Spooky Zoo Sat, 17 Oct at 10:00 am N Cannon Dr at W Fullerton Pkwy, Chicago, IL, United States, Illinois 60614 FESTIVALS
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
Jewel-Osco’s Shiploads of Celebrations & 3rd Annual Beach Volleyball Charity Classic Sat, 10 Oct at 06:00 pm North Avenue Beach SPORTS
Chicago BRA Crawl: Benefiting Breast Cancer Research Sat, 17 Oct at 12:00 pm Chicago's BEST Bars TBA USD 10 TO 28 FITNESS
Startup Networking Chicago: Founders, Investors & Talent Mixer Wed, 01 Jul at 07:00 pm Joy District USD 0 TO 66 FITNESS
Chicago Wine Fest at Hubbard Inn - Tastings Included Sat, 24 Oct at 05:00 pm Hubbard Inn USD 25 TO 42 FITNESS
Casino Uptown: Celebrating 100 Years of the Aragon Ballroom Thu, 15 Oct at 05:30 pm Aragon Ballroom MUSIC
Beyond Hunger Benefit with Death Cab for Cutie at Salt Shed - Indoor Shed Sat, 21 Nov at 07:00 pm Salt Shed - Indoor Shed
Free to Breathe Chicago Walk Sun, 18 Oct at 09:00 am 600 W Montrose Ave, Chicago, IL 60613-1500, United States CHARITIES
Sky High Puppy Yoga Sun, 04 Oct at 07:45 am 875 N Michigan Ave, Chicago, IL 60611-1770, United States HEALTH-WELLNESS
Open Books & Laugh: A Standup Comedy Show for Literacy Thu, 22 Oct at 07:00 pm Laugh Factory USD 0 TO 226 COMEDY
NIGHTMARE ON RANDOLPH - A TWO DAY HALLOWEEN EXPERIENCE Fri, 23 Oct at 06:00 pm 1249 W Randolph St, West Loop NONPROFIT
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
Journey to 30: The Miracle Center’s 30th Anniversary Benefit Sat, 17 Oct at 06:00 pm The Miracle Center USD 82 TO 135 FITNESS
Dinner with Entrepreneurs: Chicago (Giving Back Edition) Sat, 13 Jun at 07:00 pm Restaurant of the Week USD 54 FITNESS
A Walk Down the Fairway: Golf Outing, Fashion Show & Clothing Drive Sat, 10 Oct at 11:00 am South Shore Cultural Center USD 60 TO 125 FITNESS
Foodies + New Friends: Chicago Dinner + Coffee Club | Monthly Membership Wed, 05 Aug at 07:00 pm Restaurant of the Week USD 34 FITNESS
Pink Pumpkins & Petals - A Floral & Fragrance Workshop Celebrating Women Tue, 27 Oct at 07:00 pm Above Average DIY Candle Studio USD 79 WORKSHOPS
Marti & Mimi's "Back to School" Charity Ball Sun, 18 Oct at 08:30 pm Stars and Garters Theater USD 20 TO 31 FITNESS
Soulful Sounds in Chicago Sun, 11 Oct at 06:00 pm Athenaeum Center for Thought & Culture PERFORMANCES
Paulie & The Shakers @ Breakthrough Type 1 Diabetes Walk, Chicago, IL Sun, 04 Oct at 10:00 am Montrose Harbor, Chicago's Lakefront NONPROFIT
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
IPH's Fall Fest on The Riverwalk w/ Hayrides on the River & More in Chicago Sat, 10 Oct at 12:00 pm Island Party Hut (between Lake Shore Drive and Columbus on the Riverwalk) USD 40 ENTERTAINMENT
Tech Startup Networking Chicago Lincoln Park - Series A / Venture Capital Networking Event Tue, 06 Oct at 05:00 pm Parlay Lincoln Park FREE BUSINESS
Celestial Odyssey Thu, 05 Nov at 05:30 pm The Metropolitan at the Willis(Sears) Tower USD 162 TO 2,136 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
