Find cheap flights from Massachusetts to Winnipeg

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Find cheap flights from Massachusetts to Winnipeg

Round-trip
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Washington (WAS)
Winnipeg
Mon 3/8
Mon 3/15
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Good to know

Low season

AprilBest time to beat the crowds with an average 5% drop in price.

High season

DecemberMost popular time to fly with an average 20% increase in price.

Average price round-trip

$347(avg. price over the last 2 weeks)

Good deal round-trip

$149or less

Good deal one-way

$129or less

FAQs for booking flights from Massachusetts to Winnipeg

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Top 3 airlines serving Massachusetts to Winnipeg

Scores according to KAYAK customer reviews

7.9
Delta
Overall score based on 29,056 reviews
8.1
Boarding
7.8
Comfort
8.5
Crew
7.8
Entertainment
7.5
Food
Airline reviews

Cons: "For some reason, we were asked several times for Passports. This didn’t make any sense since we are US citizens with drivers license. They even had TSA talk to us. This has to be fixed. Otherwise, Delta experience was great."

Pros: "Don’t go overboard"
Cons: "Cleaner"

Pros: "Good"
Cons: "Good for now"

Cons: "Top carrier"

Pros: "Well organized and easy to check in."
Cons: "No"

Cons: "Nothing, really. Airlines unfortunately can’t make people patient or polite, & I can’t afford a private jet, so I’ll have to settle for an eye roll or twelve."

Pros: "Everything"
Cons: "Nothing"

Cons: "No mechanical failures or delays would be nice"

Cons: "The inoperative TV screens should be repaired."

Pros: "Was boarded promptly"

Pros: "this is the airline"

Cons: "Plane was late taking off. Crew did not provide water when requested. They were busy with beverages that they could sell at a cost."

Cons: "Better allergy aware food."

Cons: "Wonderful"

Pros: "I love ice cream and chocolate"
Cons: "Healthy vegetarian meal choice"

Pros: "Seating was fine"
Cons: "Did not have a wheelchair waiting for my wife when we arrived in LAX"

Pros: "room and services"
Cons: "can't think of anything"

Cons: "Even the baggage was quick (highly unusual for Columbus, Ohio)! Everything went smoothly."

Cons: "Delays due to Democrats not making deal"

Pros: "Good service this morning"
Cons: "All good"

Pros: "We left early"

Pros: "Arrived ahead of time"

Cons: "We left 30 minutes late due to congestion and I missed a layover. Otherwise it was a great experience"

Cons: "My sit changed last minute, noisy babies"

Pros: "The cheese bites were amazing!"

Cons: "My luggage is lost."

Cons: "After we boarded and were already sitting in our sits the stewardess came and removed our bags from the overhead compartment for another person with a larger bag! We ended up storing our bags under the sits in-front. The way it was done it was rude and with no consideration for our comfort."

Cons: "Delays, delays, delays... first class ticket from BOS to MSP got me a 6 hour delay and a middle seat in econ main cabin at the back of the plane. Delta you suck!"

Pros: "Easy and quick"
Cons: "No complaints"

Pros: "A3A"
Cons: "Ĺ"

Cons: "insufficient overhead luggage space"

Pros: "Food was plenty."
Cons: "Long security lines at Logan. No free WiFi"

Pros: "We were in the plane for 3 hours before we could depart. No one offered us a drink or snack."

Pros: "Comfort Plus allowed us to board early, useful USB ports."

Pros: "Service vey Good. Nice choices. Comfort seating very nice"
Cons: "WiFi awful. Useless."

Pros: "on time, good food, good films enough space to sleep in economy."
Cons: "the stewardess only went up one side of the plane offering eye shades and when i asked for one she seemed really miffed."

Pros: "The selection of movies to watch was very good."
Cons: "No snacks passed out"

Pros: "The staff. They were very helpful and polite!"
Cons: "We didn’t leave on time"

Pros: "Whole thing was easy, plane was nicely updated on the interior"

Pros: "The staff are wonderful and helpful. Best wishes to Delta. Please keep the great employees."

Pros: "I like Delta. They are organized and professional. They treat traveler with dignity."

Pros: "the service in general very nice"

Pros: "Entertainment"
Cons: "Late flight without any compensation for our trouble"

Cons: "Much older plane. Not as comfortable as some other planes I've been on."

Pros: "Nice people. Very helpful."
Cons: "LOST MY BAG IN BOSTON BEFORE EVEN TAKING OFF!!!! Did not make it, and then won't deliver it when it makes it to Kathmandu! This is most distressing."

