Chicago’s Charming Neighbor: A Walkable Village with Small-Town Appeal and Stunning Architecture

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Chicago's Charming Neighbor: A Walkable Village with Small-Town Appeal and Stunning Architecture

Just under 10 miles from downtown Chicago, Oak Park is a charming suburb that serves as an easy and interesting day trip from the city. The walkable village has a quaint, all-American feel. You might also recognize some of its landmarks from iconic movies. Remember the church scene from “Home Alone”? Yep, it was filmed at none other than Grace Episcopal Church in Oak Park. The village also borders the suburb of Berwyn, where movies like “Adventures in Babysitting” and “A League of Their Own” were filmed. Located less than 30 minutes from Chicago O’Hare International Airport (ORD) and 20 minutes from Midway International Airport (MDW), Oak Park is easy to get to if you’re visiting from out of state. Plus, it’s well connected by public transit on the Green Line CTA and Blue Line trains.



Oak Park has deep ties to two American icons: author Ernest Hemingway and architect Frank Lloyd Wright. The village is bustling with charming boutiques, a vibrant arts district, parks, and family-owned restaurants. There are also plenty of hotels and Victorian-era vacation homes to rent nearby. Once you’ve gotten a feel for Chicago and its many unwritten rules, Oak Park offers a refreshing escape. It’s the perfect place for a day or two of historical sightseeing, admiring architecture, leisurely strolls, and soaking up cozy small-town vibes.

Discover literary history and architecture in Oak Park

Many people like to revel in the historical footprints of Ernest Hemingway’s stomping grounds. The novelist lived all over the world in cities like Paris, Havana, Toronto, and Key West. However, Oak Park is actually where his story began. Hemingway called Oak Park home when he was a child, long before his career and travels abroad began. He was born in the summer of 1899 and spent the first few years of his life in the Queen Anne-style home built for his grandparents. The carefully restored home has since been converted into the Ernest Hemingway Birthplace Museum. Visitors can take a tour of the property and learn more about the iconic author’s childhood and impact on the literary world.

Another local legend is American architect Frank Lloyd Wright, who greatly influenced the area. Wright was an Oak Park resident in the late 1800s, where he built his family home and dozens of other structures. He went on to design buildings such as the Unity Temple, a UNESCO World Heritage site that demonstrates his signature style of geometrical shapes and bringing natural light indoors. While one of his best all-time works is a house hidden in the Pennsylvania mountains, Oak Park boasts the greatest number of Frank Lloyd Wright-designed buildings anywhere in the world. Guided walking tours of his studio and famous structures are available daily in Oak Park.

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Planning your visit to Oak Park

Dave Pennells

By Dave Pennells

Dave Pennells, MS, has contributed his expertise as a career consultant and training specialist across various fields for over 15 years. At City University of Seattle, he offers personal career counseling and conducts workshops focused on practical job search techniques, resume creation, and interview skills. With a Master of Science in Counseling, Pennells specializes in career consulting, conducting career assessments, guiding career transitions, and providing outplacement services. Her professional experience spans multiple sectors, including banking, retail, airlines, non-profit organizations, and the aerospace industry. Additionally, since 2001, he has been actively involved with the Career Development Association of Australia.