Find cheap flights from Winnipeg to Massachusetts

Find cheap flights from Winnipeg to Massachusetts

Round-trip
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Winnipeg (YWG)
Massachusetts
Sat 11/28
Sat 12/5
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Good to know

Low season

April Best time to beat the crowds with an average 3% drop in price.

High season

December Most popular time to fly with an average 11% increase in price.

Average price round-trip

$248 (avg. price over the last 2 weeks)

Good deal round-trip

$207 or less

Good deal one-way

$132 or less

Top tips for finding cheap flights to Massachusetts

  • Looking for a cheap flight? 25% of our users found tickets from Winnipeg to Massachusetts for the following prices or less: to Boston $132 one-way - $207 round-trip
  • High season is considered to be January, February and December. The cheapest month to fly to Massachusetts is January.

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Top airlines flying Winnipeg to Massachusetts

Scores according to KAYAK customer reviews

7.9
Delta
Overall score based on 28,796 reviews
8.1
Boarding
7.8
Comfort
8.5
Crew
7.8
Entertainment
7.5
Food
Airline reviews

Pros: "The crew was good. Now fast but good."
Cons: "The food was pretty basic."

Pros: "individual TVs"
Cons: "it would be great if you could not use all those one-use plastic cups. waste is a real issue in the US and the solution is using re-usable items like washable cups. Unboarding was a nightmare and it started to get really hot waiting to get off."

Cons: "Dripped on!!!!!!"

Pros: "Flight itself uneventful"
Cons: "Lateness"

Pros: "Crew was courteous, I asked for a blanket and a banana (I saw some being passed to delta select (?) passengers), and got both, no one snapped at me like on an earlier flight.5"
Cons: "The flight was 3.5 hrs late. (Had it been on time, I would have missed it entirely though because Atlanta airport passport control was complete chaos, I heard the airport wa closed earlier for weather related reasons). Enough said."

Pros: "Awesome customer service"
Cons: "No complaints"

Pros: "Great friendly crew. Great entertainment with movies on a short narrow body flight!"
Cons: "Boarding and disembarking was again slow. Must be a cultural thing as each flight in the US seems to be like this as people take ages to get their bags organised on arrival. Chaotic boarding is compounded by the back of the plane boarding last.... everywhere else in the world loads everyone together or does the back of the plane first and it's much quicker!"

Cons: "Seat did not recline."

Pros: "Equipment was nice and well maintained. Seats are comfortable for coach. Video at each seat. Friendly staff."

Pros: "great flight , on time, great service"

Pros: "About 10-15 yrs ago I stopped transatlantic flights on Delta. It was a scruffy airline with uninterested cabin crew & not to talk of food etc. What a change! Neat clean A330, friendly crew & food + beverages to brag (you pay outrageous prices on 'leaner-meaner' airlines if at all available). Loved the whole experience. Flying is not only getting from A to B & Delta has realized it. Looking forward to my next Delta flight!"
Cons: "NOTHING"

Cons: "the inefficiency and extra steps required to travel. Quite lacking in smooth transition between flights, significantly below expectations relative to other airlines"

Pros: "Fast boarding one way from Nashville to Boston. Smooth ride and on time."
Cons: "Trash onboard from previous flight and flight attendants texting during beverage service and seemed annoyed they were having to hand out drinks and crackers. I don’t enjoy feeling like a nuisance when I’ve paid $250 for the flight. FREE WiFi didn’t work. I always avoid Delta when possible."

Pros: "No food or entertainment on short flight"

Pros: "Free entertainment and free food was unexpected and very welcomed, especially given the trend of charging for more and more features."

Cons: "The tsa is worthless"

Pros: "aircraft is very clean. faster than imaged. the most impressed thing is it has a variety of entertainment programs."

Pros: "The crew was really friendly and helpful. The plane was really clean"
Cons: "The boarding process was too long, there was a lot of people. It was kinda a mess. The sit assignment for people who didn't have sit assign was slow."

