In 1881 Yerkes traveled to Fargo in the Dakota Territory in order to obtain a divorce from his wife. Later that year, he remarried and moved to Chicago. There, he opened a stock and grain brokerage but soon became involved with planning the city's public transportation system. In 1886, Yerkes and his business partners used a complex financial deal to take over the North Chicago Street Railway and then proceeded to follow this with a string of further take-overs until he controlled a majority of Chicago's street railway systems on the north and west sides. Yerkes was not averse to using bribery and blackmail to obtain his ends.