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YWG - BOS

Find cheap flights from Winnipeg to Boston from $181

This is the cheapest one-way flight price found by a KAYAK user in the last 72 hours by searching for a flight from Winnipeg to Boston departing on 5/26. 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
0 bags
lør. 6/8
lør. 6/15

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These are the airlines KAYAK users have selected most often from within our search results in flight searches from Winnipeg to Boston, 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 Winnipeg to Boston, as well as popular online travel agencies
In the last 7 days travelers have searched 43,895,468 times on KAYAK, and here is why:

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Cheap flight deals from Winnipeg to Boston (YWG-BOS)

Here are some of the best deals found on KAYAK recently from the most popular airlines for round-trip flights from Winnipeg to Boston 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 and deals for you by selecting your travel dates.
Choose your dates
7:30 am - 3:09 pmYWG-BOS
6h 39m1 stop
6:00 am - 11:01 amBOS-YWG
6h 01m1 stop
$318Air Canada
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tir., juli 16 - tir., juli 23
12:26 pm - 1:22 amYWG-BOS
11h 56m2 stops
11:10 am - 11:25 pmBOS-YWG
13h 15m2 stops
$327Delta
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tir., juli 16 - tir., juli 23
11:50 am - 6:05 pmYWG-BOS
5h 15m1 stop
8:15 am - 6:07 pmBOS-YWG
10h 52m2 stops
$332Porter Airlines
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tor., juni 6 - tor., juni 13
6:00 am - 7:27 pmYWG-BOS
12h 27m2 stops
8:15 am - 5:52 pmBOS-YWG
10h 37m2 stops
$336Porter Airlines
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fre., sep. 27 - man., sep. 30
12:26 pm - 1:22 amYWG-BOS
11h 56m2 stops
5:20 am - 4:37 pmBOS-YWG
12h 17m2 stops
$345Delta
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lør., juli 20 - tor., juli 25
12:25 pm - 9:17 pmYWG-BOS
7h 52m2 stops
9:15 am - 5:47 pmBOS-YWG
9h 32m2 stops
$351Porter Airlines
Find Deal
tor., maj 23 - lør., maj 25
11:50 am - 9:17 pmYWG-BOS
8h 27m2 stops
8:15 am - 6:07 pmBOS-YWG
10h 52m2 stops
$352Porter Airlines
Find Deal
tor., juni 6 - tor., juni 13
2:18 pm - 1:20 amYWG-BOS
10h 02m1 stop
6:35 pm - 1:11 pmBOS-YWG
19h 36m2 stops
$481United Airlines
Find Deal
fre., maj 31 - man., juni 3
8:15 am - 5:21 pmYWG-BOS
8h 06m1 stop
6:05 am - 11:25 amBOS-YWG
6h 20m1 stop
$484Air Canada
Find Deal
tor., maj 30 - man., juni 3
7:30 am - 10:06 pmYWG-BOS
13h 36m2 stops
8:55 pm - 11:25 pmBOS-YWG
27h 30m1 stop
$529WestJet
Find Deal
lør., juli 20 - tor., juli 25

Flights from Winnipeg to Boston - Travel Insights & Trends

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

What’s the cheapest day of the week to fly from Winnipeg to Boston?

The average price of all flights from Winnipeg to Boston clicked on KAYAK for each day over the last 12 months.
If you are looking for a flight deal from Winnipeg to Boston, look for departures on Mondays and avoid leaving on a Sunday, as it's usually the priciest day. When flying back from Boston, Sunday is the cheapest day to fly and Friday is the most expensive.

What is the cheapest month to fly from Winnipeg to Boston?

To calculate monthly average prices, KAYAK takes all prices for each month over the last year for flights from Winnipeg to Boston, removes the top 0.1% to account for outliers, and then takes the median of all values for each month.
The cheapest month for flights from Winnipeg to Boston is May, where tickets cost $386 on average. On the other hand, the most expensive months are August and December, where the average cost of tickets is $595 and $562 respectively.

How far in advance should I book a flight from Winnipeg to Boston?

To calculate daily average prices, KAYAK takes all prices for each day before departure over the last year for flights from Winnipeg to Boston, removes the top 0.1% to account for outliers, and then takes the average of all the values for each month.
To get a below average price on the flight from Winnipeg to Boston, you should book around 4 weeks before departure. For the absolute cheapest price, our data suggests you should book 32 days before departure.

Which airlines provide the cheapest flights from Winnipeg to Boston?

The cheapest price for the route for each airline clicked by KAYAK users in the last 72 hours.
The best deals for a one-way ticket found by KAYAK users over the last 3 days were on Air Canada ($181) and Delta ($190). The cheapest round-trip tickets were found on Air Canada ($318) and Delta ($327).

Good to know

Low season

November

High season

June

Cheapest flight

$181
Best time to beat the crowds with an average 0% drop in price.
Most popular time to fly and prices are also 8% lower on average.
Flight from Winnipeg to Boston

When to book flights from Winnipeg to Boston

Are your dates flexible? Find out the best times to travel from Winnipeg to Boston 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 Winnipeg to Boston

  • What is the cheapest flight from Winnipeg to Boston?

    In the last 3 days, the lowest price for a flight from Winnipeg to Boston was $181 for a one-way ticket and $318 for a round-trip.

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

    Yes

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

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

  • Which airline alliances offer flights from Winnipeg to Boston?

    Star Alliance, and SkyTeam are the airline alliances operating flights between Winnipeg and Boston, with Star Alliance being the most commonly used for this route.

  • Which is the best airline for flights from Winnipeg to Boston, Delta or WestJet?

