Coming from NW suburbs of Chi-town, I'm sure the weather won't be a problem for you. (I'm from there, too.) I would think you'd be good there. Maybe depending on very specific needs, could be better or worse - do you want indoor health clubs, other indoor winter activity options like swimming or tennis or the dreaded pickleball, etc. Do you need good medical care nearby? Culture stuff - concerts, plays, libraries, etc? Restaurants important?

I'm sure housing costs are pretty good compared to where you're coming from. But do taxes differ from one town to the next by a lot?

Have you spent a few weekends there staying in a motel or B&B? Seems like that could be a good thing to do to get the feel of the place.

Cheers.

What was his name? My dad grew up in Guttenburg. My dad refers to Clayton county as "God's Country". The only county in the state that doesn't have a stop light. I think the NE portion of Iowa is the best part of the state, extremely underrated.

OP if you end up moving to Dubuque make the venture to Clayton county and ride some of the gravel roads. Some of the best gravel roads in the country IMO.

You might also consider some parts of Indiana. I wonder how taxes compare between those two states.

I find the "weather comparison" information here to be super-useful.

https://weatherspark.com/compare

What about Galena?

Illinois taxes…

Not yet, next step.

Maybe, but I would only consider the northern part which is too flat and boring.

IA:
Social Security: Not taxable
Pensions: Not taxable
401k and IRA Distributions: Not taxable

IN:
Social Security: Not taxable
401(k) and IRA Distributions: Taxable
Pensions: Taxable

Sounds like you need to book an extended airbnb stay in IA and see for yourself.
Or rent an RV and take a tour.

Edit: Oops, someone mentioned that already. Best of luck!

How about West Michigan?

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I lived in IA for 30 years, Iowa City area to be specific, I spent quite a bit of time in the Dubuque area. My son taught skiing to kids at Sundown for several years. While he was teaching on nicer days, I would go gravel riding for 5 hours or so. It's not flat. That being said, it's a river town on the Mississippi, former manufacturing and agriculture focus, several small colleges including Loras and Clarke who both have a Catholic focus. When I lived in IA there was an active cycling community that would be easy to tap into.

IL doesn’t tax SS, pension, nor retirement distributions.

Property taxes can be very painful, however.

https://www.bankrate.com/retirement/...rement-income/

Another Iowa resident chiming in here.
Dubuque is a nice area, especially the smaller towns popping up and expanding around it like Peso, Asbury, and Farley.

Decent riding areas in all directions while also having the main amenities a small city has to offer like multiple grocery options, breweries, basic retail, etc.

If I had to pick a larger river town to live in on the Eastern side of the state - Dubuque would be my choice. Small colleges as mentioned already like Loras, Univ of Dubuque, and Clarke will keep the young people there.

Hwy 20 goes right through town, which is my only complaint as there are 15 stoplights on a major highway that starts in the country and then winds through town a bit.

Overall, lots of churches- mostly a Catholic town I believe , good school systems, with a downtown that is starting to get re-established with new businesses after the MFG stuff closed up.

Tell me about it, but they also vary a lot from township to township.
Definitely something to consider.