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Hotel Moraine-on-the-Lake opened in Highland Park in 1898 to serve vacationing Chicagoans, many from the city's exclusive Gold Coast. Hotel Moraine was designed by Highland Park architect, Ernst Mayo, for F.W. Cushing and named for the nearby granite rock shelf. Originally open solely for the summer months, many guests spent their entire summer at the hotel. The Hotel operated at maximum capacity for its first 35 years, but was negatively effected by the stockmarket crash and subsequent Great Depression. In 1943 Jules Reingold, a wealthy real estate man from Glencoe, Illinois, bought the hotel and ran it successfully until his death in 1947 The Hotel changed hands several times between 1947 and 1963. In 1963, Richard S. Wright Enterprises purchased the hotel, capitalizing on the dining room and numerous meeting rooms to attract industry conferences. By 1968, the hotel was empty again. Illinois Bell rented and redesigned the hotel's garage to serve as a school for telephone operators. In 1969, Bert Schwarz purchased the land with intentions of tearind down the hotel and building a lakeshore high-rise. Moraine Citizens Committee, a group of Highland Park residents and politicians, mobilized to block the high rise development though a city wide referendum that would granted the City of Highland Park the funds to purchase the Moraine Hotel property for a future park and nature preserve. The original Hotel Moraine-on-the-Lake was demolished in 1972. In 1999, The Highland Park City Council proposed deeded the property to the Park District of Highland Park in hopes the park built where the Hotel Moraine-on-the-Lake will be better maintained.
In 1969, construction for a modern hotel began on a 4.5 acre parcel of land in Highwood, Illinois. The hotel opened in 1970 as a Ramada Inn franchise. Between 1972 and 1985, the Ramada Inn changed hands several times and becomes the Highwood Inn. In 1985, local restaurateur William Pigati purchased the Highwood Inn and renames it the Hotel Moraine.