Pros: "Everything else"

Cons: "Missed our connection. Spent the night in Minneapolis. Luckily we had no urgent reason to get home to."

Cons: "Jet airways sucks"

Pros: "red"
Cons: "red"

Pros: "Goood everything"
Cons: "Nn"

Pros: "Nothing same useable"
Cons: "No need"

Cons: "Aka was happy with westjet"

Cons: "Nothing"

Pros: "yes every thing was good.."

Pros: "The service was really good"
Cons: "The waiting at the gate"

Cons: "Nothing"

Pros: "Boarding was fast."

Cons: "My baggage did not arrive in my final destination"

Pros: "Loved the trip"

Cons: "My tv was not working, landing was not smooth staff was rude specially Edward"

Pros: "Easy boarding and checkin"
Cons: "Westjet seating is tight"

Cons: "was delayed by an hour"

Pros: "On time. Smooth."
Cons: "Cramped seating"

Cons: "Because of the discounted fare I was placed in rear seating at the very back of the plane and to change seats was to cost me $14"

Pros: "Smooth trip."
Cons: "No one would get a wheelchair to get to cart that was on different floor. Driver didn't volunteer to carry bags to cart."

Pros: "I had a 20 minute wait to do my bag drop and I was already checked in."
Cons: "Wish there were more staff in to accept pre paid checked baggage. Very frustrating to have such a long wait time when I was already checked in. However I would definitely fly WestJet again. The staff was very friendly!"

Cons: "Later flight from Toronto delayed multiple times, finally to 2:40 am and then canceled at midnight. Way too late to find an affordable hotel, had to stay at expensive airport hotel instead."

Pros: "The ease of boarding with very nice staff!"

Pros: "Nothing"
Cons: "They kept us on the aircraft for 4 hours on the tarmac as opposed to let us sit at the gate"

Pros: "I loved how spacious the plane was. The seat was comfortable with lots of legroom."

Pros: "It was smooth and uneventful."
Cons: "It was all fine."

Pros: "I like everything else except no entertainment"
Cons: "I wish there is TV or newspaper, magazine to read or watch that helps."

Cons: "Flight was delayed due to a tire change. That’s no big deal, but the crew did not accurately keep us updated on the actual loading time in order for me to arrange my pickup upon arrival in Winnipeg."

Pros: "The plane was one of their most recent to their fleet of planes. Lots of overhead luggage space and extra leg room. Nice looking on the inside"
Cons: "I like the overall feel to the inside."

Cons: "Very few options were available to redirect me to my final destination"

Pros: "Phenomenal all around!"

Pros: "On time! Roomy cabin space and leg room"

Cons: "The very long delay, the aircraft was extremely crowded and then we arrived late"

Pros: "There is no entertainment so why ask.this question repeatedly and I understand on longer flights that is valid but on these flights it is not applicable"

Pros: "STAFF WAS GREAT"
Cons: "CHECK IN OVERHEAD BIN RULES NOT ENFORCED-NO ROOM FOR MY ONE PIECE"

Pros: "Everything was exceptional"
Cons: "Nothing to complain about"

Pros: "We got in the plane past the set time. But within reasonable tardiness. We landed a few minutes after the scheduled time. Our bags were right there when we walked out of customs"
Cons: "The cookies/nachos"

Pros: "The leg room"
Cons: "They didn’t have wifi so couldn’t watch anything"

Pros: "Friendly staff 8"

Cons: "Seats were so crammed together. When the person in front mived their headrest back my knees were crushed and I xould not sit comfortably. I am 5'10. Not super tall. Nees more leg room."

Cons: "Cabin was too cold"

Pros: "I needed assistance for my father and West jet went above and beyond in their service. Made an ol man very happy and gave him the ease of traveling alone."

Cons: "the seats are a bit confining."

Pros: "The airplane being pretty small, boarding and getting off was fast. No issues or delays either."

Pros: "Pleasant staff and adequate leg room."

Cons: "If it was noted that there would be luggage fees when I was booking I didn't see it."

Pros: "Helpful staff"

Cons: "Got there 2 minutes after check in closed and wouldn't let us fly"

Pros: "Enjoyed the flight on WestJet."
Cons: "I did not like Kayak, and will not use them again."

Pros: "Bell's live TV is probably the best feature!"

