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 Party Cruise | Pier Pressure® Black Pearl Sat, 31 Oct at 08:45 pm Spirit of Chicago Yacht USD 50 TO 94 ENTERTAINMENT
Chicago Halloween Bar Crawl 2026 Sat, 31 Oct at 04:00 pm PB&J: Pizza Beer and Jukebox USD 16 TO 46 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
Chicago Official Thanksgiving Eve Bar Crawl 2026 Wed, 25 Nov at 07:00 pm Downtown Chicago USD 0 TO 13 FITNESS
BLACK INTENTIONS | Blackout Wednesday at Y Bar Wed, 25 Nov at 10:00 pm Y Bar USD 14 TO 92 ENTERTAINMENT
Prices Going Up - Chicago - Holiday Cocktail Tasting Festival - November 14 Sat, 14 Nov at 02:30 pm Utopian Tailgate USD 0 TO 67 FITNESS
Pitch Your Peeps: Chicago's QUEER Slide Deck Dating Show Thu, 14 May at 07:00 pm Nobody’s Darling USD 13 HEALTH-WELLNESS
Chicago Social and Language Exchange (Make New Friends) ✨ Fri, 24 Apr at 05:30 pm Timothy O'Toole's Pub Chicago USD 8 MEETUPS
Chicago Riverwalk Secrets Quest Sat, 31 Oct at 10:00 am Michigan Avenue & East Wacker Place USD 23 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
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
Jinkx and DeLa Holiday Show at Auditorium Theatre Chicago Sun, 06 Dec at 07:00 pm Auditorium Theatre Chicago ART
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 PARTIES
Ornament Paint & Sip Thu, 10 Dec at 06:30 pm Cafe Con Leche, North Milwaukee Avenue, Chicago, IL, USA USD 45 ART
Breakfast with Santa Neiman Marcus Chicago Saturday, December 5, 8:30am Sat, 05 Dec at 08:30 am 737 N Michigan Ave USD 67 TO 85 BREAKFAST-WITH-SANTA
Merry, Merry Chicago! Fri, 18 Dec at 07:30 pm 220 S Michigan Ave, Chicago, IL, United States, Illinois 60604 ENTERTAINMENT
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
Black Wednesday @ PARLAY LINCOLN PARK Wed, 25 Nov at 10:00 pm Parlay Lincoln Park USD 23 TO 56 FITNESS
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
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
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
Dr. Seuss’ How the Grinch Stole Christmas! The Musical Wed, 09 Dec at 07:00 pm James M. Nederlander Theatre LIVE-MUSIC
4TH ANNUAL FREEDOM CONCERT & Early Voter Accompaniment ! Sun, 01 Nov at 01:00 pm Willye B. White Park FREE FITNESS
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, 08 Nov at 12:00 pm 1637 W 18th St USD 7 TO 13 FITNESS
Breakfast with Santa Neiman Marcus Chicago Saturday, December 12, 8:30am Sat, 12 Dec at 08:30 am 737 N Michigan Ave USD 67 TO 85 FITNESS
Chicago SantaCon Bar Crawl 2026 Sat, 19 Dec at 04:00 pm PB&J: Pizza Beer and Jukebox USD 0 TO 31 BAR-CRAWLS
Chicago, IL - First Taste Holiday @ Punch Bowl Social Fri, 06 Nov at 11:00 am Punch Bowl Social FREE FITNESS
Theater on the Lake Presents: Burning Red's 4th Annual Christmas Birth-TAY Sat, 12 Dec at 07:00 pm Theater on the Lake USD 33 HOLIDAY
Holiday-Ready Home Workshop: Chicago Sat, 07 Nov at 02:00 pm BED BATH & BEYOND + The Container Store FREE FITNESS
Holiday Pies Baking Class Sat, 21 Nov at 10:30 am 853 N Larrabee St., Chicago, IL, United States, Illinois 60610 WORKSHOPS
