I dont know if you care about schools, but a significant amount of the wisco towns just over the border don't have great schools. pleasant prairie is a nice area with good schools iirc, just pricey to me for what you're getting.
as you already alluded to- being near a highway is pretty crucial if you're going to work in IL still. getting to 94 would be pretty critical to me- being close to rt 12 wouldn't help much unless you worked lake zurich/palatine/something like that. road gets so fucking traffic-y
and of course- wisco state income taxes are higher than IL but just barely- but less property & no grocery tax.
what's your budget?
it is interesting looking at monthly payments though of course with the property tax savings...
350k house 20% down 280k mortgage is 1775 at 4.125 with 5k in taxes.
250k house 20% down 200k mortgage is 1802 at 4.125 with 10k in taxes
buuhhhhtttt youll spend 149k in interest over 30 years on the 250k house... and 210k in interest over 30 years on the 350k house.
so many ways to think about it all... for example- then if you do have to commute to IL, your time costs money not to mention fuel/vehicle wear & tear. such a mindfuck.