Chicago, IL - Festivals, Music Festivals, Wine-Beer Events, Holiday Celebrations
Illinois Cities and Towns
Addison, Algonquin, Alton, Antioch, Aurora, Barrington, Belleville, Byron, Carbondale, Carlinville, Chicago, Chillicothe, Collinsville, Crystal Lake, Darien, Decatur, Dixon, Dow, Elgin, Elmhurst, Frankfort, Glen Ellyn, Glenview, Grafton, Grayslake, Greenville, Griggsville, Harvard, Hinsdale, La Grange, Lebanon, Montgomery, Morris, Mount Vernon, New Lenox, Normal, Oak Lawn, Oakbrook Terrace, Orland Park, Rock Falls, Rock Island, Rockford, Romeoville, Rosemont, Saint Charles, Schaumburg, Springfield, Streator, Tinley Park, Tuscola, Wheaton, WinnetkaEvents in Chicago, IL - upcoming
December 31, 2025 - January 1, 2026
Chicago All Access New Years Eve (Nye) Bar Crawl
Downtown Chicago, Chicago, IL
Status: Updated 10/26/2025
This Illinois Holiday Celebration will have commercial/retail exhibitors and 2 food booths. There will be 1 stage with International, National, Regional and Local talent and the hours will be Wed 8pm-12 midnight; Thu 12 midnight-2am. Admission tickets are $10 - $20. This event will also include: nye, new year's, bar crawl, chicago, holiday, tickets, event, pub crawl.
January 24, 2026
Chicago Winter Whiskey Tasting Festival
King's, Chicago, IL
Status: Updated 12/11/2025
This Illinois Festival will have antique/collectibles exhibitors and 2 food booths. There will be 1 stage with International, National, Regional and Local talent and the hours will be Sat 2:30pm-6pm. Admission tickets are $20 - $90.
February 14, 2026
Chicago Winter Tequila Tasting Festival
King's, Chicago, IL
Status: Updated 12/22/2025
This Illinois Festival will have antique/collectibles and commercial/retail exhibitors, and 2 food booths. There will be 1 stage with International, National, Regional and Local talent and the hours will be Sat 2:30pm-6pm. Admission tickets are $20 - $90. This event will also include: food + drink, festival, tequila, tasting, chicago, tickets, event.
February 20 - 21, 2026
University of Chicago Folk Festival
University of Chicago Mandel Hall, Chicago, IL
Status: Updated 12/22/2025
This Illinois Festival Concert will have no exhibit booths and no food booths. There will be 1 stage with International, National, Regional and Local talent and the hours will be Fri 8pm-10pm; Sat 7:30pm-11pm. Admission tickets are $5 - $35.
April 24 - 26, 2026
One of a Kind Spring Show and Sale Chicago
The Merchandise Mart, Chicago, IL
Status: Updated 6/5/2025
This Illinois Art Show will have fine art and fine craft exhibitors, and no food booths. There will be 1 stage with Local talent and the hours will be Fri-Sat 10am-7pm; Sun 10am-5pm. Admission tickets are $12 - $80.
June 6 - 7, 2026
Fifty-Seventh Street Art Fair
Hyde Park Neighborhood, Chicago, IL Or Online at 57thstreetartfair.org
Status: Updated 11/5/2025
This Illinois Art Show will have fine art and fine craft exhibitors, and tba food booths.
June 13 - 14, 2026
Wells Street Art Festival
Wells Street & North Avenue, Chicago, IL
Status: Updated 10/22/2025
This Illinois Festival will have commercial/retail, corp./information, fine art and fine craft exhibitors, and 20 food booths. There will be 1 stage with National, Regional and Local talent and the hours will be Sat 10am-10pm; Sun 10am-9pm. This event will also include silent art auction.
June 26 - 28, 2026
Logan Square Arts Festival
Logan Square Centennial Monument, Chicago, IL
Status: Updated 4/9/2025
This Illinois Music Festival will have antique/collectibles, commercial/retail, corp./information, crafts, fine art, fine craft and homegrown products exhibitors, and 8 food booths. There will be 2 stages with Regional and Local talent and the hours will be Fri 5pm-10pm; Sat-Sun 12pm-10pm. This event will also include kids area; pet area.
July 18 - 19, 2026
Ravenswood on Tap
Ravenswood, Chicago, IL
Status: Updated 10/14/2025
This Illinois Festival will have antique/collectibles, commercial/retail, corp./information, crafts, film, fine art, fine craft and homegrown products exhibitors, and 4 food booths. There will be 1 stage with Local talent and the hours will be Sat 12pm-10pm; Sun 12pm-6pm.
July 24 - 26, 2026
Wicker Park Festival
Wicker Park, Chicago, IL
Status: Updated 10/14/2025
This Illinois Festival will have antique/collectibles, commercial/retail, corp./information, crafts, fine art, fine craft, flea market and homegrown products exhibitors, and 12 food booths. There will be 3 stages with National, Regional and Local talent and the hours will be Fri 5pm-10pm; Sat-Sun 12pm-10pm.
September 4 - 6, 2026
Edgewater Music Fest
5800-5930 N Broadway, Chicago, IL
Status: Updated 10/14/2025
This Illinois Festival will have antique/collectibles, commercial/retail, corp./information, crafts, film, fine art, fine craft and homegrown products exhibitors, and 10 food booths. There will be 2 stages with Regional and Local talent and the hours will be Fri 5pm-10pm; Sat-Sun 12pm-10pm.