Wine Events in Chicago

Check out happening wine events all around Chicago, IL

Lidia Bastianich - The Art of Pasta Dinner

 Sat, 07 Feb at 03:00 pm Eataly Chicago USD 156

2026 Chicago Winter Tequila Tasting Festival (February 14)

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

Uncorked: Chicago

 Sat, 14 Mar at 07:00 pm Field Museum USD 99 to 145

Graduate Council Presents: The Maroon Masquerade

 Sat, 21 Feb at 07:00 pm Joy District USD 54 to 65

Do Chicago-Style Street Art - Paint and Sip in Chicago | Classpop!™

 Sun, 01 Feb at 03:30 pm Studio W.I.P. USD 62

Vanessa Carlton

 Mon, 27 Apr City Winery - Chicago

Taste of Ravenswood

 Fri, 06 Feb at 07:30 pm Ravenswood Event Center USD 98 to 1,069

Do Chicago-Style Street Art - Paint and Sip in Chicago | Classpop!™

 Sat, 14 Feb at 03:30 pm Studio W.I.P. USD 62

Chef's Valentines Dinner: Italian Date Night

 Sat, 14 Feb at 06:30 pm Eataly Chicago USD 156

Tony Rock at City Winery - Chicago

 Wed, 11 Mar at 07:30 pm City Winery - Chicago

Love In The Making: Valentine's WineMaking Experience & Dinner

 Sat, 14 Feb at 06:00 pm Wild Blossom Meadery and Winery USD 157

Do Chicago-Style Street Art - Paint and Sip in Chicago | Classpop!™

 Wed, 11 Mar at 06:00 pm Studio W.I.P. USD 62

St. Patrick's River Dancing at Rebar 2026

 Sat, 14 Mar at 08:00 am Rebar USD 82 to 2,563

Champagne & Sparkling Wine Fest at Hubbard Inn on Valentine's Day

 Sat, 14 Feb at 05:00 pm Hubbard Inn USD 36 to 47

Early Pour Club - TABLES FOR PURCHASE

 Sat, 14 Mar at 08:00 am Joy District USD 648

Do Chicago-Style Street Art - Paint and Sip in Chicago | Classpop!™

 Sun, 08 Feb at 06:00 pm Studio W.I.P. USD 62

Clover Club | 3rd Floor Hubbard Inn | 4pm

 Sat, 14 Mar at 04:00 pm Hubbard Inn USD 56 to 109

Chicago Galentine’s Wine Tasting Experience | Hotel 55 & Lure Fishbar

 Fri, 13 Feb at 06:30 pm Lure Fishbar - Chicago USD 55

Sip Me, I'm Irish | Hubbard Inn | 12pm

 Sat, 14 Mar at 12:00 pm Hubbard Inn USD 56 to 109

Sip & Savor: Alpine Wine & Cheese

 Fri, 06 Feb at 06:30 pm Eataly Chicago USD 71

Roscoe Village Wine Walk

 Fri, 13 Feb at 05:30 pm Roscoe St from Paulina to Western USD 49 to 61

Hubbard Inn Uncorked Galentine's Edition

 Fri, 13 Feb at 07:30 pm Hubbard Inn USD 29

The R&B Trolley - Party Tour (Valentines Edition)

