BOS - YQG

$419 Find Cheap Flights from Boston to Windsor

This is the cheapest round-trip flight price found by a KAYAK user in the last 72 hours by searching for a flight from Boston to Windsor departing on 9/21. Fares are subject to change and may not be available on all flights or dates of travel. Click the price to replicate the search for this deal.
1 adult
1 adult, Economy

KAYAK searches hundreds of travel sites at once for deals on flights to Windsor

 
These are the airlines KAYAK users have selected most often from within our search results in flight searches from Boston to Windsor, as well as popular online travel agencies
These are the airlines KAYAK users have selected most often from within our search results in flight searches from Boston to Windsor, as well as popular online travel agencies
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Cheap Flights from Boston to Windsor (BOS-YQG)

 
Here are some of the best deals found on KAYAK recently from the most popular airlines for round-trip flights from Boston to Windsor that are departing in the next months. While these flights were available on KAYAK in the last 72 hours, prices and availability are subject to change and deals may expire.
Discover the best prices for you by selecting your travel dates on KAYAK.

Recent round-trip flight deals from Boston to Windsor

Sun, Sep 21 - Tue, Sep 23
Air Canada Logo
6:00 am - 3:17 pmBOS-YQG
9h 17m2 stops
Air Canada Logo
9:55 am - 3:59 pmYQG-BOS
6h 04m1 stop
$419Air Canada
Find Deal
Sun, Sep 21 - Tue, Sep 23
Air Canada Logo
6:00 am - 3:17 pmBOS-YQG
9h 17m2 stops
Air Canada Logo
9:55 am - 5:55 pmYQG-BOS
8h 00m2 stops
$424Air Canada
Find Deal
Fri, Sep 12 - Sun, Sep 14
Air Canada Logo
10:40 am - 3:27 pmBOS-YQG
4h 47m1 stop
Air Canada Logo
9:55 am - 10:39 pmYQG-BOS
12h 44m1 stop
$438Air Canada
Find Deal
Fri, Sep 12 - Sun, Sep 14
Air Canada Logo
6:00 am - 3:27 pmBOS-YQG
9h 27m2 stops
Air Canada Logo
9:55 am - 10:39 pmYQG-BOS
12h 44m1 stop
$443Air Canada
Find Deal
Fri, Sep 12 - Sun, Sep 14
Air Canada Logo
6:00 am - 3:27 pmBOS-YQG
9h 27m2 stops
Air Canada Logo
4:00 pm - 9:30 amYQG-BOS
17h 30m2 stops
$458Air Canada
Find Deal
Sun, Oct 12 - Tue, Oct 14
 Logo
9:20 am - 8:40 pmBOS-YQG
11h 20m1 stop
 Logo
8:50 am - 2:41 pmYQG-BOS
5h 51m1 stop
Fri, Sep 12 - Sun, Sep 14
 Logo
6:00 am - 8:50 pmBOS-YQG
14h 50m3 stops
 Logo
8:50 am - 5:58 pmYQG-BOS
9h 08m2 stops
Sun, Oct 12 - Tue, Oct 14
 Logo
7:00 pm - 8:50 pmBOS-YQG
25h 50m3 stops
 Logo
8:50 am - 2:41 pmYQG-BOS
5h 51m1 stop
Sun, Oct 12 - Tue, Oct 14
Air Canada Logo
6:00 am - 3:12 pmBOS-YQG
9h 12m2 stops
Air Canada Logo
10:05 am - 3:59 pmYQG-BOS
5h 54m1 stop
$571Air Canada
Find Deal
Sun, Oct 12 - Tue, Oct 14
 Logo
7:00 pm - 8:50 pmBOS-YQG
25h 50m3 stops
 Logo
8:50 am - 6:28 pmYQG-BOS
9h 38m2 stops
Booking Insights

KAYAK's insights & trends for Boston to Windsor flights

Get data-powered insights and trends into flights from Boston to Windsor to help you find the cheapest flights, the best time to fly and much more.

What is the most popular layover airport when flying from Boston to Windsor?

