Find cheap flights from Massachusetts to Windsor

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Find cheap flights from Massachusetts to Windsor

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

Round-trip
Economy
Wichita (ICT)
Windsor
Mon 4/12
Mon 4/19
Any month
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Good to know

Low season

OctoberBest time to beat the crowds with an average 15% drop in price.

High season

JanuaryMost popular time to fly with an average 59% increase in price.

Average price round-trip

$489(avg. price over the last 2 weeks)

Good deal round-trip

$373or less

Good deal one-way

$140or less

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Top airlines flying Massachusetts to Windsor

Scores according to KAYAK customer reviews

7.7
Porter Airlines
Overall score based on 2,710 reviews
7.8
Boarding
7.8
Comfort
8.3
Crew
6.8
Entertainment
7.8
Food
Airline reviews

Pros: "Crew was great. Enjoyed the free wine"
Cons: "Include baggage and seat in price. Such a bummer to pay more at the airport"

Pros: "Convenient! Love flying to Toronto on Porter. Nice glassware for drinks. Unique feel. Will definitely fly again!"

Cons: "Especially for USA and Canada travel, allow some luggage, you guys embarrassed my child by charging her luggage fee because she had to bring a device she requires. She felt embarrassed."

Cons: "Flight was delayed. It happens, I know. First time using this airline, ended up landing 1.5 hour later than planned. The boarding process in Toronto was bizantyne, with some discrepancy in the checks and balance forcing a manual check in of all passengers. Amateurish."

Pros: "Seamless checkin and boarding. Captain got us home 20mins early. Love Porter!"
Cons: "I wish the airplane had USB plugs to charge my phone. Maybe one day Porter will retrofit the airplanes with more conveniences."

Pros: "Crew was nice, free drinks of all sorts."
Cons: "Plane was 3 hours late leaving and we were given five different reasons for it. There were no weather problems. Overheads won't hold what most airlines will, and Porter's low fares lose value due to extra charges like seat reservation and luggage."

Pros: "Crew was nice"
Cons: "Flight was cancelled and rescheduled 2 days later!"

Pros: "Same"
Cons: "Same"

Cons: "Nothing"

Pros: "Great crew. Helped me move to a seat closer to the front as ones further back make me claustrophobic."
Cons: "I don’t like your new policy of not opening up fee free seats 24 hrs before the flight. You used to do that and now if you don’t pay the extra $25 you get stuck in the back row even though there are lots of available seats. You can do better than this Porter. Especially for loyal customers."

Pros: "Can’t say. Still waiting to get on plane 8:08 pm for an 8:15 pm departure!!!!!!"

Pros: "I love the in-flight food and drink service and the airport terminal comfort and amenities."
Cons: "Porter is incessantly late every single time."

Cons: "The lavatory had a terrible stench. There MUST be a way to clean it between flights."

Pros: "It was Convenient, quick , easy and fast love it"

Pros: "I like their efficiency loading the plane and leaving the gate. Perks of having a smaller plane. Also, the snacks and drinks for such a short flight."
Cons: "Notifications the night before about departure changes with confusing language that never confirms if check in deadlines also moved forward. So we end up arriving at the airport at the original time to then be told the crew could NOT fly at the original time. If that is the case they should inform us that theee is no chance that flight could leave earlier. Additionally, the flight left even later than we were told."

Pros: "I did like the crew, boarding and comfort for a short flight."
Cons: "they forgot one of our checking luggage back in Boston. it was my fiancé luggage, but good thing it wasn't my luggage since I have my work tools on my luggage that I will need for tomorrow Monday the 23-2018"

Cons: "I had to cancel the flight because at 2 am on the morning of the flight i received an email letting me know they are delaying the flight no less than 3 hours. I was forced to pay more than 600 USD to make it to Toronto on time, and in the process somehow got charged an extra 11.85 USD by JUSTFLY - the airfare seller whose "customer service" deserves an even worse review."

Pros: "the location was perfect, i was able to walk to downtown and other tourist attractions"
Cons: "it was too expensive"

Pros: "One particular flight attendant was good"
Cons: "Everything else. Delayed my first flight by 2 hours. Rude crew at boarding."

Cons: "Interior noise from plane is annoying"

Pros: "Prompt service and proximity of airport to the city. We literally walked to our hotel"

Cons: "Was not happy that the flight kept on getting delayed a 1/2 hr for a few hrs"

Pros: "Loved the Terra chips. Also the price!"
Cons: "Why did I have to take my headphones off during takeoff and descent? No other airline I’ve ridden has had that policy."

