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
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
Chicago Halloween Party 2026: Haunted Hotel Ball at Congress Plaza Hotel Sat, 31 Oct at 09:00 pm Congress Plaza Hotel Chicago USD 30 TO 1,166 PARTIES
Chicago Halloween Bar Crawl Sat, 24 Oct at 04:00 pm PB&J: Pizza Beer and Jukebox USD 16 TO 46 PARTIES
Sober October: Chicago Zero Proof Halloween Bar Crawl Sat, 10 Oct at 04:00 pm Chicago USD 0 TO 15 PARTIES
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
The Fright Crawl | Chicago's Hottest Halloween Bar Crawl 2026 | Fri, Oct 30 Fri, 30 Oct at 07:30 pm TBA USD 8 TO 71 PARTIES
A Chosen Few DJs Halloween. A House Music Event w $1,000 Costume Contest. Fri, 30 Oct at 10:00 pm Le Nocturne Chicago USD 15 TRICK-OR-TREAT
Streetlight Manifesto at House of Blues Chicago Sun, 25 Oct at 07:00 pm House of Blues Chicago TRIPS-ADVENTURES
New York City FC at Chicago Fire FC at Soldier Field Sat, 10 Oct at 01:30 pm Soldier Field TRIPS-ADVENTURES
Bottomless Mimosas on the Riverwalk - Every Saturday in Chicago Sat, 02 May at 11:00 am Island Party Hut (between Lake Shore Drive and Columbus on the Riverwalk) USD 25 TO 31 FITNESS
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 FITNESS
2026 Chicago Skechers Hot Chocolate Run Sun, 01 Nov at 07:00 am 301 S Columbus Dr, Chicago, IL 60604, United States SPORTS
NIGHTMARE IN RIVER NORTH- Chicago's BIGGEST Halloween Bar Crawl Sat, 31 Oct at 04:00 pm ĒLA Nightclub USD 13 TO 55 PARTIES
The Fright Crawl | Chicago Halloween Bar Crawl 2026 | Thursday, October 29 Thu, 29 Oct at 07:30 pm HQ Beercade USD 9 TO 80 PARTIES
Chicago's Haunted Hop 2026: Halloween Bar Crawl (Saturday, Oct 31) Sat, 31 Oct at 08:00 pm HQ Beercade USD 20 TO 38 FITNESS
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 57 FITNESS
Espresso Martini Fest at Hubbard Inn, Chicago - Tastings Included Sat, 03 Oct at 05:00 pm Hubbard Inn USD 25 TO 42 FESTIVALS
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 FITNESS
Chicago BRA Crawl: Benefiting Breast Cancer Research Sat, 17 Oct at 12:00 pm Wrigleyville's BEST Bars TBA USD 10 TO 28 FITNESS
Jewel-Osco’s Shiploads of Celebrations & 3rd Annual Beach Volleyball Charity Classic Sat, 10 Oct at 06:00 pm North Avenue Beach SPORTS
NIGHTMARE IN RIVER NORTH - Chicago’s BIGGEST Halloween Bar Crawl Sat, 31 Oct at 12:00 pm ÉLA Nightclub PARTIES
Chicago Architecture Center River Cruise at Chicagos First Lady Mon, 05 Oct at 11:59 pm Chicagos First Lady TRIPS-ADVENTURES
Chicago Halloween Bar Crawl 2026 Sat, 31 Oct at 04:00 pm PB&J: Pizza Beer and Jukebox USD 10 TO 46 FITNESS
Philadelphia Union at Chicago Fire FC at Soldier Field Wed, 14 Oct at 07:30 pm Soldier Field TRIPS-ADVENTURES
MCMF Presents...Fallapalooza (a spooky fest for teens) Fri, 16 Oct at 05:30 pm Harold Washington Library Center, Chicago Public Library FREE FITNESS
Chicago Wine Fest at Hubbard Inn - Tastings Included Sat, 26 Dec at 05:00 pm Hubbard Inn USD 25 TO 42 FITNESS
Halloween Party at Howl at the Moon Chicago Fri, 30 Oct at 06:00 pm Howl at the Moon Chicago FREE FITNESS
CHICAGO MARATHON – ABBOTT BIBAWAY EVENT Fri, 09 Oct at 12:00 pm Spirit of Music Garden in Grant Park FREE SPORTS
