Wine Events in Chicago

Check out happening wine events all around Chicago, IL

Chicago St Patty Day Exotic Paintings BYOB Wine and Paint Male Model

 Fri, 10 Oct 5425 W Lawrence Ave USD 34

Lincoln Park Wine Fest

 Fri, 03 Oct at 05:00 pm Jonquil Park

Sip & Dance: Latin vibes edition 🍷💃🕺

 Thu, 02 Oct at 07:00 pm BottlesUp

Morgan James at City Winery - Chicago

 Sun, 05 Oct at 07:00 pm City Winery - Chicago

Port Wine Fest Chicago: A Celebration of Portuguese Wine + Culture!

 Thu, 02 Oct at 05:00 pm Walden

3238 WINE TASTING CLASS-BECOME A WINE CONNOISSEUR:

 Fri, 10 Oct at 07:00 pm Discovery Center USD 42

Godfrey Wine Fest - Wine Tasting at I|O Godfrey Rooftop

 Sat, 15 Nov at 01:00 pm IO Godfrey Rooftop Lounge USD 31 to 42

“Bottle & Barrel " Fall Mini Wine and Spirits Fest

 Sun, 02 Nov at 01:30 pm Fulton Street Collective USD 34 to 62

Harvest Ball

 Sat, 18 Oct at 08:00 pm Ballroom Dance Chicago USD 87

Wine Crawl After Dark

 Sat, 04 Oct at 06:00 pm Hotel Chicago USD 208

Passages Wine and Books Audiobook Walk

 Sat, 11 Oct at 10:00 am Passages Wine and Books Free

Freddie Jackson at City Winery - Chicago

 Sun, 26 Oct at 07:00 pm City Winery - Chicago

Surabhi Ensemble & Las Guitarras de Espana

 Sun, 05 Oct at 06:00 pm City Winery - Chicago

M**der Mystery Party

 Fri, 17 Oct at 06:00 pm Passages Wine and Books USD 90

Food, Wine, Spirts, Music (Join the Waitlist for Details)

 Sun, 05 Oct at 02:00 pm TBD Free

3221 WINE TASTING CLASS: Sparkling, Rose, Orange

 Fri, 07 Nov at 07:00 pm Discovery Center USD 42

FREE Wine Club Happy Hour at Monday Coffee

 Mon, 06 Oct at 05:00 pm Monday Coffee Co. Free

Paint Night: Honor Your Lost Pet This Día de los Muertos

 Sun, 26 Oct at 06:30 pm BottlesUp! USD 54

Ireland vs. All Blacks After Party

 Sat, 01 Nov at 05:00 pm Millennium Hall USD 43 to 120

Port Wine Fest: A Festival of Portuguese Wines Chicago 2025

 Thu, 02 Oct at 05:00 pm Walden USD 77

Norman Brown

 Fri, 07 Nov City Winery - Chicago

3245 MIXOLOGY 102: SOPHISTICATED AND COMPLEX COCKTAILS

 Sat, 18 Oct at 02:00 pm Discovery Center USD 42

3238 WINE TASTING CLASS-BECOME A WINE CONNOISSEUR:

 Fri, 05 Dec at 07:00 pm Discovery Center USD 42

Global Morocco Nights of Chicago

 Fri, 03 Oct at 09:00 pm Alhambra Palace Restaurant USD 23

Sip & Paint: Celebrating the Puerto Rican Cuatro with Reynaldo ‘Guaracibo’ Rodriguez

 Sat, 25 Oct at 06:00 pm 3000 N Elbridge Ave, Chicago, IL, United States, Illinois 60618

Chicago Exotic Paintings BYOB Paint n Sip

 Sat, 10 Aug at 04:00 pm 6340 W Gunnison St USD 35

FLOURISH: A blue lotus and dance ceremony

Sat, 11 Oct at 06:00 pm Moksha Yoga Center

The Psychology of Cults at City Winery - Chicago

 Tue, 28 Oct at 07:30 pm City Winery - Chicago

Kirk Whalum at City Winery - Chicago

 Sun, 23 Nov at 05:00 pm City Winery - Chicago

Cold

 Sat, 01 Nov at 06:00 pm City Winery - Chicago

Romancing the Studio - A date night at the Gallery

 Fri, 10 Oct at 06:00 pm 5504 West Lawrence Avenue, Chicago, IL, USA USD 13

RL Book Club #103: "Our Share of the Night"

 Tue, 21 Oct at 07:30 pm Reed's Local

Damien Escobar at City Winery - Chicago

 Sun, 07 Dec at 05:00 pm City Winery - Chicago

Luenell at City Winery - Chicago

 Thu, 02 Oct at 06:00 pm City Winery - Chicago

Between the Wines Book Club - Eight Hundred Grapes

 Tue, 30 Sep at 07:00 pm WineStyles Chicago Free

Tarot Tuesday

 Tue, 11 Nov at 08:30 pm Colvin House Free

Pumpkin Spice and Date Nights

 Sat, 08 Nov at 06:30 pm 4410 N Milwaukee Ave USD 93

Boney James at City Winery - Chicago

 Sat, 15 Nov at 06:00 pm City Winery - Chicago

Chicago's BYOB Party Bus Holiday Lights Tour | Navy Pier

 Fri, 05 Dec at 05:00 pm Old Crow Smokehouse - Wrigleyville

The Whine Down : Chicago's premier Afro-Carribean late night happy hour

 Fri, 10 Oct at 09:00 pm The Wild Hare & Singing Armadillo Frog Sanctuary USD 0 to 26

