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During the 1850s and 1860s, engineers carried out a piecemeal raising of the grade of central Chicago to lift the city out of its low-lying swampy ground. Buildings and sidewalks were physically raised on jackscrews.

Many of central Chicago’s hurriedly-erected wooden frame buildings were now considered inappropriate to the burgeoning and increasingly wealthy city. Rather than raise them several feet, proprietors often preferred to relocate these old frame buildings, replacing them with new masonry blocks built to the latest grade. Consequently, the practice of putting the old multi-story, intact and furnished wooden buildings—sometimes entire rows of them en bloc—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, “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.” The function for which such a building had been constructed would often be maintained during the move, with people dining, shopping and working in these buildings as they were rollered down the street.