Cheap Flights from Windsor Airport to Massachusetts from $362 Roundtrip

Flight deals from Windsor Airport to Massachusetts

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

Boston.$362 per passenger.Departing Wed, Dec 31, returning Fri, Jan 2.Round-trip flight with Porter Airlines.Outbound indirect flight with Porter Airlines, departing from Windsor on Wed, Dec 31, arriving in Boston Logan International.Inbound indirect flight with Porter Airlines, departing from Boston Logan International on Fri, Jan 2, arriving in Windsor.Price includes taxes and charges.From $362, select.

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Flying from Windsor Airport to Massachusetts

Arm yourself with these facts on the fly.

Cheapest flight found	$362
Cheapest month to fly	December

How to find cheap flights from Windsor Airport to Massachusetts

We've compared the best online travel agents and flight providers on the internet to find the cheapest plane tickets from Windsor Airport to Massachusetts. Other savvy travelers recently found round-trip flights from $362 and one-way tickets from $182. Ready to join them? Here are a few tips to help you do it the smart way.

Fly in December

The cheapest time to fly from Windsor Airport to Massachusetts is currently December.

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 Windsor 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 Windsor 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 Massachusetts Airport to Massachusetts flight price you see when you search with us is what you pay to the provider.

Frequently asked questions

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

We looked at all of the upcoming round-trip flights from Windsor Airport to Massachusetts we could find over the next 12 months. It looks like $362 is the best price. This is good, compared to the average Massachusetts ticket price of $362.

What is the cheapest month to fly from Windsor Airport to Massachusetts?

The cheapest month to fly from Windsor Airport to Massachusetts is currently December.

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

After crunching the numbers on our flight calendar, we found that it is currently cheapest to fly from Windsor Airport to Massachusetts on Wednesday, December 31, 2025.

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

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