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Cheap flights from Massachusetts to Windsor from $515

This is the cheapest round-trip flight price found by a momondo user in the last 72 hours by searching for a flight from Massachusetts to Windsor departing on 10/13. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.
1 adult
1 adult, Economy, 0 bags

Find the cheapest flights from Massachusetts to Windsor

Cheap round-trip flights

Enter your travel dates to find the best prices.
Air Canada Logo
10:50 am - 3:22 pmBOS  Boston Logan Intl-YQG Windsor
4h 32m1 stop Toronto Pearson Intl
Air Canada Logo
10:05 am - 9:26 pmYQG  Windsor-BOS Boston Logan Intl
11h 21m2 stops Toronto Pearson Intl Montreal Pierre Elliott Trudeau Intl
$515Air Canada
Tue, Oct 13 - Sun, Oct 18
Air Canada Logo
10:50 am - 3:22 pmBOS  Boston Logan Intl-YQG Windsor
4h 32m1 stop Toronto Pearson Intl
Air Canada Logo
10:05 am - 4:10 pmYQG  Windsor-BOS Boston Logan Intl
6h 05m1 stop Toronto Pearson Intl
$522Air Canada
Tue, Oct 13 - Sun, Oct 18
Air Canada Logo
5:50 am - 3:22 pmBOS  Boston Logan Intl-YQG Windsor
9h 32m2 stops Montreal Pierre Elliott Trudeau Intl Toronto Pearson Intl
Air Canada Logo
10:05 am - 9:26 pmYQG  Windsor-BOS Boston Logan Intl
11h 21m2 stops Toronto Pearson Intl Montreal Pierre Elliott Trudeau Intl
$524Air Canada
Tue, Oct 13 - Sun, Oct 18
Porter Airlines Logo
7:00 am - 3:46 pmBOS  Boston Logan Intl-YQG Windsor
8h 46m2 stops Toronto Island Ottawa
Porter Airlines Logo
4:30 pm - 3:50 pmYQG  Windsor-BOS Boston Logan Intl
23h 20m1 stop Ottawa
$578Porter Airlines
Thu, Sep 10 - Thu, Sep 17
Multiple Airlines Logo
6:30 pm - 3:10 pmBOS  Boston Logan Intl-YQG Windsor
20h 40m1 stop Calgary
Multiple Airlines Logo
7:45 pm - 8:52 amYQG  Windsor-BOS Boston Logan Intl
13h 07m1 stop Toronto Pearson Intl
$593Multiple Airlines
Fri, Oct 2 - Thu, Oct 8
Multiple Airlines Logo
6:30 pm - 3:10 pmBOS  Boston Logan Intl-YQG Windsor
20h 40m1 stop Calgary
Multiple Airlines Logo
7:45 pm - 2:41 pmYQG  Windsor-BOS Boston Logan Intl
18h 56m2 stops Toronto Pearson Intl Montreal Pierre Elliott Trudeau Intl
$597Multiple Airlines
Fri, Oct 2 - Thu, Oct 8
Porter Airlines Logo
7:00 am - 3:46 pmBOS  Boston Logan Intl-YQG Windsor
8h 46m2 stops Toronto Island Ottawa
Porter Airlines Logo
4:30 pm - 10:30 amYQG  Windsor-BOS Boston Logan Intl
18h 00m2 stops Ottawa Toronto Island
$603Porter Airlines
Thu, Sep 10 - Thu, Sep 17
Multiple Airlines Logo
6:30 pm - 3:10 pmBOS  Boston Logan Intl-YQG Windsor
20h 40m1 stop Calgary
Multiple Airlines Logo
7:45 pm - 9:50 amYQG  Windsor-BOS Boston Logan Intl
14h 05m3 stops Toronto Pearson Intl Ottawa Montreal Pierre Elliott Trudeau Intl
$607Multiple Airlines
Fri, Oct 2 - Thu, Oct 8
Air Canada Logo
5:50 am - 3:22 pmBOS  Boston Logan Intl-YQG Windsor
9h 32m2 stops Montreal Pierre Elliott Trudeau Intl Toronto Pearson Intl
Air Canada Logo
4:05 pm - 10:40 pmYQG  Windsor-BOS Boston Logan Intl
6h 35m1 stop Toronto Pearson Intl
$619Air Canada
Thu, Sep 24 - Thu, Oct 1
Porter Airlines Logo
2:20 pm - 3:46 pmBOS  Boston Logan Intl-YQG Windsor
25h 26m1 stop Ottawa
Porter Airlines Logo
4:30 pm - 3:50 pmYQG  Windsor-BOS Boston Logan Intl
23h 20m1 stop Ottawa
$625Porter Airlines
Thu, Sep 10 - Thu, Sep 17

