Wikipedia: Raising of Chicago

During the 19th century, the elevation of the Chicago area was not much higher than the shorelines of Lake Michigan. The lack of drainage caused unpleasant living conditions, and standing water harbored pathogens that caused numerous epidemics. In 1856, engineer Ellis S. Chesbrough drafted a plan for the installation of a city-wide sewerage system. Workers then laid drains, covered and refinished roads and sidewalks with several feet of soil, and raised most buildings to the new grade with hydraulic jacks.

In January 1858, the first masonry building in Chicago to be thus raised—a four story, 21 m long, 750-ton brick structure situated at the north-east corner of Randolph Street and Dearborn Street—was lifted on two hundred jackscrews to its new grade, which was 1.88 m higher than the old one, “without the slightest injury to the building.”

Many of central Chicago’s hurriedly erected wooden frame buildings were now considered wholly inappropriate to the increasingly wealthy city. Rather than raise them several feet, proprietors often preferred to relocate these old frame buildings. Consequently, the practice of putting the old multi-story, intact and furnished wooden buildings on rollers and moving them to the outskirts of town or to the suburbs was so common as to be considered nothing more than routine traffic.

Traveller David Macrae wrote incredulously, “Never a day passed during my stay in the city that I did not meet one or more houses shifting their quarters. One day I met nine. Going out Great Madison Street in the horse cars we had to stop twice to let houses get across.