The oldest house in Chicago was built in 1836. It has been moved twice, and stands today in the Prairie District.

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The house is now a museum, and has some incredible history:

It survived fires, was a church for a short time, and during one of its moves (in 1977), was lifted entirely over the el tracks.

The house was built for Henry B Clarke, a New Yorker who moved to Chicago a few years before. According to Wikipedia, the house was built by John Rye, who later married the Clarkes' housemaid.

It is (obviously) a Chicago Landmark, and was added to the National Register of Historic Places in 1971.