Chicago's first Christmas Parade was on State Street on December 7, 1934. Gregory and a costumed Santa Claus led the caravan, which was filled with toys and various merchandise from State Street businesses. As the city's government officials had hoped, the parade contributed to desirable growth in the local economy and 1934 held the city's largest holiday buying period since 1927. This was both exciting and surprising for the entire city. Not only was it the Depression, but that day held dangerously low temperatures throughout the entire state. Some areas of Illinois were as low as fourteen degrees below zero (fahrenheit).
In 1935, the city was in even worse financial status as a result of the Depression. The city could not afford the expensive floats that were used the year before. However, the event had been so successful in the previous year that The State Street Council and the City of Chicago agreed to use an old trolley to pull the floats, as there were trolley tracks on State Street at the time.