I’m finished with Illinois! I need to retire in a small city in a neighboring state — so the place ought to I’m going?

I’m searching for a small-town ambiance, with open land round it and perhaps a physique of water close by. I all the time stated my perfect could be water within the entrance and timber within the again. I can’t be too removed from the household simply west of the Chicago suburbs, however I’m finished with Illinois! It doesn’t matter what number of purple counties you’ve gotten, Chicago votes in who they need and all of us should associate with it.

I’ve moved round quite a bit up to now and I do know I don’t need the intense humidity of the south, having lived in Georgia and Virginia. I lived within the southwest desert and I liked no mosquitoes and low humidity, however it’s means too sizzling and never sufficient flip of seasons. 

So after lots of soul-searching, and the must be close to household, I’ve focused Iowa, Indiana, and Wisconsin. I’d outline a small city as 15,000 individuals or much less, and I would really like it to have a downtown space with some locations to go to for eats. Not searching for an excellent liberal space. My value vary is $250,000 or much less.

After I do the search on the “the place ought to I retire” software, I all the time click on on average humidity in the summertime, and 10 to 25 inches of snow within the winter — with winter temperatures round 30. 

Thanks! I admire your suggestions.


Pricey Cyndi,

You may have all of the purple counties you need, however when a lot of the state’s inhabitants lives in and round Chicago and so they vote … properly, that’s how the system works.

However you need out. That’s effective, and I’m glad you’ve found our software. I’m certain you already know a spot on the water doesn’t come low-cost. And it’s exhausting to seek out someplace in Wisconsin that doesn’t get properly over 2 toes of snow every winter. Indiana is extra doable, however the tradeoff is that you just’ll must battle Chicagoland interstate site visitors everytime you go see household.

As you ponder your choices, please suppose exhausting about the way you’re going to construct your new life. It will be a disgrace if you end up driving to a bigger place for docs, buddies, group actions, even groceries. So check out your shortlist and its openness to newcomers earlier than you commit. 

Lastly, be careful for small cities (and counties) which are stagnant. Sadly, there are a lot. In the future you’ll must promote that home. 

Learn: There’s extra to selecting a spot to retire than low taxes — keep away from these 5 costly errors

Listed here are ideas to get you began in every of the three states.


Lake Shafer, by Monticello, Ind.

Courtesy Go to Indiana

The realm round Lafayette got here up first for me once I used the retirement software to go looking all three states. (It matched 100% for extra balanced politics — it went narrowly blue within the 2020 presidential election — in addition to median dwelling costs under $250,000, average humidity and snowfall of 10 inches to 25 inches.) However Lafayette, with about 73,000 individuals, is just too massive, and smaller West Lafayette, dwelling of Purdue College, not solely remains to be too massive however could have little in your value vary. But when this space appeals, look in the remainder of Tippecanoe County

The retirement software additionally advised the areas round Logansport (17,000 individuals) and Frankfort (16,000) which are extra conservative however in any other case matched your standards and are lower than 4 hours by automotive from household.

However I’m going with Monticello, a city of 5,200 by Lakes Shafer and Freeman and about three hours to household. White County is solidly conservative, and Indiana Seaside, an amusement park with, sure, a seashore, is a draw for the broader space. However you’ll be able to benefit from the lake with out the curler coasters.

If you want greater than you’ll find in Monticello, Better Lafayette is 30 miles away. Brookston is about midway to Better Lafayette if you’d like a compromise, however it’s far smaller and your water could be Moots Creek on the southern finish of city.

An alternate could possibly be Chesterton, which has 14,000 individuals and is on the jap fringe of “the Area,” as Indiana’s a part of Chicagoland known as. It’s solely two hours from household, partially as a result of the drive is just about all interstate. Porter County went purple in 2020. If you need to go to Chicago for enjoyable, you’d have the choice of selecting up a South Shore prepare from the Dune Park station just some miles away.

Chesterton is simply south of Indiana Dunes Nationwide Park alongside Lake Michigan and west of different pure areas — however lake-effect snow means extra white stuff than in Monticello (and greater than your goal). And it’s pricier, albeit proper now in a purchaser’s market.

