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Windsor

$343+ 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 8/12. Fares are subject to change and may not be available on all flights or dates of travel.
BOS — YQG
Aug 6 — Aug 131
Wed 8/6
Wed 8/13
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 August 1, 2025.

Round-trip from

$478
(Kiwi.com)

One-way from

$343
(Kiwi.com)
From Massachusetts to Windsor
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One-way flight from Massachusetts to Windsor
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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 August 1, 2025.

This Kiwi.com deal was found by Cheapflights users on 7/31. 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.
Mon 10/68:45 amBOS - YQG
1 stop12h 05mPorter Airlines
Fri 10/108:50 amYQG - BOS
1 stop13h 11mPorter Airlines
Deal found 7/31$478
This Mytrip deal was found by Cheapflights users on 7/31. 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.
Mon 10/67:00 pmBOS - YQG
3 stops25h 50mMultiple Airlines
Fri 10/108:50 amYQG - BOS
2 stops9h 38mMultiple Airlines
Deal found 7/31$693
This Air Canada deal was found by Cheapflights users on 8/1. 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.
Fri 8/155:50 amBOS - YQG
2 stops9h 29mAir Canada
Sat 8/164:00 pmYQG - BOS
1 stop6h 38mAir Canada
Deal found 8/1$779

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 August 1, 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

Mon 10/6

8:45 am-8:50 pm

1 stop12h 05m

Windsor

Fri 10/10

8:50 am-10:01 pm

1 stop13h 11m

$478

BostonWindsor

BOS - YQG

BOSYQG

Boston Logan Intl

Mon 10/6

7:00 pm-8:50 pm

3 stops25h 50m

Windsor

Fri 10/10

8:50 am-6:28 pm

2 stops9h 38m

$693

BostonWindsor

BOS - YQG

BOSYQG

Boston Logan Intl

Fri 8/15

5:50 am-3:19 pm

2 stops9h 29m

Windsor

Sat 8/16

4:00 pm-10:38 pm

1 stop6h 38m

$779

BostonWindsor

BOS - YQG

BOSYQG

Boston Logan Intl

Tue 8/12

8:35 pm-1:50 pm

3 stops17h 15m

$343

BostonWindsor

BOS - YQG

BOSYQG

Boston Logan Intl

Mon 8/11

8:45 am-1:50 pm

1 stop5h 05m

$348

BostonWindsor

BOS - YQG

BOSYQG

Boston Logan Intl

Wed 8/13

5:50 am-3:19 pm

2 stops9h 29m

$387

Flights are sorted by cheapest round-trip flights first.

Deals found on 8/1

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.

Reviews of airlines servicing Windsor

Get insights into the airlines that provide service to Windsor. Read reviews, discover amenities, and learn about the overall travel experience offered by airlines. Use this information to make informed decisions when choosing an airline for your flight to Windsor. Reviews last updated August 1, 2025.
Read reviews from past customers who have flown Porter Airlines and Air Canada from Massachusetts to Windsor. Reviews also offer insight into each airline's entertainment options, comfort, food, crew/service, and boarding process.
Porter Airlines
8.0
Very good
318 reviews

Crew

8.7

Entertainment

7.0

Boarding

8.2

Overall

8.0

Comfort

8.0

Food

7.6

Reviews

1 / 20
8.0
Excellent

Anonymous,Jul 2025

LIS - YYZ

Everything was on time and easy. Crew were nice on flights and helpful. International flight, so long and typically uncomfortable but not more than most. Food and drink service were below average but you get what you pay for. Overall, good experience
Porter Airlines
8.0
Very good
318 reviews
Porter Airlines
8.0
Very good
318 reviews

Crew

8.7

Entertainment

7.0

Boarding

8.2

Overall

8.0

Comfort

8.0

Food

7.6

Reviews

1 / 20
8.0
Excellent

Anonymous,Jul 2025

LIS - YYZ

Everything was on time and easy. Crew were nice on flights and helpful. International flight, so long and typically uncomfortable but not more than most. Food and drink service were below average but you get what you pay for. Overall, good experience
Air Canada
7.1
Good
9,855 reviews
Porter Airlines
8.0
Very good
318 reviews

Crew

8.7

Entertainment

7.0

Boarding

8.2

Overall

8.0

Comfort

8.0

Food

7.6

Reviews

1 / 20
8.0
Excellent

Anonymous,Jul 2025

LIS - YYZ

Everything was on time and easy. Crew were nice on flights and helpful. International flight, so long and typically uncomfortable but not more than most. Food and drink service were below average but you get what you pay for. Overall, good experience

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.

  • 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 August 1, 2025.
AirlineCheapestAverageFlexibilityOn-time
Porter AirlinesCheapest$511Average$658FlexibilityNo cancel feeOn-time52%
Air CanadaCheapest$648Average$659FlexibilityNo cancel feeOn-time67%

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