The White Front Hotel, built in 1851 by John Billings, was only one of the many hotels that stood in St. Charles during the mid 19th century. St. Charles had become a popular stopover for travelers on their way to and from Chicago, and so hotels proved to be a profitable business venture.

Over the years, the Italianate building has changed ownership several times. Soon after it was built, Billings sold the building to the Frellson family. They operated the building as a hotel, bar, and dining room. By 1928, following several more changes in ownership, Louis Kacheres leased the building and opened a restaurant and hotel. For the next several decades, the Kachereses ran the bustling business where local residents gathered to exchange news or to enjoy the live music offered in the open air garden behind the building. The hotel rented rooms to guests by the week.