Cons: "The plane was delayed by more than 3 hours due to "weather problems" earlier in the day. Delta did not permit re-booking to flights that left JFK for Boston earlier, even tho there seats available, instead insisting that we had to wait for our assigned flight. Small snacks (regular Coke, no Diet) did not really compensate well."

Pros: "They did eventually put out some small snacks and drinks (water and regular coke)."
Cons: "Small regional plane that was over 3 hours late in departing NY because of weather issues much earlier in the day. Delta did not permit any re-bookings to other delayed flights that were leaving in the intervening period, even though there were empty seats. Very frustrating."

Pros: "We flew a plane that had 2 row seats. I booked that for my daughter and me as well as seats ahead of an exit so we would have no one behind as. Great seats and they reclined quitea bit. We were very pleased."

Pros: "Plenty of entertainment options Frequent meals and snacks Attentive service from flight crew"
Cons: "Boarding process was slower than anticipated One of our bags did not make it"

Pros: "Everything went smoothly."
Cons: "N/A"

Pros: "Easy boarding. Due to bad weather they kept us well informed. One hour late but not their fault."
Cons: "A little chilly in the waiting are."

Pros: "Exceptional flight staff -"

Cons: "Smooth and easy"

Pros: "Great stewardesses, good food"

Pros: "Friendly crew, ok seats"
Cons: "Was not possible to even request a coffee"

Pros: "Crew was great, flight was on-time and most often overlooked (but most important) we got there safely."
Cons: "The seat on this 737-800 was uncomfortably narrow. This was likely due to the table-tray being in the seat armrest. I had to remove everything from my side pants pockets and even then was not particularly comfortable. This is particularly annoying because I usually avoid this by flying comfort plus. However, on this itinerary, Delta would not allow me to give them money for Comfort plus, because it was a domestic leg on an itinerary including stops in Asia. Such a baffling policy!?!?"

Pros: "Satellite TV on this flight was perfect! I got to watch a football game live that I really wanted to watch, but conflicted with this flight. It was great! The leg room was good and the seat was comfortable on this short flight. The lighting was appropriate for an 8pm-12am flight. Crew was nice"
Cons: "nothing to note here on this one."

Pros: "Good movies"
Cons: "Im 6'2. My knees still are hurting due to the horrible leg room"

Cons: "Same as above"

Pros: "I like the fact that I was able to get on this"
Cons: "Delta is completely messed up. My luggage was supposed to travel with me to Boston. But it didn't. Delta waisted my time. Horrible customer su"

Pros: "Crew was friendly and apologetic"
Cons: "The AC did not work and we had to get off and hang out in the jetway for probably 45 minutes. Nightmare."

Cons: "Family of 6 with 3 minors. Could not sit any of us together."

Cons: "After a grueling 14 hour flight back to the states from Asia, got notification that my Delta flight was further delayed an additional 3.5 hrs from the layover of 2hrs, so I was at the airport for a good part of the day and did not get home till midnight. Altogether 24+ hrs of no real sleep. To add insult to injury, a Delta representative called and apologized, offering a $100 voucher or gift certificate. Raised expectation that they might actually do the right thing. I then received a Delta email that says "Your day just got better", except there was nothing but ads and enter to bid for things. Overall bad experience when I really needed them to get me home on time."

Cons: "Too cramped for a flight more than 90 mins - even in the "comfort+" section. This plane configuration is fine for much shorter flight routes"

Pros: "Comfort seat upgrade. Access to Virgin Lounge in London. Food was very good."
Cons: "Video system on plane had too many commercials."

Pros: "Great flight"

Pros: "Nothing really."
Cons: "Arrived at airport at 08:00a for 09:10a flight. Delay for weather, then crew rest, then cancelled ~6 hours later. All while sitting in the airport like a dope. Put on a flight with overnight in LGA, but they could not tell us if a voucher would be provided. Usual story since the govt does not mandate the airlines do better. Was not advised to try standby on other later flights, which worked. Finally landing in BOS, we sat for 45+ min waiting for a third person to flag the plan to the gate. Understand why, but really annoying after such a long day full of delays. Felt many areas could have been handled better. Each person individually tried, but in aggregate it was a mess."

