Death By Disco: Chicago's Biggest Halloween Pop-Up Fri, 30 Oct at 08:00 pm Recess & City Hall ENTERTAINMENT
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 BLACK-FRIDAY
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
TWIN PEAKS: A Conversation with the Stars | Old Town School of Folk Music, IL | Sat. Nov 14 2026 Sat, 14 Nov at 07:30 pm Old Town School of Folk Music LIVE-MUSIC
The Greatest Love Pop Up Tour: Overflow Coffee Sat, 07 Nov at 10:00 am 1449 S Michigan Ave FREE FITNESS
OMWP Studios Vintage Camera Pop-Up at Vintage House Chicago Sat, 07 Nov at 12:00 pm Vintage House Chicago FREE FITNESS
Southside Critical Mass Chicago Bicycle Ride (1st Fridays) Fri, 04 Sep Nichols Park Plaza (South End by Fountain) FREE FITNESS
Southside Critical Mass Chicago Bicycle Ride Fri, 03 Apr 1300 E 55th St, Chicago, IL 60615-5302, United States TRIPS-ADVENTURES
Audacity: Sunshine Enterprises' Market Wed, 11 Nov at 05:30 pm The Bridgeport Art Center USD 50 TO 135 FITNESS
The Chicago Art Girls Holiday Pop-Up Shop Sat, 12 Dec at 11:00 am Alexander Graham Bell Elementary School POP-UPS
The Kibbitznest Comedy Club Sun, 24 Nov at 07:30 pm kibbitznest books, brews & blarney USD 13 TO 18 FITNESS
St. Patrick's Day Lucky Charms Lincoln Park Bar Crawl Sat, 13 Mar at 12:00 pm Lincoln Park USD 14 TO 37 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
NEON-O-WEEN a | LATE-NITE NeoN LitE HALLOWEEN PoP-uP @TimelessArtsChicago Sat, 31 Oct at 09:00 pm 3040 N. Ashland Avenue, Chicago, IL, United States, Illinois 60657 ART
AFROINTL FASHION SHOW CHICAGO Sun, 29 Nov at 07:00 pm Hilton Garden Inn Chicago Downtown/Magnificent Mile USD 44 TO 122 FITNESS
Chicago Artisan Pop-Up Market- Vendors Wanted Fri, 20 Nov at 09:00 am South Shore Cultural Center FREE FITNESS
Chicago Creative Networking Pop-Up at Chi’Tiva | Elevated Saturdays Sat, 31 Oct at 06:00 pm 1948 W North Ave USD 0 TO 181 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
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 Wrigleyville Bar Crawl Sat, 13 Mar at 10:00 am Blue Bayou USD 19 TO 37 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
Karaoke on the Chicago River with Pop Up Karaoke! Thu, 29 Oct at 06:00 pm The Water Plaza | Riverwalk USD 87 MUSIC
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
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) POP-UPS
Entourage: Scary Hours ... Halloween Event Sat, 31 Oct at 10:00 pm 2002 S Wentworth Ave ENTERTAINMENT
Brushes, Booze & Boos Sip & Paint Experience 1 year Anniversary Thu, 29 Oct at 06:00 pm Thrift LLC USD 50 TO 62 FITNESS
Brew and Bounce Skate-Dance Class Sat, 14 Nov at 11:00 am LISTEN Studio - West Loop USD 15 TO 31 WORKSHOPS
FREE Community Pop-up Thrift Boutique Sat, 21 Nov at 12:00 pm Dunning Branch, Chicago Public Library FREE FITNESS
The Chicago Pancakes & Booze Art Show (Vendor/Artist Reservations) Sat, 05 Dec at 08:00 pm Reggies ART
Pop Up Workshop (Free! Must Register) Tue, 03 Nov at 01:00 pm Chicago Public Library Black Stone Branch 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
Roast Battle at Zanies Chicago Thu, 15 Oct 1548 N Wells St, Chicago, IL, United States, Illinois 60610 COMEDY
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) FITNESS
FREE Community Pop-up Thrift Boutique Sat, 16 Jan at 12:00 pm 36th Ward Belmont Cragin Office FREE 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) FITNESS
Talking Cart: A Quarterly Meetup for Cart, Trailer & Mobile Cafe owners Thu, 10 Dec at 01:00 pm Sip Society Coffee Education Center FREE MEETUPS