I was back there in February to see a Red Wings game (I grew up in MI), I would recommend the Ford factory tour of the assembly plant in Dearborn (The Rouge Plant) they build the F-150's there. You can buy tickets at the Henry Ford and they bus you over to the plant very cool tour if you are into that kind of stuff. Also checkout Green Field Village while you are at the Henry Ford as well. I also went to a gun show while I was there the next one is June 4th and 5th in Novi, MI and it is a pretty good show, also there are plenty of ranges that offer full auto gun rentals. If I remember correctly the trip to Chicago is about a three hour drive so take that into consideration. If you are really looking for a drive I would recommend driving up to the UP (Upper Peninsula) and check out Mackinac Island https://www.mackinacisland.org/
If you decide to go into the city of Detroit there is Greektown and the HockeyTown Cafe is pretty cool too. I would just recommend getting out of the city before sundown and I am not kidding. You could also try and catch a Tigers game while you are there, there is other stuff but this all I can think of off the top of my head. Have fun and be safe man.