Investor Alert

Where Should I Retire?

Oct. 8, 2022, 3:52 p.m. EDT

I’m done with Illinois! I want to retire in a small town in a neighboring state — so where should I go?

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By Silvia Ascarelli

Dear MarketWatch,

I’m looking for a small-town atmosphere, with open land around it and maybe a body of water nearby. I always said my ideal would be water in the front and trees in the back. I can’t be too far from the family just west of the Chicago suburbs, but I am done with Illinois! It doesn’t matter how many red counties you have, Chicago votes in who they want and we all have to go along with it.

I have moved around a lot in the past and I know I don’t want the extreme humidity of the south, having lived in Georgia and Virginia. I lived in the southwest desert and I loved no mosquitoes and low humidity, but it’s way too hot and not enough turn of seasons. 

So after a lot of soul-searching, and the need to be near family, I’ve targeted Iowa, Indiana, and Wisconsin. I would define a small town as 15,000 people or less, and I would like it to have a downtown area with some places to go to for eats. Not looking for a super liberal area. My price range is $250,000 or less.

When I do the search on , I always click on moderate humidity in the summer, and 10 to 25 inches of snow in the winter — with winter temperatures around 30. 

Thanks! I appreciate your feedback.


Dear Cyndi,

You can have all the red counties you want, but when most of the state’s population lives in and around Chicago and they vote … well, that’s how the system works.

But you want out. That’s fine, and I’m glad you’ve discovered our tool . I’m sure you already know a spot on the water doesn’t come cheap. And it’s hard to find somewhere in Wisconsin that doesn’t get well over 2 feet of snow each winter. Indiana is more doable, but the tradeoff is that you’ll need to battle Chicagoland interstate traffic whenever you go see family.

As you contemplate your options, please think hard about how you’re going to build your new life. It would be a shame if you find yourself driving to a larger place for doctors, friends, group activities, even groceries. So test out your shortlist and its openness to newcomers before you commit. 

Finally, watch out for small towns (and counties) that are stagnant. Unfortunately, there are plenty. One day you’ll need to sell that house. 

Read: There is more to picking a place to retire than low taxes — avoid these 5 expensive mistakes

Here are suggestions to get you started in each of the three states.


The area around Lafayette came up first for me when I used the retirement tool to search all three states. (It matched 100% for more balanced politics — it went narrowly blue in the 2020 presidential election — as well as median home prices below $250,000, moderate humidity and snowfall of 10 inches to 25 inches.) But Lafayette, with about 73,000 people, is too big, and smaller West Lafayette, home of Purdue University, not only is still too big but will have little in your price range. But if this area appeals, look in the rest of Tippecanoe County

The retirement tool also suggested the areas around Logansport (17,000 people) and Frankfort (16,000) that are more conservative but otherwise matched your criteria and are less than four hours by car from family.

But I’m going with Monticello, a town of 5,200 by Lakes Shafer and Freeman and about three hours to family. White County is solidly conservative, and Indiana Beach, an amusement park with, yes, a beach, is a draw for the wider area. But you can enjoy the lake without the roller coasters.

When you need more than you can find in Monticello, Greater Lafayette is 30 miles away. Brookston is about halfway to Greater Lafayette if you want a compromise, but it is far smaller and your water would be Moots Creek at the southern end of town.

An alternative could be Chesterton, which has 14,000 people and is at the eastern edge of “the Region,” as Indiana’s part of Chicagoland is called. It’s only two hours from family, in part because the drive is pretty much all interstate. Porter County went red in 2020. When you want to go to Chicago for fun, you’d have the option of picking up a South Shore train from the Dune Park station just a few miles away.

Chesterton is just south of Indiana Dunes National Park along Lake Michigan and west of other natural areas — but lake-effect snow means more white stuff than in Monticello (and more than your target). And it’s pricier, albeit right now in a buyer’s market.

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