The Flight Simulator franchise was originally owned by SubLogic, before it was bought out by M$.
SubLogic published a stand alone version of Flight Simulator for many computer systems (i.e. Amiga, Atari 800, PC). After the initial release, expansion packs were released, which included more cities and locations around the world.
SubLogic's terrain modelers had a real sense of humour. At the time, CPU power was not adequate to render a realistic looking Statue of Liberty in New York. So instead, the statue was a cardboard cut-out, held up by a two-by-four in the back. As well, in the Hawaii expansion, a secret area could be found by flying into the largest volcano. The secret area contained a warp to another island, and a tunnel that went on forever, among other oddities.
To this day, all versions of Flight Simulator have Meigs Field in Chicago as their default starting location, as it was going as far back as Flight Simulator 1.