Market Garden info from a Google search:
In the hour and one-half from 1025 to 1155 Sunday morning, 17 September,
the greatest troop carrier fleet in history took off. Approximately
one-half of 3 divisions became airborne. Elements of the British 1st
Airborne Division and corps headquarters, with their equipment, were
lifted from the Newbury region by 145 United States parachute aircraft and
354 British and 4 American gliders towed by 358 British tugs. The troops
of the American 101st Airborne Division, coming from the same area, were
transported in 424 United States parachute aircraft and 70 United States
gliders towed by American tugs. From the vicinity of Grantham came
elements of the United States 82d Airborne Division in 480 United States
parachute aircraft and 50 American gliders towed by United States tugs.
The total force, including the pathfinder aircraft that led the way to
each drop and landing zone being used that day, was made up of 1,544
airplanes and 478 gliders.
That's for a three para div drop which was done in two stages. So air transports should be as expensive as they are in the game.