North to Madison St, south to I-290, west to Central Park Blvd, east to Kedzie Ave
In the 1960s, Fifth City was home to the “seven families”—a division of the nonprofit Ecumenical Institute committed to bettering the impoverished, gang-ridden neighborhood through church renewal and more. This social experiment is referenced worldwide as an example of comprehensive community development, as the members of the organizing body lived in the neighborhood while working to improve it. In the ’60s and ’70s, they established a community center and shopping center while attracting businesses, such as Bethany Hospital and a CTA bus garage, for a $40 million investment in the area. But by the late ’80s, the Ecumenical Institute’s group dissolved and crime has since spread again.
North to 115th St, south to 138th St, west to Indiana Ave, east to I-94
Kensington earned the nickname Bumtown for its many saloons. Though the taverns sustained the area through the late 1900s, ironically—thanks to the persistence of the Salem Baptist Church—Kensington was voted dry in 1998, and remains alcohol-free today.
North to 35th St, south to 43rd St, west to Cottage Grove Ave, east to Lake Michigan
Just north of Obama’s Kenwood neighborhood, Oakland (once home to 19th-century women’s and Jewish rights activist Hannah Greenebaum) is small and often overlooked. A handful of beautiful turn-of-the-century mansions along Drexel Boulevard are worth a detour. Ditto for the home at 4122 South Ellis Avenue, one of Dankmar Adler and Louis Sullivan’s few surviving residential projects.
North to 63rd St, south to 65th St, west to Long Ave, east to Lavergne Ave
This teeny-tiny area just south of Midway Airport (commonly considered part of the Clearing neighborhood) sprung up around Lawler Park during World War II to house the Chrysler Defense Plant workers building B29 bomber engines. The plant was later used by Ford; today, the site is home to the Ford City Mall and the Tootsie Roll factory.
North to 91st St, south to Kenton Line Subdivision railroad, west to Cregier Ave, east to Paxton Ave
Why the name? Beginning in the 1970s, the area was home to many affluent doctors who worked at the nearby South Chicago Community Hospital, and a play titled Pill Hill (which debuted at Yale Repertory Theatre in 1990) was set in this neighborhood. Today, the hospital is called Advocate Trinity and many of its doctors live in more far-flung ’hoods.
North to Irving Park Rd (and Forest Preserve Ave between Harlem and Narragansett Aves), south to Belmont Ave, west to Cumberland Ave, east to Austin Ave
Dunning was home to a large poorhouse and insane asylum in the mid-1800s, which was shut down by the city in the late 1800s for overcrowding and misconduct. Part of the area renamed itself West Portage Park to distance itself from the stigma of the Dunning name. The building was reopened as State Hospital in the early 1900s; in the ’70s, it became Chicago-Read Mental Health Center, which is still open today.