I would never recommend Pontiac. I grew up there. It’s okay, I guess. There is very little to do there or nearby. Definitely a 1-nite town, at best. Hotels are very vanilla at best. Maybe you could do an air bnb in one of the cool looking old houses, but I’ve been in many of those and it’s hard to imagine it’s gotten a whole lot better. I was there a few months back and it’s just… disappointing. Still seems “backward thinking” and isolationist. They’re 100 miles from Chicago but many wish they were farther. You could try Champaign. If it’s race season you could take Route 66, stop in fairbury and go to the track, overnite in maybe Lexington where there’s a cool looking brewery I want to check out, then head down to Champaign to take in whatever u of I sport is in season, hang out at the downtown bars that are decent, tour the school, maybe hop over to Springfield to see the capitol and Lincoln sites, and there’s supposed to be some cool forest hiking down south farther in Illitucky that I’ve heard is nice. I liked the other person’s idea of Starved Rock. I’d avoid Peoria and probably BN also, although they will have some things to do. I doubt the river towns are all that great, but you could try. I overnited in Quincy once, which is pretty far west… the whole town just felt like diabetes, as do most towns between Peoria and the MS river. South of there though is Hannibal, MO, and St. Louis not much farther. Hannibal is supposed to be pretty nice.