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Find cheap flights from Boston to Winnipeg

BOS - YWG

Find cheap flights from Boston to Winnipeg

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Boston (BOS)
Winnipeg
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Good to know

Low season

April Best time to beat the crowds (43% less expensive on average)

High season

February Most popular time to fly (37% more expensive on average)

Average price round-trip

C$ 391 (avg. price over the last 2 weeks)

Good deal round-trip

C$ 271 or less

Good deal one-way

C$ 110 or less

When to book flights from Boston to Winnipeg

Estimated round-trip price
Average price per month
Flight prices as travel date approaches
-1 day
-2 days

Top tips for finding a cheap flight

  • Looking for a cheap flight? 25% of our users found flights on this route for C$ 141 or less one-way and C$ 345 or less round-trip.
  • The cheapest flight from Boston to Winnipeg was found, on average, 47 days before departure.
  • Book at least 2 weeks before departure in order to get a below-average price.
  • High season is considered to be January, February and March. The cheapest month to fly is April.

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Top airlines flying Boston Logan Intl to Winnipeg

Scores according to KAYAK customer reviews

7.9
Delta
Overall score based on 28,935 reviews
8.1
Boarding
7.8
Comfort
8.5
Crew
7.8
Entertainment
7.5
Food
Airline reviews

Pros: "this is the airline"

Pros: "The crew was very friendly. The plane was very quiet (except for noisy crying babies)."
Cons: "Unless you can afford the higher priced "comfort class" or first class seats, the seating is very, very cramped on Delta's 757s. It's a good thing the flight was only 5+ hours (but that's not long enough to get any decent amount of sleep on this flight scheduled as a redeye)."

Cons: "Better allergy aware food."

Pros: "Friendly crew"
Cons: "We reserved exit row seats and when they changed the plane they gave our exit row seats to others."

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

Pros: "Movies"
Cons: "Not supplying headphones Crew not to helpful, one unpolite Refreshments ridiculous"

Pros: "The crew and service were outstanding, seat was comfortable."

Pros: "I was going for weekend trip and because of delays I would've been there less than 20 hours. But Delta was terrific in giving me a refund and essy to work with via Twitter. 2 hour phone delay but they called me back to complete refund."
Cons: "Chaos at gates. Changed gate 3 times. No real updates."

Pros: "Everything else"

Pros: "I was thankful for the early boarding with a lap infant and was very pleased with the options for entertainment on the TV monitor."
Cons: "The main issue I had was that we sat in row 34 and the noise from the engines often made it difficult to hear announcements, even with headphones in. Look into possibly zoning the audio and turning it up a click or two for rows behind the engines."

Pros: "Quick boarding, nice staff, good entertainment available."
Cons: "Nothing"

Pros: "The overall flight was good."

Cons: "My wife was told she could not board our flight from Boston to Paris because her passport was expired, even though it was not expired. We were told that in Europe passports cannot expire within 3 months of your departure. However, Delta never let us know about this rule until we literally were boarding the plane. How they could not make us aware of this until we were boarding the airplane is unbelievable and unacceptable. This has ruined our vacation which has been in planning for the last six months."

Pros: "Complimentary snack mini-meal. Early departure and arrival. Availability of extra seat and elbow room. Free movies."
Cons: "Entertainment screen would not tilt to comfortable angle when passenger in front of me reclined his seat, and the screen/system stopped functioning properly near end of flight."

Cons: "We sat on-board the aircraft, at the gate, for almost 2 hours due to a weather delay. During this time, we were not offered refreshments, nor were we offered any type of "compensatory benefit" for our delay (e.g., free Wi-Fi, vouchers good toward a future flight (a $30 voucher per passenger would seem appropriate), additional SkyMiles (3000-5000 SkyMiles would seem appropriate), etc.)."

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

Cons: "Jet airways sucks"

Cons: "The flight crew and staff were all great!"

Pros: "Crew were friendly and understanding"
Cons: "Flight was delayed 4 times, didn't land in ATL until almost 4 a.m. Still was charged for bags and when I called in to reschedule so I could get another nights sleep they said next flight wasn't until 10 the next day and there was charge for that. Also my flight from ATL to Boston earlier that week was delayed 3x. Overall not impressed with this connection. Meanwhile another flight to Boston from ATL left and I was not notified or selected for this change."

Pros: "red"
Cons: "red"

Pros: "It only took them 10 minutes to turn things around to make up time for the delay."
Cons: "The seat pockets were not cleaned."

Cons: "delayed 2+ hours due to runway maintenance. You'd think those things would be better planned..."

