Clue #1 says that everyone flew east on their first flight. By looking at the map, we can see that, out of each city, Confondre Airlines has one flight east and one flight west, except for Tokyo, where both flights go east. However, since everyone flies to a different city, the person flying from Tokyo must fly to Sydney, since the person flying from San Francisco must fly to NYC.

Here’s a diagram of all the flights (highlighted in blue) taken during the first leg of each person’s journey.

At this point, it is not possible to tell which person is on which flight.

Clue #2 says that Vanessa’s second flight had to be shorter than her first, and that Richard had a choice between a second flight shorter or longer than his first flight. Let’s compare the lengths of all possible second leg flights against the first leg flights.

From this chart, there’s only one first flight (Sydney to San Francisco) that results in two shorter second flights and only one first flight (Paris to Tokyo) that results in a choice between a shorter and longer second flight.

Thus, Richard had to go from Tokyo to NYC (he picked the longer second flight over the shorter one). Even though Vanessa could fly to either NYC and Tokyo, since Richard is flying to NYC, Vanessa must fly to Tokyo on her second flight.

Based on the flights given, Richard must then fly from NYC to Sydney (because he cannot go back to Paris), and then on to San Francisco (again, because he cannot go back to Paris). Similarly, Vanessa must fly from Tokyo to NYC (because she cannot go back to Sydney), and then on to Paris (again, because she cannot go back to Sydney). We now know two full sequences of flights.

Clues #3 and #4 compare flight lengths for the third and fourth flights. Before we get to those clues, let’s see if we can determine the remaining sequences of flights, since we’ve already established two of them.

Combining the last two charts, we can see that the person flying first from NYC to Paris must go on to San Francisco, since Vanessa is flying to Tokyo on her second flight.

We can then determine that this person must continue on to Tokyo, and then to Sydney, to avoid returning to NYC. Since this person is flying to San Francisco on their second flight, then the person first flying from Tokyo to Sydney must go on to Paris.

This person then must continue on to San Francisco, and then to NYC, to avoid returning to Tokyo. Since this person is flying to Paris on their second flight, then the last person, flying first from San Francisco to NYC, must go on to Sydney.

This person must continue on to Paris, and then to Tokyo, not only in order to avoid returning to San Francisco, but also to avoid everyone else!

Now that we have all of the flight sequences, let’s use the last two clues to see if we can figure out who goes with which sequence. Clue #3 states that Scott’s third flight was shorter than everyone else’s third flight. The flight from San Francisco to Tokyo was shorter than all the other third leg flights, so that sequence must be Scott.

Clue #4 then states that Raigan’s fourth flight was shorter than Tiffany’s fourth flight. This means that Raigan must have flown from San Francisco to NYC, and Tiffany must have flown from Paris to Tokyo.