The Fright Crawl | Chicago Halloween Bar Crawl 2026 River North | Sat, Oct 31 Sat, 31 Oct at 07:30 pm Fado Irish Pub USD 9 TO 104 PARTIES
TBD at Chicago Cubs - World Series (Home Game 4) Fri, 30 Oct at 03:30 am Wrigley Field TRIPS-ADVENTURES
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
Chicago Halloween Bar Crawl — Halloween Saturday on Sat, Oct 31st Sat, 31 Oct at 08:30 pm Fado Irish Pub USD 20 TO 50 FITNESS
The Fright Crawl | Chicago's Hottest Halloween Bar Crawl 2026 | Fri, Oct 30 Fri, 30 Oct at 07:30 pm HQ Beercade USD 9 TO 104 FITNESS
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
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 (45+ VENUES) Fri, 30 Oct at 05:00 pm Good Night John Boy USD 18 TO 55 PARTIES
NIGHTMARE IN RIVER NORTH- Chicago's BIGGEST Halloween Bar Crawl Sat, 31 Oct at 12:00 pm Tunnel USD 13 TO 55 PARTIES
Chicago Halloween Bar Crawl — Halloween Friday, Fri, Oct 30 Fri, 30 Oct at 08:30 pm HQ Beercade USD 20 TO 32 PARTIES
Chicago's Haunted Hop 2026: Halloween Bar Crawl (Saturday, Oct 31) Sat, 31 Oct at 08:00 pm Fado Irish Pub USD 20 TO 50 FITNESS
Boo Bash - A Halloween Bar Crawl in Wrigleyville Sat, 24 Oct at 06:00 pm Wrigleyville's BEST Bars TBA USD 5 TO 28 PARTIES
Beethoven 5 at Chicago Symphony Center Sat, 07 Nov at 07:30 pm Chicago Symphony Center TRIPS-ADVENTURES
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
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
NIGHTMARE IN RIVER NORTH - Chicago’s BIGGEST Halloween Bar Crawl Sat, 31 Oct at 12:00 pm ÉLA Nightclub PARTIES
Chicago Halloween Bar Crawl 2026 Sat, 31 Oct at 04:00 pm PB&J: Pizza Beer and Jukebox USD 16 TO 46 FITNESS
Charles Wesley Godwin at Salt Shed - Indoor Shed Thu, 12 Nov at 08:00 pm Salt Shed - Indoor Shed TRIPS-ADVENTURES
Chicago Northside Halloween Bar Crawl | 18 Bars, Old Town + Lincoln Park Sat, 31 Oct at 11:00 am Lincoln Park and Old Town USD 7 TO 72 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 68 HALLOWEEN
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 PARTIES
Halloween Party at Howl at the Moon Chicago Fri, 30 Oct at 06:00 pm Howl at the Moon Chicago FREE FITNESS
A Pilsen Halloween - Dance Party and Costume Contest Sat, 31 Oct at 09:00 pm Simone's USD 7 TO 18 FITNESS
Espresso Martini Fest at Hubbard Inn, Chicago - Tastings Included Sat, 03 Oct Hubbard Inn USD 25 TO 42 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
RESURRECTION ( Sunset Society, Atomic Imaging, Golan Studios ) Sat, 31 Oct at 09:00 pm Haunted Warehouse USD 17 TO 600 FITNESS
The Biggest Halloween Party in Lincoln Park Sat, 31 Oct at 10:00 pm Parlay Lincoln Park USD 50 TO 70 FITNESS
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
Kincade's Wrigleyville's Halloween DAY Party Sat, 31 Oct at 01:00 pm Kincade's Wrigley USD 20 TO 42 FITNESS
Chicago Symphony Orchestra - Jaap van Zweden & Vadim Gluzman Fri, 20 Nov Chicago Symphony Center MUSIC
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 FITNESS