Pros: "Great crew and passengers"

Pros: "Entertainment offered, USB charging options."
Cons: "Too much food offered."

Cons: "Not having a seat assignment until arriving at the gate."

Pros: "you must be kidding me!!! nothing to say good about this fly !!The sad part I'm American Express Delta SkyMiles credit card holder and they couldn't do anything for meThe only good thing we arrive in Mexico"
Cons: "flying to Mexico with. my two boys !!to begin I have to call Delta to put us seat together because the time of the fight had changed!! before we are siting by de middle of the plain when a booked r three seat together !! but than i got a imail confimatin with separete seattle for the kids!!we end up sitting all the way back on the plan!! we end up sitting all the way back on the plane l!! no TVs no windows in the last sits by the only two bathrooms on the plane with two boys that was not fun at all !!The sad part I'm American Express Delta SkyMiles credit card holder and they couldn't do anything for me when I called them"

Cons: "Didn't eat or use entertainment."

Pros: "The entertainment system worked well and was able to keep my phone charged."
Cons: "It's very cramped seating. They started boarding by rows but then gave up. Crew are nice."

Pros: "Flight on time"
Cons: "Unfriendly sataff. Not informed that we have to me know in with a difrnt confirmation number related to the operating Claire. I had to spent one hour to fit this information to be able to check in.? It was an international flight but it was treated like a domestic flight. We were not even offered the curtesy snake for a domestic flight by unfriendly stewards apparently unhappyted with her job. Apparanty all American carrier staffs has no respect for customers. It is not only s united problem. Curtesy and respects goes both ways. They need to be retrained in public relation."

Cons: "No seat assignment prior to arriving at the gate"

Pros: "The plane didn't crash."
Cons: "Everything! Flight late, seats to close, worst customer service in the skies!"

Pros: "Staff are friendly"
Cons: "No leg room compared with JetBlue; few free snacks"

Pros: "arrived early"

Pros: "We were stuck for an hour and a half on the tarmac"
Cons: "We were stuck for an hour and a half on the tarmac"

Pros: "I liked that the security line experiences very mellow, the staff all around was very friendly and nice, the TV's were great and they had free blankets and headsets. It was a very relaxing experience."
Cons: "thought the cabin could have had more heat"

Pros: "It was a really good flight minor turbulence towards the end. Flight was on time, smooth flight. NO tvs on this one."
Cons: "I wish they had more snacks like JetBlue but all was fine. TVs on every plane would be nice."

Pros: "Excellent flight and crew on a new Airbus 319"
Cons: "Lunch time flight. Only food in economy was bags of high carb salty snacks"

Pros: "Delta always has a nice professional crew. We were served within a reasonable time and I felt comfortable the whole flight."
Cons: "The pressure is the cabin with really bothering me. I've flown several times and never had the pressure to bother me but it was really hurting my head."

Cons: "You guys lied to us , you said I was getting first class flys , and it didn't happen . I'm really disappointed and I would never again get a flight with you guys!"

Pros: "The crew was friendly and boarding was easy."
Cons: "didn't provide snacks. They took a long time to retrieve the luggage that was checked at the gate."

Cons: "Row 36 is a disaster."

Pros: "flight crew was nice"
Cons: "Very old dirty plane"

Pros: "On time, leg room, entertainment, service."
Cons: "N/A"

Cons: "Old plane Zero entertainment First class seats worn thin and uncomfortable. I've been flying AA quite a bit lately and thought I'd give Delta another try. Too bad, it's clearly not up to today's standards"

Pros: "Smooth flying"
Cons: "The entertainment units were terrible. Touch screens effectively impossible to operate in this 737-800."

Cons: "I left my wallet on this flight. It was extremely frustrating that I was unable to speak to a live person to find out if the wallet had been recovered. I filled out the form online and now have to wait 2 to 3 weeks!"

Pros: "Boarding was efficient and easy. For the first time on any airline, the crew was over-the-top friendly and my special meal request was excellent."

Pros: "It's what I didn't like....as a Sky Miles member I should get a free bag. Small aircraft for a FL trip."

Pros: "I liked nothing, because the flight was 4hrs late and had 20 on standby."
Cons: "4hrs late, 20 on standby, missed connection, had to travel a day later and spent 14hrs in the airport."

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

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."

Cons: "I could not get a seat assignment or a boarding pass for my connecting flight"

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

Pros: "Good"
Cons: "Good"

Pros: "I have limited mobility and I was very well taken care of by the crew."
Cons: "flught was fine."

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: "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: "We were disappointed we couldn't order from the flight menu."