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Air Canada flights from Massachusetts to Windsor, Ontario

Our best Air Canada deals on Massachusetts to Windsor, Ontario flight tickets
Air Canada
Oct 13
BOS10:50 amBoston Logan Intl
4h 32m
1 stop
YQG3:22 pmWindsor
Oct 18
YQG10:05 amWindsor
11h 21m
2 stops
BOS9:26 pmBoston Logan Intl
$515
Air Canada
Oct 13
BOS10:50 amBoston Logan Intl
4h 32m
1 stop
YQG3:22 pmWindsor
Oct 18
YQG10:05 amWindsor
6h 05m
1 stop
BOS4:10 pmBoston Logan Intl
$522
Air Canada
Oct 13
BOS5:50 amBoston Logan Intl
9h 32m
2 stops
YQG3:22 pmWindsor
Oct 18
YQG10:05 amWindsor
11h 21m
2 stops
BOS9:26 pmBoston Logan Intl
$524

Porter Airlines flights from Massachusetts to Windsor, Ontario

Our best Porter Airlines deals on Massachusetts to Windsor, Ontario flight tickets
Porter Airlines
Sep 10
BOS7:00 amBoston Logan Intl
8h 46m
2 stops
YQG3:46 pmWindsor
Sep 17
YQG4:30 pmWindsor
23h 20m
1 stop
BOS3:50 pmBoston Logan Intl
$578
Porter Airlines
Sep 10
BOS7:00 amBoston Logan Intl
8h 46m
2 stops
YQG3:46 pmWindsor
Sep 17
YQG4:30 pmWindsor
18h 00m
2 stops
BOS10:30 amBoston Logan Intl
$603
Porter Airlines
Sep 10
BOS2:20 pmBoston Logan Intl
25h 26m
1 stop
YQG3:46 pmWindsor
Sep 17
YQG4:30 pmWindsor
23h 20m
1 stop
BOS3:50 pmBoston Logan Intl
$625

momondo Fare Finder

 
Customize your flight search to find flights from Massachusetts to Windsor, Ontario 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, momondo users made 832,500 searches. Data last updated August 11, 2026.
Use the filters below to find and compare flights from Massachusetts to Windsor, Ontario that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip

