Festivals in Chicago, IL
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(Prices Going Up) 2026 Chicago Winter Whiskey Tasting Festival (January 24)
Sat, Jan 24, 2:30 PM
Chicago · King's
(Prices Going Up) 2026 Chicago Winter Whiskey Tasting Festival (January 24)
Sat, Jan 24, 2:30 PM
Chicago · King's
Cupid's Vintage & Artisan Fest presented by Windy City Market
Sat, Feb 7, 12:00 PM
Chicago · Artifact Events
Cupid's Vintage & Artisan Fest presented by Windy City Market
Sat, Feb 7, 12:00 PM
Chicago · Artifact Events
The Chicago Pancakes & Booze Art Show (Vendor/Artist Reservations)
Sat, Feb 28, 8:00 PM
Chicago · Reggies
The Chicago Pancakes & Booze Art Show (Vendor/Artist Reservations)
Sat, Feb 28, 8:00 PM
Chicago · Reggies
2026 Chicago St Patrick’s Day Bar Crawl Saturday All Access
Sat, Mar 14, 12:00 PM
IL · Downtown Chicago
2026 Chicago St Patrick’s Day Bar Crawl Saturday All Access
Sat, Mar 14, 12:00 PM
IL · Downtown Chicago
✨ Chicago's Sweetheart Market ✨ Trinket + Artisan - Valentines Market
Sun, Feb 8, 12:00 PM
Chicago · 4432 N Kedzie Ave
✨ Chicago's Sweetheart Market ✨ Trinket + Artisan - Valentines Market
Sun, Feb 8, 12:00 PM
Chicago · 4432 N Kedzie Ave
2026 Chicago Top Shelf Tequila and Whiskey Tasting Festival (Sept 26)
Sat, Sep 26, 2:30 PM
Chicago · Downtown Chicago
2026 Chicago Top Shelf Tequila and Whiskey Tasting Festival (Sept 26)
Sat, Sep 26, 2:30 PM
Chicago · Downtown Chicago
Pickwick Vintage Show in Chicago | April 2026
Sun, Apr 19, 10:00 AM
Chicago · Chicago Athletic Association - The Unbound Collection by Hyatt
Pickwick Vintage Show in Chicago | April 2026
Sun, Apr 19, 10:00 AM
Chicago · Chicago Athletic Association - The Unbound Collection by Hyatt
ST. PATRICKS DAY WEST LOOP & RIVER NORTH GOLDEN TICKET WEEKEND PASS
Sat, Mar 14, 12:00 PM
Chicago · Good Night John Boy
ST. PATRICKS DAY WEST LOOP & RIVER NORTH GOLDEN TICKET WEEKEND PASS
Sat, Mar 14, 12:00 PM
Chicago · Good Night John Boy
2026 Chicago Summer Tequila Tasting Festival (July 25)
Sat, Jul 25, 2:30 PM
Chicago · TBA Downtown Chicago
2026 Chicago Summer Tequila Tasting Festival (July 25)
Sat, Jul 25, 2:30 PM
Chicago · TBA Downtown Chicago
West Loop Wine & Pizza Fest | Wine Tastings & Pizza Included
Saturday at 12:00 PM
Chicago · PB&J: Pizza Beer and Jukebox
West Loop Wine & Pizza Fest | Wine Tastings & Pizza Included
Saturday at 12:00 PM
Chicago · PB&J: Pizza Beer and Jukebox
Windy City Tango Festival 2026
Thu, Jul 2, 11:00 AM
Chicago · Crowne Plaza Chicago West Loop, an IHG Hotel
Windy City Tango Festival 2026
Thu, Jul 2, 11:00 AM
Chicago · Crowne Plaza Chicago West Loop, an IHG Hotel
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