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Wine tasting events in Chicago, IL

Sales end soon
Winery Spotlight Series: Chalk Hill Estate
Wednesday at 6:30 PM
Old Norwood Park · WineStyles Chicago
Sales end soon
Winery Spotlight Series: Chalk Hill Estate
Wednesday at 6:30 PM
Old Norwood Park · WineStyles Chicago
Sapori Presents Travaglini Gattinara Wine Dinner
Wed, Oct 22, 6:30 PM
Park West · Sapori Trattoria
Sapori Presents Travaglini Gattinara Wine Dinner
Wed, Oct 22, 6:30 PM
Park West · Sapori Trattoria
Soul Food Tasting with Priority Entertainment
Sat, Oct 18, 2:00 PM
The Loop · Wilma's Famous BBQ & Tavern
Soul Food Tasting with Priority Entertainment
Sat, Oct 18, 2:00 PM
The Loop · Wilma's Famous BBQ & Tavern
Selling quickly
From Vine to Wine: How Wine is Made
Thu, Nov 6, 7:00 PM
Southeast · The Wine Goddess
Selling quickly
From Vine to Wine: How Wine is Made
Thu, Nov 6, 7:00 PM
Southeast · The Wine Goddess
Nearly full
Art | Music | Wine | Community
Tomorrow at 6:00 PM
Clyde Avenue · Beards & Bellas
Nearly full
Art | Music | Wine | Community
Tomorrow at 6:00 PM
Clyde Avenue · Beards & Bellas
Trick-or-Treat Candy & Cheese Tasting
Fri, Oct 24, 7:00 PM
Maplewood · 2774 N Milwaukee Ave
Trick-or-Treat Candy & Cheese Tasting
Fri, Oct 24, 7:00 PM
Maplewood · 2774 N Milwaukee Ave
Thanksgiving Mega-Tasting, 4:30-6:00 PM Session
Sat, Nov 15, 4:30 PM
Southeast · The Wine Goddess
Thanksgiving Mega-Tasting, 4:30-6:00 PM Session
Sat, Nov 15, 4:30 PM
Southeast · The Wine Goddess
“Bottle & Barrel " Fall Mini Wine and Spirits Fest
Sun, Nov 2, 1:30 PM
West Town · Fulton Street Collective
“Bottle & Barrel " Fall Mini Wine and Spirits Fest
Sun, Nov 2, 1:30 PM
West Town · Fulton Street Collective
2026 Chicago Winter Tequila Tasting Festival (February 14)
Sat, Feb 14, 2:30 PM
South Loop · Downtown Chicago
2026 Chicago Winter Tequila Tasting Festival (February 14)
Sat, Feb 14, 2:30 PM
South Loop · Downtown Chicago
Nearly full
Passages Wine and Books Audiobook Walk
Sat, Oct 11, 10:00 AM
West Town · Passages Wine and Books
Nearly full
Passages Wine and Books Audiobook Walk
Sat, Oct 11, 10:00 AM
West Town · Passages Wine and Books
2026 Chicago Winter Whiskey Tasting Festival (January 24)
Sat, Jan 24, 2:30 PM
South Loop · Downtown Chicago
2026 Chicago Winter Whiskey Tasting Festival (January 24)
Sat, Jan 24, 2:30 PM
South Loop · Downtown Chicago
Murder Mystery Party
Fri, Oct 17, 6:00 PM
West Town · Passages Wine and Books
Murder Mystery Party
Fri, Oct 17, 6:00 PM
West Town · Passages Wine and Books
Taylor Swift Bar Crawl on November 15th: Eras, Ex's and Everything Taylor
Sat, Nov 15, 12:00 PM
Lakeview · Wrigleyville's Best Bars TBA
Taylor Swift Bar Crawl on November 15th: Eras, Ex's and Everything Taylor
Sat, Nov 15, 12:00 PM
Lakeview · Wrigleyville's Best Bars TBA
Press & Sip: DIY Press-On Nail Art + Wine Experience
Sun, Oct 19, 3:00 PM
Heart of Chicago · 2134 W 18th St
Press & Sip: DIY Press-On Nail Art + Wine Experience
Sun, Oct 19, 3:00 PM
Heart of Chicago · 2134 W 18th St
Wine-O Bingo
Tue, Oct 14, 6:30 PM
Old Norwood Park · WineStyles Chicago
Wine-O Bingo
Tue, Oct 14, 6:30 PM
Old Norwood Park · WineStyles Chicago
2026 Chicago Top Shelf Tequila and Whiskey Tasting Festival (Sept 26)
Sat, Sep 26, 2:30 PM
South Loop · Downtown Chicago
2026 Chicago Top Shelf Tequila and Whiskey Tasting Festival (Sept 26)
Sat, Sep 26, 2:30 PM
South Loop · Downtown Chicago
La Dolce Vita Cucina Patio Opening Celebration
Fri, Oct 10, 5:30 PM
Portage Park · La Dolce Vita Cucina - Chicago
La Dolce Vita Cucina Patio Opening Celebration
Fri, Oct 10, 5:30 PM
Portage Park · La Dolce Vita Cucina - Chicago
10th Annual PGMF Ales Against ALS
Sat, Nov 8, 3:00 PM
Horner Park · Heineken 2nd Star Tavern
10th Annual PGMF Ales Against ALS
Sat, Nov 8, 3:00 PM
Horner Park · Heineken 2nd Star Tavern
Nearly full
10/12- Oak Park, IL- Taste of Twenty
Sun, Oct 12, 5:00 PM
Downtown · Cooper's Hawk Winery & Restaurant- Oak Park, IL
Nearly full
10/12- Oak Park, IL- Taste of Twenty
Sun, Oct 12, 5:00 PM
Downtown · Cooper's Hawk Winery & Restaurant- Oak Park, IL
11/16- Oak Park, IL- A Grateful Gathering
Sun, Nov 16, 5:00 PM
Downtown · Cooper's Hawk Winery & Restaurant- Oak Park
11/16- Oak Park, IL- A Grateful Gathering
Sun, Nov 16, 5:00 PM
Downtown · Cooper's Hawk Winery & Restaurant- Oak Park

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