Spooky Zoo Sat, 17 Oct at 10:00 am N Cannon Dr at W Fullerton Pkwy, Chicago, IL, United States, Illinois 60614 FESTIVALS
R&B Boo Bash Sweetest Day Yacht Party (3 Levels) Chicago Sat, 17 Oct at 06:45 pm Anita Dee Yacht Charters USD 61 TO 562 FITNESS
RNB Rooftop Party @ Utopian Tailgate (Chicago) Indoor/Outdoor Sun, 18 Oct at 03:00 pm 1608 N Wells St USD 15 TO 162 ENTERTAINMENT
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
Chicago Halloween Party Cruise | Pier Pressure® Black Pearl Sat, 31 Oct at 08:45 pm Spirit of Chicago Yacht USD 38 TO 68 FITNESS
RNB Vs Hip Hop 2000s Yacht Party FT: DJ Nehpets Power 92.3 (Chicago) Sat, 10 Oct at 06:45 pm Anita Dee Yacht Charters USD 45 TO 550 FITNESS
Espresso Martini Fest at Hubbard Inn, Chicago - Tastings Included Sat, 03 Oct at 05:00 pm Hubbard Inn USD 25 TO 42 FESTIVALS
Lincoln Park Wine Fest Fri, 09 Oct at 05:00 pm 1001 W Wrightwood Ave, Chicago, IL 60614-1312, United States FESTIVALS
R&B Fall Ball Yacht Party (3 Levels) Chicago Sun, 25 Oct at 06:45 pm Anita Dee Yacht Charters USD 45 TO 562 ENTERTAINMENT
Chicago BRA Crawl: Benefiting Breast Cancer Research Sat, 17 Oct at 12:00 pm Wrigleyville's BEST Bars TBA USD 10 TO 28 FITNESS
Jewel-Osco’s Shiploads of Celebrations & 3rd Annual Beach Volleyball Charity Classic Sat, 10 Oct at 06:00 pm North Avenue Beach SPORTS
4th Annual Justice Ball | Justice • Hip Hop • Sneakers: All-White Ball Sat, 17 Oct at 05:00 pm Kennedy-King College USD 0 TO 1,197 FITNESS
Haunted Halloween Night Lake Cruise on Friday, October 30th Fri, 30 Oct at 08:00 pm Anita Dee II Boarding at Dusable Harbor (See map and directions at bottom of page for exact location) USD 20 TO 57 FITNESS
Chicago Wine Fest at Hubbard Inn - Tastings Included Sat, 26 Dec at 05:00 pm Hubbard Inn USD 25 TO 42 FITNESS
TRICK OR DRINK: River North Adult Trick-or-Treating Bar Sat, 31 Oct at 03:00 pm ROCBAR USD 14 TO 26 HALLOWEEN
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 71 FITNESS
Haunted Halloween Night Lake Cruise on Saturday, October 31st Sat, 31 Oct at 08:00 pm Anita Dee II Boarding at Dusable Harbor (See map and directions at bottom of page for exact location) USD 30 TO 58 FITNESS
The Associate Board of Endeavor Health NorthShore Hospitals 21st Annual Benefit Sat, 24 Oct at 07:00 pm Field Museum NONPROFIT
MEMENTO MORI Halloween Gala Fri, 30 Oct at 07:00 pm International Museum of Surgical Science USD 0 TO 157 FITNESS
NIGHTMARE ON RANDOLPH - A TWO DAY HALLOWEEN EXPERIENCE Fri, 23 Oct at 06:00 pm 1249 W Randolph St, West Loop NONPROFIT
Open Books & Laugh: A Standup Comedy Show for Literacy Thu, 22 Oct at 07:00 pm Laugh Factory USD 0 TO 226 FITNESS
R&B Halloween Costume Yacht Party (Chicago) Anita Dee II Sat, 31 Oct at 12:45 pm Anita Dee Yacht Charters USD 50 TO 535 BOAT-PARTIES
DCASE Presents - Under The Dome - OCTOBER 2026 Thu, 22 Oct at 05:00 pm Chicago Cultural Center FREE MUSIC