Percentage of 1-stop round-trip flights from Boston to Windsor chosen by KAYAK users via each layover airport in the last 12 months (only includes trips with the same layover airport on both legs).

Toronto (YYZ) is the top choice – 59% of KAYAK users who clicked on 1-stop flights from Boston to Windsor picked an itinerary connecting there.

What is the cheapest layover airport when flying from Boston to Windsor?

Average round-trip price for 1-stop flights from Boston to Windsor clicked by KAYAK users in the last 12 months (only includes trips with the same layover airport on both legs).

Flights via Toronto (YTZ) offer the most affordable fares, with an average round-trip price of $608.

Which layover airport offers the shortest total travel time from Boston to Windsor?

Shortest average total travel time for 1-stop one-way flights from Boston to Windsor via different layover airports, based on KAYAK user data from the last 12 months.

Consider flying via Toronto (YYZ) for the shortest journey. The average one-way travel time for flights connecting there is 4h 45m.

Which layover airport has the quickest connection when flying from Boston to Windsor?

Average layover duration at different layover airports for 1-stop one-way flights from Boston to Windsor, based on KAYAK user data from the last 12 months.

If you prefer a quick connection, Toronto (YYZ) often has the shortest layovers from Boston to Windsor, with an average of 2h 30m.

Good to know

Cheapest flight$419
Flight from Boston to Windsor

When to book flights from Boston to Windsor

Are your dates flexible? Find out the best times to travel from Boston to Windsor based on our flight data from the last year. Discover the cheapest month and even day to fly.
Estimated round-trip price
KAYAK looks at all historical flight data for each date to provide a predicted price for one-way trips or round-trips with a duration up to 40 days. While we try to provide actual minimum prices for each date, some prices are predictions and actual prices may differ.

FAQs for booking flights from Boston to Windsor

  • What is the cheapest flight from Boston to Windsor?

    In the last 3 days, the lowest price for a flight from Boston to Windsor was $419 for a round-trip ticket.

  • Do I need a passport to fly between Boston and Windsor?

    Yes

  • Which aircraft models fly most regularly from Boston to Windsor?

    We unfortunately don’t have that data for this specific route.

  • Which airline alliances offer flights from Boston to Windsor?

    Star Alliance is the only airline alliance operating flights between Boston and Windsor.

  • How does KAYAK find such low prices on flights from Boston to Windsor?

    KAYAK is a travel search engine. That means we look across the web to find the best prices we can find for our users. With over 2 billion flight queries processed yearly, we are able to display a variety of prices and options on flights from Boston to Windsor.

  • How does KAYAK's flight Price Forecast tool help me choose the right time to buy my flight ticket from Boston to Windsor?

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight to Windsor from Boston is likely to change within 7 days, so travelers know whether to wait or book now.

  • What is the Hacker Fare option on flights from Boston to Windsor?

    Hacker Fares allow you to combine one-way tickets in order to save you money over a traditional round-trip ticket. You could then fly to Windsor with an airline and back to Boston with another airline. Booking your flights between Boston and YQG can sometimes prove cheaper using this method.

  • What is KAYAK's "flexible dates" feature and why should I care when looking for a flight from Boston to Windsor?

    Sometimes travel dates aren't set in stone. If your preferred travel dates have some wiggle room, flexible dates will show you all the options when flying to Windsor from Boston up to 3 days before/after your preferred dates. You can then pick the flights that suit you best.