Right here’s what’s available on the market now in Monticello, utilizing listings on Realtor.com (which like MarketWatch is owned by Information Corp); the median listing value in October 2021 was $226,000. That is the market in Chesterton, the place the median listing value was $304,900.


Vintage Archaeology, whose authentic retailer is in LeClaire, Iowa, is dwelling base for the TV present “American Pickers.” A second location is in Nashville, Tenn.

Getty Pictures

Davenport and Scott County, a part of the Quad Cities space, come up on the “The place to Retire” software. It’s simply throughout the Mississippi from Illinois and will get a median of 26 inches of snow annually, so near what you need. It’s additionally a contact hotter than Wisconsin. Whereas Davenport is just too massive for you (simply over 100,000 individuals), LeClaire, on a bend within the Mississippi, is perhaps an choice.

This city, lower than 15 miles from Davenport, has been rising shortly however nonetheless has fewer than 5,000 residents. You could know LeClaire as the house of Vintage Archaeology, the shop behind the “American Pickers” tv present. It’s additionally the birthplace of Buffalo Invoice. Close by are well-liked winter roosting websites for bald eagles.

One different factor it’s identified for: a tug of conflict with Port Byron, Ailing., throughout the river. The rope stretches from one aspect to the opposite, however, no, the losers don’t truly fall into the water.

Annually, residents of LeClaire, Iowa, and Port Byron, Ailing., attempt to decide who’s higher with an epic recreation of tug of conflict throughout the Mississippi River. Photograph: Araby Williams for the Wall Avenue Journal

The city will entice extra day-trippers than you would possibly anticipate, however which means you additionally get extra restaurant decisions. 

If LeClaire doesn’t have the small-town really feel you need, take a look at Eldridge, with near 7,000 individuals and north of Davenport. The encircling space is extra farmland than woods, although. Underscoring the agricultural focus is the grain bin downtown.

Each small cities are near Scott County Park, with 1,280 acres and many timber. Scott County went blue in 2020 by a comparatively small margin.

Dwelling costs could shock you. Right here’s what’s listed on the market proper now in Le Claire, the place the median listing value was $319,900 in October, and in Eldridge, with a median listing value of $305,000.

If neither is true, maintain driving towards Iowa Metropolis, which is about 2½ hours by automotive from your loved ones. The house of the College of Iowa ranks extremely on lists of nice locations to dwell, and I’ve advised it right here. On condition that it’s too massive based mostly in your standards, search for an interesting spot between it and Davenport.


As soon as a lodge on the finish of a railway line in Prairie du Chien, Wis., Dousman Home is now an occasion area.

Getty Pictures

I’m struggling to discover a place that falls underneath your required snow ceiling. 

The retirement software suggests Winnebago County (the realm round Oshkosh), three hours straight north, and also you’ll discover a marina but in addition three toes of snow. (Fond du Lac to the south is smaller and could also be a greater match, however 43,000 individuals isn’t small.) There are many lakes round that space, in order that is perhaps value exploring.

I selected to observe the route south and got here to Edgerton, a city barely bigger than Monticello and largely in Rock County (which went blue in 2020). One attraction is Lake Koshkonong, a 10,595-acre lake not more than 7 toes deep. A giant bonus is that Edgerton is simply about 75 minutes from your loved ones.

Warning: Common winter highs might be under freezing, and you may depend on three toes of snow. You’re additionally a few half-hour’s drive from Madison, which might increase costs. Certainly, the median listing value in October was $275,000, based on Realtor.

A extra reasonably priced choice could possibly be equally sized Prairie du Chien, on bluffs above the Mississippi River and throughout the Wisconsin River from Wyalusing Hardwood Forest. However this extra conservative space is 3½ hours away from household and will get comparable climate.

Right here’s what’s available on the market now in each Edgerton and Prairie du Chien.

Readers, the place ought to Cyndi retire? Depart your ideas within the feedback part under.

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