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
The Chicago Art Girls Holiday Pop-Up Shop Sat, 12 Dec at 11:00 am Alexander Graham Bell Elementary School POP-UPS
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 THANKSGIVING
Kasia's Bridal 25th Anniversary Fashion Show & Customer Appreciation Event Sun, 08 Nov at 12:00 pm Kasia's Bridal & Special Occasion Boutique FREE FASHION
Holiday Artisan Showcase & Winter Social Sat, 14 Nov at 11:00 am Event Space on Thirty Third USD 0 TO 49 FITNESS
FashionCamp: WINTER HOLIDAY EDITION 2026 Sat, 12 Dec at 10:00 am FashionBar (Level 3) USD 530 FITNESS
Holiday Winter Dash Beer Run | 2026 Illinois Brewery Running Series Sun, 06 Dec at 12:00 pm Goose Island Taproom USD 0 TO 76 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
St. Patrick's Day Lucky Charms Lincoln Park Bar Crawl Sat, 13 Mar at 12:00 pm Lincoln Park USD 14 TO 37 FITNESS
Leftovers & Laughs: A Cooking Class & Comedy Night! Fri, 13 Nov at 06:00 pm Cooking with Cass USD 70 TO 93 COMEDY
Real lives Real Runways a Access 360 Activation Sun, 15 Nov at 02:00 pm Roosevelt Collection Shops (across from Old Navy) USD 0 TO 39 TOY-DRIVES
A Holiday Cabaret with The Uptones Sat, 05 Dec at 08:00 pm UncommonGround - Lakeview USD 23 ENTERTAINMENT
St. Patrick's Day Lucky Charms Wrigleyville Bar Crawl Sat, 13 Mar at 10:00 am Blue Bayou USD 19 TO 37 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
Nouveau Day with Scribe Winery at Foxtrot Thu, 19 Nov at 06:30 pm Foxtrot Lincoln Park USD 32 FITNESS
Cornelia Arts Building December Open House Fri, 04 Dec at 05:00 pm 1800 W Cornelia Ave, Chicago, IL, United States, Illinois 60657 ART
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 FITNESS
Jade Maze's Holiday Golden Hour w/ Chris Mahieu Thu, 03 Dec at 05:00 pm Epiphany Center for the Arts FREE MUSIC
Chicago Holiday Cocktail Tasting Festival Sat, 14 Nov at 02:30 pm Utopian Tailgate, 1608 N Wells St, Chicago, 60614, Chicago, US FESTIVALS
Cosmo Rotary Social at Mag Mile Holiday Lights Parade Sat, 21 Nov at 04:30 pm 875 North Michigan Avenue FREE FITNESS
Hands-On: Make your Holiday Dessert: Tiramisù Wed, 25 Nov at 04:00 pm Eataly Chicago USD 98 WORKSHOPS
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
Friendsgiving Cocktail Class: Hands-On BYOB Mixology in Chicago Wed, 18 Nov at 06:30 pm ABC Bartending School Chicago USD 71 TO 129 WORKSHOPS
St. Patrick's Day Lucky Charms River North Bar Crawl | Morning Sat, 13 Mar at 09:00 am River North USD 14 TO 37 PARTIES
Bells & Whispers - Night 2 Fri, 11 Dec at 07:00 pm International Museum of Surgical Science USD 38 NONPROFIT
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
Cat Tastrophe Charities Fundraiser Charitable Event Sat, 28 Nov at 06:00 pm Below are the details: Location: Pitch & Pour Supper Club USD 20 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 FITNESS
Jo Ann Daugherty Jazz Trio | Printmaker Deborah Maris Lader Sun, 13 Dec at 02:30 pm Artifact Events USD 34 FITNESS
In-person class: Christmas Cookie Decorating (Chicago) Wed, 13 Nov at 06:30 pm 1922 W Foster Ave USD 71 FITNESS