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Yea, I'll most likely be trainin it. As far as preference, all I know is that north is pricy and south is shootings, so somewhere in the middle???
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That's half true. The northern suburbs by the water are very expensive ($10 million estates in Winnetka along Sheridan drive), but if you go even more north (e.g. Libertyville, almost at the Wisconsin border), then it's not expensive. Also, northwest suburbs (far away from the water) are newer towns, and are cheaper. Lots of young families, etc.
The south side (like where U of C is, where the US cellular field is, etc.) is dangerous, yes. But the southwest suburbs (Oak Park, Naperville) are very nice.
Take a look at this map:
http://www.wildonions.org/Neighborhoods-Suburbs.htm
You can see the relative location of the various towns I mentioned. I forgot to mention Niles, I would lump that together with Morton Grove and Skokie.
-bigbootch