 20:00 New Year's Eve Masquerade Ball Bellagio 223
- Wednesday December 31 20:00 2026 Chicago All Access New Years Eve (NYE) Bar Crawl AE Downtown Chicago
- Wednesday December 31 21:00 NEW YEAR'S EVE BLACK TIE AFFAIR (5TH ANNUAL) 1612 W Division St
- Wednesday December 31 21:00 2026 Chicago New Years Eve Fireworks Cruise - The Midnight Kiss Chicago Elite Yacht
- Wednesday December 31 21:45 All Inclusive New Year's Eve 2026 Fireworks Cruise aboard Anita Dee II Anita Dee II TEMPORARILY LOCATED at BURNHAM HARBOR (See directions below)
- Wednesday December 31 22:00 Feliz Año Nuevo! Café Con Leche NYE Party Cafe Con Leche
- Wednesday December 31 22:00 CHICAGO BOLLYWOOD NYE 2026 @SEVEN NIGHTCLUB Seven Nightclub Chicago
Friday February 6
- Friday February 6 17:30 First Look for Charity McCormick Place
- Friday February 6 18:00 Chicago Auto Show South Building at McCormick Place
Sunday February 8
- Sunday February 8 08:00 Miles Per Hour Run McCormick Place
Friday February 27
- Friday February 27 19:30 Samay Raina "Still Alive" - Chicago - 27th Feb, 2026 Copernicus Center
Friday April 3
- Friday April 3 20:00 Ashnikko: Smoochies Tour Byline Bank Aragon Ballroom