Twenty-five letters written to William M. Doughty, one in 1844 when he resided in Cincinnati and the remaining during 1852-1858 when he resided in Chicago. Fifteen letters are from Doughty’s brother-in-law James P. Kilbreth of Cincinnati regarding real estate in Chicago. As Doughty was acting as Kilbreth’s real estate agent in Chicago, many of these letters contain information regarding various real estate transactions, deeds, and lot prices in Chicago. Several of these letters were written on the letterhead of the Cincinnati Sugar Refinery, of which Kilbreth was a partner. The remaining ten letters were written to Doughty by various family members and business associates. These correspondents include members of his wife’s family, W.W. Guthrie and R.B. Guthrie; Jon. M. Phillips of the Methodist Book Concern regarding the affairs of the Concern; M. Hollingshead regarding Chicago real estate; C.W. Sears concerning a request for a loan; Leroy Swonustedt, asking for help to place his son with a business opportunity; Wm. Glenn & Sons, inquiring after the whereabouts of a certain individual; and T.F. Baldwin on behalf of Jn. C. Harding, concerning financial matters. The letters are written mostly from Cincinnati to Doughty in Chicago, but also include letters written from Pittsburgh, Bloomington, and Chicago.