10. Oak Park
Architect Frank Lloyd Wright spent much of his career in Oak Park, a Mecca for architecture buffs with tree-lined streets that manage to rival its next-door neighbor, Chicago. Wright’s Prairie style designs dominate this upscale suburb, where the architect lived and worked for decades, and guests can choose between several tours to get up close to the design genius and his iconic, still-functional masterpieces.
While Chicago tourists board boats to learn about the buildings along the Chicago River, visitors to Oak Park can enjoy a decidedly suburban spin on the architecture tour. According to the Frank Lloyd Wright Trust, Pedal Oak Park is the most popular tour in town. Bicyclists learn all about Wright’s time in Oak Park as they pedal past world’s biggest collection of the acclaimed Illinois architect’s creations.
Well-preserved buildings throughout Oak Park include his home and studio, the Unity Temple, and the Frank Thomas, Cheney, Furbeck and Heurtley Houses. Oak Park loves its LEED-certified buildings almost as much as its Wright designs. Every year, Oak Park celebrates the planet and encourages greener living at Earth Fest, an annual event held at the city’s environmentally conscious Public Works Center.
The free festival includes kids’ activities, efficiency tutorials, vendor booths, and services such as bicycle registration, carpooling information and Recycling Alley, a popular recycling drive where residents can bring items such as cell phones, batteries, wine corks, and other items that the city doesn’t collect in its weekly blue bin pickup.
It takes approximately 40 minutes to go from Oak Park to the oldest outdoor musical festival in the whole country. Highland Park’s acclaimed Ravinia Festival is an ongoing series of outdoor concerts and picnics, and it lures high-profile entertainers outside Chicago city limits throughout the summer and fall.
According to the festival’s website, previous headliners throughout the festival’s century-long history include Willie Nelson, Carrie Underwood, Fiona Apple, Tony Bennett, Anita Baker, Sting, Heart, Jewel, Journey, Chicago, John Legend, and more. The Chicago Symphony Orchestra calls Ravinia home too; the acclaimed group has performed here every summer since 1936, according to their own archives.