@ Carry 24/7:
If you have the type of job where you seldome have to drive to work and have a pretty set schedule then the Metra is for you. My first year back here in Illinois I took the Milwaukee District North Line almost every day to my job. Unless someone/something gets hit by a train delays even in bad snow typically do not get that bad.
If you would like to live in Illinois, Closeish to the City and it is in your price range I would reccomend Deerfield. MOST of it is in Lake County so you have 0 annoying gun laws to worry about, Deerfield has good schools and it is close to both the Edens (94) and the Tristate(294) if you want to go into the city or elsewhere in the state.
Looking at western Suburbs if you go out much further than Hoffman Estates or Barrington your drive in would be a nightmare.
I can't really speak about South/SW Suburbs someone else will need to chime in on those.
I work with a guy who lives in Wisconsin ; if it is snowing driving is a joke. If you plan on taking the Train great but the further out from the city you are the more of an issue it is.