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Cheap flights from Massachusetts to Windsor, ON from C$ 339

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 17/4. Fares are subject to change and may not be available on all flights or dates of travel.
BOS — YQG
21 Apr — 28 Apr1
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 22 March 2026.

Thu 28/55:10 a.m.
BOS
-
YQG
1 stop4h 14m
Air Canada
Fri 29/54:05 p.m.
YQG
-
BOS
1 stop6h 34m
Air Canada
Deal found 18/3C$ 717
Tue 5/57:10 a.m.
BOS
-
YQG
2 stops8h 36m
Porter Airlines
Tue 12/54:30 p.m.
YQG
-
BOS
1 stop23h 30m
Porter Airlines
Deal found 20/3C$ 723
Tue 5/55:10 a.m.
BOS
-
YQG
1 stop4h 14m
Air Canada
Tue 12/54:05 p.m.
YQG
-
BOS
1 stop6h 34m
Air Canada
Deal found 20/3C$ 750
Thu 30/46:15 a.m.
BOS
-
YQG
1 stop12h 54m
Air Canada
Mon 4/54:05 p.m.
YQG
-
BOS
1 stop6h 34m
Air Canada
Deal found 17/3C$ 768

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 22 March 2026.

Round-trip from

C$ 717

One-way from

C$ 339
Air Canada
  • Air Canada
  • 28/5-29/5
  • 2 total stops
  • 10h 48m total
  • Massachusetts to Windsor
Search Deals
Porter Airlines
  • Porter Airlines
  • 17/4
  • 1 total stop
  • 6h 08m 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 22 March 2026.
Use the filters below to find and compare flights from Massachusetts to Windsor that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip

BostonWindsor

BOS - YQG

BOSYQG

Boston Logan Intl

Thu 28/5

5:10 a.m.-9:24 a.m.

1 stop4h 14m

Windsor

Fri 29/5

4:05 p.m.-10:39 p.m.

1 stop6h 34m

C$ 717
Quickest round-trip

BostonWindsor

BOS - YQG

BOSYQG

Boston Logan Intl

Mon 29/6

10:50 a.m.-3:22 p.m.

1 stop4h 32m

Windsor

Fri 3/7

10:05 a.m.-4:08 p.m.

1 stop6h 03m

C$ 750

BostonWindsor

BOS - YQG

BOSYQG

Boston Logan Intl

Tue 5/5

5:10 a.m.-9:24 a.m.

1 stop4h 14m

Windsor

Tue 12/5

4:05 p.m.-10:39 p.m.

1 stop6h 34m

C$ 750

BostonWindsor

BOS - YQG

BOSYQG

Boston Logan Intl

Thu 30/4

5:30 a.m.-7:09 p.m.

2 stops13h 39m

Windsor

Mon 4/5

4:05 p.m.-10:39 p.m.

1 stop6h 34m

C$ 779

BostonWindsor

BOS - YQG

BOSYQG

Boston Logan Intl

Tue 5/5

7:10 a.m.-3:46 p.m.

2 stops8h 36m

Windsor

Tue 12/5

4:30 p.m.-5:40 p.m.

3 stops25h 10m

C$ 1,335
Cheapest one-way
Quickest one-way

BostonWindsor

BOS - YQG

BOSYQG

Boston Logan Intl

Fri 17/4

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

1 stop6h 08m

C$ 339

BostonWindsor

BOS - YQG

BOSYQG

Boston Logan Intl

Fri 27/3

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

1 stop7h 43m

C$ 808

BostonWindsor

BOS - YQG

BOSYQG

Boston Logan Intl

Fri 17/4

6:40 p.m.-9:04 a.m.

2 stops14h 24m

C$ 870

Flights are sorted by cheapest round-trip flights first.

Deals found on 17/3

Sorted by cheapest first

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 4h 14m. Massachusetts and Windsor, Ontario are separated by a distance of 982 km.

  • 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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