Seconding IL-2 Sturmovik: 1946. It's
$10 on Good Old Games, and the US retail version is completely DRM-free, being from the time when Ubisoft was starting to wise up about that (and then went completely backwards in recent years). It actually surprised me to hear about disc checks on the 1946 release from these very forums.
Even better is the Ultr@Pack mod (currently on UP3.0 RC4 to my knowledge, compatible with the latest version, currently 4.10.1m), which adds 6DoF TrackIR support, a whole bunch of new planes (most notably Korean War-era jets like F-86s and MiG-17s), and other little tweaks and fixes.
I haven't tried multiplayer or anything beyond quick mission mode, which lets you throw together some quick dogfights with just about any aircraft of your choosing, up to 32v32 for a huge furball, 8 flights of 4 each.
$10 goes a long way these days, doesn't it?