American Presidents have flown a lot since the 20th century. One company (Lockheed Martin and Bell Aircraft) has provided much of the air transport. A Tradition of Presidential Transport: Lockheed Martin and Bell Aircraft has some details. The site notes, "Lockheed Martin first provided Presidential transport as far back as 1953 with two C-121 Constellation aircraft used by President Eisenhower. Bell Helicopter also has a long tradition providing and supporting Presidential aircraft dating to the first helicopter ride for a Commander-in-Chief in 1957 - a Bell H-13J Ranger. The Rangers were replaced by larger Sikorsky aircraft with more power and space for the President. Today, it is again time to replace the current Marine One helicopter fleet with the larger and more powerful US101 - for a true Oval Office in the Sky."
Here are some excerpts from the page:
1953: Presidential pilot Col. William G. Draper selected a C-121A Lockheed Constellation to transport the newly inaugurated President Eisenhower. Dubbed Columbine II, the four-engine aircraft was a military version of the famed Lockheed 749 airliner, recognized as one of the most beautiful commercial airliners of the piston-engine era.
1957: On July 13, President Dwight D. Eisenhower became the first Chief Executive to fly in a helicopter when he took off from the White House lawn in a Bell H-13J (a three-seat 47J Ranger) as part of Operation Alert, an emergency evacuation exercise. (Picture above.)
1960s-1980s: The Air Force's 89th Military Airlift Wing flew six Lockheed VC-140B light transport jets for special government and White House airlifts. Designed by Lockheed's celebrated Skunk Works in the late 1950s, the four-engine aircraft carried eight VIP passengers in a supplementary role to the President's 707 aircraft, and flew Presidents Johnson, Nixon, Ford, Carter and Reagan.
1982-Present: Lockheed Martin designed and built upgraded avionics systems for the VH-3D and VH-60N Marine One aircraft, which it continues to support today.