Pros: "They switched me to better seats"
Cons: "They lost my duffle bag, and when they found it, my bag was in a whole different state, and once I finally received my duffle bag my items were wet and damaged."

Pros: "Very enjoyable trip."
Cons: "Nothing"

Cons: "no food. no entertainment"

Pros: "Fast boarding the plane! Great snacks! Great flight attendants."
Cons: "We sat in the plan for 45 minutes before taking off and arrived 20 minutes late."

Pros: "Nothing"
Cons: "This flight never happened bc they didn't have a captain for the plane. Not a delay - not maintenance issues - just didn't have a captain so sorry your flight is cancelled. Ridiculous"

Pros: "Seat assignment very comfortable!!!"
Cons: "N/a"

Pros: "Great customer service"

Pros: "On time departure, friendly staff, nice free snack. Overall good experience."

Pros: "Generally there was a king of a "good buzz" among the passesgers Appreciated the good budget value. It made the trip to see my daughter possible"
Cons: "I don't have any negative feelings"

Pros: "Comfortable seat - great service"

Cons: "Delays"

Pros: "The connecting flight was with air Canada. In general the flight was fine. Landed on a Saturday afternoon."
Cons: "What was not fine was the horror at the other end when air Canada lost my bag (which had my suit and prescriptions) and couldn't tell me where it was or when it would be delivered for over two days of calling between their service centre and one the ground people at Boston. The call centre was in India, no one in Boston would tell them what was going on. It should not take three days to sort, when the bag had actually been sent on the next flight (on Saturday evening) after the one I took. Fortunately, was able to borrow BP medication from a relative and ultimately had to spend money to buy new suit and clothes before bag finally appeared because I had business meetings for which I needed appropriate attire. Every other airline I gave flown where my bag was delayed was always delivered in 24 hours. This was not Brussels airlines fault, it was the fault of air Canada."

Cons: "Everything was seamless and i have no complaints. My return flight was cancelled amd i was automatically put on a different flight, and instead of waiting more than 2 hours from boston to get to canada, i was put on an earlier flight for which i am thankful for. However we couldnt take off as delta was clogging up the way to the runaway so ended up waitimg an hour to taje off which was ridiculous. Hope delta hires more ground crew so that others arent inconvenienced in the future."

Pros: "Plesant ride"
Cons: "Flight took longer to depart due to boarding and de-icing"

Pros: "Love Air Canada. Great service and good entertainment"

Pros: "I flew through Vancouver from Boston on my way to Brisbane, Australia and back. I was nervous at first because of the 2 hour connection windows. This might be a testament to Vancouver Airport more than Air Canada, but the flight home after an initial 14 hour flight was pain free. Boarding was fast (the flight wasn't full) and we ended up pulling away from the terminal early. I slept most of the flight so I can't really comment on food. The entertainment was the same as when i left for Australia, which was ok. It had a decent variety to select from."

Pros: "The crew was professional and polite"

Pros: "Overall it was a quick and painless flight. The crew was friendly and we had no problems!"

Pros: "Nothing in particular stood out in Montreal or the flight to Boston, as better than average...meh"
Cons: "Our Swiss crew told us over the loudspeaker several times that "even if connecting we still need to get our luggage" which turned out to be false as our luggage was transferred to the Boston bound plane automatically... We were ushered out as a group to a connection security check which required electronic kiosks to be used for scanning our passports photos and fingerprints... They fraught with malfunctions then after waiting in line for s while we did the whole check all over again with s human security agent in s booth... There were only 2 security agents in the booths as well but there really needed to be several more to keep the line moving quicker... After security we walk directly out to departures but no mention of baggage claim, which was fine had we not been misinformed by Swiss initially... We ended up inquiring several times with SirCsnsda staff until it was clear Swiss had misinformed us."

Cons: "I did not take it."

