9 street fests in Chicagoland with legit fun for all

One of the joys of summer is experiencing street fairs that take over neighborhoods on the weekends. While there’s always ample entertainment for the grown-ups, it’s sometimes a toss-up whether it’s worth it to bring the kiddos. Here are a few favorite street fests worth it for kids.


West Fest (Kid Fest) 


When: July 7-8, noon-7 p.m.


Where: Chicago (West Town), on Chicago Avenue between Damen Avenue and Wood Street


Within Chicago’s West Fest is Kid Fest, a festival just for youngsters on the adjacent (Wolcott) street. Here you’ll find train rides, bounce houses, an inflatable obstacle course, pony rides, carnival games, kid-friendly vendors and live family-friendly music. Kid Fest benefits Talcott Fine Arts & Museum Academy.


Do-Division (Family Fun Fest)


When: June 2-3, noon-6 p.m.


Where: Chicago (West Town), Hoyne between Crystal and Potomac and on Crystal between Hoyne and Damen


Set along Division Street in West Town, you’ll find a plethora of local vendors, music and food. Children hone in on the Kids Stage featuring live music from Chicago favorite, Mr. Dave. Clemente High School sets up an interactive sports zone while pony and train rides, face painting, balloon animals, bounce house and more complete the fun. Proceeds from the fest exclusively benefit local elementary schools.


Art at the Glen 


When: Aug. 4-5, 10 a.m.-5 p.m.


Where: Glenview, The Glen Town Center, 2030 Tower Drive


Among the numerous shops and restaurants at The Glen Town Center, you’ll see original artwork by 185-juried artists at this 15th annual festival. The long-standing Marriott Theater will have live performances for littles in addition to fun interactive games.


Rock ’n’ Run the Runway


When: June 30, 5-10:30 p.m.


Where: Wheeling, 1070 S. Milwaukee Ave


The village of Wheeling and the city of Prospect Heights annually co-host Rock ’n’ Run the Runway, a live music and fireworks event held on the runways of Chicago Executive Airport. In addition to family-friendly live music, you’ll find food trucks, face painters, balloon artists and a kiddie train. Making their debut at the fest will be Captain America and Wonder Woman.


Strawberry Fest


When: June 22-24, hours vary


Where: Long Grove, Historic Downtown Long Grove, 308 Old McHenry Road


Downtown Long Grove’s annual Strawberry Fest has become a family favorite because who doesn’t love all things strawberry? In addition to the many strawberry-enhanced eats, kids will enjoy a classic carnival and three stages of live entertainment. At the Kid Zone, get Coachella vibes at the flower crown-making booth, try the water balloon toss or ballroom dancing and get junior knight training.


Pilsen Food Truck Social 


When: June 9-10, 11 a.m.-9 p.m.


Where: Chicago (Pilsen), 18th Street between Racine and Throop


Located in Chicago’s lower west side, the historic Pilsen neighborhood is filled with restaurants, cool shops and public art murals. More than 25 of the city’s best food trucks line up on 18th Street, including many of Pilsen’s most popular restaurants like Dusek’s Board and Beer, Honky Tonk BBQ and Dia De Los Tamales. Kids’ carnival games, face painting, live music by Thalia Hall, and of course, plenty of delicious eats, will keep kids anything but bored.


Glencoe Festival of Art


When: July 28-29, 10 a.m.-5 p.m.


Where: Glencoe, Green Bay Road and Park Avenue


The 10th annual Glencoe Festival features original artwork from more than 110 juried artists, but it’s the art scavenger hunt set up throughout the fest that makes this a draw for the kiddos. Children can put their own artistic stamp on the Graffiti Wall, create a masterpiece at the spin art machine, or participate in art fest bingo. Grab a bite to eat from one of the food vendors or at one of the charming restaurants in town.


Backlot Bash 


When: Aug. 24-26


Where: Skokie, Oakton Street between Lincoln and Laramie Avenues


This fabulous annual celebration in downtown Skokie draws people of all ages. Among the mix of live music performances, expect a carnival with classic rides and games, kids’ fun run, bingo and children’s stage.


Kids Eat Chicago


When: July 14-15


Where: Chicago (Downtown), Grant Park


The daddy of all summer street fests, Taste of Chicago, has a dedicated area for families created by Chicago Parent, the last two days of Taste, July 14-15. With inflatables provided by The Playground Games, two days full of the best children’s entertainers, a train, a diaper changing area, picnic tables under a tent, great info for parents from our trusted advertisers and more, it is the place to be at The Taste.


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