There are several housing options available. You can have a single family apartment or a shared apartment with roommates. There are two building choices, the 1400 Building or Kimbark. Either set of apartments is quite nice, it just depends on the individual student's needs which is the better choice.
Chicago has excellent ways of dealing with the weather. The only problem I've ever heard of was during "Snowpocalypse." McCormick has an open campus, so the fact that the city does a good job managing bad weather is highly important.
There really isn't a need to have a car on campus. For students who do bring cars, there is little parking available near the dorms. There are parking spaces available for rent near the main campus building.