Pour Trail

United States · Wine Travel

Illinois wine festivals & events

328 listings / 34 festivals / 294 events / peak april–august

Showing 97–102 of 102 festivals

Wine festivals in Chicago

About Wine Festivals in Chicago

Chicago is one of Illinois's notable wine festival destinations, hosting 102 ticketed tasting events where multiple wineries pour for a general audience. Events range from intimate vineyard celebrations to larger grand-tasting formats drawing hundreds of wine lovers.

Wine festival tickets in Chicago typically include multiple pours, a tasting glass, and access to food vendors or pairings. General admission prices usually run $30–$90; VIP tiers with reserve tastings and early entry often reach $60–$150. All prices on Pour Trail are shown upfront — no hidden fees or "contact for pricing."

Pour Trail verifies listing accuracy on a rolling basis. Each card shows a "Last verified" date so you know how fresh the information is before you buy tickets.

Frequently Asked Questions

How many wine festivals are there in Chicago, Illinois?
Pour Trail currently lists 102 wine festivals in Chicago, Illinois. We update our listings regularly — check back often for new events.
When is the best time to attend a wine festival in Chicago?
Peak wine festival season in Illinois typically runs from late spring through early fall (May–October), when wineries host harvest celebrations and outdoor tastings. Chicago may also have year-round indoor events. Use the date filter above to find events on your preferred dates.
How much do wine festival tickets cost in Chicago?
General admission tickets at Chicago wine festivals typically range from $30 to $90. VIP tiers with reserve tastings and early entry usually run $60–$150. Each listing on Pour Trail shows all ticket tiers and prices upfront — no hidden fees.

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Oswego

3 festivals