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On the Road: Summer Day Trips Around Chicago, IL

By Kate Silver

Chicago Day Trips

Ready to get your kicks on Route 66? You can do that, and more, as road trip season revs its engine. Chicago is surrounded by incredible family-friendly destinations brimming with history and charm -- and the best part is you don't have to go far from the Windy City. Here are some summer road trip spots, all within 100 miles of Chicago:
Chicago Day Trips

  • Frank Lloyd Wright and Ernest Hemingway's Oak Park: The homes of two of Oak Park's most famous occupants - Frank Lloyd Wright and Ernest Hemingway - remain a draw, years after their residency. Wright, the beloved American architect known for his prairie-style designs, kept his home and studio in this tony Chicago suburb, and designed a number of private homes in the area, as well as a church. (Guests can tour the , but the private homes are off-limits). Hemingway was born in Oak Park and grew up there, although you wouldn't exactly know it from his writings. You can learn about his formative years and tour the home where he was born at the Ernest Hemingway Birthplace and Museum.
  • Chicago Botanic Garden and Ravinia: First, its name is a misnomer. is actually located in the suburbs, in a town called Glencoe. The peaceful, lush gardens extend over 385 acres, and include nine islands and six miles of lake-front shoreline. Kids love the Model Railroad Garden, where 18 trains run through the foliage past miniature landmarks. The Waterfall Garden, with its 45-foot falls cascading into plant-filled pools, is mesmerizing for all ages. Other highlights include the Bonsai Garden, English Walled Garden, Rose Garden and dozens more. While you're in the area, check out the concert schedule for Ravinia, an outdoor concert space where Chicagoans laze on the lawn amid statues and sculptures, enjoy picnics and listen to live music.
  • Route 66 Roadtrip to Joliet: Want to relive the days of carhops, soda jerks and muscle cars? The Route 66 Illinois Scenic Byway actually begins (or ends, depending on your perspective) at the intersection of Jackson Boulevard and Michigan Avenue. Take the historic route from Chicago through the suburbs and into the farmland that surrounds the city. Stop in at the Joliet Area Historical Museum, where you'll find life-size statues of Jake and Elwood Blues, a.k.a. The Blues Brothers, in front. The museum sheds some light on the importance of Joliet and the Americana-filled history of Route 66. All around Joliet, you'll still find bits and pieces of that Americana.
  • Lake Geneva, Wisconsin: Once the playground for Chicago's wealthy, Lake Geneva now welcomes families from all over to enjoy the beautiful lake, charming diners and family-friendly resort scene. Outdoor activities are a given here amid the rolling Wisconsin hills and sparkling waters of Lake Geneva. Rent a boat or jet ski, bike along the Lake Geneva Bike Path, or take a stroll along the 21-mile Lake Geneva Lake Shore Path, which curves along the shores of the lake, leading you directly through the backyards of million-dollar mansions -- the path is public domain, maintained by the homeowners.

For tips on how to get your family and car ready before you head out on the road, read our road trip safety checklist.


July 1, 2014, 2:33 PM

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