Best Neighborhoods for Risk Takers

The uneven, patchwork nature of the city’s postcrash recovery has opened opportunities for speculators seeking neighborhoods with untapped potential. For this category—aimed at buyers looking to rehab and quickly sell properties or to move in hoping for a big return down the line—we confined our search to the city. We sought out neighborhoods with lots of flipping activity and factors like good transportation or proximity to gentrifying areas that make them ripe for future development.

Bradley Cole and Steve Denenberg
Two real estate brokers, Bradley Cole (left) and Steve Denenberg, recently rehabbed a three-bedroom condo in this $180,000 vintage building on North Mozart Avenue in West Ridge. Just a few months after they purchased the unit, it went under contract for $240,000—a profit of around $22,000 after renovation expenses. Photo: D.W. Johnson

Belmont Cragin

Median house sale price:$231,750
Change since 2006:–29%
Change since 2015:19%

With gentrification driving up prices in Logan Square, fans of that hip neighborhood have begun looking west to Belmont Cragin. Condo prices there were up 57 percent in 2016, house prices 19 percent, but they remain low compared with those to the east. Developers and contractors have swooped in to snap up bungalows, give them a face-lift, and turn a quick profit.


Median house sale price:$110,000
Change since 2006:–35%
Change since 2015:51%

Though its violent crime rate has been creeping up, Chatham boasts a tight-knit community of mostly working-class residents who prize the South Side neighborhood for its tidy blocks of handsome bungalows and its busy main street. Cook County recently invested in the area, naming it as one of more than a dozen places in the city to benefit from the Land Bank program, which puts vacant lots up for sale at attractive prices. A fully rehabbed bungalow goes for a little more than $200,000; an unrenovated one goes for half that.

A five-bedroom house in Belmont Cragin
A five-bedroom house in Belmont Cragin: $299,900 Photo: Courtesy of VHT

Jefferson Park

Median house sale price:$297,000
Change since 2006:–18%
Change since 2015:8%

Ask about the future of Jefferson Park, where prices have been climbing back toward their precrash peak, and real estate agents tend to point to one feature on the map: the Metra line. Count on gentrification creeping steadily into neighborhoods farther out along Metra’s northwestern corridor. “People in their late 20s and early 30s are going to start attacking this area soon,” says one local real estate agent.

West Ridge

Median house sale price:$350,000
Change since 2006:–16%
Change since 2015:6%

This staid far northern neighborhood has proximity to the Red Line, quiet streets, and excellent schools—all long-standing factors that would suggest an area where price appreciation is already built in. But the inventory in West Ridge tends to be dated and thus ripe for rehab—and investment. Older residents are moving out in increasing numbers, making now a good time to get in.

« Back to the main article