For travellers in Westchester, Fairfield County & the lower Hudson Valley
Airlines we've seen on this route recently: MX.
Right now the best HPN → Orlando round trip we can see is $169, departing Fri Aug 21 on MX. That is a real fare we found, not an average — but fares move constantly, so treat it as a starting point and confirm before you book.
Cheapest round trip we've found for each of the next few months. Every Disney blog will tell you September is cheap and spring break is not; this is what the fares actually say for your airport.
| Month | Cheapest RT | Best date found | |
|---|---|---|---|
| Jul 2026 | no fares found | — | |
| Aug 2026 cheapest | $169 | Fri Aug 21 · MX | book → |
| Sep 2026 | $261 | Tue Sep 8 | book → |
| Oct 2026 | $442 | Thu Oct 8 | book → |
For a Disney World trip the honest default is Orlando International (MCO) — it has the deepest schedule, and Disney-bound ground transport is built around it. Orlando Sanford (SFB) is worth a look only if the fare gap is large enough to cover a longer, more expensive transfer to the Disney area; it is farther out and served by far fewer airlines. The usual advice in the Disney world is to ignore Sanford entirely — that is right most of the time, but it is worth checking rather than assuming, especially if you're flying a carrier that only serves SFB.
This is the part fare sites leave out. At a smaller airport like HPN, how often the route flies matters as much as the price. A route that operates a few days a week quietly decides your trip length — you fly when it flies — and if that flight cancels, the next one may not be the same day. If you're booking a short trip, or travelling at a time you cannot flex, that risk is worth paying a little more to avoid, either by flying a bigger nearby airport or by choosing a day with more than one departure.
Southwest does not publish fares to search sites, so it never appears in the numbers above — and it serves a lot of Disney travellers. If it flies your airport, check it directly before booking anything else. Check Southwest HPN → MCO →
Fares are indicative and refresh periodically — always confirm the final price on the airline or booking site before purchasing. Prices and availability change frequently.