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$510+ Cheap flights from Massachusetts to Windsor, ON (YQG)

This is the cheapest round-trip flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 11/25. Fares are subject to change and may not be available on all flights or dates of travel.
BOS — YQG
Dec 2 — Dec 91
Tue 12/2
Tue 12/9
1 adult, Economy
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Find flight deals from Massachusetts to Windsor

Cheapest flights from Massachusetts to Windsor
Explore the most affordable flight options available from Massachusetts to Windsor. Find the lowest fares from popular airlines and budget airlines, with prices last updated on November 2, 2025.

This FlightHub deal was found by Cheapflights users on 11/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 11/251:25 pmBOS - YQG
1 stop6h 08mPorter Airlines
Tue 12/27:35 amYQG - BOS
1 stop5h 05mPorter Airlines
Deal found 11/1$510
This Air Canada deal was found by Cheapflights users on 11/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Air Canada is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 11/256:15 amBOS - YQG
1 stop12h 59mAir Canada
Tue 12/29:45 amYQG - BOS
2 stops9h 27mAir Canada
Deal found 11/1$515

Cheap flight deals from Massachusetts to Windsor

Keep the following information in mind while searching for Massachusetts to Windsor flight deals. Data was last updated November 2, 2025.

Most accurate provider

eDreams
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$441
(Air Canada)
Provider with most accurate pricing for Boston Logan Intl-Windsor flight deals.
Search Deals
Provider most trusted by Cheapflights users for Boston Logan Intl-Windsor flights.
Search Deals
From Massachusetts to Windsor
Search Deals

Cheapflights Fare Finder

 
Customize your flight search to find flights from Massachusetts to Windsor that fit within your specific budget. Explore options based on user searches and filter the results based on your desired price range. Find flights that match your budget for a cost-effective journey. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated November 2, 2025.
Use the filters below to find and compare flights from Massachusetts to Windsor that are best for you.

Fly from

Massachusetts

Fly to

Windsor

Route

Depart

Return

Price

BostonWindsor

BOS - YQG

BOSYQG

Boston Logan Intl

Tue 11/25

1:25 pm-7:33 pm

1 stop6h 08m

Windsor

Tue 12/2

7:35 am-12:40 pm

1 stop5h 05m

$510

BostonWindsor

BOS - YQG

BOSYQG

Boston Logan Intl

Tue 11/25

10:15 am-9:04 am

2 stops22h 49m

Windsor

Tue 12/2

9:45 am-7:12 pm

2 stops9h 27m

$630

Flights are sorted by cheapest round-trip flights first.

Deals found on 11/1

Best time to book a flight from Massachusetts to Windsor

Have a flexible travel schedule? Discover the best time to fly to Windsor from Massachusetts with our price prediction graph.
Estimated round-trip price
Rates are based on past data. Find the cheapest month and day to book your flight based on your travel requirements, then search for cheap deals.

Cheapflights Insights

Everything you need to know about your flight from Massachusetts to Windsor
No data available for this route at this time. Please check back soon.

Related info for your journey

Find useful and relevant information for your journey from Massachusetts to Windsor. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.

  • What airport do you fly into for flights to Windsor from Massachusetts?

    Windsor (YQG), located 5.0 mi from the city center, is the airport you fly into when you book flights from Massachusetts to Windsor.

  • How long is the flight from Massachusetts to Windsor, Ontario?

    A quick flight from Massachusetts to Windsor, Ontario can take about 6h 08m. Porter Airlines provides one of the quickest options available for as low as $510. There are 610 mi between Massachusetts and Windsor, Ontario. This flight may include one or multiple stops.

  • Can I find deals for flights from Massachusetts to Windsor that include hotel bookings?

    Yes. In addition to deals on Massachusetts to Windsor flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from Massachusetts to Windsor?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Massachusetts to Windsor.

  • Can I find deals for business class flights from Massachusetts to Windsor?

    Yes. Cheapflights offers flight deals from Massachusetts to Windsor by cabin class. In addition to browsing deals, you can also filter by cabin class on the search results page after making a search.

See more FAQs

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Top 2 airlines flying from Massachusetts to Windsor

Discover the top 2 airlines that operate flights from Massachusetts to Windsor. Compare their services, reliability, and customer satisfaction ratings to choose the airline that best suits your travel preferences and needs. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated November 2, 2025.
AirlineCheapestAverageFlexibilityOn-time
Porter AirlinesCheapest$491Average$658FlexibilityNo cancel feeOn-time52%
Air CanadaCheapest$648Average$659FlexibilityNo cancel feeOn-time67%

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