It's not that hard to discern where the deals are in Chicago. The South Loop, you will notice after a day of visiting open houses, is generally more affordable than the West Loop. As you move farther south, to Bronzeville and Hyde Park, prices are even lower. As you travel north along the lakefront, the same trend occurs, although Edgewater and Uptown are no longer the bargains they once were. One of the most basic, but easily forgotten rules in searching for real estate deals is that it's not a deal if you don't want to live there.
Neighborhoods generally change the way continents shift, so slowly movement is imperceptible.
A homeowner who bought a house near Wilson Avenue 10 years ago recently complained that prostitution and drug deals were big business near his home. He was disgusted by the trash on the streets and shocked by the size of the homeless population, the number of SROs in Uptown. These facets of the neighborhood were plainly visible when he moved in, but he chose to ignore them, thinking Uptown would soon gentrify and problems would disappear. In fact, these problems have shrunk in Uptown, but they have not gone away and perhaps never will. The real problem is that he did not buy in Uptown, but in some imaginary neighborhood, a mental landscape he created with the help of real estate brokers and developers.