Ravenswood Costume Crawl Wed, 28 Oct at 05:30 pm A variety of Ravenswood small businesses USD 34 TO 36 PARTIES
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
NIGHTMARE ON RANDOLPH - A TWO DAY HALLOWEEN EXPERIENCE Fri, 23 Oct at 06:00 pm 1249 W Randolph St, West Loop NONPROFIT
RESURRECTION ( Sunset Society, Atomic Imaging, Golan Studios ) Sat, 31 Oct at 09:00 pm Haunted Warehouse USD 17 TO 600 FITNESS
Sammy Rae at Salt Shed - Indoor Shed Fri, 23 Oct at 08:00 pm Salt Shed - Indoor Shed TRIPS-ADVENTURES
Sober October: Chicago's Zero Proof Halloween Bar Crawl Sat, 10 Oct at 04:00 pm Federales Tacos & Tequila - Logan Square, Chicago USD 0 TO 20 PARTIES
Brahms Requiem at Chicago Symphony Center Thu, 29 Oct at 07:30 pm Chicago Symphony Center TRIPS-ADVENTURES
The Biggest Halloween Party in Lincoln Park Sat, 31 Oct at 10:00 pm Parlay Lincoln Park USD 50 TO 60 FITNESS
Charles Wesley Godwin at Salt Shed - Indoor Shed Thu, 12 Nov at 08:00 pm Salt Shed - Indoor Shed TRIPS-ADVENTURES
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
Beethoven 5 at Chicago Symphony Center Sat, 07 Nov at 07:30 pm Chicago Symphony Center TRIPS-ADVENTURES
Day of the Dead Crawl - Tix Include 3 Welcome Shots Sun, 01 Nov at 01:00 pm River North's BEST Bars TBA USD 5 TO 28 FITNESS
Chicago Symphony Orchestra - How to Train Your Dragon 2 in Concert at Chicago Symphony Center Fri, 27 Nov at 07:30 pm Chicago Symphony Center MUSIC
Kincade's Wrigleyville's Halloween DAY Party Sat, 31 Oct at 01:00 pm Kincade's Wrigley USD 20 TO 37 ENTERTAINMENT
Brown Suga - A NEW BIPOC BURLESQUE COMP Sat, 24 Oct at 09:00 pm The Newport Theater USD 0 TO 429 FITNESS
The Widow's Manuscript: A Regency M**der Mystery Bookstore Crawl Fri, 23 Oct at 10:00 am Goblin Market USD 32 ART
Afrobeats Saturdayz: Halloween costume party (Up to $1000 in prizes) Sat, 31 Oct at 10:00 pm Masada USD 0 TO 176 FITNESS
The Menzingers with Hot Water Music and Weakened Friends Sat, 14 Nov at 07:00 pm The Salt Shed - Indoors TRIPS-ADVENTURES
Joffrey Ballet - The Nutcracker at Lyric Opera House Fri, 04 Dec at 07:00 pm Lyric Opera House TRIPS-ADVENTURES
Muti, Welter and Dvorak 8 at Chicago Symphony Center Thu, 03 Dec at 07:30 pm Chicago Symphony Center TRIPS-ADVENTURES
South Loop Doods Spooky Night Out at City Paws Sat, 17 Oct at 03:00 pm ChiTown Drive In FREE HALLOWEEN
JEOPARDY! Bar League - Snakes & Lattes Chicago (US) Mon, 26 Jan at 07:00 pm Snakes & Lattes Chicago FREE CONTESTS
Haunted Howl-o-ween Party for Dogs at Wag Hotels West Loop Sat, 24 Oct at 06:00 pm Wag Hotels - West Loop USD 0 TO 22 FITNESS
NEW Pub Trivia M**der Mystery Challenge: The Case of the Killer Ending Thu, 22 Oct at 05:00 pm The Book Cellar USD 13 TO 25 ART
Flummunity Fest Formal 2026 | Fluevog Chicago Sat, 17 Oct at 07:00 pm John Fluevog Shoes Chicago USD 74 TO 82 FITNESS
KIDS CHESS CLASS 8-week Series with Chess Wizards (Pre-registration) Sat, 17 Oct at 10:00 am Lemon Wedge Arts FREE WORKSHOPS
Chicago Symphony Orchestra - Jaap van Zweden & Vadim Gluzman Fri, 20 Nov Chicago Symphony Center MUSIC
Nemanja Radulović & Double Sens at Chicago Symphony Center Sun, 22 Nov at 03:00 pm Chicago Symphony Center TRIPS-ADVENTURES