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
80s vs 90s Night at the Zoo - An Adults Only Evening at Lincoln Park Zoo Sat, 19 Sep at 06:30 pm Lincoln Park Zoo USD 15 TO 48 FITNESS
Afterwork Sunset or Fireworks Social Cruises on Lake Michigan Thu, 13 Aug Anita Dee II Boarding at Dusable Harbor (See map and directions at bottom of page for exact location) USD 27 TO 42 FITNESS
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
Chicago BYOB Exotic Paintings Sip and Paint with Male Models Fri, 13 May at 07:30 pm 5425 W Lawrence Ave USD 38 FITNESS
Chicago, IL - Sunday Service: R&B + Reggaeton Brunch @ Punch Bowl Social Sun, 05 Apr Punch Bowl Social FREE BRUNCH
Chicago's Theatre of Magic at the Palmer House a Hilton Hotel Sat, 19 Sep at 04:30 pm Palmer House a Hilton Hotel USD 59 TO 99 ART
Espresso Martini Fest at Hubbard Inn, Chicago - Tastings Included Sat, 03 Oct at 05:00 pm Hubbard Inn USD 25 TO 42 FITNESS
Club Capri: Chicago's #1 Rooftop Party Series At Castaway's Beach Club Sat, 23 May Castaways Beach Club USD 31 TO 78 FITNESS
Chicago Exotic Paintings BYOB Sip and Paint with Male Models Fri, 26 Feb at 08:00 pm 5425 W Lawrence Ave USD 43 FITNESS
EmpowerHer Med Gala Fri, 25 Sep at 07:00 pm 140 E Walton Pl, Chicago, IL 60611-1545, United States HEALTH-WELLNESS
SATURDAY SEPTEMBER 19: CHICAGO'S BEST COMEDY SHOW Sat, 19 Sep at 09:00 pm The Comedy Bar - Chicago Main Stage FREE FITNESS
Grand Opening of The Champagne Room Featuring Moët & Chandon Sat, 19 Sep at 08:00 pm Ambassador Gold Coast - The Chicago Hotel Collection USD 30 TO 66 FITNESS
Moe's Wrigleyville's $30 Wristband Pkg - Every Fri & Sat in Chicago Sat, 11 Jul at 10:00 pm Moe's Cantina (Wrigleyville) USD 34 FOOD-DRINKS
ALL THE FEELS: "PRETTY & TOXIC" (R&B • Breakup • Real Feelings) Sat, 10 Oct at 10:00 pm BAR22 USD 0 TO 38 FITNESS
Chicago Halloween Bar Crawl 2026 - Lincoln Park - Fri, Oct 30 Fri, 30 Oct at 05:00 pm Brando's Lincoln Park USD 13 TO 48 FITNESS
Chicago Exotic Paintings BYOB Wine and Paint Male Model Fri, 10 Mar at 09:00 pm 5425 W Lawrence Ave USD 44 FITNESS
TAMALES Y ROCK AT PIZZA CANTINA: Live Performance by Sin Anestesia Sat, 19 Sep at 11:00 am Pizza Cantina USD 0 TO 14 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 PARTIES
Chicago Friday and Saturday Halloween Bar Crawl - West Loop - Fri, Oct 30 Fri, 30 Oct at 05:00 pm Esco USD 13 TO 48 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
The Boos & Booze Chicago Halloween Bar Crawl | Lincoln Park Sat, 31 Oct at 02:00 pm Lincoln Park USD 8 TO 31 FITNESS
JEOPARDY! Bar League - Snakes & Lattes Chicago (US) Mon, 17 Aug Snakes & Lattes Chicago FREE CONTESTS
CHICAGO ZOMBIE CRAWL - Halloween Bar Crawl - Wrigleyville Party Pass Fri, 30 Oct at 07:00 pm Wrigleyville FITNESS
Sakura - Paint and Sip in Chicago | Classpop!™ Sat, 19 Sep at 03:30 pm Pinot's Palette - Logan Square USD 56 ART
The Second City Improv Social at Sheraton Grand Chicago Riverwalk Sat, 15 Aug Sheraton Grand Chicago Riverwalk USD 119 WORKSHOPS
Beyond Bliss | Chicago Male Revue Show at Fame Nightclub Sat, 19 Sep at 07:00 pm 157 W Ontario St USD 20 TO 25 PARTIES
Laughs in the CITY at Renaissance Bronzeville (Formerly Jokes and Notes) Mon, 16 Mar Renaissance Bronzeville FREE COMEDY
Offshore Rooftop Halloween Party in Chicago — Oct 31 Sat, 31 Oct at 08:00 pm Offshore Rooftop USD 33 HALLOWEEN-PARTIES
