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 PARTIES
Beyond Hunger Benefit with Death Cab for Cutie at Salt Shed - Indoor Shed Sat, 21 Nov at 07:00 pm Salt Shed - Indoor Shed
Espresso Martini Fest at Hubbard Inn, Chicago - Tastings Included Sat, 03 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
Kincade's Wrigleyville's Halloween DAY Party Sat, 31 Oct at 01:00 pm Kincade's Wrigley USD 20 TO 37 FITNESS
NIGHTMARE ON RANDOLPH - A TWO DAY HALLOWEEN EXPERIENCE Fri, 23 Oct at 06:00 pm 1249 W Randolph St, West Loop NONPROFIT
Startup Networking Chicago: Founders, Investors & Talent Mixer Wed, 01 Jul at 07:00 pm Joy District USD 0 TO 66 FITNESS
Pink Pumpkins & Petals - A Floral & Fragrance Workshop Celebrating Women Tue, 27 Oct at 07:00 pm Above Average DIY Candle Studio USD 49 FITNESS
Celestial Odyssey Thu, 05 Nov at 05:30 pm The Metropolitan at the Willis(Sears) Tower USD 162 TO 2,136 FITNESS
River North Pole - A family fun indoor event with Santa and Mrs. Claus! Sat, 21 Nov at 11:00 am Trump International Hotel & Tower® Chicago USD 0 TO 146 FITNESS
Gourmand Gala - A Symphony of Senses Thu, 12 Nov at 06:30 pm 500 W Jackson Blvd, Chicago, IL 60661, USA FOOD-DRINKS
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
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 FITNESS
11th Annual PGMF Ales Against ALS Sat, 07 Nov at 03:00 pm Heineken 2nd Star Tavern USD 0 TO 109 NONPROFIT
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
Dinner with Entrepreneurs: Chicago (Giving Back Edition) Sat, 13 Jun at 07:00 pm Restaurant of the Week USD 54 FITNESS
GSDC 2026 Gala: Greater Together Wed, 28 Oct at 05:30 pm South Shore Cultural Center USD 189 TO 375 FITNESS
Foodies + New Friends: Chicago Dinner + Coffee Club | Monthly Membership Wed, 05 Aug at 07:00 pm Restaurant of the Week USD 34 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 FITNESS
Soulful Holiday Lights Trolley Celebrating Motown, R& B & House Sat, 28 Nov at 06:30 pm 230 W North Ave USD 79 HOLIDAY
Marti & Mimi's "Back to School" Charity Ball Sun, 16 Aug at 08:30 pm Stars and Garters Theater USD 20 TO 31 FITNESS
Chicago Wicker Park Naughty Santa Bar Crawl Sat, 05 Dec at 06:00 pm DSTRKT and Wicker Park Venues USD 0 TO 18 FITNESS
Lavender Virtual Race 1M 5K 10K 13.1 26.2 | Language of Flowers Collection Sat, 27 Jun at 01:00 pm Chicago USD 4 TO 47 SPORTS
The Swedish Hospital Foundation Luminescence Gala Sat, 14 Nov at 06:00 pm Hilton Chicago Hotel NONPROFIT
Bee Happy Race 2026 | Fun Virtual 5K, 10K, Half Marathon Sat, 16 May at 01:00 pm Chicago USD 4 TO 47 FITNESS
Zeus Virtual Race 2026 | Gods & Warriors Virtual Running Series Sat, 13 Jun at 01:00 pm Chicago USD 4 TO 47 SPORTS
Howl-O-Ween Pet Costume Contest for PAWS Chicago Sat, 31 Oct at 11:30 am Harry Caray's Navy Pier USD 13 CONTESTS
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
Chicago Wine Fest at Hubbard Inn - Tastings Included Sat, 26 Dec at 05:00 pm Hubbard Inn USD 25 TO 42 FITNESS
Look At Me 2026: Domestic Violence Awareness Month Wed, 28 Oct at 05:00 pm 2150 S Canalport Ave FREE ART
"Bourbon & Blazers" @ 2112 Studios supporting Breast Cancer Awareness Month Tue, 27 Oct at 06:00 pm 4319 N Knox Ave USD 23 FITNESS
Race Through Hawaii Virtual Race | 5K, 10K, Marathon | Run Anywhere Sat, 16 May at 01:00 pm Chicago USD 6 TO 47 SPORTS
All Systems Grow! Grant Writing And Management Master Class Fri, 06 Nov at 09:00 am Impact House USD 597 FITNESS
Race Through Alaska 1M 5K 10K 13.1 26.2 Virtual Race Sat, 18 Apr at 01:00 pm Chicago USD 6 TO 47 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
WHIMSICAL TOY BOX- Kids Aerial Arts Student Showcase Fundraiser Sat, 05 Dec at 03:30 pm Chicago Aerial Arts USD 32 TO 44 FITNESS
Foodies + New Friends: Chicago | 30's Dinner Meet Fri, 03 Apr at 07:00 pm Restaurant of the Week USD 23 FITNESS
