Must-Try Events for the Second Half of Summer – Chicagoland Edition

Summer is in full swing with plenty to do, see, taste and enjoy throughout Chicagoland! We’ve pulled together some of our favorite “must-try” events – many of which are free! – to help you squeeze every ounce of fun from this sizzlin’ summer! Click on the event title for complete details.

Lombard Cruise Nights & Summer Concerts | Saturdays through Aug. 25; 6-10pm | Downtown Lombard: St. Charles & Main St. | Lombard, IL
Check out some great classic and custom cars and rock out to free concerts. Highlights: July 14: Neverly Brothers + Cadillac Night; July 28: Heartache Tonight (Eagles tribute band) + ’70s Muscle Cars; August 11: Breakfast Club Band + ’80s and Newer cars.

Summer Evening Concerts | Monday-Thursday, various times | Through Sept. 3 | Chicago Botanic Garden | Glencoe, IL
The Garden stays open until 9 pm in the summer with free concerts nightly, Monday-Thursday. Set up your picnic any time after 4 pm. Monday: Carillon bell concerts, 7-8pm; Tuesday: Different each week, from jazz to swing to country, 6-8pm; Wednesday: Dancin’ Sprouts features musical entertainment for kids, 5:30-7:30pm; Thursday: Get ready to dance to reggae, flamenco, classic rock and more, 6-8pm.

Chicago Park District: Movies in the Parks | Through Sept. 12 | Various Parks throughout the City | Chicago, IL
This free movie series has something for everyone! Enjoy such classics as Roman Holiday, Sunset Boulevard and The Wizard of Oz; family favorites like The Boss Baby, Jumanji: Welcome to the Jungle, and Finding Dorie; sing-alongs like Grease and Mary Poppins; or recent blockbusters including Wonder Woman, Black Panther and Hidden Figures. All movies begin at dusk.

U-Pick Berries | Open daily through October; 8am-5pm (weather + supply permitting) | Heider’s Berry Farm | Woodstock, IL
Pick plump, juicy strawberries and raspberries in July and September. Daily updates including hours and available berry supply are published on their website. Heider’s currently accepts cash and checks only; no credit or debit cards.

Jazz Up Glen Ellyn | Sat., July 14; 2:30-9:30pm | Downtown Glen Ellyn, 286 N. Park Blvd. | Glen Ellyn, IL
Curated by artistic director and jazz guitarist Fareed Haque, this year’s theme is the music and rhythms of Brazil! Pack a picnic and enjoy an afternoon of great music. Get ready to samba!

Walking Plays: The Brothers Grimm Woodland Tales | Weekends in July & August; 6pm | Morton Arboretum | Lisle, IL
The Brothers Grimm emerge from the past to tell their favorite stories in fast-paced, interactive and hilarious fashion. Using only the suitcases they arrive with, their wit and a little help from the crowd, classics come to life among the trees. These plays are suitable for all ages. Plays are approximately 90-minutes long and do not exceed 2 miles in hiking distance.

Fiesta del Sol | Thurs., July 26, 5-10pm; Fri.-Sat., July 27-28, 11am-11pm; Sun., July 29, 11am-10pm| Cermak Rd. & Loomis St. | Chicago, IL
This free, family-friendly festival is the largest Latino festival in the Midwest and offers live entertainment, local art, a variety of food, carnival rides, a children’s area, educational resources for parents and more.

Hot Dog Fest | Fri.- Sat., Aug. 10-11, 11am-9pm; Sun., Aug. 12, 11am-8pm | Chicago History Museum | Stockton & LaSalle Dr. | Chicago, IL
Three-day festival celebrating the Chicago-style hot dog features a line-up of bands, family activities and hot dogs prepared in various regional and ethnic styles by the city’s top hot dog vendors.

Chicago Air & Water Show | Sat.-Sun., Aug. 18-19; 10am-3pm | North Avenue Beach | 1600 N. Lake Shore Drive | Chicago, IL
Featuring military and civilian flight aerobatics, historic aircraft, simulated water rescues and parachute teams, the Chicago Air and Water Show will feature the U.S. Air Force Thunderbirds as well as the U.S. Army Parachute Team Golden Knights and the U.S. Navy Leapfrogs.

Taste of Polonia | Labor Day Weekend: Fri.., Aug. 31, 5-10pm; Sat.-Sun., 12-10pm; Mon., Sept. 3, 12-9pm | Copernicus Center | Chicago, IL
The largest Polish festival in the country features live music (polka, ’80s, classical, jazz), ethnic food, carnival rides and a craft beer tent.

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