Golden Hour Featuring Vince Lazarus & DJ Woodi Sat, 26 Sep at 05:00 pm Epiphany Center for the Arts FREE MUSIC
Chicago Halloween Bar Crawl 2026 Sat, 31 Oct at 04:00 pm Kitchen + Kocktails By Kevin Kelley - Chicago USD 13 TO 18 FITNESS
Drunk Dracula in Chicago | Chicago Sat, 19 Sep at 03:00 pm Drunk Shakespeare Chicago TRIPS-ADVENTURES
The Boos & Booze Chicago Halloween Friday & Saturday Bar Crawl | West Loop Fri, 30 Oct at 12:00 am Punch Bowl Social USD 10 TO 15 PARTIES
The Boos & Booze Chicago Friday Halloween Bar Crawl | River North & West Loop Fri, 30 Oct at 05:00 pm River North Bar (Headquarters Beercade) USD 10 TO 15 PARTIES
The Boos & Booze Chicago Friday & Saturday Halloween Bar Crawl | River North Sat, 31 Oct at 12:00 am Headquarters Beercade USD 10 TO 15 PARTIES
I|O Godfrey Halloween 2026 Sat, 31 Oct at 08:00 pm I|O Godfrey Rooftop Lounge USD 50 TO 2,136 FITNESS
The Official Halloween Bar Crawl - Chicago Sat, 31 Oct at 05:00 pm Black Hole Bar USD 17 TO 86 FITNESS
OneOne Club Happy Hour Fri, 29 May Chef Art Smith’s Reunion, Navy Pier, East Grand Avenue, Chicago, IL, USA FREE FOOD-DRINKS
Shuck & Sundresses Oyster Experience Day Party Sat, 26 Sep at 03:00 pm Pitch & Pour Supper Club USD 46 TO 354 PARTIES
RNRA "I Love River North" Happy Hour hosted by F1®Arcade Chicago Tue, 29 Sep at 05:30 pm 1 W Grand Ave USD 45 TO 55 SPORTS
Grand Opening of The Lair (Under Stardust River North) Sat, 19 Sep at 08:00 pm Stardust Lounge FREE PARTIES
The Boos & Booze Chicago Halloween Bar Crawl | Lincoln Park Fri, 30 Oct at 06:00 pm Lincoln Park Plaza USD 10 PARTIES
FRIDAY OCTOBER 16: CHICAGO'S BEST COMEDY SHOW Fri, 16 Oct at 09:00 pm The Comedy Bar - Chicago Main Stage FREE COMEDY
"DANCE OF THE DEAD" | Chicago's Ultimate Halloween Party Fri, 30 Oct at 10:00 pm BAR22 USD 0 TO 44 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
SATURDAY OCTOBER 17: CHICAGO'S BEST COMEDY SHOW Sat, 17 Oct at 09:00 pm The Comedy Bar - Chicago Main Stage FREE COMEDY
Let's Get Toasty - Date Night - Paint and Sip in Chicago | Classpop!™ Wed, 23 Sep at 07:00 pm Pinot's Palette - Logan Square USD 49 ART
The Boos & Booze Chicago Friday & Saturday Halloween Bar Crawl | West Loop Sat, 31 Oct at 02:00 pm Headquarters Beercade USD 14 TO 43 PARTIES
Chicago, IL - First Taste Halloween @ Punch Bowl Social Fri, 02 Oct at 11:00 am Punch Bowl Social Chicago FREE FITNESS
Love Songs & Liquor Brunch Karaoke With a live Band Sat, 10 Oct at 12:00 pm Haymarket Pub & Brewery USD 19 TO 25 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
Chicago Official Thanksgiving Eve Bar Crawl 2026 Wed, 25 Nov at 07:00 pm Downtown Chicago USD 0 TO 13 FITNESS
Exclusive Verity Experience: Secrets on Still Water - Paint and Sip in Chicago | Classpop!™ Sat, 10 Oct at 08:00 pm Pinot's Palette - Logan Square USD 62 FITNESS
In Another Life: Chicago's Vintage Fashion Show Wed, 14 Oct at 06:00 pm 247 E Ontario St USD 50 TO 61 FITNESS
Chicago Exotic Paintings BYOB Wine & Paint Male Models Fri, 29 Jul at 07:00 pm 5425 W Lawrence Ave USD 44 FITNESS
Chicago Riverwalk Bar Crawl | Includes 2 Welcome Shots! Sat, 15 Aug Starting at AceBounce then off to the Best Bars on the Chicago Riverwalk USD 22 TO 28 PARTIES
Chicago Boricua Women event: One last San Juan sunset Sun, 20 Sep at 04:00 pm Humboldt Park Beach FREE FITNESS