Saturday, 31st of October, 2026: Annual Nocturna All Hallows’ Eve Ball w/ DJ Scary Lady Sarah + more Sat, 31 Oct at 10:00 pm Metro Chicago ENTERTAINMENT
Chicago Halloween Bar Crawl Sat, 24 Oct at 04:00 pm PB&J: Pizza Beer and Jukebox USD 16 TO 46 PARTIES
Chicago Halloween Party Cruise | Pier Pressure® Black Pearl Sat, 31 Oct at 08:45 pm Spirit of Chicago Yacht USD 38 TO 68 FITNESS
CHICAGO ZOMBIE CRAWL - Halloween Bar Crawl - Wrigleyville Party Pass Fri, 30 Oct at 07:00 pm Wrigleyville FITNESS
Chicago Halloween Bar Crawl 2026 Sat, 31 Oct at 04:00 pm PB&J: Pizza Beer and Jukebox USD 10 TO 46 FITNESS
Chicago Social and Language Exchange (Make New Friends) ✨ Fri, 24 Apr at 05:30 pm Timothy O'Toole's Pub Chicago USD 8 FITNESS
Volunteers Needed! 92nd Chicago Thanksgiving Parade 2026 Thu, 26 Nov at 06:00 am HI Chicago, The J. Ira and Nicki Harris Family Hostel FREE FITNESS
The Metropolitan Jazz Octet with Dee Alexander Sat, 24 Oct at 08:30 pm 3111 N Western Ave Chicago IL 60618 MUSIC
Chicago Official Thanksgiving Eve Bar Crawl 2026 Wed, 25 Nov at 07:00 pm Downtown Chicago USD 0 TO 13 FITNESS
Chicago - Holiday Cocktail Tasting Festival - November 14 Sat, 14 Nov at 02:30 pm Utopian Tailgate USD 0 TO 67 FITNESS
Monster Jammies: A Halloween Pajama Dance Party For Kids Sun, 25 Oct at 03:00 pm Mathew Bieszczat Volunteer Resource Center USD 0 TO 45 KIDS
Soulful Sounds in Chicago Sun, 11 Oct at 06:00 pm Athenaeum Center for Thought & Culture PERFORMANCES
Jinkx and DeLa Holiday Show at Auditorium Theatre Chicago Sun, 06 Dec at 07:00 pm Auditorium Theatre Chicago ART
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
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
Merry, Merry Chicago! Fri, 18 Dec at 07:30 pm 220 S Michigan Ave, Chicago, IL, United States, Illinois 60604 ENTERTAINMENT
Dr. Seuss’ How the Grinch Stole Christmas! The Musical Wed, 09 Dec at 07:00 pm James M. Nederlander Theatre LIVE-MUSIC
Future Travel World™ Chicago — International Travel & Experience Show Thu, 29 Oct at 09:00 am Marriott Marquis Chicago USD 187 TO 396 FITNESS
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
Black Wednesday @ PARLAY LINCOLN PARK Wed, 25 Nov at 10:00 pm Parlay Lincoln Park USD 23 TO 56 FITNESS
4TH ANNUAL FREEDOM CONCERT & Early Voter Accompaniment ! Sun, 01 Nov at 01:00 pm Willye B. White Park FREE FITNESS
2026 Arts in the Dark Halloween Parade Sat, 24 Oct at 06:00 pm N Columbus Dr, Chicago, IL, United States PARADES
Chicago's BYOB Party Bus Holiday Lights Tour 'Tis The Season Fri, 04 Dec at 04:00 pm Headquarters Beercade USD 66 TO 2,136 FITNESS
2nd Annual DAY OF THE DEAD MARKET Sat, 24 Oct at 12:00 pm 2102 W Cermak Rd, Chicago, IL 60608-4006, United States WORKSHOPS
Godfrey Holiday Cocktail Fest - Cocktail Tasting at I|O Godfrey Rooftop Sat, 05 Dec at 12:00 pm IO Godfrey Rooftop Lounge USD 25 TO 48 FITNESS
Breakfast with Santa Chicago Neiman Marcus Saturday, December 5, 8:30am Sat, 05 Dec at 08:30 am 737 N Michigan Ave USD 67 TO 85 FITNESS
Soulful Holiday Lights Trolley Celebrating Motown, R& B & House Sat, 28 Nov at 06:30 pm 230 W North Ave USD 79 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
Festival del Arte Popular 2026 Tue, 13 Oct at 10:00 am 1852 W 19th St, Chicago, IL, United States, Illinois 60608 FESTIVALS
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
Chicago SantaCon Bar Crawl 2026 Sat, 19 Dec at 04:00 pm PB&J: Pizza Beer and Jukebox USD 0 TO 31 FITNESS
Family Craft Corner: Spooky Decor Sun, 18 Oct at 01:00 pm Idea Box Integrated Arts USD 8 TO 32 FITNESS
Fa La La Fabulous Holiday Market - Chicago Sat, 14 Nov at 11:00 am 3656 N Halsted St, Chicago, IL, United States, Illinois 60613 HOLIDAY