 Fri, 13 Feb at 10:00 pm Chalet USD 69 to 85

Do Chicago-Style Street Art - Paint and Sip in Chicago | Classpop!™

 Fri, 20 Feb at 06:00 pm Studio W.I.P. USD 62

Do Chicago-Style Street Art - Paint and Sip in Chicago | Classpop!™

 Thu, 12 Feb at 08:30 pm Studio W.I.P. USD 62

Do Chicago-Style Street Art - Paint and Sip in Chicago | Classpop!™

 Tue, 17 Feb at 08:30 pm Studio W.I.P. USD 62

Do Chicago-Style Street Art - Paint and Sip in Chicago | Classpop!™

 Sat, 07 Mar at 03:30 pm Studio W.I.P. USD 62

Valentine's Day Festa

 Fri, 13 Feb at 06:00 pm Eataly Chicago USD 49 to 240

Do Chicago-Style Street Art - Paint and Sip in Chicago | Classpop!™

 Wed, 18 Mar at 06:00 pm Studio W.I.P. USD 62

Valentines Day Hands on: The Art of the Salumi & Formaggi Board

 Sat, 14 Feb at 12:00 pm Eataly Chicago USD 87 to 130

Valentine's Painting + Wine Night

 Fri, 13 Feb at 06:30 pm Vault Gallerie USD 61

Do Chicago-Style Street Art - Paint and Sip in Chicago | Classpop!™

 Sat, 21 Mar at 08:30 pm Studio W.I.P. USD 62

Do Chicago-Style Street Art - Paint and Sip in Chicago | Classpop!™

 Sat, 07 Mar at 09:30 pm Studio W.I.P. USD 62

Do Chicago-Style Street Art - Paint and Sip in Chicago | Classpop!™

 Wed, 25 Mar at 06:00 pm Studio W.I.P. USD 62

Do Chicago-Style Street Art - Paint and Sip in Chicago | Classpop!™

 Thu, 26 Feb at 08:30 pm Studio W.I.P. USD 62

Wild Wander - Paint and Sip in Chicago | Classpop!™

 Fri, 06 Feb at 07:30 pm Pinot's Palette - Logan Square USD 56

RATIO: ROSÉ LOUNGE

 Sat, 21 Feb at 03:00 pm Bodega Taqueria y Tequila USD 13 to 23

Simply Starry Night "Your City" - Paint and Sip in Chicago | Classpop!™

 Fri, 20 Mar at 08:00 pm Pinot's Palette - Logan Square USD 56

Sushi Making With Chef Janet at a Local Distillery - Sushi Making Cooking Class in Chicago | Classpop!™

 Sat, 07 Feb at 05:30 pm Wolf Point Distilling USD 74

Waterfall Beach - Paint and Sip in Chicago | Classpop!™

 Wed, 04 Feb at 07:30 pm Pinot's Palette - Logan Square USD 49

Do Chicago-Style Street Art - Paint and Sip in Chicago | Classpop!™

 Thu, 26 Mar at 06:00 pm Studio W.I.P. USD 62

Jim Messina

 Sat, 21 Mar at 06:00 pm City Winery - Chicago

City Reflections - Paint and Sip in Chicago | Classpop!™

 Fri, 06 Mar at 08:00 pm Pinot's Palette - Logan Square USD 56

Glowing Starry Night - Chicago - Paint and Sip in Chicago | Classpop!™

 Sat, 14 Feb at 07:30 pm Pinot's Palette - Logan Square USD 56

Moon Over the Pines - Paint and Sip in Chicago | Classpop!™

 Thu, 19 Feb at 07:30 pm Pinot's Palette - Logan Square USD 49

Do Chicago-Style Street Art - Paint and Sip in Chicago | Classpop!™

 Wed, 18 Feb at 06:00 pm Studio W.I.P. USD 62

Homemade Chocolate Confections - Cooking Class in Chicago | Classpop!™

 Mon, 23 Feb at 07:00 pm Illuminated Brew Works USD 74

Psychedelic Paradise - Paint and Sip in Chicago | Classpop!™

 Fri, 06 Feb at 08:00 pm Pinot's Palette - Logan Square USD 56

Monet’s Water Lilies II - Paint and Sip in Chicago | Classpop!™

 Wed, 25 Feb at 07:00 pm Pinot's Palette - Logan Square USD 49

Perfecting the Preparation of Pasta - Pasta Making Cooking Class in Chicago | Classpop!™

