Chicago is a very nice city, but it is a big city. Obviously, living downtown is expensive. You would get more bang for your buck if you lived in the burbs.
However, the suburbs are very nice, and there is a LOT of stuff to see/do. I personally live in Naperville (
www.naperville.il.us, crappy website.. i know..), a city of about 140,000 that is about 30minutes train ride or 30minutes(no traffic)/1.25hours(BAD traffic) commute from chicago. It is one of (if not THE) largest suburb, and is pretty typical of greater chicagoland. Housing ranges anywhere from $110,000 (townhouse/condo) to $2,000,000 or so. I assume you probably don't/won't have kids in the next 2 years, but the schools are top notch if you do. I'd suggest that you come visit chicago, check out the city for a bit (esp. if you will be working there), but also check out the suburbs.
I can attest that the costs of living are somewhat high (well at least compared to eastern Iowa where i go to school), but definitely lower than the west/east coasts. I would say that Chi-town is probably on par cost-wise with Houston.
It does get hot in the summer (downtown usually isnt too bad due to the lake breeze), and it does get cold in the winter (probably not as bad as you're used to in Canada, but close). In the winter, there is skate on state (outdoor ice skating rink in the middle of downtown), as well as the window-murals (best word i can use to describe em, not very accurate though) in the shop windows on state st. In the summer, there is Taste of Chicago in grant park, basically a festival of all different kinds of food. Plus there are Cubs / White Sox / Bears / Bulls / Blackhawks games all year round (heh.. no hockey in Houston or Seattle, that might mean something to a Canuck
). hmm.. what else.. The club/bar scene is really fun too, though somewhat expensive (i guess anything's expensive compared to 25 cent bottles we get here in college
). Anyway, all around its a really fun town.
The food is excellent, you haven't lived until you've eaten chicago-style pizza made the right way (Gino's East/Lou Malnati's/Leonardo's/Giordano's all make great Chi-style pizzas, sauce on top of course). Chicago style hot-dogs / italian beefs are excellent as well (Portillo's can't be beat in this regard), and you won't find them anywhere else. There are many good cultural restaurants as well, both in the city and in the suburbs.
hmm.. anything else..
well there prolly is but i can't think of it right now.. i should get to bed
anyway, give chicago+suburbs a look, I love em and you could too
ebaycj