Chicago is the largest city in the Midwest, and although there are plenty of attractions in The Windy City, there are several smaller towns close by that have a lot to offer. The towns surrounding the city range from popular suburban cities with attractions to charming farm towns with ample activities. This list encompasses some, but not all, of the best small towns near Chicago.

St. Charles

A view of a tall building in St Charles Illinois from behind an autumnal tree
St. Charles is known for its greenspaces and its history.

St. Charles is a popular destination approximately an hour’s drive from The Loop. This city is located west of Chicago off of I-355 along the Fox River. The intimate city, known for its ample greenspaces and historic sites, offers a variety of spacious home styles with expansive outdoor spaces for buyers.

Points of Interest:

Arcada Theatre: As host to local musicals and musicians, Arcada Theatre is the area’s premier event venue, hosting such acts such as David Bowie and Elvis tribute bands as well as nationally known singers like Michael Bolton and Johnny Rivers.

Pottawatomie Park: Among the many greenspaces along the banks of the Fox River, Pottawatomie Park allows visitors to explore a variety of trails and enjoy a scenic view of the river. The park is also home to a public pool, a golf course, and tennis courts.

Beith House Museum: A tour of St. Charles wouldn’t be complete without the historic home of stonemason William Beith turned museum. Built in 1850, the museum highlights interior and exterior design from the mid 19th century and hosts tours for all ages.

DeKalb

A castle-like building at Northern Illinois University rises above green trees in DeKalb
DeKalb is home to Northern Illinois University.

DeKalb is a college town just over an hour from Chicago. The city of nearly 50,000 residents is home to Northern Illinois University and offers a scenic setting with a secluded feel. This destination is a popular choice for Chicagoans looking to get out of the city.

DeKalb allows visitors to embrace a country lifestyle while not missing out on local entertainment and attractions. As you leave the Windy City and drive west to open terrain, here are just a few of the things to look forward to.

Points of Interest:

Whiskey Acres Distilling Co.: Whiskey enthusiasts can enjoy spending a day at Whiskey Acres Distilling Co. Founded in 1999, the distillery offers a large patio space where visitors can sip on neat pours and craft cocktails.

Jonamac Orchard: During the autumn months Jonamac Orchard is a highlight of the DeKalb area. This apple orchard is just a few minutes away from downtown DeKalb and offers a cider house, a petting zoo, a gift shop, and plenty of apples for the picking.

Ellwood House Museum: History buffs will love exploring the Ellwood House Museum. This historic site is home to the estate of barbed wire entrepreneur Issac Ellwood. Dating back 1879, the museum campus offers tours of seven historic structures.

Flossmoor 

Located off Chicago’s Metra Electric line, Flossmoor is a quaint southside suburb that offers thoughtfully designed neighborhoods, breweries, and ample parks and natural space to explore. This Cook County Village is a popular spot for Chicago commuters looking for small-town charm in a convenient location close to the city. 

Points of Interest:

Flossmoor Station: Whether you’re in search of a quick bite or a cold brew, Flossmoor Station Brewing Company offers plenty of options. The brewpub is located in the area’s historic train station, originally built in 1906. The pub offers several beers made in the facility as well as imports, craft cocktails, and comfort food.

Leavitt Avenue Park: Home to public art, ample greenspace, and a baseball field, Leavitt Avenue Park is a relaxing area within walking distance of the Metra line and Flossmoor Station. The playground and statue installation make it an ideal setting for all ages. 

Coyote Run Golf Course: Golfers can enjoy several courses in the area. One local favorite is Coyote Run Golf Course. This a public course that offers an on-site restaurant and 18-holes across 6,478 yards with challenges for golfers of all skill levels.

Frankfort 

Located in Will County, just under an hour from Chicago is the village of Frankfort. This town is a prime example of a suburb that offers some of the best parts of both urban and rural living. Although there's ample access to major expressways and retail options, Frankfort is also close to Midewin National Tallgrass Prairie and Illinois River Country. Frankfort is known for being a fast-growing suburb with a historic downtown of boutiques, restaurants, and more.

Points of Interest:

White Street Cafe: Locals come to White Street Cafe for their brunch-like cuisine with a variety of tea options and mimosas. The cafe is located at the intersection of White Street and Kansas Street, which is home to some of the area’s most popular dining and retail spots. 

KidsWork Children’s Museum: Families can enjoy visiting the KidsWork Children’s Museum. The museum offers programs such as storytime and yoga for kids.

Frankfort Farmers Market: During the spring and summer months, Frankfort hosts a farmers market on Sundays. The market features goods from local artisans, makers, and artists.