TBD at Chicago Cubs - World Series (Home Game 1) Fri, 23 Oct at 03:30 am Wrigley Field TRIPS-ADVENTURES
American League Championship Series: Chicago White Sox vs. TBD - Home Game 2 Series Game 4 (If Necessary) Fri, 16 Oct at 03:30 am Rate Field SPORTS
TBD at Chicago Cubs - World Series (Home Game 4) Fri, 30 Oct at 03:30 am Wrigley Field TRIPS-ADVENTURES
World Series: Chicago White Sox vs. TBD - Home Game 1 (Date: TBD - If Necessary) Fri, 23 Oct at 03:30 am Rate Field
American League Division Series: Chicago White Sox vs. Cleveland Guardians - Home Game 2 Series Game 4 (If Necessary) Thu, 08 Oct at 04:00 pm Rate Field
American League Championship Series: Chicago White Sox vs. TBD - Home Game 3 Series Game 5 (If Necessary) Sat, 17 Oct Rate Field SPORTS
TBD at Chicago White Sox - World Series (Home Game 3) Wed, 28 Oct at 03:30 am Rate Field TRIPS-ADVENTURES
TBD at Chicago Cubs - World Series (Home Game 3) Wed, 28 Oct at 03:30 am Wrigley Field TRIPS-ADVENTURES
Winnipeg Jets at Chicago Blackhawks at United Center Thu, 15 Oct at 07:00 pm United Center TRIPS-ADVENTURES
Chicago Blackhawks vs. Winnipeg Jets Thu, 15 Oct at 07:00 pm United Center USD 25 TO 744 TRIPS-ADVENTURES
Jewel-Osco’s Shiploads of Celebrations & 3rd Annual Beach Volleyball Charity Classic Sat, 10 Oct at 06:00 pm North Avenue Beach SPORTS
NBA Cup - Atlanta Hawks at Chicago Bulls at United Center Fri, 13 Nov at 07:00 pm United Center SPORTS
NBA Cup - Washington Wizards at Chicago Bulls at United Center Fri, 20 Nov at 07:00 pm United Center SPORTS
Chicago Bulls vs. Cleveland Cavaliers Mon, 23 Nov at 07:00 pm United Center USD 39 TO 499 TRIPS-ADVENTURES
Chicago Bulls vs. Indiana Pacers Sat, 28 Nov at 07:00 pm United Center USD 39 TO 499 TRIPS-ADVENTURES
Loyola Ramblers Mens Basketball vs. Calumet College Crimson Wave Mens Basketball Mon, 26 Oct at 12:00 am Gentile Arena SPORTS
Marquette Golden Eagles vs Missouri Tigers Mens Basketball at United Center Sun, 15 Nov at 11:59 pm United Center TRIPS-ADVENTURES
Players Grass Series #12 😎 BLOCK PARTY | Saturday 10/24/26 at Montrose Cricket Hill in Chicago 🏐 Sat, 24 Oct at 09:00 am The Dock at Montrose Beach SPORTS
JEOPARDY! Bar League - Snakes & Lattes Chicago (US) Mon, 26 Jan at 07:00 pm Snakes & Lattes Chicago FREE CONTESTS
Pass The Aux Chicago at Classick Studios (Something Dope) Sun, 11 Oct at 06:00 pm Classick Studios USD 45 TO 162 FITNESS
LOSTNFADED Presents: Faded Game Night Sun, 11 Oct at 06:00 pm Replay Lincoln Park USD 20 TO 32 FITNESS
Chicago Bulls vs. Detroit Pistons Sat, 26 Dec at 07:00 pm United Center USD 39 TO 499 TRIPS-ADVENTURES
Second City Karaoke League | Mondays @ The River - Fall 2026 Mon, 05 Oct at 07:30 pm The River Kitchen & Bar USD 82 FITNESS
Meet IRL | Singles Trivia Night: Spooky Theme! Thu, 15 Oct at 06:30 pm Fatpour Wicker Park: Ultimate Chicago Sports Bar USD 35 TO 39 FITNESS
DePaul Blue Demons Volleyball vs. Butler Bulldogs Sun, 25 Oct at 03:00 pm McGrath-Phillips Arena SPORTS
Utah Mammoth at Chicago Blackhawks at United Center Sat, 12 Dec at 06:00 pm United Center TRIPS-ADVENTURES
Illinois Fighting Illini vs UConn Huskies Mens Basketball at United Center Fri, 04 Dec at 11:59 pm United Center TRIPS-ADVENTURES
Marquette Golden Eagles vs Missouri Tigers Basketball Tickets Sun, 15 Nov at 12:00 am United Center EUR 68
Tuesday Trivia Night at The Welcome Back Lounge! - Logan Square Tue, 13 Oct at 08:00 pm The Welcome Back Lounge FREE FITNESS
UConn Huskies vs Illinois Fighting Illini Mens Basketball Fri, 04 Dec at 03:30 am United Center TRIPS-ADVENTURES
Players Grass Series #13 😎 HOODIE TOURNEY | Saturday 11/14/26 at Montrose Grove 16 in Chicago 🏐 Sat, 14 Nov at 09:00 am The Dock at Montrose Beach SPORTS
Chicago Steel vs. Youngstown Phantoms Sat, 24 Oct at 06:00 pm USG Arena at Blackhawks Ice Center SPORTS
Euchre League 2026 Session III at Hopsmith Tue, 25 Aug at 06:30 pm Hopsmith Chicago USD 23 TO 45 FITNESS
Orlando Magic at Chicago Bulls at United Center Mon, 15 Mar at 07:00 pm United Center TRIPS-ADVENTURES
Kahoot Trivia Night Thu, 16 Apr at 06:00 pm Solar Intentions Non-Alcoholic Beverage Shop FREE FITNESS
Chicago Puzzle Club - Teams Family-Friendly Speed Puzzle Competition & Puzzle Swap - Oct. 24, 2026 Sat, 24 Oct at 01:00 pm Clarendon Park CONTESTS
Traitors: A Real Life Competition of Traitors and Faithfuls Thu, 12 Nov at 07:00 pm Uptown Taproom USD 20 TO 30 FITNESS
Whaddayaknow? Trivia at Carol's Pub Wed, 07 Oct 4659 N Clark St, Chicago, IL, United States, Illinois 60640
Alabama A&M Bulldogs at DePaul Blue Demons Mens Basketball at Wintrust Arena Mon, 09 Nov at 11:59 pm Wintrust Arena
CATAN Championship Qualifier - Snakes and Lattes Chicago US Sun, 01 Nov at 11:30 am Snakes & Lattes Chicago USD 26 SPORTS
Wingspan Board Game Tournament Snakes & Lattes Chicago Sat, 10 Oct at 02:00 pm Snakes & Lattes Chicago USD 10 SPORTS
Lower Levels Only Barn Hunt Trial (Chicago) Sat, 17 Oct at 01:00 pm City Sniffers Dog Sports LLC SPORTS
HamBingo for the Haitian American Museum of Chicago Sun, 01 Nov at 07:00 pm 1055 W Bryn Mawr Ave, Chicago, IL, United States, Illinois 60660 NONPROFIT
DePaul Blue Demons Mens Basketball vs. Creighton Blue Jays Mens Basketball Sat, 27 Feb at 12:00 am Wintrust Arena SPORTS
DePaul Blue Demons Mens Basketball vs. North Alabama Lions Mens Basketball Tue, 01 Dec at 12:00 am Wintrust Arena SPORTS
Creighton Bluejays Women's Volleyball vs. Creighton Bluejays Sat, 31 Oct at 05:00 pm McGrath-Phillips Arena SPORTS