Pros: "The flight itself was fine, free WiFi on board, movies to watch, stewards and stewardesses on board were very kind and attentive."
Cons: "I was originally flying WestJet, and the 7:05 AM flight I booked was cancelled. I hopped online and booked the 8:10 AM flight via Air Canada back to Boston. First, the flight was oversold, so only AFTER I was able to check my bag did I learn that I was flying stand-by. Completely nerve wracking. If I had known in advance I would have booked with another airline. I was able to get on the flight thanks to some volunteers who gave up their seats on the 8:10 AM flight for the next flight out (10:10 AM) in return for some monetary compensation. I arrived in Boston, and after waiting for 45 minutes, I learned my bag was put on the 10:10 AM flight rather than the 10:10 AM flight, but only after dealing with a snappy and disrespectful check-in attendant that seemed to not believe me that my bags indeed did not arrive. The office for baggage services for Air Canada was vacant and locked next to the carousel. Myself and a couple of other travelers, upon getting to the check-in counter and explaining the situation mistakenly lumped us all together and said "okay so you're all traveling together and your bags need to go the same place". Me: "No, that's incorrect, we are not related or traveling together, we just all have the same issue--none of our bags have arrived". Other Air Canada representative, who up to this point had not been involved in the exchange: "She didn't ask you if you were related, she asked you if your bags were lost" and then proceeded to roll her eyes and walk away from the counter. I suppose she misinterpreted my concern for rudeness and felt the need to put me in my place. Granted, my early morning flight cancellation and the stress associated with flying standby had nothing to do with them, but the attitude I was given as a concerned traveler whose bag was potentially lost was completely unwarranted. Compounded with the frustration of the entire morning I cannot describe how infuriating this exchange added up to being. I was told my bag would be delivered to my home by 4 PM that day. No bag. Got a phone call at 7 PM - they'd be there in the next hour. 10:00 PM and going to bed: No bag. I gave up and prepared to make a claim in the morning. 8:30 AM Sunday morning - my bag is sitting on my front porch wrapped in a trash bag. What a fiasco."

Cons: "Flight crew not helpful. Despite empty space in first class overheads, would not allow coach passenger to put anything there."

Cons: "The flight left almost 1 hour late because paperwork wasn't signed off"

Cons: "Flight was delayed. They lost my baggage. TV in my seat didn't work and they didn't do anything about it."

Pros: "Spacious flight Cozy environment Comfortable sitting"

Pros: "-Staff offered free things like headphones and 15 minutes of wifi access to compensate for multiple delays -Cheap! -I was rescheduled to this flight after my previous flight was delayed and prevented me from taking my original flight back, but I was moved up to boarding zone 3 in return"
Cons: "-Significant delay prevented me from checking in to my room, which was highly inconvenient. Fortunately I had a friend who was willing to have me, but if not (and because the nearby hotels are filled up due to the beginning of freshman orientation at my college), I would have had nowhere to stay after 13+ hours of flying and exhaustion. This alone significantly hurt the experience."

Cons: "2h and 4h30 h late"

Pros: "Everything excep boarding on return flight."
Cons: "Delay on return & boarding was really slow! Not sure if it was the computers or attendants."

Cons: "Our inbound flight was two hours late. When connecting through Toronto, they lied to us. They said that the outbound connection was on time, that we'd likely missed it. Then, after standing through their requisite customer service line with only one open desk for two full flights, we were told to sprint through customs. We arrived, breathless to find the connection was delayed. We were told that they don't post the delayed connections for fear that passengers won't run or that U.S. customs will close. Uncommunicative and untruthful, their service is atrocious."

Pros: "Flight crew was friendly. They were dealing with a lot of crabby people due to a 4 hour weather delay. They handled it, some better than others."
Cons: "I checked my bag. It got soaked. I am talking drenched like dumped in a lake and left there for the 4 hours we were delayed in Toronto. When we contacted air canada the luggage complaint rep told us to complete an online claim. We haven't heard a peep out of Air Canada in a week. Unacceptable Air Canada. You must would at least acknowledge that something was done wrong by a baggage crew even if they aren't on your payroll and on an airports."

Pros: "Nothing"
Cons: "Absolute joke of an airline with zero customer service. I would never travel with them again and would recommend anyone else not too."

Pros: "I liked waiting to fly until weather was good."
Cons: "I disliked the long delay, no time for the drink cart."

