Chasing Sun(Sets) III — JOEZI x MASSUMA Sat, 19 Sep at 12:00 pm Castaways Beach Club USD 30 TO 65 ART
Masquerade Ball On The Yacht (3 Levels) Chicago Sat, 19 Sep at 06:45 pm Anita Dee Yacht Charters USD 55 TO 562 PARTIES
Lakeview East Festival of the Arts Sat, 19 Sep at 06:30 pm Lakeview East Festival of the Arts FESTIVALS
Juke Vs Hip Hop Yacht Party (3 Levels) Chicago Fri, 25 Sep at 06:45 pm Anita Dee Yacht Charters USD 40 TO 500 ENTERTAINMENT
RnB Vs Hip Hop Yacht Party (Black Attire) Anita Dee 2 Sat, 03 Oct at 12:45 pm Anita Dee Yacht Charters USD 45 TO 535 ENTERTAINMENT
MOULIN ROUGE: Fashion, Drag & Cabaret Experience at Kit Kat Club Sun, 20 Sep at 05:00 pm Kit Kat Club USD 45 ART
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 - West Loop - Sat, Oct 24 Sat, 24 Oct at 05:00 pm Esco USD 13 TO 27 PARTIES
R&B Boo Bash Sweetest Day Yacht Party (3 Levels) Chicago Sat, 17 Oct at 06:45 pm Anita Dee Yacht Charters USD 45 TO 562 ENTERTAINMENT
The Halloween Bar Crawl - Chicago - River North - Sat, Oct 31 Sat, 31 Oct at 05:00 pm Joy District USD 13 TO 15 PARTIES
Chicago's Hottest Halloween Bar Crawl 2026 - River North - Fri, Oct 30 Fri, 30 Oct at 05:00 pm Joy District USD 15 TO 50 FITNESS
Chicago Official Halloween Bar Crawl - West Loop - Sat, Oct 31 Sat, 31 Oct at 05:00 pm Esco USD 13 TO 44 FITNESS
The Boos & Booze Chicago Halloween Bar Crawl | Lincoln Park Sat, 31 Oct at 02:00 pm Lincoln Park USD 8 TO 31 FITNESS
Gallery Guichard Presents Soul of the Stone at South Shore Cultural Center! Sat, 26 Sep at 12:00 pm South Shore Cultural Center FREE EXHIBITIONS
Act One: A Century in the Making / Book Signing & Panel Discussion Thu, 24 Sep at 06:00 pm Green Relish LLC USD 0 TO 250 BUSINESS
Chicago Halloween Bar Crawl 2026 Sat, 31 Oct at 04:00 pm Kitchen + Kocktails By Kevin Kelley - Chicago USD 13 TO 18 FITNESS
2026 Filter Photo Festival Kick Off! Wed, 23 Sep at 06:00 pm Leica Store and Gallery Chicago FREE FESTIVALS
First Look of Intentionality, 1960: Whose Dreams? Sat, 19 Sep at 06:00 pm Washington Park Arts Incubator FREE FITNESS
The Official Halloween Bar Crawl - Chicago Sat, 31 Oct at 05:00 pm Black Hole Bar USD 17 TO 86 FITNESS
Foursided Mini Art Show Opening - Andersonville Fri, 25 Sep at 06:00 pm Foursided Card + Gift - Andersonville FREE FITNESS
In A Pickle - Neelie Hespen Solo Showcase Fri, 02 Oct at 06:00 pm The Dill Pickle Food Co-op FREE FITNESS
Our Side of the Story: A Youth Media & Storytelling Event Sat, 26 Sep at 01:00 pm Legler Library FREE FITNESS
Moravian Glory: From Folk Heritage to Modern Expression Fri, 25 Sep at 04:30 pm Consulate General of The Czech Republic in Chicago FREE EXHIBITIONS
Signature Event: Running Tour of Freed to K*ll with Gera-Lind Kolarik Sun, 27 Sep at 10:00 am Haymarket House USD 0 TO 39 ART
Soul Sabbatical: A Rest Retreat For The Culture Sat, 19 Sep at 11:00 am Ellis (Samuel) Park FREE FITNESS
Through Our Eyes Youth Art Exhibition + Celebration Sat, 26 Sep at 02:00 pm SZNL Chicago LLC FREE ART
Intentionality, 1960: Whose Dreams? Thu, 24 Sep at 06:00 pm Washington Park Arts Incubator FREE FITNESS
Art Exhibit: The Sound Barriers Vol. 4 @ Definition Theatre Mon, 14 Sep Definition Theatre USD 18 FITNESS
R&B Vs Hip Hop Black Attire Yacht Party (3 Levels) Chicago Sat, 07 Nov at 06:45 pm Anita Dee Yacht Charters USD 45 TO 562 FITNESS
Libations for Nigeria - Photo Book Release and Immersive Art Exhibition Sun, 27 Sep at 03:00 pm ALT SPACE CHICAGO USD 0 TO 150 ART
Juke Me Til I Scream Friday The 13th Yacht Party (3 Levels) Chicago Fri, 13 Nov at 06:45 pm Burnham Harbor S Dock - Anita Dee 2 - Temporary Docking Area USD 45 TO 562 FITNESS
Lincoln Park Uncovered: From Swans to Lions & Beyond! ️✨ Sat, 19 Sep at 11:00 am 2001 N Clark St USD 23 WORKSHOPS
Czechia Unveiled: Top Sights, Travel Tips, and Czech Treat Wed, 23 Sep at 12:30 pm Consulate General of The Czech Republic in Chicago FREE FITNESS
Fisk University Legacy Through the Lens of Art Sun, 04 Oct at 01:00 pm Saint Ignatius College Prep USD 0 TO 5,898 FITNESS
