The ClarkeFord house claims to be Chicago’s oldest, built in 1836. It’s now a museum.
The NobleSeymourCrippen house also claims that title, but Norwood Park wasn’t technically in Chicago when it was built in 1833.  It is now the Norwood Park Historical society.
The Netterstrom House in Lake View is among the oldest houses in the city – but this one is still a home.