This first map shows a possible progression of Benjamin from his possible birthplace in Alabama (where his father Abraham lived) to the Cherokee lands in Arkansas, to upper New York just south of Lake Ontario, to Dowagiac, Michigan where he obtained a medical license and he and his wife had their first 2 children, to Chicago where their son Benjamin was born, to Deerfield, IL where he died.
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This map shows the area north of the Finger Lakes and south of Lake Ontario in upstate New York where all of Benjamin's letters are from.
We also know that he was preaching in Chicago in late 1844, early 1845, as evidenced by an article in a Welsh publication describing an encounter and conversation with him.
Given the time period, I assume he would have come to Dowagiac and Cass County, Michigan, and eventually Chicago on the Sauk Trail / Chicago Road that connected Detroit to Chicago at the time.
Cass County, Michigan has a rich history and Dowagiac is home to the Pokagon Band of Potawotomie.
Benjamin stated that he preached among the Potawatomie in Michigan, and we know he was registered there as an Indian Physician (scroll down for that image.) He lived there when Abraham and Hattie were born there.
Here is a newspaper from Cass County in 1863. It does not mention Benjamin, but it shows what it was like at that time. http://discovercasscounty.com/historic-public-structures/
Benjamin is listed in the Chicago City Directory in 1869, a year before his death.
Name: Benjamin M Whitecloud
Residence Year: 1869
Street address: 99 Butterfield
Residence Place: Chicago, Illinois, USA
Occupation: Physician
Publication Title: Chicago, Illinois, City Directory, 1869
Benjamin is listed in the Chicago City Directory in 1867 living at 259 21st Street.
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Benjamin is listed in the Chicago Business City Directory in 1866 as a physician with an office at 131 E. Adams. This would have been where the Art Institute stands today. After the great fire in 1871 (only 5 years after this publication and one year after his death) the great fire destroyed everything on Michigan Avenue from Congress north to the River. Lake Michigan used to run just east of Michigan Ave past the train tracks. So his office would have been right on the lake in what was a mostly residential area in 1866. The shoreline of the lake was moved east after the fire, with the debris from the fire creating what is now Grant Park.
Benjamin is in the 1865 Tax list in Dowagiac, Michigan where he is listed as a physician. We know his children Abraham and Hattie were already born by then, both being born in Michigan. His son Benjamin was born in Chicago in 1865, this same year. So we can assume he moved to Chicago in 1865. (He is listed toward the bottom)
Benjamin is listed as living in Kalamazoo, Michigan in this 1863 Tax Roll from Michigan.
