Kenwood- A previously redlined community in Chicago’s Southside and now a success story for building African American generational wealth

Kenwood was once one of Chicago’s most affluent neighborhoods, and  still contains some of the largest single-family homes in the city. Kenwood was originally settled in the 1850s by wealthy Chicagoans seeking respite from the City. The first of these residents was John A. Kennicott, who built his home near the Illinois Central Railroad at 48th Street. He named his home Kenwood after his ancestral land in Scotland. Kenwood continued to prosper through the 1880s and 1890s, and new concentrations of large single-family homes began to emerge along Drexel Boulevard. By the early 1930s signs of deterioration emerged within the community, as the population exploded but with many of the older homes being converted in rooming houses and subdivided into apartments. Sadly with a large influx of African American’s in the neighborhood, White flight took root in the 60s and 70s and Kenwood’s population plummeted from 41K in 1950s to 21k in 1980. This was also the period when Kenwood’s commercial districts along 43 and 47 streets fell into disrepair and the neighborhood lost a significant amount of its retail and cultural amenities from which it still has not recovered.

Thankfully a large number of middle class homeowners (mostly African American) stuck it out in Kenwood and helped stabilize many gorgeous historic streets in the neighborhood. By the late 70s historic districts were created and by the late 90s the population stabilized. By 2000 in-fill construction began in earnest as the City pushed for the redevelopment of many vacant lots. Kenwood is now an economically diverse neighborhood and what I would consider a success story for a previously redlined African American community. There is now a strong Black middle class here and many of them own their homes and are building generational wealth. The next step for Kenwood is to reconstruct its blighted commercial districts along 43rd & 47th streets so this can truly become a mixed-use walkable community more akin to nearby Hyde Park. Even without strong retail amenities Kenwood is a solid urban neighborhood thanks to its great public transit access, wonderful park amenities, decent walkable schools, diverse and often affordable housing stock, gorgeous historic architecture, and comfortable tree lined streets.

Click here to view my Kenwood album on Flickr


* Excellent urban density.
* Great public transit access and easy access to Dwtn as its only a 15-20 minute train ride.
* Decent bike amenities with two main north-south bike routes and several dedicated bike stations.
* Great sidewalk and ADA infrastructure overall.
* Good diversity overall, especially economic.
* Good number of walkable schools but with mixed ratings.
* Good diversity of for sale options with lots of affordable options. Some 1-beds selling btwn 75K-300K, 2-beds generally sell btwn 100K-350K with some more expensive luxury product. 3 & 4 beds sell btwn 200K and 1 M.
* Good rental supply ranging from moderate to pricy. 1-beds lease in the 1Ks, 2-beds 1.5K-2K. 3-beds btwn the high 1Ks-3Ks. Limited 4 bed rentals.
* Great park amenities including the expansive lakefront parks, several small-medium parks spread through the neighborhood, and the lengthy  Drexel Blvd. Promenade running along the western border.
* Solid tree canopy.
* Generally solid architecture including some very excellent brownstones and 1920s apts bldgs that have been preserved. Wide range of in-fill including some crummy autocentric strip malls, early residential infill attempts and better more recent infill.


* Generally a safe neighborhood but still vestiges of blight and disinvestment that used to blight the neighborhood. Higher crime average than North Chicago neighborhoods.
* Ok cultural amenities: some restaurants, bars, & cafes, an art gallery, local ballet school, a local community theater, and the Hyde Park Arts Center. Convenient access to the many cultural assets in Hyde Park to the south.
* Decent retail amenities including a right sized Walmart, Whole foods, drug store, a couple banks, a Marshall’s & Ross’s, a couple boutiques, plenty of salons/barbers, some gyms, a local post office and library. Many retail amenities nearby in Hyde Park as well.
* Much of the historic commercial fabric has been wiped away along 47th, 43rd but good intact nodes at 47th & Drexel Blvd and Hyde Park & Lake Park Ave.
* Due to a lack of retail amenities pedestrian activity is pretty underwhelming but some activity thanks to Kenwood’s density.
* Kenwood still struggles with a historic negative image and bias, but it seems to be improving as the White population has increased in recent decades.