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
INTL FESTIVAL OF LIFE/JSVFest -COMBINED, SEPT. 25-27, UNION PK-Promo tix Fri, 03 Jul at 12:00 pm Union Park USD 21 TO 156 FITNESS
Just Announced - Chicago - Top Shelf Tequila and Whiskey Tasting Festival - September 26 AE Sat, 26 Sep at 02:30 pm Kings Dining & Entertainment USD 20 TO 85 FESTIVALS
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
Spooky Zoo Sat, 17 Oct at 10:00 am N Cannon Dr at W Fullerton Pkwy, Chicago, IL, United States, Illinois 60614 FESTIVALS
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
Masquerade Ball On The Yacht (3 Levels) Chicago Sat, 19 Sep at 06:45 pm Anita Dee Yacht Charters USD 55 TO 562 PARTIES
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
NIGERIAN INDEPENDENCE DAY YACHT CRUISE Sun, 27 Sep at 12:00 pm Anita Dee Yacht Charters USD 55 TO 802 FITNESS
Espresso Martini Fest at Hubbard Inn, Chicago - Tastings Included Sat, 03 Oct at 05:00 pm Hubbard Inn USD 25 TO 42 FITNESS
Ascend Beyond (Featuring DJ Chava + Everywhere Between) Thu, 24 Sep at 07:30 pm Peggy Notebaert Nature Museum USD 0 TO 162 FITNESS
FashionBar THE SHOWS: October 2026 - The Trans Media Fashion Show Fri, 02 Oct at 06:00 pm Water Tower Place, Level 3 USD 0 TO 189 FITNESS
EmpowerHer Med Gala Fri, 25 Sep at 07:00 pm 140 E Walton Pl, Chicago, IL 60611-1545, United States HEALTH-WELLNESS
Lincoln Park Wine Fest Fri, 09 Oct at 05:00 pm 1001 W Wrightwood Ave, Chicago, IL 60614-1312, United States FESTIVALS
Aawaz for Nepal: an open mic featuring queer artists Sun, 20 Sep at 07:00 pm Dorothy USD 5 TO 28 FITNESS
"Final Look" Chicago River Swim Weekend Cruise & Celebration Sat, 19 Sep at 10:00 am 600 W Chicago Ave USD 29 TO 55 FITNESS
FashionBar THE SHOWS: October 2026 - The Collective Runway Show Sat, 03 Oct at 05:00 pm Water Tower Place, Level 3 USD 0 TO 402 FITNESS
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
Chicago Halloween Party Cruise | Pier Pressure® Black Pearl Sat, 31 Oct at 08:45 pm Spirit of Chicago Yacht USD 33 TO 62 ENTERTAINMENT
LIVING QUEER MONTHLY-Latine Edition by LQM Team | Destinos 2026 Fri, 02 Oct at 07:30 pm Center on Halsted USD 13 TO 55 FESTIVALS
Makers & Shakers Bash Fri, 18 Sep at 06:00 pm 22W Washington St., Chicago, IL 60602 | Morningstar’s HQ, 7th Floor Venue & Patio ART
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
FashionBar THE SHOWS: Evening Wear Collections & Closing Show Sun, 04 Oct at 03:00 pm Water Tower Place, Level 3 USD 26 TO 397 ART
5k Fun Run x Alarmist Brewing | 2026 IL Brewery Running Series Sat, 26 Sep at 11:00 am Alarmist Brewing & Taproom USD 53 TO 76 FITNESS
Listening Hours with Marvin Tate: 4th Shift Album & Book Release Sat, 19 Sep at 06:00 pm The Land School FREE FITNESS
Move, Breathe, Connect: A Pilates in the Park summer series Sun, 05 Jul at 12:00 pm Humboldt Park, Chicago FREE FITNESS
Equity & Transformation (EAT) Film Festival - 2026 Sat, 19 Sep at 04:00 pm ACX Harper Theater- Hyde Park FREE FITNESS
❤️⚾ Congenital Heart Disease Day with Team CHD Illinois at the White Sox! ⚾❤️ Sun, 27 Sep at 12:00 pm Guaranteed Rate Field MEETUPS
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 HALLOWEEN