Pros: "Porter was very prompt on their loading and take off. Complementary wine and beer in delight was a bonus. Complementary beverages and he mix was a nice surprise during my layover as well. Their waiting area was large, adequate in seating and comfortable."
Cons: "The bathroom stalls at the waiting luge were small. You can barely fit your luggage in there with you."

Pros: "Nothing"
Cons: "Getting an email as I was going to sleep advising my flight is cancelled and rescheduled on next available 640am two days later. Wow talk about leaving me stranded Who is paying my two extra nights hotel and food? Pretty unprofessional service Been on hold over an hour Come on porter Is that the best you can do?"

Pros: "That is lands clise to town"
Cons: "Lateness on runway for a long time before parking at gate Not pleasant experience My first tome On top of an hour late leaving with no announcements at the terminal Luggage was wet arriving as well All together not a fun day"

Cons: "Started with long delay instantly. After waiting in line to rebook my connecting flight which was missed because of daly I was given a boarding pas with the wrong name on it. I had to leave security line and go back to the counter. I was told it was no big deal and these things happen. After waiting a couple of hours for my next flight I was told my boarding pass had the wrong flight number on it. So once again I had to leave the boarding area to get the matter taken care of. It was a very frustrating experience."

Pros: "Quiet plane! Excellent crew."
Cons: "Logan Terminal E..."

Pros: "Crew was very friendly and sincere."
Cons: "Delayedx3."

Pros: "I loved the waiting area with free snacks and drinks while we waited for our next flight. So comfortable! I wish Porter had other flights in the United States :)"

Pros: "I love the space on the plane. Not many passengers. I had the row all to myself!"
Cons: "The last minute call for passport validation. I thought I was all set and then a call came over the loud speaker to come forward and check passports. I didn't know where to go and I thought I with going to miss the plane. Other passengers asked me what was going on and where should they go. I figured it out and just made it back for boarding in the nick of time. I wish the call had of been made earlier or that a big sign was posted."

Pros: "Price and timing"
Cons: "Noisy children; mediocre food"

Pros: "I like Mr. Porter"
Cons: "Schedule could be a bit more precise, but as long as Porter manages its fine..."

Pros: "First time using Porter and won't be the last. Great airport right in the center of Toronto and customs was fast and efficient. The flight was short so no food/entertainment but there wasn't a N/A choice, only stars..."

Pros: "Staff was extremely professional and knew their job."
Cons: "Flights were short so did not have entertainment, which is fine."

Pros: "Seats were good, service was excellent I felt, good drink selections. I'd say it's regional version of Southwest. Please be mindful the overhead space is like that of Spirit (very small!)."
Cons: "Landing. Both times the landing steps were shaky and uncomfortable. Taking off was no problem at all so really not sure why landing was so hard to swallow... as in I wouldn't bring my baby on board just because of this."

Cons: "When i booked my ticket online there was no indication or warning that i needed to complete eta online as i was not traveling on a us or canadian passport. At the ticket desk i was initially told i could not fly because of this and that it was up to me to know about the eta requirement. Then i was told how to complete the form online and the problem was solved."

Pros: "Excellent service"
Cons: "No wifi or screen"

Pros: "Every thing was the best and I loved it The best airport, crew , landing , service and on time flight."

Pros: "Travel was seamless Flights were surprisingly punctual Staff was friendly and planes are comfy for short flights - Lounge is the best ! definitely the highlight of flying porter. They stand behind their slogan... " Flying Refined ""

Pros: "The service was usual, of good quality"
Cons: "I paid for the first row seat and got row 10 and the agent said I did not pay the difference. You can check my ticket"

Pros: "- frequency of shuttle - free wifi - free refreshments at the airport and on board - friendly check in staff - short line ups - quick customs process"

Cons: "Specifically purchased a $350 USD one way ticket with 2 1/2 hr travel time from Montreal to Windsor with a 30 min layover in Toronto, After landing in Toronto, same plane flies to Windsor once some passengers de-board and others board. There were only a 6 or 7 passengers left on the plane after landing in Toronto and in 5 min Porter announced that they are cancelling the flight without giving a reason. The actual reason is there was not enough passengers to make it worth for them to fly plane to Windsor, so gave us the option to be booked on the next flight in 3hrs or the following in 6hrs. Issued a $50 CAN voucher (good for 6 month on Prorter) for the inconvenience and a $10 meal credit. NOT really a good deal, as they value your time at $20 per hour in voucher credits, but charged $350 for the ticket in real money. No representatives there can help in any other way or offer anything other than the $50 voucher. Just sit and wait in an overcrowded lounge. The flight to Windsor 3 hrs later was completely full,"

Pros: "The carry-on space was too small. My flight leaving Toronto was delayed one hour. I enjoyed the free coffee and cookies at the airport."

