Inaugurated July 17, 1928, Contract Air Mail Route 27, as originally placed in operation, was unique in that it serviced a greater number of cities than any earlier Contract Air Mail route. The inaugural service covered the vast automotive district of Michigan and had three distinct northern terminals: from Chicago to Kalamazoo, where it split into three segments to Muskegon, Detroit, and Bay City.

This cover was carried on the inaugural Contract Air Mail Route 27 flight from Detroit, Michigan to Kalamazoo, Michigan (where it was backstamped) and is listed in the Contract Air Mail Flights (CAM) Section of The American Air Mail Catalogue as 27W10.

During 1931 the airline changed its name to Transamerican Airlines Corporation. The airline was later purchased by American Airlines.