Espresso Martini Fest at Hubbard Inn, Chicago - Tastings Included Sat, 03 Oct at 05:00 pm Hubbard Inn USD 25 TO 42 FITNESS
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
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
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
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
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) FITNESS
NATURAL HAIR FEST Kick-Off Celebration -Vendor Opportunity -Evening Event Sun, 29 Nov at 06:00 pm Hilton Garden Inn Chicago Downtown/Magnificent Mile USD 122 FITNESS
NATURAL HAIR FEST CHICAGO - DAYTIME VENDOR OPPORTUNITY Sun, 29 Nov at 10:00 am Hilton Garden Inn Chicago Downtown/Magnificent Mile USD 122 TO 301 FITNESS
AFROINTL FASHION SHOW CHICAGO Sun, 29 Nov at 07:00 pm Hilton Garden Inn Chicago Downtown/Magnificent Mile USD 44 TO 122 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
Chicago Wine Fest at Hubbard Inn - Tastings Included Sat, 26 Dec at 05:00 pm Hubbard Inn USD 25 TO 42 FESTIVALS
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 FITNESS
The Chicago Pancakes & Booze Art Show (Vendor/Artist Reservations) Sat, 05 Dec at 08:00 pm Reggies 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
Chicago Handmade Vendor Market- Call for Vendors Fri, 06 Nov at 09:00 am Maxwell Street Polish FREE BUSINESS
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
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
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
Chicago Bacon Fest: Live Band & Bacon Everything: Food, Drink & Photo Ops Sat, 06 Mar at 12:00 pm Old Crow Smokehouse USD 11 TO 41 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
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 FITNESS
The Shops - Single Day Pop-up - January Edition #2 Sat, 16 Jan at 11:00 am Water Tower Place (Level 3 Next to JJill and White House Black Market) FITNESS
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 Hilton Garden Inn Chicago Downtown/Magnificent Mile USD 32 TO 5,898 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 Hilton Garden Inn Chicago Downtown/Magnificent Mile USD 32 TO 5,978 FITNESS
Natural Hair Fest® Returns & Strengthens Natural Hair Movement in Chicago Sun, 29 Nov at 10:00 am Hilton Garden Inn Chicago Downtown/Magnificent Mile USD 32 TO 5,978 FITNESS