You do not have to open all umbrellas at the same time. They just all have to be open eventually. Allow the planes move over big groups and helicopters over smaller groups.
Allow the helicopters to circle in front of the helipad and land the other planes. If you have five helicopters near the helipads, land them and allow the planes circle somewhere until all of them land.
To do get quick game completions, get to the "Game Over screen quickly by crashing two planes. Then, repeat the process. Consider doing this on level 2 due to the frequency of aircraft. Note: You must exit the game from the main menu for your progress to increment. Quitting during game play will not count.