Pros: "Friendly, helpful staff"
Cons: "Typical stuff, Cramped space, crappy food"

Pros: "Crews"
Cons: "Should be more hearty food and more entertainment like tv, movies and radio"

Pros: "The crew was OK, just a bit too patronising and hyper"
Cons: "Seats were damn uncomfortable and tight. The attendant making the announcements spoke soon fast, you had to wonder if she is running a marathon....I could hardly hear her full sentences. One of the serving attendant was a tad patronising and slightly annoying. Like no one wants to listen to "innuendos" at that time of the night."

Pros: "It was a little bit delayed but after the airplane arrived everything was very fast."
Cons: "I don't have any problem about the west jet, I know that some delays is complete normal because the weather or air traffic."

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"

Cons: "Took 45 minutes to get through Calgary security, long line ups"

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

Cons: "Seat didn't recline and touch screen on TV was working but it took some work -- I had to press and hold and the little arrow would fly all over the screen"

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: "5 hours delayed because captin was late."

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: "Very cramped like sardine tin. Not enough flight info boards in airport and they were hard to read m"

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: "Delayed without notice and broken sound system for tv screen."

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: "Ease of booking"
Cons: "No complaints"

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."

Pros: "The landing..."
Cons: "Left late and overall once again did not find the staff to be exceptionally helpful."

Pros: "Friendly"
Cons: "French annoying"

Pros: "Liked being distracted by a free movie."

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

Pros: "Quick easy, I hate that I have to go through sercurity again... but oh well."
Cons: "Refer to last one."

Pros: "Good service"

Pros: "Service on the flight is always good and the transfer in Toronto was seamless."
Cons: "The departure area in Boston is dreadful. no room and no amenities. Straight out of the 60's."

Pros: "We checked in online and were able to very quickly and efficiently check our bags and board."
Cons: "We did not have in flight entertainment. We had to pay $10 to rent an iPad."

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"

Cons: "1h15 late"

Pros: "Everything was fantastic. Great flight crew. Great stuff."

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

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: "Price good; seat comfort OK."
Cons: "Late to board, late to take off, late to land: no explanations other than "We're third in line.""

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"

Cons: "Connecting from London through Toronto to Winnipeg couldn't be accomplished in a 2.25 hr layover. Long line for immigration and and enormous line to go through security again meant I missed my flight and the next one was full. It gave me 5 hours to think of all the reasons why I won't connect through Toronto again."

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: "Flight and in flight service"
Cons: "Bit chaotic in the departure area and at the gate"

Pros: "Organized boarding and in flight service"
Cons: "Late departure"

Pros: "I liked the entertainment selection. It had starwars, that was a big plus."
Cons: "The seating accommodations were terrible l. No leg room, and no room beteween passengers. I Could not relax for a 12hr flight. Im debating of booking a new flight altogether home. WHyde do all converges have to be spring ruxe ("

Pros: "I am happy that Air Canada is unionized; the personnel are fine. I also like the tvs on the backs of the seats, with their wide range of shows. Particularly, I like Portlandia, though there was only one episode of that."
Cons: "I disliked that the airline forced me to miss my connection (inevitable, I suppose, given the excessive security and the lack of direct, affordable connections between Manitoba and the US) and I had to take a later flight to Toronto and didn't get home until 2 am."

Cons: "Air canada just didn't even show up, I had to take a different plane to Japan which made me late for my last flight so I had to stay in a hotel and wait til the morning to catch a new plane. So ya, not impressed."

Pros: "Short flight, as expected on smaller older plane"

Read more about Delta
COVID-19 information

Safety measures for airlines flying from Massachusetts to Winnipeg

Airlines flying from Massachusetts to Winnipeg 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 Winnipeg

Mandatory masks

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

Social distancing seating

Middle seats unavailable to book on flights from Massachusetts to Winnipeg

Pre-flight testing

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

Book cheap flights from Massachusetts to Winnipeg

Recent round-trip flight deals

8/5
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Air Canada
5h 53m
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8/10
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6h 23m
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5h 53m
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10h 13m
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7h 38m
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5h 53m
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5h 28m
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5h 53m
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8/10
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Air Canada
10h 13m
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5/11
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WestJet
6h 10m
BOS - YWG
5/14
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WestJet
5h 36m
YWG - BOS
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Delta
10h 44m
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Delta
8h 15m
YWG - BOS
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47h 50m
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3/31
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25h 25m
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46h 20m
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38h 10m
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14h 30m
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29h 02m
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