If you can’t find something fun to do around Illinois this May, you’re not trying hard enough. But we get busy schedules, so we’ve taken some of the work out of it with this list of can’t-miss events.
There’s plenty going on during Memorial Day Weekend, May 23-25 this year, but farmers markets and spring festivals are starting, and artists of all kinds are showing their skills.
In Chicago, the fifth annual Chicago Cabaret Week will be from May 8 to May 17. This annual ten-day festival showcases Chicago’s top cabaret artists performing blues, Broadway, burlesque, jazz, R&B, American Songbook, and international music.
Here's a roundup of some more events taking place this May in the Chicagoland:
May 15 at Arts Center, 200 N Oak Park Ave at 6:30 p.m.
Candlelight concerts bring the magic of a live, multi-sensory musical experience to awe-inspiring locations like never seen before in Chicago. Get your tickets now to discover the music of The Beatles at Arts Center of Oak Park under the gentle glow of candlelight.
May 15 at Joliet Area Historical Museum, 204 N Ottawa St at 7 p.m.
The South Side Exiles play on the Joliet Museum's Outdoor Rooftop Music Series Friday, May 15th at 7pm (doors open at 6:15pm)!
The Chicago rock crew known as South Side Exiles play original and cover songs written and performed in the classic American style of the 1970s rock tradition, inspired by Chuck Berry, The Stones, Lou Reed, The Faces, Muddy Waters, & more!
May 16 at 1000 Elm St, Glenview at 2:30 p.m.
The award-winning New Tradition Chorus, proudly announces its 43rd Annual Spring Show at the Glenview Community Church,1000 Elm St. The show will present many of the great songs by past and contemporary American Musical Masters at 2:30 on Saturday, May 16 and Sunday, May 17.
May 16 at Peace Village, 10300 Village Cir Dr, Palos Park at 10 a.m.
Bring the whole family for a day filled with festive games, interactive entertainment, and unique shopping from a variety of vendors—including handcrafted and curated items created by our talented residents.
May 16 at 100 South US 45, Grayslake at 9 a.m.
University of Illinois Extension Master Gardeners will hold its annual plant sale on Saturday, May 16, 2026. This year our plant sale will feature a beautiful selection of nursery grown varieties not readily available at traditional garden centers – natives, new cultivars of perennials, grasses and pollinator-friendly plants.
May 16 at Good Templar Park Association, 528 East Side Dr, Geneva at 10 a.m.
Don't miss the ONLY public Open Day event this month to tour the World Famous 1893 VIKING SHIP! This full sized, 78 foot, oak and iron Viking Ship was hand built in Norway. Its hardy crew of 12 sailed it nonstop though raging storms across the North Atlantic to become a star attraction of the 1893 World's Columbian Exposition Chicago.
May 17 at Apple Chevrolet, INC, 8585 W 159th St, Tinley Park at 9 a.m.
If you’ve been searching for car shows near me or exciting Chicago events, mark your calendar for an unforgettable morning at Apple Chevrolet. On Sunday, May 17th, we’re proud to host the NCCC Corvette Show alongside the Windy City Corvettes at our Tinley Park Chevy dealership.
May 23 at 171 Central St., Evanston at 9 a.m.
The Evanston Art Center (EAC) is excited to welcome the public to our upcoming exhibition, Excerpts of Imagination | Louis De Guzman. The exhibition will be on display from May 23–June 21, 2026 with an opening reception on Sunday, May 31, 1–4pm that will be free and open to the public.
May 30 at The Promenade Bolingbrook, 631 E Boughton Rd at 11 a.m.
Join us for an exciting two days at the Taste of Bolingbrook on May 30th and 31st, where local flavors, live entertainment, and community come together!
Are you planning an event this spring or summer? Feature it so nearby readers see it all across Patch — including in roundups like this!
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