April 10, 2026 · Carbondale, IL
River Radio Southern Illinois Barrel Fest
$50–$150
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Collectors
United States · Wine Travel
Illinois wine festivals & events
257 listings / 30 festivals / 227 events / peak april–august
Showing 1–24 of 30 festivals
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April 18, 2026 · Chicago, IL
Godfrey Wine Fest - Wine Tasting at I|O Godfrey Rooftop in Chicago
$25–$49
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Beginners
May 7, 2026 · Downers Grove, IL
Shop, Sip & Stroll Downtown Downers Grove Wine Walk 2026
$35
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May 29, 2026 · Chicago, IL
Wine Fest on the Beach - Wine Tasting at North Ave. Beach
$25–$35
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Beginners
June 12, 2026 · Chicago, IL
Rosé Fest on the Beach - Wine Tasting at North Ave. Beach
$25–$35
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August 1, 2026 · Oswego, IL
CabCab Concert + Wine Fest: Last Call | August 1st
$30
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Groups
September 12–13, 2026 · Chicago, IL
Saborea Chicago's Latino Gourmet: Food, Wine and Spirits Festival
$40–$500
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September 13, 2026 · Lemont, IL
Uncorked: The Forge Wine Festival
$20–$100
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Groups · Foodies
October 24, 2026 · Chicago, IL
Chicago Wine Fest at Hubbard Inn - Tastings Included
$25–$35
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Beginners
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