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Weeeeell, hotels in Chicago are hurting, maybe not as badly as in some areas, but things are not rosy. If you have solid experience you can do OK in the places oriented to business travelers, but if that falls much further...
In Illinois CNAs are pretty common, the community colleges and "for proft" schools turn out too many. Wages in nursing homes and such are not the greatest. Pay is better for the hospital based medical specialists (radiology tech, resp. therapist, ophthalmological surg tech, that sort of thing) pays MUCH better (but if folks cut back on RK the "vital" stuff might be smarter...).
Chicago ain't cheap! With specific skills you can use Career Builder and other online sites to get a sense for how many jobs there are / what wages are, but my sense is that out of town resumes are not in demand -- when labor was tighter a few years back you could probably get an interview before you moved. I would suggest trying that route. If you get some employers to show intrest BEFORE you move it could really make things go much more smoothly.
Depending on how the broader economy goes it could be real hard to move here without jobs pre-arranged. Even with solid skills lots of people are hunkering down for a loooooong period of joblessness / underemployment...
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