According to Forbes and the Chicago Tribune, the twin communities of Homewood and Flossmoor are among the most livable places in Chicagoland.
Southwest of the city, both ‘burbs are acclaimed for their quality homes and award-winning schools. Residents love their community’s safety, leafy parks, and vibrant downtown areas. With many commuting to Chicago for work and play, getting to the city is easy via the Metra and the Dan Ryan Expressway!
Homewood-Flossmoor Village Guide
While it’s undeniable Homewood and Flossmoor are quiet communities, that doesn’t mean that there isn’t fun to be had in the area.
Charming downtown districts, local restaurants, and community festivals keep residents active. So while Chicago’s big-name attractions may beckon, sometimes things are just nicer in the ‘burbs!
Great Downtowns

The center of life in Homewood and Flossmoor are their acclaimed downtown areas. Shops in the area range from local boutiques and well-known franchises. One can spend a weekend afternoon leisurely browsing or a quick after-work stop for daily necessities.
These downtown areas also host the area’s eclectic restaurant scenes. With options ranging from fine dining spots for date night, casual places for the family, and dives for lunch, the area has you covered. Local favorites include the Bellagio Restaurant, for great family Italian, Cilantro Cocina, for delicious Mexican cuisine, and Flossmoor Station Restaurant and Brewery, a local brewpub featuring American classics and seafood with a New Orleans twist.
Community Events
Great outdoor festivals throughout the year showcase Homewood and Flossmoor’s fun-loving community. Great events include a Fourth of July Parade and Celebration and the Artisan Street Fair. In February, Homewood’s Chocolate Festival features demonstrations, bake-offs, and, of course, tastings!
Other great activities in the area include several bowling alleys, movie theaters, and bars. Need somewhere to watch the game? Try Lassen’s Sports Bar and Grill or 5th Quarter.
Parks and Recreation

Homewood and Flossmoor share a park district. With 32 lovely parks, two public pools, a public golf course & driving range, and two fitness centers and sports complexes, excellent amenities are available.
The area also has great nature preserves, including the Izaak Walton Preserve. Over 193-acres of lakes, woodlands, and sand dunes, the Preserve is great for a relaxing hike or summer picnic. The park district also offers youth sports, arts programming, and great summer day camps.
Homewood-Flossmoor History
Settlement and Early History
Homewood is the older of the two towns. The first Euro-American settlers came to the area in the 1830s. Located along an ancient glacial shoreline, the early settlers found the soil especially fertile. Homewood’s historic downtown, then named Hartford, was established by James Hart in 1853. Many more settlers arrived when the area was connected to Chicago via the Illinois Central Railroad. The town was incorporated as Homewood in 1893.
Flossmoor has its roots in the Chicago World’s Fair (the “Columbian Exposition”) of 1892. With the intention of transporting soil for the Exposition, the Illinois Central Railroad purchased 160 acres west of the rail line. When the plan was deemed untenable, the railroad sold the land for development. A contest was held to determine the name of the new village. The winning name was “Flossmoor”, a Scottish name meaning “gentle rolling countryside”. The community quickly gained popularity as numerous golf courses and country clubs were built in the area.
Post-World War II

The years after World War II saw significant growth. Many new businesses opened and subdivisions were built. Homewood and Flossmoor grew more diverse in the 1970s as Jewish, Italian-American, and African-American communities settled in the area. The post-war period saw partnerships between the two towns form including a joint park district and high school.
Today, both communities are thriving and vibrant. With an excellent school system and a warm, welcoming vibe, Homewood and Flossmoor are well-loved by Chicagoland renters or buyers.
Homewood-Flossmoor Homes
Homewood and Flossmoor are great areas for both buyers and renters. A highly livable suburb, the area is well-loved by families for its lovely homes and excellent schools. While housing in the area tilts heavily towards single-family homes in a variety of architectural styles, some townhomes and apartment buildings are available.
Characterized by tree-lined neighborhoods, well-kept homes, and great parks, Homewood and Flossmoor are well worth your time. Come check the area out!