Tucked Next To Chicago Is A Scenic Walkable Suburban City Full Of Arts, Culture, And Affordable Homes

Home to nearly three million people, Chicago is the third largest city in the US. In addition to its permanent residents, the Windy City attracts around 50 million visitors per year, luring people from near and far with its rich history, iconic food scene, cultural institutions, and even a few tourist traps that are best to avoid.

Apart from the array of attractions in Chicago proper, the area surrounding the city is sparkling with hidden gem destinations, comprising inviting suburbs with green parks, peaceful trails, and local shopping gems like Deerfield, and walkable villages with small-town charm and immaculate architecture like Oak Park.

Situated just 20 minutes west of Chicago, Berwyn is another delightful suburb to visit. Perfect for a day trip, Berwyn's offerings are similar to its big city neighbor's, tucked neatly into a bite-sized suburban package. Boasting a vibrant live music scene, public art, delicious restaurants, and walkable charm, Berwyn is not only a desirable destination to visit; its affordable homes listed at 21% under the national median also make it a cheaper alternative to Chicago-style living. Whether you're visiting for a day or looking for a home to stay in, Berwyn is an ideal Windy City suburb you don't want to miss.

If you're flying to the area, you have two options. You can land at Chicago O'Hare International Airport (ORD) or Chicago Midway International Airport (MDW). The latter will place you about 6 miles south of Berwyn. Unless you're renting a car, public transit is the easiest way to go. From the Midway Orange Line Station at the airport, you can hop on the 54th/Cermak Pink Line to reach Berwyn in about 40 minutes.

Once you've reached your suburban destination, explore Berwyn's rich offerings by heading to the downtown Depot District. Colored with vibrant outdoor murals and charming brick-and-mortar buildings housing shops and restaurants, the district also boasts local live music venues like Fitzgerald's. Set in a historic building dating back to the early 1900s, the lively nightclub hosts an array of musical acts, from jazz and blues to rock n' roll. If you're visiting in early July, stop in for the annual American Music Festival, a four-day lineup of live music that features over 40 incredible acts.

Just up the street from Fitzgerald's, you'll find another live music gem, Friendly Tap. Housing a taproom, a coffee lounge, and a music lesson space, the local venue offers a cozy communal gathering spot for musicians and music listeners alike. Catch live shows on Fridays and Saturdays, or pop in on a Wednesday night to take the stage at open mic.

Beyond Berwyn's walkable charm and live music spots in The Depot District, the city flourishes in its beautiful residential homes. Brimming with Chicago-style bungalows, you'll find a generous collection of the early 1900s charmers dotting Berwyn's tree-lined neighborhoods, as well as stunning examples of English Tudor, Victorian, and American Foursquare homes. If you're in the market to buy, Berwyn has some of the most affordable homes in the Chicago area, with median home sales around $350,000 as of 2024.

Not only does Berwyn have plenty of historic homes on display, but it's also home to a historic road. Running along Ogden Avenue, Route 66 passes through the heart of Berwyn, immortalized with a variety of kitsch-filled attractions. If you're visiting during August, head to the Route 66 Car Show. Held on the last Saturday of the month, the show features an impressive lineup of vintage automobiles, motorcycles, and plenty of retro charm. No matter what time of year you visit, you can check out roadside attractions like the original White Castle on the corner of Harlem and Ogden Avenues, the World's Largest Laundromat on Cermak Road, and Berwyn's Toys & Trains, a local hobby shop packed with Route 66-era toys and memorabilia. To explore another Route 66 suburb with walkable downtown charm, head southwest to Plainfield, Illinois.