- $499,999
- 4Bd
- 3Ba
- 2,405 Sq Ft

You might know the Chicago area as a great place to be young, to be single, or even in love. In fact, Chicago and the surrounding cities and towns are great places to be pretty much anyone—and that includes a soon-to-be retiree. That’s why we looked at business listings, the cost of living, median home prices, the percentage of the population who are seniors, and crime data to determine the 10 best Chicago suburbs to retire.
If you’re getting ready for retirement, chances are, Palos Heights is slightly younger than you are. Yep, at just about 40-years-old, this relatively new community has all of the creature comforts you’d expect from a place with modern planning, like quarter-acre (or larger) lots for houses, broad lawns, and streets lined with trees. The oldest homes in the area are along Harlem Avenue, and to the south, the homes get newer—and bigger. So where you’ll be really just depends on your budget, your preference, and how close you want to be to all those senior amenities—which does include four retirement communities, in case you’d prefer that. No matter what you’re looking for, though, you’ll be well taken care of in Palos Heights, both by your community (there are more people over 65 here than anywhere else) and the plethora of doctors.
If saving money is the most important thing to you when you retire, your search should begin and end with Monee. Not only is the cost of living a whole lot lower than Chicago’s cost of living, it’s even lower than most of Illinois! Matter of fact, it’s flat out the most affordable place in the area. Monee also has 17 restaurants and, for all you golfers out there, the local Golf Vista Golf Course. If you’re up for a bit of a drive, you can head to the nearby and larger Deer Creek Golf Club.
Sure, Winfield might be a great place for young couples, but it’s also a good place to retire. This is largely due to a lower cost of living and crime rate here than in Chicago, but it’s also because of the sheer number of things to do—for any age. There’s the Klein Creek Golf Club and the park district for the summers, a library to warm up in during the winter, and there are over 15 restaurants, from southern food so good you’ll think you’re in Texas to Gnarly Knots Pretzel Co., where the name kind of speaks for itself. But if a retirement community is important to you—either in an actual retirement home or just in the age of most of your peers, the next spot on our list might be a better fit.
Not only does Northfield have some of the most residents above the age of 65, it also has one of the best retirement communities around. Which in this case, you might want to consider, because the median home price here is over $653,000. Of course you get what you pay for, and in Northfield what you’re paying for is safety, more doctors than you can count on all your fingers and toes, hiking and biking trails, boating areas, and of course, and bridle paths for your horses. (Northfield is one of the few north shore communities which issues licenses for keeping horses.)
Lincolnshire is basically a ready-made retirement community. There are already many residents over the age of 65 here, some of whom live in the retirement community Sedgebrook, some of whom live in luxurious homes, and some, in smaller townhomes or condos. Basically, Lincolnshire has something for everyone—and that includes amenities. For seniors, Lincolnshire has two retirement communities, a library, three golf courses, two nonprofit options for volunteering, six arts and entertainment options, and thirty restaurants.
Of all the places in our top 10, Des Plaines is easily the largest with nearly 60,000 residents, and you know what that means—lots of things to do. There are over 200 restaurants, a rec center, a library, seven retirement homes, and five golf courses. If you’re more interested in the arts than the art of swinging a club, there’s the beautiful Des Plaines Theatre, the Des Plaines Historical Society, festivals year round, The Barefoot Hawaiian for some dance lessons, and even the McDonald’s No. 1 Store Museum—a memorial site to the first Micky D’s ever.
Highland Park has everything you’ll need in your retirement years—plus a whole lot more. This city is well known as an arts community, with the Ravinia Festival, a world-class summer event for the performing arts. It’s a festival of music and dance that lasts literally the entire summer, from May until late September. Of course if you aren’t so much into art, don’t forget there are also eight golf courses, 75 restaurants, a library, a rec center, and a handful of nonprofit options to choose from. And if you’re not into any of that, you can always just relax at home… which wouldn't be a bad choice here, really—the neighborhoods in Highland Park are dotted with everything from historic colonials from the mid-1800s to more contemporary homes and condos downtown.
If you love nature or you happen to have a dog that’s coming along for the retirement ride with you, Lake Bluff might just be perfect for you. This beautiful community has more parks and green areas per capita than anywhere outside of Chicago, along with several beaches and trails for walking. There are also four golf courses nearby, including the Lake Bluff Golf Club, the Lake Bluff History Museum, art galleries, a summertime farmers’ market, and about 30 restaurants. The homes here might be a little more expensive than most homes in the Chicago area, but since they’re mostly large single family homes with sprawling lawns, we can see why.
Westchester is a great option for those looking to spend a little less money on a home—but who can still afford a pretty high cost of living. Here’s where your money will likely go in Westchester—goods and services are much more expensive here than in the rest of Illinois, as are groceries and transportation. On the other hand, utilities and healthcare are much less expensive than the Illinois average. This is good news, particularly for a retiree who might need more medical attention than most. Not only will you have about 50 doctors to choose from, it seems you’ll also likely be paying less.
Remember how we said Westchester was an affordable option for housing? Well that was nothing compared to the homes, and overall cost of living, in Crest Hill. Said houses here range from single family ranch-style homes to townhomes and condos. The residential areas are mostly white picket fences and well manicured lawns. And if you’re looking for something a little more communal, Crest Hill is also home to the highly rated Willow Falls Senior Living Community.
You’ve done the work, you’ve made a plan, and at this point, you’re about ready to wrap things up. Don’t worry, we are too. Like we said in the beginning, the Chicago area is great for many things—perhaps you’ve been there for years and you’ve experienced all it has to offer. But whether you’re arriving brand new or you’re a Windy City expert, we hope this list has helped you on the road to retirement. If you’re interested in finding a home in the area, get in touch.
When we create Big Deal Lists like this one, we make sure to rely solely on facts and figures—not our own opinions. In this case, we used the U.S. Census, AreaVibes, and local business listings to research all of the places near Chicago with populations of 5,000 or more in terms of these criteria:
We then ranked each of these 106 places with scores from one to 106 in each category above. From there, we weighted these scores so that both the “65 and up” and “crimes” categories were worth 20 percent of the overall score, while the rest were worth 15 percent. Finally, we averaged all of these weighted scores into one overall Big Deal Score, where our lowest scores went to our 10 best places to retire.
Feature Image Source: Willow Falls Senior Living Community via Facebook Like This Post? You’ll Definitely Love These: