Bottomless Margaritas on the Riverwalk - Every Weds & Sun! Wed, 19 Aug Island Party Hut (between Lake Shore Drive and Columbus on the Riverwalk) USD 25 TO 58 FITNESS
33rd African/Caribbean Intl Fest of Life combined with 10th JSVFest Fri, 25 Sep at 12:00 pm Union Park USD 21 TO 743 FITNESS
Oktoberfest Chicago Fri, 25 Sep at 05:00 pm 1429 W Wellington Ave, Chicago, IL 60657-4121, United States FESTIVALS
INTL FESTIVAL OF LIFE/JSVFest -COMBINED, SEPT. 25-27, UNION PK-Promo tix Fri, 03 Jul at 12:00 pm Union Park USD 21 TO 156 FITNESS
Just Announced - Chicago - Top Shelf Tequila and Whiskey Tasting Festival - September 26 AE Sat, 26 Sep at 02:30 pm Kings Dining & Entertainment USD 20 TO 85 FESTIVALS
Bottomless Mimosas on the Riverwalk - Every Saturday in Chicago Sat, 15 Aug Island Party Hut (between Lake Shore Drive and Columbus on the Riverwalk) USD 25 TO 31 PARTIES
Before Midnight - A Cinderella Tea Experience at The Ritz-Carlton, Chicago Sat, 19 Sep The Ritz-Carlton, Chicago FREE
Chicago, IL - Sunday Service: R&B + Reggaeton Brunch @ Punch Bowl Social Sun, 05 Apr Punch Bowl Social FREE BRUNCH
Espresso Martini Fest at Hubbard Inn, Chicago - Tastings Included Sat, 03 Oct at 05:00 pm Hubbard Inn USD 25 TO 42 FITNESS
International Festival of Life (IFOL) combined with JSVFest Fri, 03 Jul at 12:00 pm Union Park USD 21 TO 743 FESTIVALS
Club Capri: Chicago's #1 Rooftop Party Series At Castaway's Beach Club Sat, 23 May Castaways Beach Club USD 31 TO 78 FITNESS
DJ Sean Mac and Joe Global - RnB Brunch at City Winery - Chicago Sat, 03 Oct at 12:00 pm City Winery - Chicago BRUNCH
Second Hand Soul Band | Old Town Oktoberfest | Sat Sep 19 1:45pm | 1360 N Wells St Chicago Sat, 19 Sep at 01:30 pm 1360 N Wells St, Chicago, IL 60610-1908, United States ENTERTAINMENT
Día de los Muertos Dinner with Chef Richard Sandoval Sat, 03 Oct at 06:00 pm Toro by Chef Richard Sandoval FREE FITNESS
SATURDAY SEPTEMBER 19: CHICAGO'S BEST COMEDY SHOW Sat, 19 Sep at 09:00 pm The Comedy Bar - Chicago Main Stage FREE FITNESS
Bronzeville Summer Nights September 2026 (Fall Finale!) Sat, 26 Sep at 01:00 pm Grand Boulevard FREE MUSIC
20th Annual St. Helen Carnival Thu, 24 Sep at 05:00 pm 2347 W Augusta Blvd, Chicago, IL, United States, Illinois 60622 CARNIVALS
Island Soul Experience: Sea & Provisions – A Seven-Course Bahamian Tasting Sat, 26 Sep at 06:00 pm Dining Room At Kendall College USD 125 WORKSHOPS
Beyond Lifestyle™ — Wellness Travel & Biohacking Expo in Chicago Sat, 26 Sep at 09:00 am Marriott Marquis Chicago USD 84 TO 292 FITNESS
Grand Opening of The Champagne Room Featuring Moët & Chandon Sat, 19 Sep at 08:00 pm Ambassador Gold Coast - The Chicago Hotel Collection USD 30 TO 66 FITNESS
Handmade Pappardelle with Creamy Alfredo - Chicago Sat, 17 Oct at 06:15 pm Sip & Savor | 53rd Street - Hyde Park USD 69 ART
Meet Me on Milwaukee - September Edition Sun, 27 Sep at 10:00 am N Milwaukee Ave, Chicago, IL, United States MUSIC
Grand Opening of The Lair (Under Stardust River North) Sat, 19 Sep at 08:00 pm Stardust Lounge FREE PARTIES
Jewel-Osco’s Shiploads of Celebrations & 3rd Annual Beach Volleyball Charity Classic Sat, 10 Oct at 06:00 pm North Avenue Beach SPORTS
The Judgment of Paris Wine Dinner - Mastro's Chicago Steakhouse Wed, 07 Oct at 07:00 pm Mastro's Steakhouse USD 325 WORKSHOPS
Moe's Wrigleyville's $30 Wristband Pkg - Every Fri & Sat in Chicago Sat, 11 Jul at 10:00 pm Moe's Cantina (Wrigleyville) USD 34 FOOD-DRINKS
Festa Italiana with Jewel-Osco - N Des Plaines St, Chicago Sat, 03 Oct at 12:00 pm Jewel-Osco FREE MUSIC
🔥🎲 PASEO BORICUA SALSA SATURDAY POP-UP @ PE ERRE! 🎲🔥 Sat, 19 Sep at 07:00 pm La Familia Domino League ENTERTAINMENT
