I played a lot of MS Flight Simulator 4.0. Probably older versions too. I think I had one on a 286 but don't really remember. I definitely crashed a lot. Landings were the hardest. As I recall you could change the weather and customize planes. For really interesting flying.
I also played a lot of fighter pilot games. Which seem to have died off. Leaving arcade style ones or junk not as detailed as commercial plane simulators. Which makes no sense as I'd rather fly a F/A-18 hornet than a Boeing 747.
Jane's flight simulators have been around a very long time.
Their latest 1999USAF has some fun planes to fly if you like fighter jets.
I remember high mem DOS booting my old Pentium 75 to be able to play some of the older ones.