"John" wrote in message ...
A passenger wins a raffle prize or makes a donation to a charity, school
fund-raiser etc to win something. The winning item is an airplane
ride. [...] In other words, the
passenger paid money, with the expectation of an airplane ride, although
the money isn't spent on the plane or pilot. Is this legal?

Yes.

Change the scenario to the pilot has a commercial rating. Does this
change the answer to the question?

No.

Finally, if the airplane ride is to a destination at another airport and
then returning (after a few hours, overnight, weekend etc.) How does
this change the answers?

As far as I know, it doesn't. The key to the flight is the charitable
donation aspect, and I don't recall seeing any exclusion with respect to the
exact nature of the flight.

I have heard differing opinions from people with respect to whether their
local FSDO requires a drug test for such donations, but that's the only
complication I'm aware of.

Pete