The so-called “Windy City” — which is home to lakefront beaches, must-visit restaurants for deep-dish pizza, and sweeping views at the top of the John Hancock Tower — is surrounded by historic Southland suburbs worth exploring in themselves. About 30 miles from downtown, for instance, you’ll find Flossmoor. The village, which began as a picturesque golfing community for wealthy Chicagoans in the late 19th century, is now home to about 9,700 people.
Today, you’ll find homes designed by world-famous architects, fine-dining restaurants serving farm-fresh plates, and annual activities to keep residents and visitors entertained. Downtown, small businesses are housed in a historic, Tudor-style shopping center, and a central train station offers rides all the way to Chicago aboard the Metra Electric (ME) line. There are still stunningly-landscaped golf courses here like Flossmoor Country Club, which dates all the way back to the village’s early days.
In other words, whether you’re planning to spend an afternoon shopping, dining, or you’re simply hoping to tee off at a historic, picturesque course, Flossmoor’s got you covered; plus it’s an easy day trip — or even a half-day trip — from the heart of the Windy City.
Restaurants, shops, and historic architecture in Flossmoor
Although Flossmoor is tiny, especially compared to Chicago, which has a population of over 2.7 million, there are still plenty of boutiques, restaurants, and breweries to check out in the quaint downtown. Many of these are housed in the former Civic Center, which was built in the Tudor style back in 1929. Today, it’s home to Dunning’s Gourmet Market and Deli, where you can pick up Italian subs and turkey clubs to go. There’s also Flossmoor Social, just a few steps away, which has become the go-to place in town for modern fine-dining. Since opening in 2025, it’s received primarily five-star reviews, with one former customer writing on Google, “The food was absolutely delectable—shout out to their phenomenal chef!”…