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$217+ Cheap flights from Massachusetts to Windsor, ON (YQG)

This is the cheapest one-way flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 1/16. Fares are subject to change and may not be available on all flights or dates of travel.
BOS — YQG
Jan 17 — Jan 241
Sat 1/17
Sat 1/24
1 adult, Economy
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Cheap flight deals from Massachusetts to Windsor

Best flights from Massachusetts to Windsor
Discover carefully curated flight deals from Massachusetts to Windsor that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated December 18, 2025.

This Gotogate deal was found by Cheapflights users on 12/17. 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 Gotogate is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 1/241:00 pmBOS - YQG
1 stop6h 14mAir Canada
Sat 1/319:45 amYQG - BOS
1 stop6h 12mAir Canada
Deal found 12/17$440
This Porter Airlines deal was found by Cheapflights users on 12/16. 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 Porter Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 1/301:30 pmBOS - YQG
1 stop6h 03mPorter Airlines
Fri 2/67:35 amYQG - BOS
1 stop3h 30mPorter Airlines
Deal found 12/16$508
This Air Canada deal was found by Cheapflights users on 12/15. 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.
Sun 2/81:00 pmBOS - YQG
1 stop6h 14mAir Canada
Tue 2/109:45 amYQG - BOS
1 stop6h 12mAir Canada
Deal found 12/15$511
This Kiwi.com deal was found by Cheapflights users on 12/17. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 1/169:00 amBOS - YQG
1 stop10h 33mPorter Airlines
Fri 1/237:35 amYQG - BOS
2 stops10h 35mPorter Airlines
Deal found 12/17$513
This Porter Airlines deal was found by Cheapflights users on 12/17. 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 Porter Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 2/811:50 amBOS - YQG
1 stop7h 43mPorter Airlines
Tue 2/107:35 amYQG - BOS
1 stop4h 30mPorter Airlines
Deal found 12/17$543

Find flight deals from Massachusetts to Windsor

Keep the following information in mind while searching for Massachusetts to Windsor flight deals. Data was last updated December 18, 2025.

Most accurate provider

eDreams
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$440
(Gotogate)

One-way from

$217
(Kiwi.com)
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.
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From Massachusetts to Windsor
Search Deals
One-way flight from Massachusetts to Windsor
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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 December 18, 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

Sat 1/24

1:00 pm-7:14 pm

1 stop6h 14m

Windsor

Sat 1/31

9:45 am-3:57 pm

1 stop6h 12m

$440

BostonWindsor

BOS - YQG

BOSYQG

Boston Logan Intl

Fri 1/30

1:30 pm-7:33 pm

1 stop6h 03m

Windsor

Fri 2/6

7:35 am-11:05 am

1 stop3h 30m

$508

BostonWindsor

BOS - YQG

BOSYQG

Boston Logan Intl

Sun 2/8

1:00 pm-7:14 pm

1 stop6h 14m

Windsor

Tue 2/10

9:45 am-3:57 pm

1 stop6h 12m

$511

BostonWindsor

BOS - YQG

BOSYQG

Boston Logan Intl

Fri 1/16

9:00 am-7:33 pm

1 stop10h 33m

Windsor

Fri 1/23

7:35 am-6:10 pm

2 stops10h 35m

$513

BostonWindsor

BOS - YQG

BOSYQG

Boston Logan Intl

Sun 2/8

11:50 am-7:33 pm

1 stop7h 43m

Windsor

Tue 2/10

7:35 am-12:05 pm

1 stop4h 30m

$543

BostonWindsor

BOS - YQG

BOSYQG

Boston Logan Intl

Fri 1/16

1:30 pm-7:33 pm

1 stop6h 03m

$217

BostonWindsor

BOS - YQG

BOSYQG

Boston Logan Intl

Fri 1/16

5:30 am-7:14 pm

2 stops13h 44m

$275

Flights are sorted by cheapest round-trip flights first.

Deals found on 12/17

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 03m. Air Canada provides one of the quickest options available for as low as $508. 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 December 18, 2025.
AirlineCheapestAverageFlexibilityOn-time
Porter AirlinesCheapest$491Average$658FlexibilityNo cancel feeOn-time52%
Air CanadaCheapest$648Average$659FlexibilityNo cancel feeOn-time67%

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