Are there any games where you can just casually fly about and explore kinda like in Pilot Wings 64 (especially like with the USA map level where there was a ton of crap to see)? Preferably with a regular analog game pad.

I'm not even kidding with this:Google Earth Flight Simulator

https://support.google.com/earth/answer/148089?guide=22385&ref_topic=23746

Not sure if that's what you're looking for but I figured it couldn't hurt.

PW64 was awesome, one of the few games I owned for that system that I refused to trade away to friends who kept losing cartridges.

I would suggest Sky Odyssey for the Playstation 2. It's fairly old now and was never very popular; you can probably buy a used copy for fairly cheap.