Face Your Giants Virtual Race 2026 | Christian Virtual Run Sat, 06 Jun at 01:00 pm Chicago USD 4 TO 47 FITNESS
Just One More Mile Virtual Race 2026 | Global Running Day Virtual Wed, 03 Jun at 01:00 pm Chicago USD 4 TO 47 FITNESS
Community Yoga and Sound Bath at The Parlor (a Trash People Fundraiser) Sun, 25 Oct at 04:00 pm Grace Church USD 20 TO 38 FITNESS
Great Lake Jumper DJ Set - 11/7 Sat, 07 Nov at 03:00 pm 3740 N Clark St, Chicago, IL, United States, Illinois 60613 NONPROFIT
Harvesting Hope: Food Bank Volunteer Day- Chicago Chapter Sat, 14 Nov at 09:00 am 4100 W Ann Lurie Pl FREE VOLUNTEERING
Talent at the Table: Chicago Film | Benefit for Hope Connections for Cancer Thu, 27 Aug at 07:00 pm Restaurant of the Week USD 34 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 PARTIES
ChiKaGo - Celebration of Life & Spirit for John Sacelli Sun, 01 Nov at 07:00 pm Yoga Now Chicago HEALTH-WELLNESS
HamBingo for the Haitian American Museum of Chicago Sun, 01 Nov at 07:00 pm 1055 W Bryn Mawr Ave, Chicago, IL, United States, Illinois 60660 NONPROFIT
California Interchange at I-290 Cleanup + Coffee Social Sun, 25 Oct at 10:00 am 2718 W Van Buren St USD 0 TO 13 FITNESS
Peony Virtual Race | 1M 5K 10K 13.1 26.2 | Language of Flowers Collection Sat, 30 May at 01:00 pm Chicago USD 4 TO 47 SPORTS
Buccaholics Illinois - Bucs vs Bears Meet and Greet Sat, 07 Nov at 07:00 pm 1956 W 35th St, Chicago, IL 60609-1204, United States MEET-AND-GREET
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
2026 New Year Challenge -Year of the Horse 2.026 Mile 20.26 Mile 202.6 MILE Sun, 15 Feb at 01:00 pm Chicago USD 4 TO 42 FITNESS
Burrito Brigade Chicago Bike Distribution Sun, 13 Jul at 02:30 pm Plaza Tenochtitlán FREE TRIPS-ADVENTURES
How to Make a Mosaic for Beginners Sat, 14 Nov at 01:00 pm The WasteShed Humboldt Park USD 74 WORKSHOPS
Race Through Colorado Virtual Race | 5K, 10K, Half Marathon | Run Anywhere Sat, 09 May at 01:00 pm Chicago USD 6 TO 47 FITNESS
Race Through Georgia Virtual Race | 5K, 10K, Half Marathon & More | Run Sat, 02 May at 01:00 pm Chicago USD 6 TO 47 FITNESS
Teacher Appreciation Virtual Race 2026 | Teach Love Inspire Sat, 23 May at 01:00 pm Chicago USD 4 TO 47 SPORTS
CFW's Annual Fundraiser: Fall Fete at Midwest Coast Brewing Company Tue, 17 Nov at 05:00 pm Midwest Coast Brewing Company USD 82 TO 109 NONPROFIT
"STARTUP-INVESTOR PITCH LUNCH" - FUNDRAISING PROGRAM IN SILICON VALLEY Mon, 22 Jun at 10:00 am The Congress Plaza Hotel & Convention Center FREE FITNESS
Jokes for Coats - Comedy Show & Coat Drive Thu, 19 Nov at 08:00 pm Chicago Theater Works USD 13 FITNESS
HACIA Holiday Party to Benefit HACIA Scholarship & Education Foundation Thu, 03 Dec at 05:30 pm East Bank Club USD 0 TO 26,679 FITNESS
Above and Beyond Family Recovery Center’s 2026 Gala: Redefining Recovery, Transforming Lifetimes Fri, 06 Nov at 06:00 pm The Drake Hotel (140 E Walton Pl, Chicago)
Chicago Tech Startups, Investors, Experts Networking & Pitch Event Tue, 17 Nov at 07:00 pm Ten Cat Tavern USD 11 TO 37 BUSINESS
Chicago Santa Bar Crawl | Wrigleyville's SantaCon | Twelve Bars of XMas Sat, 12 Dec at 10:00 am Wrigleyville's Best Bars: Full List In Event Details USD 10 TO 40 PARTIES
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
Yeti Frostbite Miles Virtual Race| Cryptid Quest Series 1M 5K 10K 13.1 26.2 Sat, 11 Jul at 01:00 pm Chicago USD 4 TO 47 SPORTS
FREE Community Pop-up Thrift Boutique Sat, 16 Jan at 12:00 pm 36th Ward Belmont Cragin Office FREE POP-UPS
Art After Work: Appliqué Quilted Clothing with feltgirlworld Thu, 17 Dec at 05:30 pm Intuit Art Museum USD 5 TO 20 FITNESS
SERGELATO & Friends: Friendsgiving Party 2026 Fri, 13 Nov at 06:30 pm South Loop Market Logan Square NONPROFIT
Honey Pie’s Slice of Relief Sat, 12 Dec at 03:30 pm Solar Intentions Non-Alcoholic Beverage Shop USD 14 FITNESS