Rovelstad followed conventions dating back at least as far as the Columbian Exposition. On the front of the coin (above, left) the Water Tower, the ruins of the Second Presbyterian Church, and a fragment of the Chicago Historical Society building can be seen in front of the flames. Behind them, representing the city a hundred years later, are the First National Bank Building, Marina City, Lake Point Tower, and the John Hancock Building. The four stars stand for Fort Dearborn, the fire, the Columbian Exposition, and the Century of Progress. On the reverse (above, right) the twenty-one stars encircling the seal of Chicago are in honor of the fact that Illinois was the twenty-first state to join the Union. The Society explained the meaning of the city seal: "The shield represents the national spirit of Chicago; the Indian, the original inhabitants of the area. The ship in full sail symbolizes the rise of civilization and commerce in Lake Michigan. The sheaf of wheat represents the cultural riches of the area that surrounds Chicago, and the babe in the shell symbolizes a pearl, signifying that Chicago shall be the 'gem of the lakes.' The city's Latin motto, 'Urbs in Horto' means 'The City in a Garden.' The date, March 4, 1837, is the date of incorporation of the city."

The classic size (2 1/2" in diameter) and coin size (1 1/2") were available in both silver and antique bronze (pictured above). The silver medallions (.999 fine) were serially numbered and priced at $35 and $10, the bronze at $6 and $1. They were sold at 120 participating banks and savings and loan associations, as well as in the museum store, in order to raise money for the Society. The project failed to meet expectations. In 1975 an Atlanta company named East Coast Coin Exchange, noting that only half of the planned total of 15,000 silver medals were minted, offered a remaining stock of 1800 in the two sizes for sale. The larger medal was now $80.