in chicago, there's not many hotels that are in the neighborhoods. so if you stay downtown, you will get raped on parking. and u can't do shyt about that. you stay by ohare, you gotta commute to get to the neighborhoods. and the driving commute from ohare to the southside is HELLISH to put it mildly. there's a few hotels in the neighborhoods, but some are pricey. If you stay in a hotel near midway airport, those will have parking. midway is on the south west side, so you can easily get to the south side. midway borders the suburbs, and those neighborhoods are safe. that's actually probably your best bet if you want to have rental car and get around. midway also has train and expressway access to get you downtown fairly quickly.
the cost of living in chicago is cheap for the most part compared to any other comparable major city in the country. try places like NYC, the bay area, boston, DC or LA, and those housing prices will blow your mind