Illinois

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Shows we know about in Illinois in May Back May Sun Mon Tue Wed Thu Fri Sat 1 Mr. Blotto 8:30 PM Jamo's Live Mokena ---- Grateful String Band 7 PM EDT/6 PM CDT Frankfort Bluegrass Fest Fundraiser | May 1st 2026 Frankfort 2 Mr. Blotto 8:30 PM Pollyanna Brewing Co. St. Charles ---- Head's All Empty 10 PM EDT/9 PM CDT Head's All Empty: Winter Residency 2025-2026 McHenry ---- Sunshine Daydream 7 PM EDT/6 PM CDT Nickipalooza - Sunshine Daydream & Positively 4th St. - Danenberger New Berlin 3   4   5 Mr. Blotto 8:30 PM Reggies Music Venue Chicago 6   7   8 Caution 11 PM EDT/10 PM CDT CAUTION Live at 115 Bourbon St. Chicago 9 Old Shoe 6 PM EDT/5 PM CDT Jam For Jamboree - A Benefit for Jamaica at High Noon Saloon Madison ---- Sunshine Daydream 7 PM EDT/6 PM CDT Sunshine Daydream Grateful Dead Tribute Alto Vineyards Champaign Champaign 10 Mr. Blotto 2:00 PM Broken Oar Port Barrington ---- The Garcia Project 7:30 PM EDT/6:30 PM CDT Live Jerry Garcia Band show recreation with The Garcia Project at The Bloomington 11   12 Mr. Blotto 8:30 PM Reggies Music Venue Chicago 13   14   15 Old Shoe 9 PM EDT/8 PM CDT Old Shoe & Horseshoes & Hand Grenades Chicago 16 Sunshine Daydream 7 PM Sunshine Daydream Grateful Dead Tribute Times Theater Rochester Rochester 17 Mr. Blotto 4:00 PM Long Grove Chocolate Fest Long Grove ---- Dark Star Orchestra 5 PM An Evening with Dark Star Orchestra Wilmington 18   19 Mr. Blotto 8:30 PM Reggies Music Venue Chicago 20   21   22   23 Mr. Blotto 9:00 PM Evenflow Geneva 24   25   26   27   28   29   30 Mr. Blotto 9:30 PM Max Happy fest Woodstock ---- Lazy Lightning Band 7 PM EDT/6 PM CDT Ryans Pier Presents The Lazy Lightning Band Aroma Park ---- Sunshine Daydream 4 PM EDT/3 PM CDT Chatham Chatham ---- Terrapin Flyer 9 PM EDT/8 PM CDT Terrapin Flyer Performs LIVE at Q Bar Darien Darien 31