 Mon, 09 Feb at 07:00 pm Illuminated Brew Works USD 74

Do Chicago-Style Street Art - Paint and Sip in Chicago | Classpop!™

 Sun, 01 Mar at 01:00 pm Studio W.I.P. USD 62

The Christi Show at City Winery - Chicago

 Sun, 08 Mar at 07:00 pm City Winery - Chicago

Chicago Rum Fest 2026

 Sat, 25 Apr at 02:00 pm Logan Square Auditorium USD 26 to 301

IAN MAKSIN & GABRIEL DATCU in CHICAGO: "WINTER BLUES" (House Concert)

 Tue, 03 Feb at 07:00 pm Private Residence USD 39

Sunset City - Paint and Sip in Chicago | Classpop!™

 Wed, 11 Mar at 07:30 pm Pinot's Palette - Logan Square USD 32

Valentine's Day Pizza Cooking Classes and Dinner

 Wed, 11 Feb at 06:00 pm Pizzeria Due USD 178

Monet's Chicago Twilight - Paint and Sip in Chicago | Classpop!™

 Sat, 28 Mar at 07:30 pm Pinot's Palette - Logan Square USD 56

A Spirited Affair: Candle Making + Wine Pairing Experience at The Gwen

 Thu, 12 Feb at 06:00 pm The Gwen, a Luxury Collection Hotel, Michigan Avenue Chicago USD 89

2026 Grace Giving Trivia Night

 Sat, 11 Apr at 05:30 pm Irish American Heritage Center Free

Goldentide - Paint and Sip in Chicago | Classpop!™

 Sat, 21 Mar at 07:30 pm Pinot's Palette - Logan Square USD 56

Learn the Essentials of Homemade Sushi - Sushi Making Cooking Class in Chicago | Classpop!™

 Mon, 02 Feb at 07:00 pm Illuminated Brew Works USD 74

SIP, SPA, SLAY BEAUTY EVENT: February 21, 2026

 Sat, 21 Feb at 11:00 am The Sculpt Spot

Joanna Connor Blues Band/TBD

 Thu, 19 Feb at 06:00 pm Kingston Mines - Chicago Blues Center USD 18

Sweetheart Gnome - Paint and Sip in Chicago | Classpop!™

 Wed, 11 Feb at 07:00 pm Pinot's Palette - Logan Square USD 56

Make Ravioli & Fettuccine With Chef Amerilis - Pasta Making Cooking Class in Chicago | Classpop!™

 Thu, 12 Feb at 05:30 pm Wolf Point Distilling USD 74

River to My Heart (Date Night) - Paint and Sip in Chicago | Classpop!™

 Sun, 15 Feb at 06:00 pm Pinot's Palette - Logan Square USD 56

Amore Borealis Date Night - Paint and Sip in Chicago | Classpop!™

 Fri, 13 Feb at 07:30 pm Pinot's Palette - Logan Square USD 56

Van Gogh's Blue Vase - Paint and Sip in Chicago | Classpop!™

 Fri, 13 Feb at 08:00 pm Pinot's Palette - Logan Square USD 56

Flash Class: Italian Caviar and Bubbles

 Sat, 14 Feb at 03:00 pm Eataly Chicago USD 107

Perfecting the Preparation of Pasta - Pasta Making Cooking Class in Chicago | Classpop!™

 Mon, 06 Apr at 07:00 pm Illuminated Brew Works USD 74

Sushi Making With Chef Janet at a Local Distillery - Sushi Making Cooking Class in Chicago | Classpop!™

 Thu, 02 Apr at 05:30 pm Wolf Point Distilling USD 74

Serene Sunrise - Paint and Sip in Chicago | Classpop!™

 Sun, 22 Feb at 01:00 pm Pinot's Palette - Logan Square USD 56

Wine Tasting with Winebow Importers at Spirits & Spice Chicago

 Sat, 07 Feb at 04:00 pm Spirits & Spice Chicago Free

Midnight Glow - Paint and Sip in Chicago | Classpop!™

 Sat, 28 Feb at 07:30 pm Pinot's Palette - Logan Square USD 56

Ghostly Gardens - Paint and Sip in Chicago | Classpop!™

 Wed, 25 Feb at 07:30 pm Pinot's Palette - Logan Square USD 49

Golden Hour featuring Vivian Garcia

 Thu, 26 Feb at 05:00 pm 201 S. Ashland Avenue, Chicago, IL, United States, Illinois 60607

