2026 Chicago Bears Season Tickets at Soldier Field Sat, 19 Sep at 12:55 pm Soldier Field TRIPS-ADVENTURES
TBD at Chicago White Sox - AL Wild Card (Home Game 1) Tue, 29 Sep at 03:30 am Rate Field TRIPS-ADVENTURES
TBD at Chicago White Sox - AL Wild Card (Home Game 2) Wed, 30 Sep at 03:30 am Rate Field TRIPS-ADVENTURES
TBD at Chicago White Sox - AL Wild Card (Home Game 3) Thu, 01 Oct at 03:30 am Rate Field TRIPS-ADVENTURES
Noel Miller: Special Taping Fri, 02 Oct at 07:15 pm 1331 N Milwaukee Ave, Chicago, IL, United States, Illinois 60622 COMEDY
TBD at Chicago Cubs - World Series (Home Game 1) Fri, 23 Oct at 03:30 am Wrigley Field TRIPS-ADVENTURES
NBA Preseason - Memphis Grizzlies at Chicago Bulls at United Center Fri, 09 Oct at 07:00 pm United Center SPORTS
Chicago White Sox vs. Detroit Tigers (Post Game Concert by Cole Swindell) Thu, 17 Sep at 06:00 pm Rate Field CONCERTS
TBD at Chicago Cubs - World Series (Home Game 2) Sat, 24 Oct at 03:30 am Wrigley Field TRIPS-ADVENTURES
NBA Preseason - Phoenix Suns at Chicago Bulls at United Center Wed, 07 Oct at 07:00 pm United Center SPORTS
Winnipeg Jets at Chicago Blackhawks at United Center Thu, 15 Oct at 07:00 pm United Center 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
World Series: Chicago White Sox vs. TBD - Home Game 2 (Date: TBD - If Necessary) Sat, 24 Oct at 03:30 am Rate Field
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 4) Fri, 30 Oct at 03:30 am Wrigley Field TRIPS-ADVENTURES
TBD at Chicago Cubs - World Series (Home Game 3) Wed, 28 Oct at 03:30 am Wrigley Field TRIPS-ADVENTURES
New England Patriots at Chicago Bears at Soldier Field Thu, 22 Oct at 07:15 pm Soldier Field TRIPS-ADVENTURES
Meet IRL | Friday Night Pickleball for Singles | SPF Lincoln Park Fri, 25 Sep at 06:15 pm SPF Pickleball USD 29 TO 50 FITNESS
NIGERIAN INDEPENDENCE DAY YACHT CRUISE Sun, 27 Sep at 12:00 pm Anita Dee Yacht Charters USD 55 TO 802 FITNESS
World Series: Chicago White Sox vs. TBD - Home Game 3 (Date: TBD - If Necessary) Fri, 30 Oct at 03:30 am Rate Field
Chicago Blackhawks vs. Winnipeg Jets Thu, 15 Oct at 07:00 pm United Center USD 25 TO 744 TRIPS-ADVENTURES
Pro Wrestling Tees presents: ALL ELITE COMEDY Live in Chicago! Fri, 25 Sep at 10:00 pm The Lincoln Lodge USD 24 TO 66 COMEDY
Toronto Tempo at Chicago Sky at Wintrust Arena Tue, 22 Sep at 07:00 pm Wintrust Arena TRIPS-ADVENTURES
Second Hand Soul Band | Old Town Oktoberfest | Sat Sep 19 1:45pm | 1360 N Wells St Chicago Sat, 19 Sep at 01:30 pm 1360 N Wells St, Chicago, IL 60610-1908, United States ENTERTAINMENT
New York City FC at Chicago Fire FC at Soldier Field Sat, 10 Oct at 01:30 pm Soldier Field TRIPS-ADVENTURES
Players Grass Series #10 😎 OktoberFest | Saturday 9/26/26 at Montrose Grove 16 in Chicago 🏐 Sat, 26 Sep at 09:00 am The Dock at Montrose Beach SPORTS
Champions Classic: Michigan State vs Duke, Kansas vs Kentucky Tue, 10 Nov at 06:00 pm United Center KENTUCKY-DERBY
Chicago Bulls vs. Philadelphia 76ers Sun, 08 Nov at 02:30 pm United Center USD 75 TO 700 TRIPS-ADVENTURES
Beyond Lifestyle™ — Wellness Travel & Biohacking Expo in Chicago Sat, 26 Sep at 09:00 am Marriott Marquis Chicago USD 84 TO 292 FITNESS
Champions Classic: Michigan State vs. Duke & Kansas vs. Kentucky Tue, 10 Nov at 03:30 am United Center KENTUCKY-DERBY
"Final Look" Chicago River Swim Weekend Cruise & Celebration Sat, 19 Sep at 10:00 am 600 W Chicago Ave USD 29 TO 55 FITNESS
Colin Kaepernick: The Perilous Fight — Book Signing & Author Talk Fri, 30 Oct at 07:00 pm Rainbow PUSH Coalition USD 48 TO 106 FITNESS
Bloomingdale Trail Run 2026 Sat, 26 Sep at 07:30 am 1600-3000 W Bloomingdale, Chicago, IL, United States, Illinois 60647 TRIPS-ADVENTURES
Volunteering Event: Bank of America Chicago Marathon Sun, 11 Oct at 08:30 am Grant Park, Chicago, Illinois SPORTS
2026 Chicago Skechers Hot Chocolate Run Sun, 01 Nov at 07:00 am 301 S Columbus Dr, Chicago, IL 60604, United States SPORTS
Welcome to Logan Square - LIVE PRO WRESTLING Fri, 02 Oct at 08:00 pm Logan Square Auditorium USD 26 TO 50 FITNESS
Remix Rumble Presents: Chicago Wrestling Nightclub (21+) Fri, 25 Sep at 09:00 pm Emporium Wicker Park USD 17 TO 40 SPORTS
Captured Cubs Player in Chicago - Outdoor Exploration Game Thu, 01 Oct at 12:00 am Wrigley Field USD 10 SPORTS