Boo Bash - A Halloween Bar Crawl in Wrigleyville Sat, 24 Oct at 06:00 pm Wrigleyville's BEST Bars TBA USD 5 TO 28 PARTIES
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 FITNESS
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 Wrigleyville's BEST Bars TBA USD 10 TO 28 FITNESS
Kincade's Wrigleyville's Halloween DAY Party Sat, 31 Oct at 01:00 pm Kincade's Wrigley USD 20 TO 37 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
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 65 FITNESS
IPH's Fall Fest on The Riverwalk w/ Hayrides on the River & More in Chicago Sat, 19 Sep at 12:00 pm Island Party Hut (between Lake Shore Drive and Columbus on the Riverwalk) USD 40 ENTERTAINMENT
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
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
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 FESTIVALS
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
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
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
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
NATURAL HAIR FEST CHICAGO - DAYTIME VENDOR OPPORTUNITY Sun, 29 Nov at 10:00 am Hilton Garden Inn Chicago Downtown/Magnificent Mile USD 301 FITNESS
Chicago Wine Fest at Hubbard Inn - Tastings Included Sat, 26 Dec at 05:00 pm Hubbard Inn USD 25 TO 42 FESTIVALS
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 Creative Networking at Chi’Tiva Downtown | CLVR LABs Sun, 18 Oct at 03:00 pm THC by Chitiva South Loop USD 0 TO 122 FITNESS
AFROINTL FASHION SHOW CHICAGO Sun, 29 Nov at 07:00 pm Embassy Suites by Hilton Chicago Downtown River North USD 44 TO 122 FASHION
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 Bagel Fest: Bagel Tastings, Live Music, Bagel Photo Ops & More! Sat, 27 Feb at 10:00 am Old Crow USD 15 TO 48 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 - 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
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 - 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 - 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) FITNESS
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) POP-UPS
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
TBOX: Twelve Bars of Xmas - Chicago's 30th Annual Xmas Crawl - Wrigleyville Sat, 12 Dec at 10:00 am Wrigleyville's Best Bars: Full List In Event Details USD 5 TO 40 NONPROFIT
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