Free to Breathe Chicago Walk Sun, 18 Oct at 09:00 am 600 W Montrose Ave, Chicago, IL 60613-1500, United States CHARITIES
Casino Uptown: Celebrating 100 Years of the Aragon Ballroom Thu, 15 Oct at 05:30 pm Aragon Ballroom MUSIC
Ravenswood Costume Crawl Wed, 28 Oct at 05:30 pm A variety of Ravenswood small businesses USD 34 TO 36 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
Kincade's Wrigleyville's Halloween DAY Party Sat, 31 Oct at 01:00 pm Kincade's Wrigley USD 20 TO 37 ENTERTAINMENT
Fall Clothing Swap 2026 Fri, 16 Oct at 06:00 pm Chicago Fair Trade Museum & Store USD 13 TO 55 NONPROFIT
Haunted Howl-o-ween Party for Dogs at Wag Hotels West Loop Sat, 24 Oct at 06:00 pm Wag Hotels - West Loop USD 0 TO 22 FITNESS
Skip the Small Talk Night at kibbitznest Wed, 01 Apr kibbitznest books, brews & blarney USD 24 FOOD-DRINKS
Zombie Bugs Informational Talk and Pinning Session with Neuroparasitologist Sat, 17 Oct at 12:00 pm The Insect Asylum FREE WORKSHOPS
Journey to 30: The Miracle Center’s 30th Anniversary Benefit Sat, 17 Oct at 06:00 pm The Miracle Center USD 82 TO 135 ART
Investing in the Next Generation: A Side Event at SOCAP 2026 Tue, 13 Oct at 05:00 pm The Metropolitan (67th Floor - East Room) FREE FITNESS
5k Fun Run x Spiteful Brewing | 2026 IL Brewery Running Series Sun, 25 Oct at 11:00 am Spiteful Brewing Tap Room USD 0 TO 76 FITNESS
Lavender Laugh Lounge (Sober Friendly, Queer Stand Up Comedy) Sat, 06 Dec at 06:30 pm Loaves & Witches FREE FITNESS
FIND YOUR THING at the Fall 2026 Volunteer Fair! Sun, 18 Oct at 12:00 pm Royal Palms Shuffleboard Club FREE FITNESS
Dinner with Entrepreneurs: Chicago (Giving Back Edition) Sat, 13 Jun at 07:00 pm Restaurant of the Week USD 54 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
Barks & Brews Halloween: Rescue Puppy Yoga at Midwest Coast Brewing Sun, 01 Nov at 10:00 am Midwest Coast Brewing Company USD 50 FITNESS
R&B Vs Hip Hop Black Attire Yacht Party (3 Levels) Chicago Sat, 07 Nov at 06:45 pm Anita Dee Yacht Charters USD 45 TO 562 ENTERTAINMENT
Legado Cultural - Concierto de 50 Aniversario Sat, 14 Nov at 07:00 pm Benito Juarez Community Academy USD 40 TO 50 MUSIC
Men Having Babies 2026 Midwest Surrogacy Conference & Expo in Chicago Fri, 16 Oct at 05:00 pm Center on Halsted USD 50 FITNESS
Principal Storytelling Evening Thu, 15 Oct at 05:30 pm Griffin Museum of Science and Industry, Chicago FREE FITNESS
5k Fun Run x Printer's Row Brewing | 2026 IL Brewery Running Series Sat, 17 Oct at 11:00 am Printer's Row Brewing USD 0 TO 76 WORKSHOPS
Paranormal Prom- An Adult Aerial Student Showcase Fri, 16 Oct at 06:30 pm Chicago Aerial Arts USD 29 TO 39 FITNESS
American Heart Association EmPOWERED to Serve Business Accelerator Demo Day Thu, 22 Oct at 10:00 am 222 W Merchandise Mart Plaza, Suite 228 FREE FITNESS
Listos para el museo: Colorful Calaveras Sat, 17 Oct at 12:30 pm 1852 W 19th St, Chicago, IL, United States, Illinois 60608 ART
