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Well I think you're going to have a hard time finding an uncool neighborhood with no teens and kids. I don't know if that really exists anywhere in the country, let alone Chicago.
Downtown itself is really an option, given that rental rates are still really low from the condo boom (that's now a bust). There are lots of rental units in The Loop, River North and Greektown, all of which are within easy walking distance of just about anything "downtown", which is sort of a nebulous term. Greektown has lots of great restaurants, and the Green and Blue Lines are close.
Stay out of Lincoln Park and Lakeview.
Uptown (north of Lakeview and Wrigleyville) might be pretty good, although there are some serious pockets of poverty, so be careful. There's also a big halfway house for the mentally ill in the northeast corner of the neighborhood (roughly Sheridan and Foster), so be aware of that. Farther west is better. You can get downtown on the Red Line in about 30 minutes or 15 on the Metra if you're within walking distance of Lawrence and Ravenswood. There's also some fantastic arcitecture and the neighborhood really is on its way back.
Edgewater is also pretty good and is just north of Uptown. It's farther along in the transition than Uptown, and there are lots of interesting ethnic pockets still. It will probably take you 40 minutes in by El, and there's no Metra stop.
Bridgeview is the political seat of power for the city, and it's on the Near South Side. It's....homogenous, so if you're looking for an ethnic restaurant that's not Irish, it might not be your spot.
Any other requirements?
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