Skokie
Skokie was once heavily Jewish and middle class. It's diversified lately and gotten more upscale, however it is suburban, if inner ring post-war suburb (mostly, it was platted out before WWII and there are a few apartment buildings and bungalows from just before the depression). Some of it is very, well, kitschy, in a 50's/60's suburban way. Lincolnwood is also similar as are some of the immediately adjacent areas of the city. Evanston is immediately to the east, which is similar in parts to Skokie (in terms of housing stock) and much more upscale in other parts. Keep in mind for purchasing that taxes will be higher than in the city, much higher in fact, with lower asking prices. Example, the asking prices for property in West Rogers Park will be 1/3 more than in Southwest Evanston, but the property taxes in Evanston are double (and Evanston city services aren't all that, they don't plow as well as the CoC).
The immediately adjacent neighborhoods of the city West Rogers Park (sometimes called West Ridge now), Sauganash and Edgebrook are mostly quite nice and have bigger houses overall than Skokie. Skokie has the Swift (CTA Yellow line, which now has two stations in Skokie) which connects to the Red Line downtown (or Purple express, though really, no faster due to poor maintenance, during rush hour) at Howard. The Swift may eventually connect to Old Orchard (local mall, one of the older malls and still an outside mall).