Chatham

Chatham runs roughly from 79th to 95th between the Dan Ryan and Cottage Grove. It became a center of Black professional and business life in Chicago in the mid-twentieth century and has held that character since, with unusually high owner-occupancy and unusually long tenure.

The housing is brick: bungalows, two-flats, and some larger courtyard buildings, most of it built in a twenty-year window and much of it maintained by owners who have been there for decades. Walk the blocks and you can see it.

County records put the median two unit sale at $250,500 over the two years ending May 2026, across 34 arms length sales, with the middle half between $147,000 and $340,000. On three year medians the figure ran $193,000 for 2019 through 2021 and $268,000 for 2023 through 2025. Note the last three year medians: $240,000, then $250,000, then $268,000. It moves in steps rather than a smooth line, which is normal in a market this owner-occupied.

What that owner-occupancy means for an investor is fewer distressed sellers and better average condition, but also less inventory. You will wait for the right building here rather than choosing among five.

I like Chatham for someone buying one good building to hold. It is not where you go to assemble a portfolio quickly, and anyone telling you otherwise has not tried.