Oak Park IL

Courtesy of Brian Crawford under a CC 2.0 license.

#7. Oak Park IL

Though it’s less than five square miles in size, Oak Park offers its 50,000 residents access to top-notch public transportation, great schools and beautiful tree-lined streets. There is a seemingly endless supply of family-friendly events happening in this Chicago suburb, such as an old-fashioned carnival, summer movies in the park and a long-running ice show. Oak Park parents have even turned the first day of school into an annual celebration, going so far as to hire a marching band to accompany local kids to class.

Adults here will appreciate the diverse and historically significant architecture throughout Oak Park (there are a number of houses designed by Frank Lloyd Wright, including his own home and studio). Plus, the school district in Oak Park prioritizes diversity, social and emotional learning and the arts, in addition to providing a quality education to students.

Best Way to Keep Everyone Entertained on a Saturday Afternoon: Visit the Oak Park Conservatory, a relaxing (and free!) indoor escape with lush green plants everywhere.

Kid-Friendly Restaurant: George’s Restaurant, a family-owned and family-friendly joint where you can get a hearty meal that tastes like it was cooked at home.

Best Date Night Spot (for frazzled parents): Grab a bite at The Little Gem Cafe, a cozy and romantic hangout with great cocktails.

Where to Score the Sweet Stuff: Hole in the Wall Custard Shoppe, an Oak Park institution and the perfect place to cool off on summer evenings.

Coolest Indoor Playground: Wonder Works Children’s Museum is more like a playground than your average museum — it’s a shoe-free zone where kids can play in a treehouse, pretend to work in a country market or put on a theater show.

Dog-Friendly Hangout Spot (because they’re part of the family too!): BeerShop, which is like a combination tap room and liquor store (that only sells beer). They have 16 beers on tap, plus more than 250 cans or bottles you can drink there or take home. Dogs are a big part of BeerShop’s atmosphere (just take a quick peek at their Instagram), so be sure to bring your four-legged family members when you visit.

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