Chicago's Cute Next-Door Neighbor Is A Walkable Village With Small-Town Charm And Immaculate 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.

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.

In addition to the historic landmarks in the Hemingway and Pleasant Districts, there is so much to discover in this vibrant village. Downtown Oak Park is where you'll find the majority of shops, restaurants, and annual events. The Jazz Thaw is a series of concerts in March that kick off the thawing of winter. In May, the Wright Plus Architectural Housewalk invites visitors inside the privately-owned homes designed by Wright. The Microbrew Review in August is known as the largest zero-waste craft beer festival in the Midwest.

The Oak Park Arts District is exactly what it sounds like; a thriving hub for the arts brimming with galleries, independent shops, theaters, and more. On the third Friday of every month, art galleries stay open late for the Third Friday Gallery Walk. It's a great opportunity to explore new exhibitions and try some of the restaurants in the area, like Taco Mucho's tequila tastings and delicious Mexican cuisine made from scratch.

A must-visit sweet spot in Oak Park is the sister-owned Broken Tart. Reminiscent of European and old-school Chicago bakeries, the cafe features familiar items with a modern twist; think coconut cakes topped with espresso glaze and kale salad scones. For those seeking vintage gems, Grateful Threads Resale Emporium and Brown Elephant are full of hidden treasures. Die-hard vintage lovers can head to nearby Woodstock, a whole town full of vintage shops and nostalgic vibes. Conscious shoppers must pay a visit to Ten Thousand Villages, a marketplace that ethically sources products from around the world and directly supports the artisans.