One Day at a Time, Inc Annual Breast Cancer Awareness 5k Sat, 10 Oct at 07:00 am St.Luke Missionary Baptist Church FREE NONPROFIT
Paris with Purpose - Cancer Benefit & Scholarship Dinner Fri, 09 Oct at 06:00 pm Malcolm X College USD 0 TO 500 NONPROFIT
Gourmand Gala - A Symphony of Senses Thu, 12 Nov at 06:30 pm 500 W Jackson Blvd, Chicago, IL 60661, USA FOOD-DRINKS
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 PARTIES
Saving Tiny Hearts Brazilian Carnival Charity Event Sat, 24 Oct at 06:00 pm Loews Chicago Hotel CARNIVALS
GSDC 2026 Gala: Greater Together Wed, 28 Oct at 05:30 pm South Shore Cultural Center USD 189 TO 375 FITNESS
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
11th Annual PGMF Ales Against ALS Sat, 07 Nov at 03:00 pm Heineken 2nd Star Tavern USD 0 TO 109 FITNESS
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 FITNESS
A Seat at the Table | A Fundraiser Dinner for Logan Square Families Thu, 15 Oct at 06:30 pm Armitage Baptist Church FREE FITNESS
AASSC 5th ANNUAL CANCER WALK Sun, 18 Oct at 10:00 am Dr. Conrad Worrill Track & Field Center FREE FITNESS
Soulful Holiday Lights Trolley Celebrating Motown, R& B & House Sat, 28 Nov at 06:30 pm 230 W North Ave USD 79 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
Burrito Brigade Chicago Bike Distribution Sun, 13 Jul at 02:30 pm Plaza Tenochtitlán FREE TRIPS-ADVENTURES
Chicago Wicker Park Naughty Santa Bar Crawl Sat, 05 Dec at 06:00 pm DSTRKT and Wicker Park Venues USD 0 TO 18 PARTIES
2026 Domestic Violence Awareness Walk & Run Sat, 10 Oct at 08:45 am Universal Family Connection FREE PARTIES
Costume Drive for our Upcoming Annual BOOOtique Sun, 20 Sep at 09:30 am Portage Park Farmers Market FREE FITNESS
KPAC 2026 Chili Cookoff Fundraiser Sat, 24 Oct at 01:00 pm Gracie O'Malley's Portage Park USD 18 TO 29 FITNESS
Chicago Positive Impact Fundraiser- After School Programming 2026/2027 Fri, 09 Oct at 06:00 pm 1251 W Taylor St USD 0 TO 18 NONPROFIT
Chicago Walk for Borderline Personality Disorder 2026 Sun, 04 Oct at 09:30 am Jackson Park FREE 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
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
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
Wine and Wills with Evermore Law Group Wed, 07 Oct at 06:00 pm Biagio Events and Catering FREE FITNESS
Talent at the Table: Chicago Film | Benefit for Hope Connections for Cancer Thu, 27 Aug Restaurant of the Week USD 34 FITNESS
The Swedish Hospital Foundation Luminescence Gala Sat, 14 Nov at 06:00 pm Hilton Chicago Hotel NONPROFIT
Race Through Hawaii Virtual Race | 5K, 10K, Marathon | Run Anywhere Sat, 16 May at 01:00 pm Chicago USD 6 TO 47 FITNESS
Kellogg Cares Day: Supporting Sarah's Circle Sat, 10 Oct at 08:00 am Sarah's Circle FREE ENTERTAINMENT
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
Pink Threads Culture Walk: United By Style Sat, 24 Oct at 06:00 pm Hairpin Arts Center USD 37 TO 90 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 NEW-YEAR
Mud Stencils! An Intro to Green Graffiti with Ari Mulch Sun, 11 Oct at 01:00 pm 1754 N Kimball Ave USD 34 FITNESS