Joffrey Ballet - The Nutcracker at Lyric Opera House Fri, 04 Dec at 07:00 pm Lyric Opera House TRIPS-ADVENTURES
Afrobeats Saturdayz: Halloween costume party (Up to $1000 in prizes) Sat, 31 Oct at 10:00 pm Masada USD 0 TO 176 FITNESS
Chicago Architecture Center River Cruise at Chicagos First Lady Mon, 26 Oct at 11:59 pm Chicagos First Lady TRIPS-ADVENTURES
Nemanja Radulović & Double Sens at Chicago Symphony Center Sun, 22 Nov at 03:00 pm Chicago Symphony Center TRIPS-ADVENTURES
Brahms Requiem at Chicago Symphony Center Thu, 29 Oct at 07:30 pm Chicago Symphony Center TRIPS-ADVENTURES
Bo Johnson at The Lincoln Lodge - one night only 11/8/26 Sun, 08 Nov at 06:00 pm The Lincoln Lodge USD 30 FITNESS
Muti, Welter and Dvorak 8 at Chicago Symphony Center Thu, 03 Dec at 07:30 pm Chicago Symphony Center TRIPS-ADVENTURES
Lyric Opera of Chicago - Wagner - Myth and Music at Lyric Opera House Sun, 22 Nov at 02:00 pm Lyric Opera House TRIPS-ADVENTURES
Godfrey Wine Fest - Wine Tasting at I|O Godfrey Rooftop in Chicago Sat, 14 Nov at 01:00 pm IO Godfrey Rooftop Lounge USD 25 TO 42 FESTIVALS
Chicago Riverwalk Secrets Quest Thu, 29 Oct at 10:00 am Michigan Avenue & East Wacker Place USD 23 FITNESS
Jaap van Zweden at Chicago Symphony Center Fri, 20 Nov at 07:30 pm Chicago Symphony Center TRIPS-ADVENTURES
IPH's Fall Fest on The Riverwalk w/ Hayrides on the River & More in Chicago Sat, 19 Sep at 12:00 pm Island Party Hut (between Lake Shore Drive and Columbus on the Riverwalk) USD 40 FITNESS
Barrio Bugalú - Brujería Edition Feat DJ Bongohead Fri, 30 Oct at 06:00 pm Segundo Ruiz Belvis Cultural Center USD 10 TO 18 ENTERTAINMENT
Crawl to Christkindlmarket: A Holiday Pub Crawl to Christkindlmarket Fri, 27 Nov at 04:00 pm River North's BEST Bars On Your Way to Christkindlmarket USD 28 FITNESS
Handels Messiah at Chicago Symphony Center Sat, 19 Dec at 07:30 pm Chicago Symphony Center TRIPS-ADVENTURES
Parranda Bar Crawl en Wrigleyville | Tix Include Brunch Buffet & 2 Shots! Sat, 28 Nov at 12:00 pm Wrigleyville's Best Bars TBA USD 11 TO 41 PARTIES
UConn Huskies vs Illinois Fighting Illini Mens Basketball Fri, 04 Dec at 03:30 am United Center 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
Reese's Book Club - Big Little Truths (The Sequel to Big Little Lies) Tue, 10 Nov at 06:30 pm Lilliput Books FREE FITNESS
New Year's Eve Sunset Cocktail Cruise on Thursday, December 31st Thu, 31 Dec at 04:30 pm Anita Dee II TEMPORARILY LOCATED at BURNHAM HARBOR (See directions below) USD 20 TO 42 NEW-YEAR
Cosplay Contest Fridays Fri, 16 Oct 2833 N. Sheffield, Chicago, IL, United States, Illinois 60657 CONTESTS
The Oz Experience in Chicago: Escape the Wicked Glitch! Sun, 01 Nov at 01:00 am Chicago History Museum USD 8 TRIPS-ADVENTURES
Midnight in the Enchanted Forest: Fall Ball Sat, 31 Oct at 07:00 pm Spill The Beans USD 26 TO 62 FITNESS
Chicago Wicker Park Naughty Santa Bar Crawl Sat, 05 Dec at 06:00 pm DSTRKT and Wicker Park Venues USD 0 TO 18 FITNESS