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$383+ Cheap flights from Massachusetts to Windsor, ON (YQG)

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 6/21. Fares are subject to change and may not be available on all flights or dates of travel.
BOS — YQG
Apr 5 — Apr 121
Sat 4/5
Sat 4/12
1 adult, Economy
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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 March 31, 2025.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$383
(FlightHub)
Provider with most accurate pricing for Boston Logan Intl-Windsor flight deals.
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Provider most trusted by Cheapflights users for Boston Logan Intl-Windsor flights.
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From Massachusetts to Windsor
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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 March 31, 2025.

This FlightHub deal was found by Cheapflights users on 3/30. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 6/217:15 amBOS - YQG
1 stop5h 55mPorter Airlines
Sat 6/282:30 pmYQG - BOS
1 stop5h 06mPorter Airlines
Deal found 3/30$383
This Air Canada deal was found by Cheapflights users on 3/30. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Air Canada is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 5/110:40 amBOS - YQG
1 stop4h 46mAir Canada
Sun 5/44:10 pmYQG - BOS
1 stop6h 28mAir Canada
Deal found 3/30$399
This Mytrip deal was found by Cheapflights users on 3/30. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 5/1410:04 amBOS - YQG
3 stops27h 06mMultiple Airlines
Wed 5/211:50 pmYQG - BOS
1 stop5h 46mMultiple Airlines
Deal found 3/30$469

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 2,558,603 searches. Data last updated March 31, 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 6/21

7:15 am-1:10 pm

1 stop5h 55m

Windsor

Sat 6/28

2:30 pm-7:36 pm

1 stop5h 06m

$383

BostonWindsor

BOS - YQG

BOSYQG

Boston Logan Intl

Thu 5/1

10:40 am-3:26 pm

1 stop4h 46m

Windsor

Sun 5/4

4:10 pm-10:38 pm

1 stop6h 28m

$399

BostonWindsor

BOS - YQG

BOSYQG

Boston Logan Intl

Wed 5/14

10:04 am-1:10 pm

3 stops27h 06m

Windsor

Wed 5/21

1:50 pm-7:36 pm

1 stop5h 46m

$469

Flights are sorted by cheapest round-trip flights first.

Deals found on 3/30

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

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 2.4 - 3.7 inches per month. September is typically the wettest month, when rainfall can reach 3.7 in. January is typically the driest time to visit Windsor, Ontario when rainfall is around 2.4 in.

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 73.4 F. Travelers looking to avoid the cold should look outside of January, when temperatures are typically at their lowest (around 24.8 F).

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 March 31, 2025.
Porter Airlines
7.9
Good
277 reviews

Boarding

8.2

Crew

8.7

Comfort

8.1

Overall

7.9

Entertainment

6.9

Food

7.6

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
277 reviews
Porter Airlines
7.9
Good
277 reviews

Boarding

8.2

Crew

8.7

Comfort

8.1

Overall

7.9

Entertainment

6.9

Food

7.6

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
9,004 reviews
Porter Airlines
7.9
Good
277 reviews

Boarding

8.2

Crew

8.7

Comfort

8.1

Overall

7.9

Entertainment

6.9

Food

7.6

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), located 5.0 mi from the city center, is the airport you fly into when you book flights from Massachusetts to Windsor.

  • 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

Traveling to a place near Massachusetts?

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Top airline flying from Massachusetts to Windsor

Discover the top airline that operate flights from Massachusetts to Windsor. Compare their services, reliability, and customer satisfaction ratings to choose the airline that best suits your travel preferences and needs. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated March 31, 2025.
AirlineCheapestAverageFlexibilityOn-time
Porter AirlinesCheapest$511Average$658FlexibilityNo cancel feeOn-time52%
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