Pros: "The crew members were also friendly"
Cons: "The boardung gate was changed but no announcement was made"

Cons: "Flight delayed out of Boston. This seems to be the normal state of things. I dont think I've ever flow this route on and had an om time arrival This caused me to miss my flight in Toronto, forcing me to spend the night. I pressed their customer service rep for a hotel, but they refused claiming it was a weather related incident and they were were therefore mot responsible. The weather in Boston and Toronto was fine and at no poi t on the flight did anyone offer Any Reason Whatsoever for the delay. Moreover when i protested the customer service agent mocked me for not realizing it was a 'weather related incident'. I spent the night on the floor on YYC. Needless to say, Ill never fly Air Canada again."

Cons: "Wireless system slow and costly."

Pros: "The staff was helpful and courteous. I liked the tv selection especially the Canadian content."
Cons: "The flight was delayed because of electric problems. The complimentary snacks aren't as good as other airlines."

Pros: "It was such a nice normal flight compared to the other flights on this trip."
Cons: "Still too much carry on to deal with before take off."

Pros: "Paid for the "upgraded" seat only to be told we had to be in the back of the plane. Moving back all rows had one person and one chair open, so we had to sit apart. Useless crew as an elder couple asked to sit together and were told to check with passengers. Oh and the flight was delayed 3 times."

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

Pros: "I never got in my flight home for my aunts funeral and to get back to work because nothing on your website warned or notified me that I needed a visa just for a connecting flight on Air Canada so not only did I lose my money I was denied my flight denied the chance to be at my aunts funeral and get back to work. So my honest opinion is that I am extremely disappointed and deeply saddened by this evtire ordeal now I have to spend more money to purchase another ticket with another airline to go home. Thanks for the hassle! Aslim Hosein."
Cons: "Seriously? NOTHING AT ALL and I wish I could select no stars"

Pros: "I liked the service crew and flight attendants help. It was amazing to come home safe. I enjoyed my flight."
Cons: "Nothing at all."

Pros: "Genial crew"
Cons: "Disorganization in Boston, we almost missed our connecting flight"

Pros: "The flight was on time!!!"
Cons: "I find over the past 25 years that I have been flying with Air Canada the customer service has really went to the dumps !!! Every body is rude and don't understand why."

Pros: "My flight was delayed and I did not get my baggage when I arrive at Boston airport.. I had no clothes or anything to wear for three weeks when I got to Boston. I complain the very day I got to Boston airport. Up till now the bag I checked in at Toronto airport has not been given to me. The funny thing is after I checked in, it was not scan at any other place except Toronto. So it got lost at Toronto where I checked in. All that am told of is the baggage can not be located. Three weeks I spend at Boston, I had nothing."

Pros: "Quick, cheap, great service"
Cons: "Nothing bad, really"

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: "I was happy to be on the flight."

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

Cons: "The USB port in seat 26A was pushed in and wouldn't connect for power. Unless this was exactly the same plane it was true on both flight to and return from Boston. The LCD entertainment system is very slow to respond to touch. The default sound level is always too loud. The commercials take up the first 10 minutes (or longer) of the experience and make for an excruciating long wait."

Cons: "Flight was 45 min late leaving & I only had 1 hr between the next flights. Because Winnipeg is a small airport, I just made the next connection but no time to go to the restroom."

Cons: "Flight was late taking off"

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: "The crew was nice and the flight landed on schedule."

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: "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: "Excellent crew and comfortable cabin."
Cons: "I have no criticisms to offer."

Pros: "The crew at the gate and onboard were exceptional! At the gate they made sure I could get on this flight even though the computer auto booked me for 2 days later."
Cons: "My bags didn't make it on the flight because of a close connection. Then I was rebooked on a flight 2 days later. This is unacceptable. I was expected to stay in Toronto for two days."

Pros: "entertainment,"
Cons: "crew are polite but cold and strict. it was a night flight and they were very noisy when serving the food."

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"

Cons: "gate was changed without an announcement flight was twice delayed"

Pros: "Great service"

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."

Pros: "getting to my connecting flight on time"
Cons: "There was nothing to hate"

Cons: "Food was not that good"

Read more about Delta
COVID-19 information

Safety measures for airlines flying from Boston to Winnipeg

Airlines flying from Boston to Winnipeg have enacted additional safety measures and adjusted policies to better accommodate travellers. Policies vary by airline.

Heightened sanitation

Daily cleaning, installation of cabin HEPA filters on flights from Boston to Winnipeg

Mandatory masks

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

Social distancing seating

Middle seats unavailable to book on flights from Boston to Winnipeg

Pre-flight testing

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

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