Lavender Laugh Lounge (Sober Friendly, Queer Stand Up Comedy) Sat, 06 Dec at 06:30 pm Loaves & Witches FREE FITNESS
Chicago Wine Fest at Hubbard Inn - Tastings Included Sat, 24 Oct at 05:00 pm Hubbard Inn USD 25 TO 42 FITNESS
Chicago BRA Crawl: Benefiting Breast Cancer Research Sat, 17 Oct at 12:00 pm Chicago's BEST Bars TBA USD 10 TO 28 FITNESS
Dinner with Entrepreneurs: Chicago (Giving Back Edition) Sat, 13 Jun at 07:00 pm Restaurant of the Week USD 54 FITNESS
Skip the Small Talk Night at kibbitznest Wed, 01 Apr kibbitznest books, brews & blarney USD 24 FOOD-DRINKS
BA NIA INC'S ANNUAL MATERNAL HEALTH WALK 2026 Sat, 19 Sep at 10:00 am Chicago Forest Preserves - Major Marshall Trail, Dan Ryan Loop - Central Picnic Grove #3 FREE FITNESS
Growing Home's Annual Backyard Barbecue Sun, 20 Sep at 02:00 pm Growing Home Urban Farm USD 100 FITNESS
Scrimmage Fundraiser: BJJ, Muay Thai, MMA, Fitness Sat, 26 Sep at 12:00 pm Mission MMA & Fitness USD 0 TO 1,069 NONPROFIT
September Free Day at the American Writers Museum Sun, 20 Sep at 10:00 am American Writers Museum FREE FITNESS
Mom Ish:The Experience Sat, 19 Sep at 09:00 am Malcolm X College Conference Center USD 135 TO 189 FITNESS
2026 Annual Jazz Brunch , benefiting Advocate Masonic OBG Residency Sun, 20 Sep at 12:30 pm Jazz Showcase USD 109 MUSIC
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
Workshop! PHYSICAL ACTING: Lessons from a Puppet by Glass Half Full Theatre Sat, 19 Sep at 11:00 am Virginia Wadsworth Wirtz Center for the Performing and Media Arts in Chicago (Wirtz Center Chicago) USD 34 ART
QUEER QUENTOS by Norma Seledon | Destinos Festival 2026 Tue, 29 Sep at 07:30 pm Center on Halsted USD 13 TO 55 FITNESS
SCRATCH NIGHT - Destinos Ed. by Physical Theater Festival | Destinos 2026 Mon, 28 Sep at 07:00 pm Center on Halsted USD 18 TO 55 FITNESS
The Associate Board of Endeavor Health NorthShore Hospitals 21st Annual Benefit Sat, 24 Oct at 07:00 pm Field Museum NONPROFIT
TRICK OR DRINK: River North Adult Trick-or-Treating Bar Sat, 31 Oct at 03:00 pm ROCBAR USD 14 TO 26 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
Black is Gold 6: Culture Xchange (Supported by Tito's Handmade Vodka) Sat, 17 Oct at 05:00 pm Vjosa Cafe & Events USD 0 TO 71 FITNESS
MEMENTO MORI Halloween Gala Fri, 30 Oct at 07:00 pm International Museum of Surgical Science USD 0 TO 157 FITNESS
2026 Chicago Walk to End Lupus Sat, 19 Sep at 09:00 am 1199 E Oakwood Blvd, Chicago, IL 60653 NONPROFIT
Free to Breathe Chicago Walk Sun, 18 Oct at 09:00 am 600 W Montrose Ave, Chicago, IL 60613-1500, United States CHARITIES
Listening Hours with D-Composed's Khelsey Zarraga & Wilfred Farquharson Fri, 18 Sep at 06:00 pm The Land School FREE ENTERTAINMENT
LSQP Art After Dark - Featuring artists SunshineUnit and Kramer Fri, 18 Sep at 07:00 pm Logan Square Pilates + Core Studio FREE ART
The Running Joke: A Marathon Fundraiser Show Sun, 20 Sep at 07:30 pm Cornservatory Theatre FREE FITNESS
City in an Orchard - Tree Planting at Dante Farm Sat, 26 Sep at 10:00 am 6801 S Dante Ave FREE WORKSHOPS
Fall Clothing Swap 2026 Fri, 16 Oct at 06:00 pm Chicago Fair Trade Museum & Store USD 13 TO 55 FITNESS
No Sleep Til Kyiv - Screening and Q&A | Ukrainian Cinema Month Sun, 27 Sep at 05:00 pm 2842 W Chicago Ave FREE FITNESS