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Cheap flights from Massachusetts to Windsor, ON from C$ 661

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 6/10. Fares are subject to change and may not be available on all flights or dates of travel.
BOS — YQG
6 Aug — 13 Aug1
1 adult

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 1 August 2025.

Round-trip from

C$ 661
Porter Airlines
  • Porter Airlines
  • 6/10-10/10
  • 2 total stops
  • 25h 16m total
  • 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 1 August 2025.

Mon 6/108:45 a.m.BOS - YQG
1 stop12h 05mPorter Airlines
Fri 10/108:50 a.m.YQG - BOS
1 stop13h 11mPorter Airlines
Deal found 31/7C$ 661
Mon 6/107:00 p.m.BOS - YQG
3 stops25h 50mMultiple Airlines
Fri 10/108:50 a.m.YQG - BOS
2 stops9h 38mMultiple Airlines
Deal found 31/7C$ 959

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 629,999 searches. Data last updated 1 August 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 6/10

8:45 a.m.-8:50 p.m.

1 stop12h 05m

Windsor

Fri 10/10

8:50 a.m.-10:01 p.m.

1 stop13h 11m

C$ 661

BostonWindsor

BOS - YQG

BOSYQG

Boston Logan Intl

Mon 6/10

7:00 p.m.-8:50 p.m.

3 stops25h 50m

Windsor

Fri 10/10

8:50 a.m.-6:28 p.m.

2 stops9h 38m

C$ 959

Flights are sorted by cheapest round-trip flights first.

Deals found on 31/7

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 1 August 2025.
Read through reviews of airlines operating flights from Massachusetts to Windsor, such as Porter Airlines. You can also see how each airline stacks up in terms of entertainment options, comfort, food, crew/service, and boarding process.
Porter Airlines
8.0
Very good
318 reviews
Check prices

Crew

8.7

Entertainment

7.0

Boarding

8.2

Comfort

8.0

Food

7.6

Overall

8.0

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
Check prices

Crew

8.7

Entertainment

7.0

Boarding

8.2

Comfort

8.0

Food

7.6

Overall

8.0

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) is the airport you will fly into if you book a flight from Massachusetts to Windsor. It is only a 8.0 km journey from Windsor (YQG) to Windsor’s city centre.

  • 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.

  • What is the cheapest month to book a flight from Massachusetts to Windsor, Ontario?

    Currently, February is the cheapest month in which you can book a flight from Massachusetts to Windsor, Ontario (average of C$ 352). Flying from Massachusetts to Windsor, Ontario in March is currently the most expensive (average of C$ 530). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

See more FAQs

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