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As far as I can tell, in the U.S., 49 USC 46317(a) makes flying without a proper certificate a crime punishable by fine and/or imprisonment. However, the FAA is a regulatory agency, which means it can only assess civil penalties (e.g., civil fines or revocation of certificates).

In practice I've heard (and would expect) the FAA gets quite exercised over "airmen" found to be carrying passengers for hire without current and proper certificates.

What I'm wondering is whether individuals have ever been, or are routinely, subject to any scrutiny or regulatory or prosecutorial action if they fly without certificates and don't commit any other egregious violations of FAA regulations? E.g., if you only fly registered aircraft for your own amusement, and you never break a serious airspace rule, but you never get an FAA certificate, could you expect to go your whole life without any trouble from the FAA? If not, what sort of trouble might you expect and how would you get into it?

And has anyone ever faced criminal prosecution for flying without proper certificates who did not also commit a gross violation of safety while operating an aircraft for hire, or some other felony (e.g., smuggling)?

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    $\begingroup$ Some estimates indicate that up to half of all pilots in Alaska don't have any kind of license.. $\endgroup$ – pericynthion Dec 6 '15 at 1:12
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    $\begingroup$ Sentenced for Flying Without a License $\endgroup$ – mins Dec 6 '15 at 2:05
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    $\begingroup$ @mins - Good find. But I wonder if the triggering circumstance was that he was flying an unregistered plane ... and how air traffic control would have known it wasn't registered? (Also, he had previously falsified applications for certificates, and he is "owner of two aircraft parts/salvage businesses," so this may have been the equivalent of finally nabbing Capone for tax evasion, or a scofflaw for jaywalking?) $\endgroup$ – feetwet Dec 6 '15 at 2:36
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    $\begingroup$ You are right, just a track to follow, there are many cases. $\endgroup$ – mins Dec 6 '15 at 11:00
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    $\begingroup$ @mins - Wow, excellent resource! I wonder if somebody is familiar enough with these to deduce customs or practices: E.g., all reported "sentencings* I've browsed seem to be associated with other infractions like operating unregistered aircraft. Meanwhile, everywhere I've checked this general question I seem to find that mention that a majority of Alaska pilots have no certificates at all. $\endgroup$ – feetwet Dec 6 '15 at 19:19
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First, if you fly privately without a license can you avoid trouble with the FAA? Yes, if you don't attract attention to yourself.

It's essentially the same as driving a car without a license or insurance: it happens because some people just don't see why they should have to get a license, and it's possible because no one regularly checks every car and every driver. Anecdotally, there are plenty of pilot stories about unlicensed pilots in rural, remote areas who fly out of private strips or small, uncontrolled airports. Alaska in particular is notorious: I've heard the 'joke' several times that the FAA used to have the goal of getting at least 50% of Alaskan pilots certificated.

Second, if you do get caught by the FAA or by law enforcement, what happens? As you said, the FAA can revoke your certificate but state or federal officials can go after you with criminal charges. This is from the criminal indictment of someone who was accused of lying about his pilot's and mechanic's certificates:

At sentencing he faces a maximum of five years in prison and a \$250,000 fine for each of the two criminal counts of making false statements to the FAA, and a maximum of three years in prison and a \$250,000 fine for each of the three counts of flying without proper authorization.

I couldn't find out what happened with that case, though, so I don't know if he was found guilty or not and penalties - if any - he really faced. @mins found another example that did result in a prison sentence.

Finally, there is one legal way to fly in the US without a license: fly an ultralight under part 103.

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    $\begingroup$ For the first case: "60 days incarceration, three years of probation, and a $5,000 fine [...] also ordered to sell his airplane and not enter an airport, unless [...] as a passenger, for three years" $\endgroup$ – mins Dec 6 '15 at 11:10
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    $\begingroup$ Only prosecution in UK recently was in 2011, guilty of being pilot in command on 3 occasions, once on UK registered, twice on US registered passenger aircraft. Fined £4500 plus £1100 costs. $\endgroup$ – user23614 Dec 7 '15 at 13:13
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    $\begingroup$ @user23614 still cheaper than flight training. $\endgroup$ – RaajTram Aug 2 '16 at 21:37
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As it was explained to me by an unlicensed pilot and an FAA inspector having lunch in rural Alaska, the punishment if any is determined by how serious the infraction. If you are caught like this guy was, having a quaint conversation along with a sandwich, probably nothing. If you were doing something that endangered only yourself, the FAA will insist you get certified before operating the aircraft. If you endanger others the penalties get more severe. Etc etc. it also depends on the mood of the official and your response to his inquiry. long and short of it, could walk away with a snicker and a warning, might get the book thrown at you.

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