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Cheap flights from Massachusetts to Windsor, ON from C$ 792

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 5/4. Fares are subject to change and may not be available on all flights or dates of travel.
BOS — YQG
5 Mar — 12 Mar1
1 adult
1 adult, Economy, 0 bags

Cheap flight deals from Massachusetts to Windsor

Enter your travel dates to find the best prices.

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 3 February 2026.

Sun 5/41:25 p.m.
BOS
-
YQG
1 stop6h 08m
Porter Airlines
Tue 7/47:35 a.m.
YQG
-
BOS
1 stop5h 05m
Porter Airlines
Deal found 1/2C$ 792
Fri 20/311:50 a.m.
BOS
-
YQG
1 stop7h 43m
Porter Airlines
Fri 27/37:35 a.m.
YQG
-
BOS
2 stops10h 32m
Porter Airlines
Deal found 3/2C$ 800
Fri 20/36:15 a.m.
BOS
-
YQG
1 stop12h 59m
Air Canada
Fri 27/37:50 p.m.
YQG
-
BOS
1 stop14h 12m
Air Canada
Deal found 3/2C$ 830
Sun 5/46:45 p.m.
BOS
-
YQG
1 stop14h 19m
Air Canada
Tue 7/49:45 a.m.
YQG
-
BOS
2 stops8h 12m
Air Canada
Deal found 2/2C$ 847

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 3 February 2026.

Round-trip from

C$ 792
Porter Airlines
  • Porter Airlines
  • 5/4-7/4
  • 2 total stops
  • 11h 13m total
  • 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 629,999 searches. Data last updated 3 February 2026.
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

Sun 5/4

1:25 p.m.-7:33 p.m.

1 stop6h 08m

Windsor

Tue 7/4

7:35 a.m.-12:40 p.m.

1 stop5h 05m

C$ 792

BostonWindsor

BOS - YQG

BOSYQG

Boston Logan Intl

Fri 20/3

11:50 a.m.-7:33 p.m.

1 stop7h 43m

Windsor

Fri 27/3

7:35 a.m.-6:07 p.m.

2 stops10h 32m

C$ 800

BostonWindsor

BOS - YQG

BOSYQG

Boston Logan Intl

Fri 20/3

6:15 a.m.-7:14 p.m.

1 stop12h 59m

Windsor

Fri 27/3

7:50 p.m.-10:02 a.m.

1 stop14h 12m

C$ 830

BostonWindsor

BOS - YQG

BOSYQG

Boston Logan Intl

Sun 5/4

6:15 a.m.-7:09 p.m.

1 stop12h 54m

Windsor

Tue 7/4

9:45 a.m.-5:57 p.m.

2 stops8h 12m

C$ 847

Flights are sorted by cheapest round-trip flights first.

Deals found on 1/2

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) 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.

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

    Departing from Massachusetts to Windsor, Ontario will take you 6h 08m. Massachusetts and Windsor, Ontario are separated by a distance of 982 km. Both multi-stop and direct flights can be found to your destination and back.

  • 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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