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$490+ 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 10/29. Fares are subject to change and may not be available on all flights or dates of travel.
BOS — YQG
Oct 15 — Oct 221
Wed 10/15
Wed 10/22
1 adult, Economy
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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 September 15, 2025.

Round-trip from

$490
(Kiwi.com)
From Massachusetts to Windsor
Search Deals

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 September 15, 2025.

This Kiwi.com deal was found by Cheapflights users on 9/13. 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.
Wed 10/291:25 pmBOS - YQG
1 stop6h 08mPorter Airlines
Wed 11/57:35 amYQG - BOS
1 stop5h 05mPorter Airlines
Deal found 9/13$490
This Gotogate deal was found by Cheapflights users on 9/13. 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.
Tue 9/3010:10 amBOS - YQG
1 stop10h 40mPorter Airlines
Sun 10/58:50 amYQG - BOS
1 stop6h 16mPorter Airlines
Deal found 9/13$550
This Mytrip deal was found by Cheapflights users on 9/13. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/305:50 amBOS - YQG
3 stops15h 00mMultiple Airlines
Sun 10/58:50 amYQG - BOS
1 stop6h 16mMultiple Airlines
Deal found 9/13$578
This Mytrip deal was found by Cheapflights users on 9/13. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/292:15 pmBOS - YQG
3 stops29h 18mMultiple Airlines
Wed 11/57:35 amYQG - BOS
1 stop5h 05mMultiple Airlines
Deal found 9/13$608
This KAYAK deal was found by Cheapflights users on 9/13. 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 KAYAK is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/2310:10 amBOS - YQG
1 stop10h 40mPorter Airlines
Sun 9/288:50 amYQG - BOS
1 stop13h 11mPorter Airlines
Deal found 9/13$864
This KAYAK deal was found by Cheapflights users on 9/13. 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 KAYAK is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/236:30 pmBOS - YQG
2 stops14h 52mAir Canada
Sun 9/284:00 pmYQG - BOS
1 stop26h 10mAir Canada
Deal found 9/13$907

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 September 15, 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

Wed 10/29

1:25 pm-7:33 pm

1 stop6h 08m

Windsor

Wed 11/5

7:35 am-12:40 pm

1 stop5h 05m

$490

BostonWindsor

BOS - YQG

BOSYQG

Boston Logan Intl

Tue 9/30

10:10 am-8:50 pm

1 stop10h 40m

Windsor

Sun 10/5

8:50 am-3:06 pm

1 stop6h 16m

$550

BostonWindsor

BOS - YQG

BOSYQG

Boston Logan Intl

Tue 9/30

5:50 am-8:50 pm

3 stops15h 00m

Windsor

Sun 10/5

8:50 am-3:06 pm

1 stop6h 16m

$578

BostonWindsor

BOS - YQG

BOSYQG

Boston Logan Intl

Wed 10/29

2:15 pm-7:33 pm

3 stops29h 18m

Windsor

Wed 11/5

7:35 am-12:40 pm

1 stop5h 05m

$608

BostonWindsor

BOS - YQG

BOSYQG

Boston Logan Intl

Tue 3/3

1:25 pm-7:33 pm

1 stop6h 08m

Windsor

Wed 3/4

7:35 am-12:40 pm

1 stop5h 05m

$714

BostonWindsor

BOS - YQG

BOSYQG

Boston Logan Intl

Tue 3/3

1:00 pm-7:14 pm

1 stop6h 14m

Windsor

Wed 3/4

9:45 am-7:12 pm

2 stops9h 27m

$722

Flights are sorted by cheapest round-trip flights first.

Deals found on 9/13

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 $490. There are 610 mi between Massachusetts and Windsor, Ontario.

  • 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 September 15, 2025.
AirlineCheapestAverageFlexibilityOn-time
Porter AirlinesCheapest$511Average$658FlexibilityNo cancel feeOn-time52%
Air CanadaCheapest$648Average$659FlexibilityNo cancel feeOn-time67%

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