Chicago's Historic Suburb Is An Illinois Village With A Quaint Downtown And Stunning Golf Courses

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.

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!"

You'll also find Conservatory Vintage and Vinyl in the former Civic Center, a store that sells, as the name suggests, everything from records to antique decor. A short walk away on Brassie Avenue is the Frederick Nichols House, which was constructed by famed architect Frank Lloyd Wright in 1906. Wright, who's responsible for the "best all-time work of American architecture" in the Pennsylvania mountains, designed hundreds of other homes across the country, many of which were in Illinois. Although the Nichols house is a private residence, it's occasionally open for public tours.

Finally, given that this is the Chicago suburbs, you'll also want to try a slice or two deep-dish pizza. Flossmoor has its own Lou Malnati's location, which is often considered to be one of the best deep-dish pizza stops in the city.

Flossmoor Golf Club, which anchored the village in the late 19th and early 20th centuries, is still just as important to the community today. It's ranked among the best golf courses in all of Illinois thanks to its stunning landscaping and reputation for attracting A-list golfers. "[It's an] Old school golf course with lots of history and fun to play," reads one review on Google, noting, "[There's a] Unique bunker pattern and old school greens which can be hard to putt on the first time."

Nearby, you'll also find Idlewild Country Club, which was founded a few years later in 1908. Reviews here are similarly positive, with hundreds of five-star ratings on Google. Olympia Fields Country Club, which has also been ranked among the best courses in the region, is just a few minutes outside the village. Before heading out to golf, you can swing by the Flossmoor Farmer's Market outside the public library from June through October to pick up baked goods or fresh produce. 

Flossmoor is about 20 miles south of Chicago Midway International Airport and a little over 40 miles south of Chicago O'Hare International Airport. Although Flossmoor doesn't offer many overnight options, you can always stay in the historic La Banque Hotel in Homewood, an artsy Chicago suburb with a quaint downtown, boutique shops, and trails located just a few minutes away via train. Downtown Chicago is about 40 minutes to an hour away, just a straight shot north along the ME line.