OCT 18 – 5PM | CHICAGO| Sip & Stretch Couples Yoga Date Night

 Sat, 18 Oct at 05:00 pm Dance Center Chicago USD 125

Chicago's BYOB Party Bus Holiday Lights Tour | Navy Pier

 Sat, 27 Dec at 05:00 pm Old Crow Smokehouse - Wrigleyville

Tarot Tuesday

 Tue, 14 Oct at 08:30 pm Colvin House Free

NO SOMMS ALLOWED: Burgundy and Beaujolais

 Sat, 22 Nov at 02:00 pm Rogers Park Social USD 50

Sweetest Day Wine, Spirits & Beer Tasting

 Sat, 18 Oct at 01:00 pm 1060 E 47th St USD 23 to 82

Classic Encounter with Terri Hemmert

 Thu, 20 Nov at 06:00 pm 220 S Michigan Ave, Chicago, IL, United States, Illinois 60604

2026 Chicago Winter Tequila Tasting Festival (February 14)

 Sat, 14 Feb at 02:30 pm Downtown Chicago USD 0 to 440

Laugh Learn And Lead-Hosted By /Comedian Jeremiah Frazier

 Tue, 28 Oct at 05:00 pm North Oak Park Avenue USD 20 to 25

Friday Night - Haunted Carnival

 Fri, 31 Oct at 10:00 pm LOFT 22 USD 26 to 34

Tarot Tuesday

 Tue, 09 Dec at 08:30 pm Colvin House Free

An Exploration of the South Africa: Overview of a New Landscape

 Tue, 30 Sep at 06:00 pm Grand Cru Chicago USD 50

Classic Encounter with Terri Hemmert

 Thu, 05 Feb at 06:00 pm 220 S Michigan Ave, Chicago, IL, United States, Illinois 60604

Press & Sip: DIY Press-On Nail Art + Wine Experience

 Sun, 19 Oct at 03:00 pm 2134 W 18th St USD 26 to 61

PAWS, PINTS & DANCE HAFLA @ NAVIGATOR TAPROOM

 Sun, 16 Nov at 01:30 pm 2211 N Milwaukee Ave, Chicago, IL 60647-2061, United States

BYOB Party Bus Holiday Lights Tour 'Tis The Season

 Fri, 19 Dec at 05:00 pm Headquarters Beercade

Get Lit: Santa's Book Fair

 Tue, 02 Dec at 05:30 pm American Writers Museum USD 8 to 29

Chicago's BYOB Party Bus Holiday Lights Tour 'Tis The Season

 Fri, 28 Nov at 05:00 pm Headquarters Beercade

Chicago's BYOB Party Bus Holiday Lights Tour 'Tis The Season

 Fri, 05 Dec at 05:00 pm Headquarters Beercade

Chante Moore

 Sun, 02 Nov City Winery - Chicago

3rd Fridays Free Admission Night with Museum Tour

 Fri, 21 Jul at 05:00 pm Heritage Museum of Asian Art Free

Survivor 49 ULTRA VIP Viewing Party Jonny Fairplay & Yam Yam Arocho Chicago

 Wed, 15 Oct at 05:30 pm Randolph Tower City Apartments USD 120

Chat & Cheers - Free Weekly Chicago Social Hour Every Thursday!

 Thu, 03 Apr at 07:00 pm Hopsmith Chicago Free

George Wallace at City Winery - Chicago

 Sun, 12 Oct at 05:00 pm City Winery - Chicago

Meet and Create! - Paint and Sip

 Sat, 10 Jul at 06:30 pm 1438 E 52nd St USD 39

Open Paint Night at Studio15 Art Gallery

 Fri, 11 Jul at 06:00 pm Studio15 / TVP Tech Solutions LLC USD 30

Waltz DanceSport Classes

 Tue, 02 Sep at 07:45 pm Ballroom Dance Chicago USD 45

The Halloween Bloom Bar - Create A Candle & A Halloween Floral Mini Pumpkin

 Sat, 25 Oct at 12:00 pm 3414 W Foster Ave USD 71 to 210

Chicago Wine Fest at Hubbard Inn - Tastings Included

 Sat, 18 Oct at 05:00 pm Hubbard Inn USD 31 to 69

Napoli Night at La Pizza & La Pasta

 Mon, 01 Sep at 07:00 pm Eataly Chicago USD 37

Chicago's BYOB Party Bus Holiday Lights Tour 'Tis The Season

 Sun, 21 Dec at 04:00 pm Headquarters Beercade

Bingo at ALK

 Wed, 18 Sep at 05:00 pm About Last Knife Free

Godfrey Wine Fest - Wine Tasting at I|O Godfrey Rooftop - Multiple Dates

 Sat, 15 Nov IO Godfrey Rooftop Lounge

Bottomless Mimosas on the Riverwalk - Every Weekend at Island Party Hut

 Sat, 03 May at 11:00 am Island Party Hut (between Lake Shore Drive and Columbus on the Riverwalk) USD 31

Wine Down Wednesday

 Wed, 26 Feb at 06:30 pm Creative Sippin USD 35