Pros: "Seating was fine on their "normal" flights."
Cons: "Regarding Air Canada Rouge service: If you are over 6' in height your knees will not fit in the assigned space."

Pros: "Nothing"
Cons: "After waiting 30 minutes after our boarding time, I got an email on my phone saying the gate had changed. No one at the current gate knew anything about it and I went to ask but no one could be found. I asked a man sitting behind the gate, who happened to be the pilot, and he also knew nothing about it. Needless to say, the gate changed and absolutely nobody was told about it. 2 hours later, our flight finally took off, and I was thanked by the pilot for getting us to the right gate... At least he provided a little humor to the situation! Plane also wasn't cleaned, pretzels and trash all over the floor."

Pros: "This was the smoothest flight I've ever had. Great pilot."
Cons: "It was a bit delayed."

Pros: "The crew was fantastic, really lovely and chipper!"
Cons: "There were only pretzels as a food option and I have celiac disease so I'm allergic to gluten. You can't just have one food option stop skimping. ALSO - I was put on a standby list which is entirely unacceptable. I purchased my ticket, therefore I should have a seat on a flight. Luckily in the end I was printed a ticket, but being on standby was just bullshit. Totally unacceptable."

Pros: "It left ontime and got me to where I needed to be."
Cons: "Pretzels are gross and dry. Jet Blue has much better snack choices. Overheard bins were really small on this small aircraft."

Pros: "cruising slightly high to avoid turbulence, the way from Toronto to Winnipeg we were flying on altitude 26,000 and then 30,000 feet. on west jet we were flying on altitude 39,000 feet with less turbulence. thanks"

Pros: "Leg room is comfortable"
Cons: "Flight had one and half hour delay. I did not get E-mail reminder for Check-in, for my return flight from Toronto."

Cons: "Same movies"

Cons: "Crew stopped severing prematurely. He said we were about to land and failed to serve my row and the one behind me. In the end we still had 30 minutes before we started the initial descent. When the person behind me spoke to him about it the steward was rude to him."

Cons: "The woman at ticket counter was rude and not helpful"

Pros: "It was a pleasant experience , the whole travel"
Cons: "Nil"

Pros: "Great flight, entertainment system, flight staff made me feel at home"

Pros: "The saftey"
Cons: "Food"

Pros: "I enjoy flying and being in the air at high altitude in any air line. Away from everyone else and with a new family who are flying with me."
Cons: "The charge per bag is ridiculous. It should be included as part of fare paid. Understood another bag charge as a separate fee."

Cons: "The flight was late"

Pros: "short flight with a good seat. fast baggage service"

Pros: "Check in was excellent"
Cons: "Flight was 4 and half hours late for weather and mechanical reasons. Airline responded very well but such a long delay is annoying"

Pros: "Despite the crew being on strike, the only attendant on board did an excellent job of handling everybody's needs."

Pros: "On time or early"

Pros: "Direct service is nice! Clearing customs in Ottawa makes life easier."
Cons: "Buttery pretzels in both directions that are way too buttery. Crew is never overly happy to be there."

Pros: "On the plus side, the service was great."
Cons: "There is just not enough space in the seats! I am not a tiny person and my trip was not helped by the fact that the seats are too narrow to comfortably seat people larger than a size 10!"

Pros: "This flight always takes off and lands on time, and has a friendly flight crew."

Cons: "The screen at my seat did not function properly."

Pros: "Fast boarding and takeoff"
Cons: "Delayed 1.5 hours"

Pros: "Everything"

Pros: "The information screen did not work... Air Canada booth at Winnipeg staff excellent.. Calgary terrible"

Pros: "Everything was great"

Read more about Delta

Book cheap flights from Winnipeg to Massachusetts

Recent round-trip flight deals

1/20
Wed
2 stops
Delta
12h 12m
YWG - BOS
1/28
Thu
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Delta
13h 37m
BOS - YWG
2/11
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6h 50m
YWG - BOS
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YWG - PVC
1/31
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Multiple Airlines
14h 41m
PVC - YWG

Recent one-way flight deals

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Air Canada
7h 15m
YWG - BOS
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Delta
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YWG - BOS
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