July 21, 1919
Chicago, Illinois
A dirigible, the Wingfoot Air Express, crashes into the Illinois Trust and Savings Building, killing 13

The dirigible caught fire while in flight. When it was clear the dirigible could not be saved, the 3 crew members and 2 passengers parachuted from the craft. Two of the crew were able to reach the ground safely. However, the third member of the crew died when his parachute caught fire, one passenger’s parachute tangled with the dirigible and was killed when it crashed, and the other passenger broke his legs while parachuting and later died in the hospital.

The dirigible crashed into the Illinois Trust and Savings Building’s skylight just as the bank’s employees were closing for the night, and flaming debris and shattered glass rained upon them. Ten bank employees were killed from the wreckage and a further 27 were injured.

A view of the crash site

Debris litters the lobby floor

Last Flight of the Wingfoot Express
Eric Edward Esper, 2014
[Source]