Illinois: Pekin? I’m not optimistic about Trump anywhere in the suburban areas. The fact that he lost the 6th and 14th congressional districts is flat out embarrassing.
Massachusetts: Braintree
South Dakota: Sioux Falls
Trump won the 14th, but I don't expect him to do so this year. I'm really not sure what the biggest IL city he'll carry is, since I don't see him carrying Springfield, Peoria, Rockford, Belleville, any of the big Chicago suburbs or college towns (Champaign, Bloomington/Normal). Maybe somewhere like Quincy?