Best Small Towns for Retirement Near Chicago and All Around Illinois

Illinois is one of the most populated states in the country, with many living around the Chicago metro area. Though perhaps most known for popular sights like Wrigley Field or the Skydeck at Willis Tower, more and more of the 55+ community are finding that the small towns of Illinois are just where they want to be. Why swap big-city amenities for small-town living when you can easily have both? If you look closer, you’ll see that a Chicago suburb has the same beautiful architecture, the same great people, and delicious food (like Chicago hot dogs—yum!)—with just less traffic! Here’s a list of my favorite small towns for retirement near Chicago, Illinois!

Carol Stream, IL

Named after the developer’s daughter, this town boasts a population of 40,000 and a charming atmosphere. Carol Stream is what many picture as the perfect small town, with several well-groomed parks, churches of many denominations, and small-town pride beaming from the residents. The town is home to many yearly festivals including Swedish Days, Geneva Arts Fair, Fall Festival of the Vine, and the Christmas Walk. The town has several affordable restaurants, an outdoor amphitheater, and a new Town Center.

Glen Ellyn, IL

The suburb or Village of Glen Ellyn is located less than 25 miles outside of Chicago and is one of the area’s premier suburbs. Many recognize this town for its giving spirit and volunteerism. Retirees who want to live in a small, charming town but have close access to the city will love Glen Ellyn. The town has 29 parks, a wildlife preserve, and a great golf course thriving with cultural amenities.

Oswego, IL

CNN Money recently named the city of Oswego as one of the 100 towns to live. It’s just 50 miles from Chicago at the south end of Fox River. The community strives to keep a small-town feel while offering modern amenities. The Oswego Park District offers retirees several activities, recreational programs, and facilities. The village features hundreds of acres of parks, a 183-bed hospital, bike trails, and a new aquatic center. The village is also home to the Fox Bend Golf Course which is one of the top-rated in Illinois.

South Elgin, IL

The village of South Elgin is home to approximately 22,000 people. Money Magazine recently named it one of the top 100 places. Some of the main attractions in the city are the Fox River Trolley Museum, South Elgin Riverfest, and the World of Faeries Festival. South Elgin has everything a retiree would want including great weather, parks, golf courses, restaurants, and a senior center.

Addison, IL

Addison is located just west of the Chicago metro area and has a population of approximately 37,000 residents. The town has many modern amenities, shops, and activities but remains a great place to retire or raise your family. The Addison Public Library and Parks and Recreation District offer multiple events each month including movie nights, craft classes, golf lessons, live performances, and more.

Pontiac, IL

This town, with a population of 12,000 people, is a hidden gem in the state! Pontiac is home to the Route 66 Museum, Livingston County War Museum, and the International Walldog Mural.

Crystal Lake, IL

Crystal Lake is located 50 miles northwest of Chicago and is one of the most popular suburbs in Illinois because of its small-town charm and proximity to the water. The population is currently 42,000 people. There are many things to do in Crystal Lake year round including historic sites such as the Colonel Palmer House, Lights on the Lake, Johnny Appleseed Festival, and of course, boating and swimming on the lake.

Glenview, IL

Glenview is a small town that is located just 18 short miles north of Chicago. Once known as Northfield, residents ushered in the name Glenview back in 1895. Glenview became incorporated in 1899. The Park is one of Glenview’s oldest and best neighborhoods. A religious community established the town in 1894. The original church still stands today. The center of town called The Glen contains homes, businesses, and shopping centers.

Oak Park, IL

Oak Park is one of the best towns near Chicago. It is adjacent to Chicago on the west side. There is easy access to Chicago from Oak Park by way of public transportation. There are several famous people who hail from Oak Park and its college prep school, Oak Park River Forest High School. They include Ray Kroc, founder of McDonald’s, and Ernest Hemingway. Oak Park is very rich in arts and culture.

Woodstock, IL

Woodstock is home to the famous Woodstock Opera House as well as Old McHenry County Courthouse. The town was the main location for the filming of the Movie Groundhog Day. In addition, a handful of scenes from the movie Trains, Planes, and Automobiles starring Steve Martin and John Candy were filmed in Woodstock. In 2007, the National Trust for Historic Preservation named Woodstock one of the Dozen Distinctive Destinations.

Lake Bluff, IL

Lake Bluff is a nice, quaint town that is near the Great Lakes Navy Base. As a former railroad town, the town has a haunted history. In fact, every other year, the Lake Bluff History Museum holds ghost walks to celebrate the haunted history of the town. Philip D. Armour who founded Armour and Company hails from Lake Bluff as does actor Mark Morenttini and singer Richard Marx.

Geneva, IL

Geneva is a great small town located along the Fox River and is well-known for its many shops and restaurants. The Fox River Trail and the Illinois Prairie Path have extensive biking and walking trails. Geneva is rich in history and in downtown Geneva, at the Geneva History Center, there is the Fabyan Windmill. This windmill is an old Dutch windmill that is from the 1850s. Back in the day, Geneva manufactured goods such as packed meat, milled grains, butter, and cheese.

Long Grove, IL

Long Grove is located 35 miles northwest of Chicago. Its business district boasts over 120 businesses. To protect the business district, strict rules exist to maintain the integrity of the shops and buildings. Geneva is also famous for its amazing shopping establishments.

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