[tptacek]

Oak Park is significantly more expensive than Chicago.

I don't think you can legitimately call Jefferson Park "remote" while saying you'd like to live in Evanston, which is much farther from the center of the city.

Jefferson Park is a straight shot down Milwaukee from the center of the city, and a pretty good chunk of every restaurant or bar you'd want to go to is along that shot. It's also got a Blue Line station, with better service than the Purple Line. For that matter, Jefferson Park is bisected by I-90. Have you ever had to commute between downtown (or anywhere else) and Evanston? It's a nightmare: you're a 20 minute drive from any major commuter road.

(I was born and raised on the south side of Chicago and moved to Evanston, and then Lakeview, when I was 18).

Bringing this all back to the point of the thread: a decent house in a nice neighborhood in Chicago will cost you $200, maybe $250 if you're optimizing. Well within reach of anyone in our industry. You can spend more. You can spend $500, or even a million. But it would be weird to do that. The fact that there are family-oriented neighborhoods in Chicago that people have barely heard of with all the conveniences of (say) Jefferson Park is the reason you can get such good deals on houses here. Chicago is just a well-designed city.

[willu]

I guess there are a lot of weirdos in Chicago by your estimation. Virtually every decent north-side neighborhood in Chicago (including Jefferson Park) has a median sales price above your $250k point and that includes all types and sizes of homes:

http://www.trulia.com/home_prices/Illinois/Chicago-heat_map/