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Cheap flights from Massachusetts to Windsor, ON from C$ 625

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 3/4. Fares are subject to change and may not be available on all flights or dates of travel.
BOS — YQG
25 Feb — 4 Mar1
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 20 February 2025.

Round-trip from

C$ 625
Air Canada
  • Air Canada
  • 3/4-11/4
  • 3 total stops
  • 29h 01m 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 20 February 2025.

Thu 3/47:55 p.m.BOS - YQG
1 stop13h 39mAir Canada
Fri 11/46:45 p.m.YQG - BOS
2 stops15h 22mAir Canada
Deal found 20/2C$ 625
Sat 21/67:15 a.m.BOS - YQG
1 stop5h 55mPorter Airlines
Sat 28/62:30 p.m.YQG - BOS
1 stop5h 06mPorter Airlines
Deal found 20/2C$ 811
Thu 3/45:15 a.m.BOS - YQG
3 stops32h 38mMultiple Airlines
Fri 11/42:30 p.m.YQG - BOS
2 stops28h 05mMultiple Airlines
Deal found 20/2C$ 973

Find flights from Massachusetts to Windsor within your budget

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 20 February 2025.

Fly from

Massachusetts

Fly to

Windsor

Route

Depart

Return

Price

BostonWindsor

BOS - YQG

BOSYQG

Boston Logan Intl

Thu 3/4

7:55 p.m.-9:34 a.m.

1 stop13h 39m

Windsor

Fri 11/4

6:45 p.m.-10:07 a.m.

2 stops15h 22m

C$ 625

BostonWindsor

BOS - YQG

BOSYQG

Boston Logan Intl

Sat 21/6

7:15 a.m.-1:10 p.m.

1 stop5h 55m

Windsor

Sat 28/6

2:30 p.m.-7:36 p.m.

1 stop5h 06m

C$ 811

BostonWindsor

BOS - YQG

BOSYQG

Boston Logan Intl

Thu 3/4

5:15 a.m.-1:53 p.m.

3 stops32h 38m

Windsor

Fri 11/4

2:30 p.m.-6:35 p.m.

2 stops28h 05m

C$ 973

Flights are sorted by cheapest round-trip flights first.

Deals found on 20/2

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.

Travel insights for flights from Massachusetts to Windsor

Get recent, data-driven insights about flights from Massachusetts to Windsor including ideal travel times, pricing trends, and more.

Rainfall in Windsor by month

Plan your trip to Windsor by taking into account the average rainfall totals by month.

In terms of precipitation, rainfall in Windsor, Ontario ranges from 62.0 - 94.0 mm per month. September is typically the wettest month, when rainfall can reach 94.0 mm. January is typically the driest time to visit Windsor, Ontario when rainfall is around 62.0 mm.

Temperature in Windsor by month

Plan your trip to Windsor by taking into account the average temperature totals by month.

If weather is an important factor for your trip to Windsor, Ontario, use this chart to help with planning. For those seeking warmer temperatures, July is the ideal time of year to visit, when temperatures reach an average of 23.0 C. Travellers hoping to avoid the cold should look outside of January, when temperatures are typically at their lowest (around -4.0 C).

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 20 February 2025.
Porter Airlines
7.9
Good
276 reviews
Check prices

Comfort

8.0

Entertainment

6.9

Food

7.6

Overall

7.9

Crew

8.7

Boarding

8.2

Reviews

1 / 17

10.0
Excellent

Anonymous,Dec 2024

YYZ - LAS

Everything about the rescheduled (cost me $180) flight great. ***Being denied boarding because I was few minutes under 1.5 hours was not. Stuck at the Kiosk for about 15 minutes before it directed me to the Porter counter was strange. Do not know why checking in online at home was not successful? I think something was up...what can you do?

Porter Airlines
7.9
Good
276 reviews
Porter Airlines
7.9
Good
276 reviews
Check prices

Comfort

8.0

Entertainment

6.9

Food

7.6

Overall

7.9

Crew

8.7

Boarding

8.2

Reviews

1 / 17

10.0
Excellent

Anonymous,Dec 2024

YYZ - LAS

Everything about the rescheduled (cost me $180) flight great. ***Being denied boarding because I was few minutes under 1.5 hours was not. Stuck at the Kiosk for about 15 minutes before it directed me to the Porter counter was strange. Do not know why checking in online at home was not successful? I think something was up...what can you do?

Air Canada
7.0
Good
8,748 reviews
Porter Airlines
7.9
Good
276 reviews
Check prices

Comfort

8.0

Entertainment

6.9

Food

7.6

Overall

7.9

Crew

8.7

Boarding

8.2

Reviews

1 / 17

10.0
Excellent

Anonymous,Dec 2024

YYZ - LAS

Everything about the rescheduled (cost me $180) flight great. ***Being denied boarding because I was few minutes under 1.5 hours was not. Stuck at the Kiosk for about 15 minutes before it directed me to the Porter counter was strange. Do not know why checking in online at home was not successful? I think something was up...what can you do?

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, November is the cheapest month in which you can book a flight from Massachusetts to Windsor, Ontario (average of C$ 357). Flying from Massachusetts to Windsor, Ontario in March is currently the most expensive (average of C$ 517). 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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