2026 Chicago Bears Season Tickets at Soldier Field Sat, 19 Sep at 12:55 pm Soldier Field TRIPS-ADVENTURES
Bottomless Margaritas on the Riverwalk - Every Weds & Sun! Wed, 19 Aug Island Party Hut (between Lake Shore Drive and Columbus on the Riverwalk) USD 25 TO 58 FITNESS
Oktoberfest Chicago Fri, 25 Sep at 05:00 pm 1429 W Wellington Ave, Chicago, IL 60657-4121, United States FESTIVALS
Sofi Tukker at Huntington Bank Pavilion at Northerly Island Fri, 25 Sep at 07:00 pm Huntington Bank Pavilion at Northerly Island TRIPS-ADVENTURES
Johnny Blue Skies and the Dark Clouds at United Center Tue, 29 Sep at 08:00 pm United Center TRIPS-ADVENTURES
TBD at Chicago Cubs - World Series (Home Game 4) Fri, 30 Oct at 03:30 am Wrigley Field TRIPS-ADVENTURES
Bottomless Mimosas on the Riverwalk - Every Saturday in Chicago Sat, 15 Aug Island Party Hut (between Lake Shore Drive and Columbus on the Riverwalk) USD 25 TO 31 PARTIES
TBD at Chicago Cubs - World Series (Home Game 3) Wed, 28 Oct at 03:30 am Wrigley Field TRIPS-ADVENTURES
Sober October: Chicago Zero Proof Halloween Bar Crawl Sat, 10 Oct at 04:00 pm Chicago USD 0 TO 15 PARTIES
Espresso Martini Fest at Hubbard Inn, Chicago - Tastings Included Sat, 03 Oct at 05:00 pm Hubbard Inn USD 25 TO 42 FITNESS
Chicago Architecture Center River Cruise at Chicagos First Lady Mon, 14 Sep at 11:59 pm Chicagos First Lady 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
Haunted Hotel Halloween Ball 2026 at Congress Plaza Hotel Sat, 31 Oct at 09:00 pm Congress Plaza Hotel Chicago USD 30 TO 1,166 HALLOWEEN
Zoo Brews: Howls and Growls Fri, 23 Oct at 06:30 pm N Cannon Dr at W Fullerton Pkwy, Chicago, IL, United States, Illinois 60614 HALLOWEEN
Jewel-Osco’s Shiploads of Celebrations & 3rd Annual Beach Volleyball Charity Classic Sat, 10 Oct at 06:00 pm North Avenue Beach SPORTS
Robot Apocalypse: Journey to the End of Night - 2026 Sat, 26 Sep at 05:00 pm Walsh (John) Park USD 0 TO 29 FITNESS
Saturday, 31st of October, 2026: Annual Nocturna All Hallows’ Eve Ball w/ DJ Scary Lady Sarah + more Sat, 31 Oct at 10:00 pm Metro Chicago ENTERTAINMENT
Beyond The Gate: Cate Le Bon & Horsegirl Thu, 24 Sep at 06:00 pm Bohemian National Cemetery TRIPS-ADVENTURES
NIGHTMARE IN RIVER NORTH- Chicago's BIGGEST Halloween Bar Crawl Sat, 31 Oct at 04:00 pm ĒLA Nightclub USD 13 TO 55 FITNESS
2026 Chicago Skechers Hot Chocolate Run Sun, 01 Nov at 07:00 am 301 S Columbus Dr, Chicago, IL 60604, United States SPORTS
RIVER NORTH/WEST LOOP 2 DAYS OF HALLOWEEN BAR CRAWL PARTY PASS (18 VENUES) Fri, 30 Oct at 04:00 pm Good Night John Boy USD 18 TO 55 PARTIES
Chicago BRA Crawl: Benefiting Breast Cancer Research Sat, 17 Oct at 12:00 pm Chicago's BEST Bars TBA USD 10 TO 28 FITNESS
Jorge Luis Pacheco Trio: "Live from Havana" Wed, 30 Sep at 08:30 pm 201 S. Ashland Avenue, Chicago, IL, United States, Illinois 60607 MUSIC
Haunted Halloween Night Lake Cruise on Friday, October 30th Fri, 30 Oct at 08:00 pm Anita Dee II Boarding at Dusable Harbor (See map and directions at bottom of page for exact location) USD 20 TO 42 FITNESS
JEOPARDY! Bar League - Snakes & Lattes Chicago (US) Mon, 17 Aug Snakes & Lattes Chicago FREE CONTESTS
Philadelphia Union at Chicago Fire FC at Soldier Field Wed, 14 Oct at 07:30 pm Soldier Field TRIPS-ADVENTURES
Jekyll and Hyde at Broadway Playhouse at Water Tower Place Sun, 27 Sep at 01:00 pm Broadway Playhouse at Water Tower Place CONTESTS
NIGHTMARE IN WEST LOOP - Chicago's BIGGEST Halloween Bar Crawl Sat, 31 Oct at 12:00 pm Good Night John Boy USD 13 TO 55 PARTIES
Sober October: Chicago's Zero Proof Halloween Bar Crawl Sat, 10 Oct at 04:00 pm Three Dots and a Dash USD 0 TO 15 FITNESS
HighQ - a comedy game show at The Lincoln Lodge Sun, 01 Feb at 06:00 pm The Lincoln Lodge USD 18 FITNESS
Chicago Wine Fest at Hubbard Inn - Tastings Included Sat, 24 Oct at 05:00 pm Hubbard Inn USD 25 TO 42 FITNESS
Chicago Halloween Bar Crawl 2026 Sat, 31 Oct at 04:00 pm PB&J: Pizza Beer and Jukebox USD 10 TO 46 PARTIES
The Official Halloween Bar Crawl - Chicago Sat, 31 Oct at 05:00 pm Black Hole Bar USD 17 TO 86 FITNESS
Definition Theatre: How We Got On by Idris Goodwin Fri, 11 Sep Definition Theatre USD 29 TO 39 FITNESS
The Oz Experience in Chicago: Escape the Wicked Glitch! Thu, 01 Oct at 01:00 am Chicago History Museum USD 8 TRIPS-ADVENTURES
From Day One - Chicago Live 2026: People & HR Tue, 29 Sep at 08:30 am Venue SIX10 USD 268 TO 1,999 FITNESS
Haunted Halloween Night Lake Cruise on Saturday, October 31st Sat, 31 Oct at 08:00 pm Anita Dee II Boarding at Dusable Harbor (See map and directions at bottom of page for exact location) USD 30 TO 58 FITNESS
Unplugged R&B 1-Year Anniversary ft. Eric Bellinger Fri, 30 Oct at 06:00 pm Pitch and Pour Supper Club USD 45 TO 482 MUSIC
Charles Wesley Godwin at Salt Shed - Indoor Shed Thu, 12 Nov at 08:00 pm Salt Shed - Indoor Shed TRIPS-ADVENTURES
Joffrey Ballet - The Nutcracker at Lyric Opera House Fri, 04 Dec at 07:00 pm Lyric Opera House TRIPS-ADVENTURES
Lectures on Tap - "Why Humans Speak: The Evolution and Origins of Language" Tue, 29 Sep at 06:30 pm Logan Square USD 39 CONTESTS