Find cheap flights from Boston to Kissimmee - Compare and Save

When flying out of Boston you’ll be using Boston Logan Intl. Kissimmee does not have its own airport so you’ll be flying into nearby Orlando airport, which is 11.0 mi away.

Direct flights cover the 1,121 miles separating Boston and Kissimmee in about 3h 10m.

65 direct flights run between Boston and Kissimmee on a daily basis. On average, there are about 459 departures each week.

Consider leaving on a Wednesday and avoid Saturdays if you are looking for the best rates. For your return to Boston, you’ll find the best rates on Thursdays and the most expensive ones on Mondays.

KAYAK is a travel search engine. That means we look across the web to find the best prices we can find for our users. With over 2 billion flight queries processed yearly, we are able to display a variety of prices and options on flights from Boston to Kissimmee.

KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight to Kissimmee from Boston is likely to change within 7 days, so travelers know whether to wait or book now.

Hacker Fares allow you to combine one-way tickets in order to save you money over a traditional round-trip ticket. You could then fly to Kissimmee with an airline and back to Boston with another airline.

Sometimes travel dates aren't set in stone. If your preferred travel dates have some wiggle room, flexible dates will show you all the options when flying to Kissimmee from Boston up to 3 days before/after your preferred dates. You can then pick the flights that suit you best.

In the last 5 days, the cheapest one-way ticket between Boston and Kissimmee found on KAYAK was with Frontier for $43. Breeze Airways offered a round-trip connection from $61 and Frontier from $72.