Jerk, Seafood & Vegan Festival (JSVFest) combined with Int'l Festival of Li Sat, 25 Jul at 12:00 pm Union Park USD 23 FITNESS
SECOND SERVICE | Chicago’s Monthly Sunday Kickback Sun, 19 Jul at 03:00 pm BAR22 USD 0 TO 180 FITNESS
Asian Dumplings Class - Chicago Fri, 25 Sep at 06:00 pm Pilot Project Brewing - Wrigleyville USD 69 WORKSHOPS
'Forever Summer' Event at LondonHouse Rooftop Tue, 22 Sep at 11:00 am LondonHouse Chicago, Curio Collection by Hilton POP-UPS
The Bacon Brothers People in the World Tour – Concert Cruise Sat, 17 Oct at 06:00 pm 600 E Grand Ave Chicago, IL CONCERTS
Money Breakthrough Intensive Sat, 26 Sep at 10:00 am Barack Obama Presidential Library USD 62 TO 357 FITNESS
Chicago BRA Crawl: Benefiting Breast Cancer Research Sat, 17 Oct at 12:00 pm Chicago's BEST Bars TBA USD 10 TO 28 FITNESS
Homemade Pasta Cooking Class (Fresh Pasta Carbonara!) Fri, 25 Sep at 06:30 pm Bettie's Chicago USD 151 FITNESS
In-person class: Pasta Perfection: Fresh Pasta from Scratch (Chicago) Thu, 09 Jul at 06:30 pm Gateway To Learning (4925 N Lincoln Ave, Chicago, IL 60625) USD 65 FITNESS
In-person class: Asian Dumplings (Chicago) Thu, 30 Apr at 06:30 pm Pilot Project Brewing - Wrigleyville USD 65 FITNESS
JEOPARDY! Bar League - Snakes & Lattes Chicago (US) Mon, 17 Aug Snakes & Lattes Chicago FREE CONTESTS
Hispanic Heritage Month Celebration Sat, 19 Sep at 12:00 pm Caldwell Woods Wellness Center FREE FITNESS
The Beer Garden at Gallagher Way Sat, 17 Oct at 11:00 am Gallagher Way, North Clark Street, Chicago, IL, USA USD 37 FITNESS
The Second City Improv Social at Sheraton Grand Chicago Riverwalk Sat, 15 Aug Sheraton Grand Chicago Riverwalk USD 119 WORKSHOPS
Borshch Fest 2026 — Celebrating Ukrainian Heritage Sun, 27 Sep at 01:00 pm Catherine Chevalier Woods Picnic Grove #1 USD 0 TO 34 FITNESS
Woodford Reserve Whiskey & Chocolate Pairing with Women Who Whiskey Chicago Tue, 29 Sep at 06:30 pm Brownstone USD 26 KENTUCKY-DERBY
Foodies + New Friends: Chicago Dinner + Coffee Club | Monthly Membership Thu, 13 Aug Restaurant of the Week USD 34 FITNESS
Golden Hour Featuring Vince Lazarus & DJ Woodi Sat, 26 Sep at 05:00 pm Epiphany Center for the Arts FREE MUSIC
Chicago Wine Fest at Hubbard Inn - Tastings Included Sat, 24 Oct at 05:00 pm Hubbard Inn USD 25 TO 42 FITNESS
In-person class: The Ramen Experience: From Broth to Bowl (Chicago) Fri, 05 Jun at 06:15 pm Sip & Savor | 53rd Street - Hyde Park USD 65 FITNESS
Whisky Jewbilee Chicago 2026! Celebrating 15 years of Single Cask Nation Thu, 15 Oct at 06:00 pm Artifact Events USD 82 TO 125 FITNESS
Festival of Wood and Barrel Aged Beers Fri, 13 Nov at 05:00 pm 525 S. Racine Ave., Chicago, IL, United States, Illinois 60607 FESTIVALS
Dinner with Entrepreneurs: Chicago (Giving Back Edition) Sat, 13 Jun at 07:00 pm Restaurant of the Week USD 54 FITNESS
Skip the Small Talk Night at kibbitznest Wed, 01 Apr kibbitznest books, brews & blarney USD 24 FOOD-DRINKS
Orange Crush S.A.C. - WHITE SOX Hispanic Heritage Tailgate Outing Fri, 25 Sep at 03:00 pm Guaranteed Rate Field USD 85 TO 103 TRIPS-ADVENTURES
Bryn Mawr Block Party 2026 Sun, 20 Sep at 10:00 am Bryn Mawr Avenue (Between Kimball Ave & Sawyer Ave) FREE FITNESS
Growing Home's Annual Backyard Barbecue Sun, 20 Sep at 02:00 pm Growing Home Urban Farm USD 100 FITNESS
Monster Mall Chicago: Boo's and Brews Sun, 20 Sep at 12:00 pm Midwest Coast Brewing Company FREE FITNESS
OneOne Club Happy Hour Fri, 29 May Chef Art Smith’s Reunion, Navy Pier, East Grand Avenue, Chicago, IL, USA FREE FOOD-DRINKS
REAL HOUSEWIVES OF SLC TRIVIA NIGHT Thu, 24 Sep at 07:00 pm Cultivate by Forbidden Root USD 23 FITNESS