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
This town of 40,000 is named after the developer’s daughter and has become one of the best small towns to live in. The town 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. The village is known for its giving spirit and takes pride in 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
The city of Oswego was recently named one of the top 100 towns to live in by CNN Money. 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 and was recently named one of the top 100 places to live by Money Magazine. Some of the main attractions in the city are the Fox River Trolley Museum, South Elgin Riverfest, and 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 offers 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 that is being discovered by more retirees every year. 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. Glenview used to be called Northfield until the name Glenview was voted on in 1895. Glenview became incorporated in 1899. The Park is one of Glenview’s oldest and best neighborhoods. It was established in 1894 as one of the religious communities. 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 were filmed in Woodstock. In 2007, the National Trust for Historic Preservation named Woodstock one of the Dozen Distinctive Destinations.
Recommended: 5 Reasons I Love Living In A Small Town Retirement Community!
Lake Bluff, IL
Lake Bluff is a nice, quaint town that is near the Great Lakes Navy Base. Lake Bluff used to be a railroad town and the town has a very 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. It is well known for its business district with downtown Geneva being home to 120 businesses. To protect the business district, there are strict rules on the size and use of all buildings, the paint color, and the signs that are hung. Geneva is also famous for its amazing shopping establishments.
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Robert Fowler
Contributing WriterRobert Fowler is a retired blogger who lives with his wife, Mary Ann at Village at Deaton Creek, a Del Webb Community in North Georgia. Robert was previously the President of Retirement Media Inc. He has visited numerous 55+ Active Adult Communities over the years, sharing his experiences along the way with readers. View more posts