BostonWindsor

BOS Boston Logan Intl - YQG Windsor

BOSYQG

Boston Logan Intl

Tue 10/13

10:50 am-3:22 pm

1 stop4h 32m

Windsor

Sun 10/18

10:05 am-9:26 pm

2 stops11h 21m

$515
Quickest round-trip

BostonWindsor

BOS Boston Logan Intl - YQG Windsor

BOSYQG

Boston Logan Intl

Tue 10/13

10:50 am-3:22 pm

1 stop4h 32m

Windsor

Sun 10/18

10:05 am-4:10 pm

1 stop6h 05m

$522

BostonWindsor

BOS Boston Logan Intl - YQG Windsor

BOSYQG

Boston Logan Intl

Tue 10/13

5:50 am-3:22 pm

2 stops9h 32m

Windsor

Sun 10/18

10:05 am-9:26 pm

2 stops11h 21m

$524

BostonWindsor

BOS Boston Logan Intl - YQG Windsor

BOSYQG

Boston Logan Intl

Thu 9/10

7:00 am-3:46 pm

2 stops8h 46m

Windsor

Thu 9/17

4:30 pm-3:50 pm

1 stop23h 20m

$578

BostonWindsor

BOS Boston Logan Intl - YQG Windsor

BOSYQG

Boston Logan Intl

Fri 10/2

6:30 pm-3:10 pm

1 stop20h 40m

Windsor

Thu 10/8

7:45 pm-8:52 am

1 stop13h 07m

$593

BostonWindsor

BOS Boston Logan Intl - YQG Windsor

BOSYQG

Boston Logan Intl

Fri 10/2

6:30 pm-3:10 pm

1 stop20h 40m

Windsor

Thu 10/8

7:45 pm-2:41 pm

2 stops18h 56m

$597

BostonWindsor

BOS Boston Logan Intl - YQG Windsor

BOSYQG

Boston Logan Intl

Thu 9/10

7:00 am-3:46 pm

2 stops8h 46m

Windsor

Thu 9/17

4:30 pm-10:30 am

2 stops18h 00m

$603

BostonWindsor

BOS Boston Logan Intl - YQG Windsor

BOSYQG

Boston Logan Intl

Fri 10/2

6:30 pm-3:10 pm

1 stop20h 40m

Windsor

Thu 10/8

7:45 pm-9:50 am

3 stops14h 05m

$607

BostonWindsor

BOS Boston Logan Intl - YQG Windsor

BOSYQG

Boston Logan Intl

Thu 9/24

5:50 am-3:22 pm

2 stops9h 32m

Windsor

Thu 10/1

4:05 pm-10:40 pm

1 stop6h 35m

$619

BostonWindsor

BOS Boston Logan Intl - YQG Windsor

BOSYQG

Boston Logan Intl

Thu 9/10

2:20 pm-3:46 pm

1 stop25h 26m

Windsor

Thu 9/17

4:30 pm-3:50 pm

1 stop23h 20m

$625

Flights are sorted by cheapest round-trip flights first.

Sorted by cheapest first

Cheap Massachusetts to Windsor, Ontario flight deals and tips

Find info about flight duration, direct flights, and airports for your flight from Massachusetts to Windsor, Ontario

Fastest flight time

8h 36m

Direct flights

None
The fastest flight from Massachusetts to Windsor, Ontario takes 8h 36m
There are no direct flights from Massachusetts to Windsor, Ontario. There are no popular flight routes from Massachusetts to Windsor, Ontario.
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Frequently asked questions about flying from Massachusetts to Windsor, Ontario

  • When did momondo last update prices for flights from Massachusetts to Windsor Airport?

    Prices for flights from Massachusetts to Windsor Airport are refreshed on a daily basis.

  • How old do you have to be to fly from Massachusetts to Windsor Airport?

    The minimum age a child must be to fly alone is five but airlines that offer an unaccompanied minor (UNMR) service will have their own age restrictions, including rules around flight length, timings, and stopovers. We always recommend checking with the individual airline you are booking with to travel from Massachusetts to Windsor Airport.

  • What documentation or ID do you need to fly to Windsor Airport?

    The required travel and health documents for your Windsor Airport trip may vary depending on your itinerary and personal circumstances. As a general rule, you should carry multiple documents, including a national ID card or driver's license and a passport valid for six months after your intended arrival at Windsor Airport. We recommend that you seek guidance from your airline or a reliable third party such as IATA.

Frequently asked questions about flying from Massachusetts to Windsor, Ontario

  • How do I get Price Alerts for flights from Massachusetts to Windsor, Ontario?

    You can take advantage of momondo’s Price Alerts by first searching for your flights to Massachusetts from Windsor, Ontario. Flight offers will be shown to you in real-time. From there you can create a Price Alert by using our on-site widget.

  • How can I save money on flights from Massachusetts to Windsor, Ontario with momondo?

    Plan your trips smart with the “Price Forecast” feature, which uses flight data to help you pick the best days to fly for the lowest fares. Our “Price Calendar” helps you get the most for your money by showing you when it’s most advantageous to fly. Curate your own travel experiences for less with “Explore”. Expert travel hacks to fuel your next adventure are a click away with “Discover” by momondo. Set up our “Price Alerts” to track fare changes and book when prices are at their lowest point.

  • How does momondo find its flight prices?

    We aggregate our prices from over 700+ competitors from airlines to OTAs. We operate in over 30 markets worldwide to show you a wide range of travel options.

Traveling to a place near Windsor?

Book flights to Windsor if you plan to visit one of these locations
Pelee Island

Why use momondo?

Why should I use momondo to find a flight deal from Massachusetts to Windsor?

Finding the right flight to Windsor from Massachusetts is quick and easy when you have a range of options in front of you, from reputable agents and recognisable airlines. Options that can then be filtered down to find the best fit. That is what momondo does. We make finding flights to Windsor quick and easy, saving you time and money.

Can I find flights from Massachusetts to Windsor with flexible booking policies on momondo?

Yes. momondo enables you to select and highlight flights to Windsor from Massachusetts with this policy.

How can momondo help me find flights from Massachusetts to Windsor?

Once you have performed a search for Massachusetts to Windsor flights, momondo helps you find the right one by offering useful filters to narrow down your flight selection. Flights can be filtered by multiple factors such as airline, airport and price; but also by other criteria like aircraft type and payment method.

I’m not ready to book a flight from Massachusetts to Windsor right now. Can momondo alert me if prices change?

Yes momondo offers price alerts on flights to Windsor from Massachusetts. After performing a search on this page you should be able to see the price alert set up feature. Simply provide a valid email address and momondo will instantly alert you when prices change.

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