Singles Meet Up at the Museum of Contemporary Art 21-36 Tue, 29 Sep Museum Of Contemporary Art Chicago USD 15 TO 29 ART
The Face of African American Spirit Fri, 16 Oct at 06:00 pm St Benedict the African Catholic Church FREE ART
Singles Meet Up at The Farmers Market 21-35 and 36-50 Sun, 04 Oct 1425 N Damen Ave USD 15 TO 29 TRIPS-ADVENTURES
St. Patrick's Day Lucky Charms Lincoln Park Bar Crawl Sat, 13 Mar at 12:00 pm Lincoln Park USD 14 TO 37 PARTIES
Dan Ryan Woods Stewardship Kickoff: Info Session, Tutorials, and Art! Sat, 10 Oct at 10:00 am Dan Ryan Woods-91st Street FREE ART
TYFM OPEN SHOOT x CHICAGO (FREE HEADSHOT EVENT) Sat, 26 Sep at 10:00 am LACUNA by Catalyst Suites FREE FITNESS
St. Patrick's Day Lucky Charms River North Bar Crawl | Afternoon Sat, 13 Mar at 12:00 pm Headquarters Beercade USD 14 TO 37 FITNESS
Opening of the Photo Exhibition: TEMPUS FUGIT II Wed, 23 Sep at 08:30 am St Procopius Catholic Church FREE EXHIBITIONS
St. Patrick's Day Lucky Charms Wicker Park Bar Crawl Sat, 13 Mar at 12:00 pm Chop Shop USD 8 TO 25 FITNESS
St. Patrick's Day Lucky Charms West Loop Bar Crawl Sat, 13 Mar at 12:00 pm West Loop USD 14 TO 37 FITNESS
The Darkroom Chicago: Film Development Workshop in Logan Square Sun, 16 Aug at 02:00 pm Mobile Makers Chicago USD 87 TO 151 FITNESS
COFFEE + CONNECTION + PORTRAITS "The Empowered You" Sun, 11 Oct at 11:00 am Blue Bottle Coffee USD 55 BUSINESS
Singles Meet Up at the Museum of Contemporary Art 31-45 Tue, 06 Oct at 05:00 pm Museum Of Contemporary Art Chicago USD 15 TO 29 ART
Dorothy's Trials of Oz: City Exploration Quest in Chicago Thu, 01 Oct at 12:00 am Oz Park Basketball Court USD 10 TRIPS-ADVENTURES
St. Patrick's Day Lucky Charms River North Bar Crawl | Morning Sat, 13 Mar at 09:00 am River North USD 14 TO 37 FITNESS
St. Patrick's Day Lucky Charms Wrigleyville Bar Crawl Sat, 13 Mar at 10:00 am Blue Bayou USD 19 TO 37 PARTIES
Book Signing & Q&A with Ronnie Frey Sun, 18 Oct at 10:00 am necessary & sufficient coffee - Printers Row, South Dearborn Street, Chicago, IL, USA FREE FITNESS
1893 World’s Fair & Filming Locations: Chicago Midway Walking Tour Sun, 27 Sep at 10:30 am Midway Plaisance ENTERTAINMENT
Singles Meet Up at The Green City Market 21-35 and 36-50 Sat, 24 Oct at 11:00 am Green City Market Lincoln Park USD 15 TO 29 FITNESS
BORNVAIN ART PRESENTS: THE COLLECTION Sat, 07 Nov at 04:00 pm David Rubenstein Forum at the University of Chicago USD 29 FITNESS
Mud Stencils! An Intro to Green Graffiti with Ari Mulch Sun, 11 Oct at 01:00 pm 1754 N Kimball Ave USD 34 WORKSHOPS
Singles Meet Up at The Museum of Contemporary Art 45-55 Tue, 27 Oct at 05:00 pm Museum Of Contemporary Art Chicago USD 15 TO 29 FITNESS
Screening of George Tice: Seeing Beyond the Moment Mon, 21 Sep at 12:30 pm Chicago Cultural Center ART
AFROINTL FASHION SHOW CHICAGO Sun, 29 Nov at 07:00 pm Embassy Suites by Hilton Chicago Downtown River North USD 44 TO 122 FITNESS
FashionCamp: WINTER HOLIDAY EDITION 2026 Sat, 12 Dec at 10:00 am FashionBar (Level 3) USD 530 HOLIDAY
Perfume Festival & Exchange at Pullman Block House Gallery Sat, 24 Oct at 12:00 pm Pullman Artspace Lofts USD 0 TO 7 FITNESS
Spooky Student Showcase: Pole Icons & Brass Ring ‘26 Fri, 23 Oct at 07:00 pm The Brass Ring USD 0 TO 18 FITNESS
Runway Walking Class & Compcard Shoot 2027- FashionBar The Shows Session 3 Sat, 12 Dec at 02:00 pm Water Tower Place (FashionBar Space on Level 3) USD 82 TO 226 FITNESS
Runway Walking Class & Compcard Shoot 2027- FashionBar The Shows Session 1 Sat, 17 Oct at 02:00 pm Water Tower Place (FashionBar Space on Level 3) USD 82 TO 226 WORKSHOPS
Runway Walking Class & Compcard Shoot 2027- FashionBar The Shows Session 2 Sat, 14 Nov at 02:00 pm Water Tower Place (FashionBar Space on Level 3) USD 82 TO 226 FITNESS
Runway Walking Class & Compcard Shoot 2027- FashionBar The Shows Session 5 Sat, 13 Feb at 02:00 pm Water Tower Place (FashionBar Space on Level 3) USD 82 TO 226 FITNESS