FREE Community Pop-up Thrift BOOOtique Sat, 24 Oct at 12:00 pm 36th Ward Belmont Cragin Office FREE FITNESS
Marti & Mimi's "Back to School" Charity Ball Sun, 16 Aug at 08:30 pm Stars and Garters Theater USD 20 TO 31 FITNESS
Juke Me Til I Scream Friday The 13th Yacht Party (3 Levels) Chicago Fri, 13 Nov at 06:45 pm Burnham Harbor S Dock - Anita Dee 2 - Temporary Docking Area USD 45 TO 562 FRIDAY-THE-13TH
Soulful Sounds in Chicago Sun, 11 Oct at 06:00 pm Athenaeum Center for Thought & Culture PERFORMANCES
Painting Dreamscapes - Fantasy & Dreamscape Painting Workshop Fri, 16 Oct at 06:00 pm Awakenings FREE FITNESS
City of Chicago's OEMC Whole Community Training Summit 2026 Tue, 27 Oct at 08:00 am DePaul University - Lincoln Park Student Center FREE 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
Project Management ( PMP ) Exam Prep Classroom Training in Chicago, IL Tue, 03 Feb Regus - Chicago - Hyde Park USD 1,599 WORKSHOPS
Celestial Odyssey Thu, 05 Nov at 05:30 pm The Metropolitan at the Willis(Sears) Tower USD 162 TO 2,136 NONPROFIT
Chicago's Hottest Networking Event For Young Professionals Wed, 28 Oct at 07:00 pm Joy District USD 10 TO 21 BUSINESS
Gourmand Gala - A Symphony of Senses Thu, 12 Nov at 06:30 pm 500 W Jackson Blvd, Chicago, IL 60661, USA FOOD-DRINKS
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
Monthly Group Ukulele Lessons in Pilsen. FREE Ukulele Giveaway! Sun, 11 Oct at 12:00 pm 1637 W 18th St USD 7 TO 13 FITNESS
Saving Tiny Hearts Brazilian Carnival Charity Event Sat, 24 Oct at 06:00 pm Loews Chicago Hotel CARNIVALS
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
GSDC 2026 Gala: Greater Together Wed, 28 Oct at 05:30 pm South Shore Cultural Center USD 189 TO 375 FITNESS
Foodies + Fears: Chicago | Dinner with Paranormies Sat, 25 Apr at 07:00 pm Restaurant of the Week USD 23 MEETUPS
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
HeRose + Heroines: Chicago | Christians in the Creative Arts Fri, 22 May at 07:00 pm Restaurant of the Week USD 23 MEETUPS
Kerry Kennedy: Ethel Kennedy - The Extraordinary Life and Bold Legacy Tue, 27 Oct at 07:30 pm City Winery - Chicago
New Year's Eve Sunset Cocktail Cruise on Thursday, December 31st Thu, 31 Dec at 04:30 pm Anita Dee II TEMPORARILY LOCATED at BURNHAM HARBOR (See directions below) USD 20 TO 42 NEW-YEAR
One Day at a Time, Inc Annual Breast Cancer Awareness 5k Sat, 10 Oct at 07:00 am St.Luke Missionary Baptist Church FREE FITNESS
Risen Fest at Mindful Baking Sun, 25 Oct at 12:00 pm Mindful Baking Kitchen & Cafe (Gluten-free & Vegan) USD 20 MUSIC
In-Person Support Group for Women Narcissistic Abuse Survivors Thu, 08 Oct at 07:00 pm 4801 W Peterson Ave suite 608 FREE NONPROFIT
Paris with Purpose - Cancer Benefit & Scholarship Dinner Fri, 09 Oct at 06:00 pm Malcolm X College USD 0 TO 500 FITNESS
Club Millennial (MLNL) - Chicago - Stereo Nightclub - 10/31 Sat, 31 Oct at 05:00 pm Stereo Nightclub USD 14 TO 38 FITNESS