Reviews of the top airlines flying from Boston to Windsor

 
See real verified KAYAK customer reviews for airlines flying from Boston to Windsor. Airline scores are aggregated from all reviews left by passengers on KAYAK after flying with an airline. KAYAK doesn’t show reviews that are older than 5 years. Learn how KAYAK collects reviews.
Need help choosing which airline to fly with from Boston to Windsor? KAYAK airline reviews give an overall score for each airline based on loads of factors, including comfort, boarding, in-flight entertainment and more, to make your decision easier. See airline scores according to verified KAYAK customer reviews.
8.0
Porter AirlinesOverall score based on 318 reviews
7.6Food
7.0Entertainment
8.0Comfort
8.2Boarding
8.7Crew
Airline reviews

All good the seats a little tight and no I pad screen

10.0 ExcellentAnonymous, Jul 2025YYZ - RSW
Read more Porter Airlines reviews

All good the seats a little tight and no I pad screen

Everything was good except the fact you charge more for a carry on bag vs a check in bag and to top it off in US$ that was not impressive

Our flight was cancelled at the last minute for maintenance reasons and we were rebooked on a late flight when we purposefully booked our flight to be home early due to work.

Seemed like an old plane. Very noisy. The seat cushions were so old that the metal bracing of the seats were poking through. There was plenty of leg room though.

Flight was delayed over 2 hours, then landed at a different airport!

The whole experience from check in to deboarding was fantastic.

Just an evening before they canceled my ticket and offered me ticket costing 3 x times more than. I will not fall prey to these scams,Will never book through kayak now. Such a bad experience.

was okay except.. 1)the porter check in webpage doesn't let you print your boarding pass from home 2)that there was a 90 min cut off for checking in on the kiosk in general, and to print a boarding pass, even tho i checked in online already....

Great! Personable crew. I love that they pour complimentary beer and wine.

I love the 2 seats per row. More room. The crew were excellent.

I booked my flight months ago, and checked-in online about 12 hours before the flight. I received an email confirmation of check-in. I had no subsequent communication from Air Canada after my original booking. After arriving at the airport three hours before the flight, as instructed, I waited 90 minutes for an agent to appear to check my bag. I was informed that my flight had been canceled many weeks before, and that flight was no longer being run!! I showed a copy of my check-in confirmation, but no explanation could be found. I was placed on standby for the next flight and the connection. Luckily, those flights were not full and I arrived at my destination. I double checked my email, but I received no update about the flight from Air Canada until the day of the flight.

I had a good experience. I liked being informed about the status of my luggage

I was forcefully re-routed to another destination and was delayed a total of 8hours. I have still not received my bags, no one is taking responsibility. The agents at the airport lied to me that I will get to my destination same time as my previous flight where I was forcefully re-routed from.

Flight was delayed by 1.5hrs. Once inside, people had their small handbags on the storage. The crew (male guy) was not helpful in making some space in the storage. Instead, he asked few bags to be checked-in and it was not a great experience. No attempt to help but just followed the things with a straight face. People had their literally small bags and he wouldnt not move from one storage to another even if there was space and would not let us do i as well. Once flight was on, they ran out of Orange juice, really running out of orange juice when the temp were 32.degrees outside. didnt made the sense. Onasking for a extra snack, he made a face as if he was giving me out of his pocket. if the flight was delayed, there could have an attempt to provide something extra incase people did asked.

Our flight was canceled at the last minute. Someone on the flight said the exact same thing happened to her the day before. I will say they helped us book a flight on another airline so that we could still make our vacation with little delay.

We had a very long delay. First the inbound flight took a while, then maintenance, they “fixed it” to then do boarding and leave the gate, and waste a lot of time to have to go back to the gate and eventually deplane. Had to wait for a new aircraft, wait for a gate, and do the whole thing again. Instead of leaving at 9:50am we left until past 1. I could’ve not woken up at 5am, or spend some more time with my family if they gave more grace period of time between flights to give some time in case of any issues. But they have to make all and every dollar possible

Abandoned me in hallway in a wheelchair… which I asked for because I sprained my back. After waiting in the hallway, I decided to walk the rest of the way since someone respecting me up.. My experience with the united was totally the opposite. Wheelchair access, propped swift and save me a lot of grief. Air Canada totally disorganized.

Bad experience boarding and flight got delayed didn’t make it to my next flight

The food on the trip Toronto to Athens could be better: the chicken didn’t taste good.

Conflicting information provided about baggage allowance. One screen said I had a carry on and another said I didnt.

Everything you need to know for your flight from Boston to Windsor

Information on your arrival and departure airports

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