Learn the Essentials of Homemade Sushi - Sushi Making Cooking Class in Chicago | Classpop!™

 Mon, 02 Mar at 07:00 pm Illuminated Brew Works USD 74

Adam Weiner

 Mon, 02 Mar at 06:00 pm City Winery - Chicago

World's Best Barista Competition

 Wed, 11 Feb at 06:00 pm TRUCE USD 32

Sushi Making With Chef Janet at a Local Distillery - Sushi Making Cooking Class in Chicago | Classpop!™

 Thu, 05 Mar at 05:30 pm Wolf Point Distilling USD 74

Your City Night Glow - Paint and Sip in Chicago | Classpop!™

 Thu, 12 Mar at 07:30 pm Pinot's Palette - Logan Square USD 49

Pasta Making With Chef Janet at a Local Distillery - Pasta Making Cooking Class in Chicago | Classpop!™

 Thu, 12 Mar at 05:30 pm Wolf Point Distilling USD 74

Van Gogh's Daisies and Poppies - Paint and Sip in Chicago | Classpop!™

 Sun, 15 Mar at 01:00 pm Pinot's Palette - Logan Square USD 56

Galaxy Lake - Paint and Sip in Chicago | Classpop!™

 Fri, 13 Mar at 08:00 pm Pinot's Palette - Logan Square USD 56

Make Potstickers From Scratch - Cooking Class in Chicago | Classpop!™

 Mon, 16 Mar at 07:00 pm Illuminated Brew Works USD 74

3238 WINE TASTING CLASS-BECOME A WINE CONNOISSEUR:

 Fri, 13 Feb at 07:00 pm Discovery Center USD 42

Classic Encounter with Terri Hemmert

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

BYOB Sip & Paint Class “Northern Lights”

 Wed, 04 Feb at 07:00 pm Sip & Paint USD 43

Fur Coats & Wine Tour

 Sat, 07 Feb at 06:00 pm Bronzeville Winery Free

Learn the Essentials of Homemade Sushi - Sushi Making Cooking Class in Chicago | Classpop!™

 Mon, 13 Apr at 07:00 pm Illuminated Brew Works USD 74

Richard Elliot

 Sat, 11 Apr at 06:00 pm City Winery - Chicago

Homemade Chocolate Confections - Cooking Class in Chicago | Classpop!™

 Thu, 16 Apr at 05:30 pm Wolf Point Distilling USD 74

Sip & Dance: Valentine’s Night Edition

 Thu, 12 Feb at 07:00 pm BottlesUp! USD 55

Cortina Night at La Pizza & La Pasta

 Tue, 03 Feb at 07:00 pm Eataly Chicago USD 33

Live Cooking Class with Chef Saul Ramos

 Wed, 11 Feb at 06:30 pm Sapori Trattoria USD 149

Valentine's Comedy Show Hosted by Def Comedy Jam's Joe Torry

 Fri, 13 Feb at 07:00 pm CineCity Studios Chicago USD 0 to 109

A Spooky Valentine’s Shopping Soirée

 Fri, 13 Feb at 03:00 pm The Pleasure Chest Free

Homemade Chocolate Confections - Cooking Class in Chicago | Classpop!™

 Mon, 20 Apr at 07:00 pm Illuminated Brew Works USD 74

Valentines Swing Class For Couples (West Loop)

 Fri, 13 Feb at 06:15 pm Ballroom Dance Chicago West Loop USD 107

Gamer Gathering @ Kinowerks!

 Fri, 06 Feb at 07:00 pm Kinowerks USD 0 to 18