Pros: "Lounge had complimentary beverages and snacks, security was a breeze, no line up. The complimentary snack and beverage (alcohol too!) was great."
Cons: "Lounge was a little run down looking. My flight home was cancelled, having just received the news as I was on the bus to the airport. So my 11:20am flight became a 6:30pm flight, no reason given. Later on in the afternoon that flight got moved to 7:30pm... At the airport, they changed the gate and then my final boarding time ended up being 8:00pm. So not impressed!! I had pre-purchased a bus ticket home which I lost the money on, Porter has not responded to my request for them to pay for that. PLUS my husband having to then drive 1.5 hours to pick me up and then drive us home another 1.5 hours at 10:30 at night. What a total mess, I had work booked the entire next day and night that I was now exhausted for."

Cons: "Shaky and noisy flight, the transportation offered by porter could be vastly improved."

Pros: "smooth"

Pros: "The aircraft crew were very polite and helpful."
Cons: "I could have used more leg room being so tall."

Pros: "Nice to offer chips"
Cons: "Very delayed, but with only vague and confusing explanations. Delay before taking off, delay on the runway. First they could not find plane, then could not find crew."

Pros: "The crew was amazing"
Cons: "Wish there had been any kind of entertainment available or if there was it would have been better advertised"

Pros: "I was only a few minutes late and was not allowed to check in my bag or to board the flight."
Cons: "They could have let me board!!"

Pros: "There was a problem with the aircraft in the middle of boarding, so the gate agent delayed boarding so that we wouldn't have to stay in the cold."
Cons: "Plane was tight. Over an hour late. Bags didn't arrive."

Pros: "Nice seats fast boarding"
Cons: "Snack can be more richer"

Cons: "In a flight that is only 1:45, to have an incoming flight delayed by 1:45 for non-mechanical issues can create a lot of havoc. On the turnaround, we boarded and arrived very late. We missed our connection to Sydney and had to wait 24 hours for the next flight out."

Cons: "i got to the airport 2.5 hours befor my flight to play it safe and waited at the check in for about a hour befor a air canada employe even showed up. vary poor service on the airlines part i will never fly with air canada again."

Cons: "Took off late."

Pros: "It was on time."
Cons: "I wish the entertainment system had had closed captioning, and/or that the inflight wifi had worked."

Cons: "Air canada regularly delayed. It’s their trademark"

Cons: "Air Canada declined to accommodate in next available flight even though the originating flight was on a single Ticket."

Cons: "5 hours delayed because captin was late."

Pros: "On board entertainment"
Cons: "No real food for purchase"

Pros: "T"
Cons: "The waiting area at the Boston airport is poor. It is very small, rundown and with limited access to refreshments. It's ok but certainly not a selling point."

Pros: "New system with Canadian customs was fantastic. Went through really quickly."

Cons: "Basic connection flight. Music was only entertainment."

Pros: "To like food, service."
Cons: "At Check in, the guy give me the seat number is too big:("

Pros: "Actually, everything was perfect."
Cons: "I don't have any complaints at all. Except a ticket agent who tried 2 give me hard time, fortunately I handled the issue. After all, everything was well done."

Cons: "All good"

Cons: "I'm 6ft tall and paid for a coach ticket. This aircraft wasn't built for tall people in coach."

Pros: "Ground personnel"
Cons: "The overall service on board"

Pros: "Good"
Cons: "Good"

Pros: "Crew was very nice"

Cons: "Flight was delayed by 10 minutes but had to wait 45 minutes on the plane before take off. Quite stressful and tiring!"

Pros: "Quick little hop . . . I find that everyone (passengers and flight crew) tend to be in a good mood on these."

Pros: "Employee in Boston terminal great help in sign in process. Volunteer, I believe, in Air Canada terminal in Toronto helped me find my way to another terminal."

Cons: "Wireless system slow and costly."

Pros: "Service was amazing. Flight was intime and they helped me with my luggages to be transferd directly to the last country eventhough they are two seperate booking"

Pros: "We didn't crash"
Cons: "Terrible service by the Air Canada stewardess. She was surly and unprofessional. Just flat out rude."

