To match Del Tachi, but in the Midwest:
IL-Cook County: Chicago or Dearborn; Chicago is obvious, but maybe a suburb like Oak Park or Evanston?
IL-Chicago Suburbs: Lincoln or Chicagoland; Aurora or Naperville
IL-Northwest: Illinois (The river flows right through here); Peoria or Springfield
IL-South: Shawnee (National Forest and Indigenous Tribe) or Little Egypt; Not a great central location here, maybe Effingham (have not heard positive things about the place) or Decatur?
IN-North: Wabash (Not a huge fan of naming a state famous for an
Indian battle); South Bend
IN-South: Hoosier (Never been a fan of the Indiana name); keep Indianapolis
MI-North: Superior or Huron; Traverse City or Midland
MI-West: Michigan or Ford; Grand Rapids or Lansing
MI-East: Motown; Ann Arbor, Livonia or Detroit itself (Detroit could use the boost)
MN-Twin Cities: Twin Cities; St. Paul
MN-Remainder: Minnesota; St. Cloud or Mankato
MO-North: Missouri; Columbia
MO-South: Ozark; Jefferson City or Springfield
OH-Southeast: Ohio; Athens
OH-Northeast: Western Reserve or Erie or Cuyahoga; Cleveland (Cleveland could use the boost)
OH-Southwest: Miami or Grant; Dayton
OH- Northwest: Maumee or Scioto (Not great choices here); Columbus
WI-East: Menominee or Michigan; Fond du Lac or Sheboygan
WI-West: Wisconsin; Madison or LaCrosse