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Cheap flights from Massachusetts to Windsor, ON from C$ 299

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 16/1. Fares are subject to change and may not be available on all flights or dates of travel.
BOS — YQG
17 Jan — 24 Jan1
1 adult
1 adult, Economy, 0 bags

Cheap flight deals from Massachusetts to Windsor

Enter your travel dates to find the best prices.

Best flights from Massachusetts to Windsor
Discover carefully curated flight deals from Massachusetts to Windsor that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated 18 December 2025.

Sat 24/11:00 p.m.BOS - YQG
1 stop6h 14mAir Canada
Sat 31/19:45 a.m.YQG - BOS
1 stop6h 12mAir Canada
Deal found 17/12C$ 606
Fri 30/11:30 p.m.BOS - YQG
1 stop6h 03mPorter Airlines
Fri 6/27:35 a.m.YQG - BOS
1 stop3h 30mPorter Airlines
Deal found 16/12C$ 700
Sun 8/21:00 p.m.BOS - YQG
1 stop6h 14mAir Canada
Tue 10/29:45 a.m.YQG - BOS
1 stop6h 12mAir Canada
Deal found 15/12C$ 704
Fri 16/19:00 a.m.BOS - YQG
1 stop10h 33mPorter Airlines
Fri 23/17:35 a.m.YQG - BOS
2 stops10h 35mPorter Airlines
Deal found 17/12C$ 707
Sun 8/211:50 a.m.BOS - YQG
1 stop7h 43mPorter Airlines
Tue 10/27:35 a.m.YQG - BOS
1 stop4h 30mPorter Airlines
Deal found 17/12C$ 748

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 18 December 2025.

Round-trip from

C$ 606

One-way from

C$ 299
Air Canada
  • Air Canada
  • 24/1-31/1
  • 2 total stops
  • 12h 26m total
  • Massachusetts to Windsor
Search Deals
Porter Airlines
  • Porter Airlines
  • 16/1
  • 1 total stop
  • 6h 03m 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 18 December 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

Sat 24/1

1:00 p.m.-7:14 p.m.

1 stop6h 14m

Windsor

Sat 31/1

9:45 a.m.-3:57 p.m.

1 stop6h 12m

C$ 606

BostonWindsor

BOS - YQG

BOSYQG

Boston Logan Intl

Fri 30/1

1:30 p.m.-7:33 p.m.

1 stop6h 03m

Windsor

Fri 6/2

7:35 a.m.-11:05 a.m.

1 stop3h 30m

C$ 700

BostonWindsor

BOS - YQG

BOSYQG

Boston Logan Intl

Sun 8/2

1:00 p.m.-7:14 p.m.

1 stop6h 14m

Windsor

Tue 10/2

9:45 a.m.-3:57 p.m.

1 stop6h 12m

C$ 704

BostonWindsor

BOS - YQG

BOSYQG

Boston Logan Intl

Fri 16/1

9:00 a.m.-7:33 p.m.

1 stop10h 33m

Windsor

Fri 23/1

7:35 a.m.-6:10 p.m.

2 stops10h 35m

C$ 707

BostonWindsor

BOS - YQG

BOSYQG

Boston Logan Intl

Sun 8/2

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

1 stop7h 43m

Windsor

Tue 10/2

7:35 a.m.-12:05 p.m.

1 stop4h 30m

C$ 748

BostonWindsor

BOS - YQG

BOSYQG

Boston Logan Intl

Fri 16/1

1:30 p.m.-7:33 p.m.

1 stop6h 03m

C$ 299

BostonWindsor

BOS - YQG

BOSYQG

Boston Logan Intl

Fri 16/1

5:30 a.m.-7:14 p.m.

2 stops13h 44m

C$ 379

Flights are sorted by cheapest round-trip flights first.

Deals found on 17/12

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 03m. 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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