Cons: "Onced arrived to my Montreal destination, I get informed my bag never made it onto the flight once we connected in Boston... Now dealing with AC to get it back. Very dissapointing"

Pros: "The flight had to abort take off due to an issue with the pilot seat. We had to return to the gate for them to fix the problem. Left the gate a second time only to sit on the runway with no explanation from the pilot."

Pros: "The tremendous effort to support our making our connecting flight."
Cons: "The nightmare between flights in Toronto airport"

Pros: "On time departure"
Cons: "I had visa on expired passport ,staff on duty took too long nearly an hour to clear me."

Pros: "Very nice new plane. The special "natural" lighting made it easier to sleep and wake up."
Cons: "Both flights were significantly delayed and the boarding process for the flight to Tel Aviv for some reason took absolutely forever. Then we waited on the tarmac for almost two hours."

Pros: "Good service"

Pros: "Wish the longer portion of our flight was as pleasant as the short leg to Toronto."

Pros: "Wheel chair request on arrival in Toronto was very poorly implemented resulting in two long delays"
Cons: "If Air Canada can't get these basics right it will be difficult to be competitive with Porter Air"

Pros: "Logan checking with own security checkpoint Boston to Toronto tv great Staff professional"

Pros: "Clean plane, attentive efficient staff, easy boarding."
Cons: "Flight staff forgot to pass out customs forms upon landing in Toronto - caused some confusion at customs entry."

Pros: "The fast boaring"
Cons: "The 3hr delay. Not many announcements. No one at the gate/desk. Had to be in a crowded gate area with no choice."

Pros: "Good movie selection"
Cons: "Poor organization and late takeoff"

Cons: "fitst leg was late. no communication about the connection. was not not clear whether we're going to make the connection - too much stress"

Pros: "i didn't like anything about this flight"
Cons: "The flight was over an hour delayed and everything else since boarding was a mess. It was hard for the fly hostess to keep her calm and we knew she was stressed, as much as many passengers who lost their connection or who had really tied ones. I noticed also that it wasn't the only flight delayed so I am not sure if this is usual with Air Canada."

Pros: "Seating in two's very good."
Cons: "Both going and return had to wait an extra hour."

Pros: "Not much"
Cons: "It was delayed which caused my connection to be cancelled and rebooked for next day. Was extremly uncomfortable and very expensive"

Cons: "Late and overbooked Toronto Airport Dodd is bad. --- no veggie optional"

Cons: "The waiting room in Boston was awful and behind security, hot, small crowded. Delayed"

Pros: "Bos->Toronto Good Air Canada at Boston Logan airport has there own gate area with only 3 gates. This reduces the security line for faster security check. However this also causes problems with PreCheck. See below."
Cons: "Bad There is only one line for security at Air Canada Boston Logan because of the small volume at this check point. Because of this, PreCheck passages need to hold onto there bording pass as they go through security. The first security person who checks ID and boarding pass only told my wife not to take off her shoes. He did not tell her to hold on to her boarding pass, so she put it into the bin for x-ray stuff. So later security personnel then told her to take off her shoes and gave her a body scan because her boarding pass was already in the x-ray machine. I always hold on to my boarding pass thru security but had to take my computer out of my carry-on."

Pros: "Great service"

Pros: "great hotel paid for by Air Canada"
Cons: "5 hours late - missed connecting flight"

Pros: "Great air fare. Small airport--easy parking---quick check in."
Cons: "Small plane with limited seat size, but well worth taking to Toronto to connect to major flights."

Read more about Porter Airlines
COVID-19 information

Safety measures for airlines flying from Massachusetts to Windsor

Airlines flying from Massachusetts to Windsor have enacted additional safety measures and adjusted policies to better accommodate travelers. Policies vary by airline.

Heightened sanitation

Daily cleaning, installation of cabin HEPA filters on flights from Massachusetts to Windsor

Mandatory masks

Masks required on board, masks provided on flights from Massachusetts to Windsor

Social distancing seating

Middle seats unavailable to book on flights from Massachusetts to Windsor

Pre-flight testing

Testing for antibodies, testing for symptoms for flights from Massachusetts to Windsor

Book cheap flights from Massachusetts to Windsor

Recent round-trip flight deals

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Porter Airlines
4h 20m
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5h 18m
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3h 55m
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4h 18m
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28h 33m
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