Bottomless Margaritas on the Riverwalk - Every Weds! Wed, 03 Jun at 06:30 pm Island Party Hut (between Lake Shore Drive and Columbus on the Riverwalk) USD 25 TO 58 ENTERTAINMENT
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
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
Espresso Martini Fest at Hubbard Inn, Chicago - Tastings Included Sat, 03 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
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
Chicago Wine Fest at Hubbard Inn - Tastings Included Sat, 24 Oct at 05:00 pm Hubbard Inn USD 25 TO 42 FESTIVALS
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 DAY-OF-THE-DEAD
The Shops - Fall Edition Pop-up Sat, 24 Oct at 11:00 am Water Tower Place (Level 3 Next to JJill and White House Black Market) POP-UPS
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 FITNESS
Meet New People Bar Crawl Chicago - Welcome Shots at Every Bar! Sat, 09 Sep at 09:00 pm Wrigleyville's BEST Bars TBA (Check your email before the crawl for full schedule!) USD 22 FITNESS
The Shops - BLACK FRIDAY Edition! 1/2/3 Day Vending Opportunities! Fri, 27 Nov at 11:00 am Water Tower Place (Level 3 Next to JJill and White House Black Market) USD 29 TO 349 FITNESS
Chicago Singles Bar Crawl - Welcome Shots at Every Bar! Sat, 23 Sep at 09:00 pm Wrigleyville's BEST Bars TBA (Check your email before the crawl for full schedule!) USD 22 PARTIES
The Shops - Single Day Pop-up - November Reps Capital Edition Sat, 07 Nov at 11:00 am Water Tower Place (Level 3 Next to JJill and White House Black Market) POP-UPS
West Loop Chicago NYE 2027 Party – Live DJs, Champagne Toast, Appetizers Thu, 31 Dec at 09:00 pm PB&J and Grapes & Grains (Two Venues!) USD 20 TO 40 NEW-YEAR
NATURAL HAIR FEST Kick-Off Celebration -Vendor Opportunity -Evening Event Sun, 29 Nov at 06:00 pm Embassy Suites by Hilton Chicago Downtown River North USD 122 FITNESS
NATURAL HAIR FEST CHICAGO - DAYTIME VENDOR OPPORTUNITY Sun, 29 Nov at 10:00 am Embassy Suites by Hilton Chicago Downtown River North USD 32 TO 301 FITNESS
Chicago Bagel Fest: Bagel Tastings, Live Music, Bagel Photo Ops & More! Sat, 27 Feb at 10:00 am Old Crow USD 15 TO 48 FITNESS
AFROINTL FASHION SHOW CHICAGO Sun, 29 Nov at 07:00 pm Embassy Suites by Hilton Chicago Downtown River North USD 44 TO 122 FITNESS
National Redhead Fest in Chicago | Fireball Shots, Live Music & More! Sat, 20 Feb at 12:00 pm The Cubby Bear Chicago USD 10 TO 16 MUSIC
The Shops - Holiday Edition #2 - Final 2026 Pop-up! Sat, 19 Dec at 11:00 am Water Tower Place (Level 3 Next to JJill and White House Black Market) FITNESS
The Shops - Holiday Edition #1 Sat, 12 Dec at 11:00 am Water Tower Place (Level 3 Next to JJill and White House Black Market) USD 29 TO 290 FITNESS
The Shops - FashionBar’s Single Day Pop-up - January Edition Sat, 09 Jan at 11:00 am Water Tower Place (Level 3 Next to JJill and White House Black Market) POP-UPS
The Shops - Black History Month Edition Sat, 20 Feb at 11:00 am Water Tower Place (Level 3 Next to JJill and White House Black Market) POP-UPS
The Shops - Valentines Day Edition Sat, 13 Feb at 11:00 am Water Tower Place (Level 3 Next to JJill and White House Black Market) FITNESS
Natural Hair Fest® Kicks Off NATIONAL Natural Hair Initiative in Chicago Sun, 29 Nov at 10:00 am Embassy Suites by Hilton Chicago Downtown River North USD 31 TO 5,884 FESTIVALS
New Year's DAY Bar Crawl in Wrigleyville, Chicago - Happy New Year! Fri, 01 Jan at 12:00 pm Wrigleyville's Best Bars TBA USD 10 TO 28 FITNESS
Natural Hair Fest® KICK-OFF for the NATIONAL 24+ City TOUR de Naturelle’ Sun, 29 Nov at 10:00 am Embassy Suites by Hilton Chicago Downtown River North USD 32 TO 5,978 FITNESS
TBOX | Chicago's 30th Annual 12 Bars of Xmas/Santa Crawl | 12+ Wrigley Bars Sat, 12 Dec at 10:00 am Wrigleyville's Best Bars TBA USD 5 TO 40 BAR-CRAWLS
Natural Hair Fest® Returns & Strengthens Natural Hair Movement in Chicago Sun, 29 Nov at 10:00 am Embassy Suites by Hilton Chicago Downtown River North USD 32 TO 5,978 FITNESS