Cheap Flights from Orlando International Airport to Massachusetts from $104 Roundtrip

Flight deals from Orlando International Airport to Massachusetts

Looking for cheap flights from Orlando International Airport to Massachusetts, or a last-minute trip? Find the cheapest prices on one-way and round-trip flights right here.

Boston.$104 per passenger.Departing Tue, Aug 5, returning Wed, Aug 6.Round-trip flight with Spirit Airlines.Outbound direct flight with Spirit Airlines departing from Orlando International on Tue, Aug 5, arriving in Boston Logan International.Inbound direct flight with Spirit Airlines departing from Boston Logan International on Wed, Aug 6, arriving in Orlando International.Price includes taxes and charges.From $104, select.

Hyannis.$313 per passenger.Departing Thu, Aug 21, returning Thu, Aug 28.Round-trip flight with American Airlines.Outbound indirect flight with American Airlines, departing from Orlando International on Thu, Aug 21, arriving in Hyannis.Inbound indirect flight with American Airlines, departing from Hyannis on Thu, Aug 28, arriving in Orlando International.Price includes taxes and charges.From $313, select.

Nantucket.$460 per passenger.Departing Tue, Jul 22, returning Sat, Jul 26.Round-trip flight with Delta.Outbound indirect flight with Delta, departing from Orlando International on Tue, Jul 22, arriving in Nantucket.Inbound indirect flight with Delta, departing from Nantucket on Sat, Jul 26, arriving in Orlando International.Price includes taxes and charges.From $460, select.

Worcester.$597 per passenger.Departing Thu, Jul 10, returning Mon, Jul 14.Round-trip flight with jetBlue.Outbound direct flight with jetBlue departing from Orlando International on Thu, Jul 10, arriving in Worcester.Inbound direct flight with jetBlue departing from Worcester on Mon, Jul 14, arriving in Orlando International.Price includes taxes and charges.From $597, select.

Flying from Orlando International Airport to Massachusetts

Arm yourself with these facts on the fly.

Cheapest flight found	$104, Boston
Cheapest month to fly	August
Average flight time	2 hrs, 57 mins
Average flights per week	432
Most popular airline	Azul Airlines

How to find cheap flights from Orlando International Airport to Massachusetts

We've compared the best online travel agents and flight providers on the internet to find the cheapest plane tickets from Orlando International Airport to Massachusetts. Other savvy travelers recently found round-trip flights from $104 and one-way tickets from $49. Ready to join them? Here are a few tips to help you do it the smart way.

Fly in August

The cheapest time to fly from Orlando International Airport to Massachusetts is currently August.

Fly on a Wednesday

From our data, we can see that Wednesday seems to be the cheapest time to fly from Orlando International Airport to Massachusetts.

Flex your dates for the best rates

If you’re flexible on your departure dates, you can use Skyscanner's whole month tool to find the cheapest day of the year to fly from Orlando International Airport to anywhere you choose in Massachusetts.

Watch as flight prices go up and down

With Price Alerts, we'll let you know when flight prices from Orlando International Airport to your chosen airport in Massachusetts go up or down so you can book when the time is just right.

Relax – these are fee-free plane tickets

With us, there are no added fees – the Orlando International Airport to Massachusetts flight price you see when you search with us is what you pay to the provider.

Frequently asked questions

Are there any direct flights from Orlando International Airport to Massachusetts?

Yes – direct flights currently operate from Orlando International Airport to Boston Logan International Airport and Worcester Airport in Massachusetts.

What is the average price of a flight from Orlando International Airport to Massachusetts?

We looked at all of the upcoming round-trip flights from Orlando International Airport to Massachusetts we could find over the next 12 months. It looks like $104 is the best price. This is good, compared to the average Massachusetts ticket price of $336.

What is the cheapest month to fly from Orlando International Airport to Massachusetts?

The cheapest month to fly from Orlando International Airport to Nantucket Airport is currently July.
The cheapest month to fly from Orlando International Airport to Hyannis Airport is currently August.
The cheapest month to fly from Orlando International Airport to Worcester Airport is currently July.
And the cheapest month to fly from Orlando International Airport to Boston Logan International Airport is usually August.

On which upcoming date is it cheapest to fly from Orlando International Airport to Massachusetts?

After crunching the numbers on our flight calendar, we found that it is currently cheapest to fly from Orlando International Airport to Massachusetts on Tuesday, August 5, 2025.

If I'm flying from Orlando International Airport, where in Massachusetts is cheapest to fly to?

If you're flying from Orlando International, the cheapest city in Massachusetts to fly into is Boston. The cheapest airport serving Boston at the moment is Boston Logan International.