Home Alone 2: Lost In New York - Live In Concert Sat, 19 Dec at 07:00 pm 50 E Ida B Wells Dr, Chicago, IL, United States, Illinois 60605 ENTERTAINMENT
Theater on the Lake welcomes back Burning Red a Tribute to Taylor Swift! Sat, 12 Dec at 07:00 pm Theater on the Lake USD 33 TAYLOR-SWIFT
St. Patrick's Day Lucky Charms Lincoln Park Bar Crawl Sat, 13 Mar at 12:00 pm Lincoln Park USD 14 TO 37 PARTIES
St. Patrick's Day Lucky Charms River North Bar Crawl | Afternoon Sat, 13 Mar at 12:00 pm Headquarters Beercade USD 14 TO 37 PARTIES
Book Event: The Spirits by Bonnie Jo Campbell Thu, 15 Oct at 07:00 pm Women & Children First FREE 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 River North Bar Crawl | Morning Sat, 13 Mar at 09:00 am River North USD 14 TO 37 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 Chicago Art Girls Holiday Pop-Up Shop Sat, 12 Dec at 11:00 am Alexander Graham Bell Elementary School POP-UPS
Holiday Winter Dash Beer Run | 2026 Illinois Brewery Running Series Sun, 06 Dec at 12:00 pm Goose Island Taproom USD 0 TO 76 HOLIDAY
Thanksgiving Dinner Buffet at The Ambassador Room Thu, 26 Nov at 12:00 pm Ambassador Gold Coast - The Chicago Hotel Collection USD 0 TO 89 FITNESS
May 5, 2026 * * GET- READY TO START "Free" Strength & Line Dance @ 10:30am! Tue, 20 Oct at 10:30 am 6550 S Harvard Ave FREE FITNESS
Family Recipe Archive Lab: Preserve One Dish & Its Story Sat, 10 Oct at 10:20 am 1541 W Belmont Ave USD 5 TO 65 FITNESS
Late Wednesdays: Festival After Hours Wed, 14 Oct at 05:00 pm 1852 W 19th St, Chicago, IL, United States, Illinois 60608 FESTIVALS
It's A Wonderful Life: A Live Radio Play at Paradiso at Athenaeum Theatre - IL Fri, 11 Dec The Chicago Theatre PERFORMANCES
FashionCamp: WINTER HOLIDAY EDITION 2026 Sat, 12 Dec at 10:00 am FashionBar (Level 3) USD 530 FITNESS
Felt Decor- Friday, December 4th Fri, 04 Dec at 07:00 pm Revolution Brewing - Brewery & Taproom USD 45 TO 50 HOLIDAY
Tony P's Ugly Sweater Holiday Party @ The Scout: Wednesday December 9th Wed, 09 Dec at 06:00 pm The Scout Waterhouse + Kitchen USD 24 TO 30 UGLY-CHRISTMAS-SWEATER-DAY
PROMCHELLA: The Art of Becoming — A Holiday Fashion Show Sat, 07 Nov at 03:00 pm 6330 S Stony Island Ave USD 0 TO 55 FASHION
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
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
Jo Ann Daugherty Jazz Trio | Printmaker Deborah Maris Lader Sun, 13 Dec at 02:30 pm Artifact Events USD 34 FITNESS
Jingle Jammies: A Holiday Pajamas Dance Party For Kids Sun, 13 Dec at 03:00 pm Mathew Bieszczat Volunteer Resource Center USD 0 TO 45 FITNESS
Historic Pullman Model Train Experience-2026 Sat, 26 Dec at 11:00 am HPF Pullman Exhibit Hall FREE FITNESS
Gourd Ornament Decorating with Abeni Pierson Sun, 08 Nov at 12:00 pm DuSable Black History Museum and Education Center USD 55 FITNESS
The Balzekas Museum Guild Holiday Craft Fair Sat, 21 Nov at 11:00 am Balzekas Museum Of Lithuanian Culture, South Pulaski Road, Chicago, IL, USA FREE CHRISTMAS-MARKETS-AND-FAIRS
Fair Trade Holiday Market Sun, 15 Nov at 08:00 am 625 W Adams St, Chicago, IL 60661-3603, United States BUSINESS
Holiday Swing Social: Class + Social Dancing Sat, 19 Dec at 07:00 pm Ballroom Dance Chicago USD 18 TO 34 FITNESS
Graham Byrne is Back in Chicago and Performing A Brand New Hour Sat, 19 Dec The Lincoln Lodge USD 18 FITNESS
Harvest & Harmony: Thanksgiving Ohara-Ryu Ikebana Workshop Sat, 21 Nov at 10:00 am Japanese Culture Center USD 82 WORKSHOPS
Third Coast Symphony presents Handel's Messiah Thu, 10 Dec at 06:30 pm South Shore Cultural Center CONCERTS