I don't think you can find Fat Tire in these parts either.....
I live in Chicago.
As for "upscale" -- a pilot cannot afford some of the areas
Housing isn't too bad -- a building with a 24 hour doorman, security, etc. runs about $250K (2 Bedrooms, 2 Baths) but wait, don't forget the parking space. These days they are running from $30K to $50K depending on the property IN ADDITION TO THE COST OF THE CONDO. Being a pilot, alas, not living in that building.......
Then there are the suburbs. How far do you want to commute. Which airports will you be doing Contract work? The Northern Subs are nice, but then you are limited to PWK; if NW (nice too), then DPA. If you want to work out of MDW, expect long drives and commuting if not living downtown or in LaGrange (partial to that little community

).
I would suggest going to the Chicago Tribune and the Chicago Sun Times and looking at their classifieds -- just to familiarize yourself with pricing in the area. Also go to Barnes & Noble or Borders and pick-up a map of the Chicago area. This will help you visualize the interstates with the areas you are interested in living. For example, Schaumburg is nice, but working out of MDW would be an unhappy commute -- if done on a regular basis -- expect 1 1/2 hours each way because there no "straight" shot to the airport. If working out of ORD, it would be an easy commute.
I think this is an awesome town, however, it is stretched North/South/West and depending on where you live and the airport you want to work at, the commute could take upwards of 2+ hours (during rain, snow, traffic, etc).
As for the winters, well I grew up in the Midwest and I don't think that they are "that" bad......it does get cold. I would suggest investing in a car starter if you will not have a garage. I would suggest lots of warm clothing too!! At least you aren't coming from FL and have seen some snow in NY.