As tptacek says, Jefferson Park is the bang for your buck winner in Chicago. My sister in law just bought for under 200 with a yard, and a decent 2 floor home. House next door was listed for 150 (incredibly small though), and these aren't garbage homes in a bad neighborhood over there.

I'd buy there too if I wasn't planning on leaving this city in the next year or so. Housing prices are not what make me want to leave here, the climate and congestion are.

Jeff Park was one of the first neighborhoods I lived in Chicago, and it has proved to be one of the best. Quiet, clean, friendly.

My sister just last year bought a house in Jefferson Park for around that, and her neighbor's house just went up for less than 200. I'm sure it's not the best house in the world, but it's a nice neighborhood walking distance from a blue line station.

I don't know about the particulars of their places. The only properties I've seen in Jeff Park for that cheap have been Bank Owned, in need of serious rehab, or have some other mitigating issue like being on a short lot.

My sister's place is almost as big as mine in Oak Park. We could haggle over whether nice houses cost 200 or 250k, but for starter homes (the kind you'd pay over 1MM for in SFBA) in the city itself, that's the range.

Obviously, if you're looking to buy in Lakeview or Logan Square or Lincoln Square, the numbers change. But I don't know why you'd want to do that.