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Hi EMU!
We're waiting on a job offer tomorrow, and depending on what it all entails, we could find ourselves in Chicago this fall! I am VERY excite to move there, as crazy as it sounds to everyone I've run into- the thought of actually having seasons, great public schools, communities that don't up and move every year, public transportation, and a major city to play in- I love the idea! 
I will miss my beaches, dearly, but, my parents and sister are here, so we'll be visiting. 
We've been looking into the different villages for awhile now, since we knew the offer was coming, and are able to narrow it down quite a bit- but, no definite picks yet. We have the unique issue of having SIX dogs in our family- and a great number of the villages have limits around 2 or 3- not going to work for us, unless they make exceptions if you obtain a kennel license or such. DH will be working in the city, so we have to worry about commute, too. And schools, of course- I don't want to move up there and pick the worst schools (though, even the worst probably beat out most of the ones here- LOL!).
I'll come back and pick your brain tomorrow, if all goes well with the offer!
Re: Hi EMU!
Congrats!
I'm actually from Chicago (not the burbs but actually Chicago)...born and raised...I've been in CF for only about 6 years now....
IMO you are moving to a fantastic city! Although I've grown accustomed to CF great weather, there's nothing like Chi Town...I'm a Chicago girl no matter how long I've lived here...
Just so you know, commuting in Chicago is great, even if you live in the burbs....If you are in the Chicagoland area, the Metra can take you into the city...in truth, its usually better that way to just park at the Metra station and commute in if working DT, I4 has nothing on the Dan Ryan, Eisenhower, Kennedy, Edens, or Stevenson Expressway...(yea, we call our expressways by name for the most part vs. by number...LOL, you'll get used to it)... If you are planning to move to one of the closer burbs, you may even be able to take the EL train into DT....
If you have any questions about the city, let me know, I'll be happy to help...definitely drastically different than CF IMO...It took me a while to get used to CF and I still have issues with some things, considering myself a city girl...but I love the friendliness of CF.