US to South Africa - Less than $500

You have to go through Europe—but who doesn't want a European stopover? Conde Nast Traveler

The flight from New York to Johannesburg is long—not the longest in the world, technically, but certainly one of them. It clocks enough hours in the sky that you start thinking about deep vein thrombosis and how many Amazon TV series (not episodes—series) you need to download before the trip. It's ideal to break up the 16-hour direct flight with a layover in, say, London, and Qatar Airways—one of the world's top airlines—currently has multi-stop fares for under $500. There's a lot of availability all year for a flight that normally costs upwards of $1,500–$1,800. It just takes a little creative planning and flexible timing to make this work.

As discovered by Scott Keyes of How to Fly for Free today, it's best to start with a Google flight search and some weekday departure times. Try Tuesdays in May: One outbound flight, from New York-JFK to Johannesburg via Doha, Qatar, with a return flight from Johannesburg to Berlin via Doha—costs $399. (That's crazy!) You'll need to tack on a one-way flight from Berlin (or your European city of choice), but you can still do all of this for under $1,000, and you'll feel very worldly by the time you're done.