    The two airlines most popular with KAYAK users for flights from Winnipeg to Boston are Delta and WestJet. With an average price for the route of $579 and an overall rating of 8.0, Delta is the most popular choice. WestJet is also a great choice for the route, with an average price of $495 and an overall rating of 7.5.

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

    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 Winnipeg to Boston.

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

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight to Boston from Winnipeg 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 Winnipeg to Boston?

    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 Boston with an airline and back to Winnipeg with another airline. Booking your flights between Winnipeg and BOS 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 Winnipeg to Boston?

    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 Boston from Winnipeg up to 3 days before/after your preferred dates. You can then pick the flights that suit you best.

See more FAQs

Top 4 airlines serving from Winnipeg to Boston

 
See real verified KAYAK customer reviews for airlines flying from Winnipeg to Boston. 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 Winnipeg to Boston? 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
DeltaOverall score based on 10778 reviews
8.6Crew
8.2Boarding
7.9Comfort
7.4Food
8.0Entertainment
Airline reviews

The gate area was incredibly short staffed, with one representative manning 4-5 flights, which caused a 3 hr delay in boarding even though the plane was all ready to leave. Other flights also were delayed because of this. The flight crew was awesome and I feel bad for the only gate worker on call, but Delta needs to hire more employees.

2.0 MediocreAnonymous, May 2024AVL - LGA
Read more about Delta reviews

The gate area was incredibly short staffed, with one representative manning 4-5 flights, which caused a 3 hr delay in boarding even though the plane was all ready to leave. Other flights also were delayed because of this. The flight crew was awesome and I feel bad for the only gate worker on call, but Delta needs to hire more employees.

Very frustrated with boarding gate crew. She announced the plane was small and they would be limiting us to one item to carry on. Not a problem for me as I understand the tiny planes have limited space!! Not the case here! It was a rather large plane and had plenty of room for bags! So because I don’t want to be one of “those people” who ignores the request to check a carry on I did so asking if I would be able to pick it up at the bottom of the ramp on arrival in Knoxville to which she responded “yes”! Then I watched as every other passenger held onto their 2 items and boarded!! Then when we arrived in Knoxville our 2 carry ons had been put with all the other luggage and we had to go to baggage pick up and wait for all the big checked bags to come off the carousel! So she lied!! Frustrating. Next time I won’t be so nice!

Everything was great. The big planes could still stand to have a bit more leg room. Crew was amazing!!

It was a good experience except when boarding a female flight attendant did not go out of her way to assist my teenage daughters in finding space for their carry-ons after their compartments were full.

It was a Red-Eye flight so was not comfortable enough to sleep, but seat was as expected. Crew was great and in-flight entertainment was excellent. Flight was smooth

Terrible. Delta delays caused us to miss our flight and they did nothing to fix it.

The A330-200 was showing its age but otherwise this was a pleasant flight with friendly crew. The meals/snack provided were pretty good.

The most unprofessional and disorganized experience I’ve ever had with an airlines. After the flight was diverted on the runway and we returned to the gate, there was no communication about the plans and it took an additional 5 hours to get set up with a hotel and a new flight, information that was not readily given to the passengers and mostly gotten second hand from what other passengers heard from each other. Based on this experience I cannot recommend flying delta again

I received the two differed meals: chicken and pasta. I asked and I received. I am anti-wasting food!

I was traveling with my 85 years old grandma and 60 years old mother. Which I requested to get a wheelchair. I went to the Delta Kiosk and asked for a wheelchair.  They brought a wheelchair and 2 minutes (without exaggerating, time is important for me as I am well disciplined with a military background) later they said that the wheelchair belongs to American Airlines, so we need to switch it.  We were like where is the other one so my grandma can use it? They are like, "it's on its way, she has to wait for the other one" I asked them why does she have to wait? Is it ok for her to sit on this one when the other one arrives. Answer was "NO". I guess lack of common sense was the issue. I started to explain to the agent that she can not stand still or wait. Finally, someone said that in spanish "she can not stand, let's wait for the other one" . Delta's wheelchair came, without an attendant or helper. They brought that wheelchair and left it in the middle of the airport. Nobody seemed to care. I had to push her to the gate. Then they finally realized that "wait a minute, there is something wrong with that". So they send someone, who later started harassing us, to tell us how he works for cash tips. Then a "Private Security Interviewer" approached us. I think his name was Carlos (His descriptions - tall for an average worker, ginger curly hair, wears glasses, overweight). He did not represent himself. All he did was show his badge for two seconds and when (later on) I asked him what his name was, he said "I already told you at the beginning". At that point we were waiting to be called at the Delta Kiosk (this is prior to the Customs first check in point). So, Delta Airlines hired "Private security interviewers" to make sure that nobody brings anything illegally to the US. Which is great, makes me feel safe and secure. But, it does not serve the purpose. Let me explain to you why. These interviewers do not know what they are doing or saying and you can clearly see that. They think that they are CBP or Immigration officers. They will get angry If you ask them any questions. Then they will put all these stickers on the back of your passport like they caught "Pablo Escobar". At one point I was sarcastic and told the interviewer that "I like those stickers, It's my hobby and I am collecting them. Can I have more of those?"  and interviewers eyes and brain goes like "error 404". He did not know how to react or respond to that. Then he flags my itinerary on his iPad. Trying to give me a hard time since I asked him about his name, so I can call him by his name. But of course that did not change the fact that his lack of english made everything even harder. After 45 mins of wait and clearing the "Private Security Interviewer" you would think that we are going to be all set to depart. I was wrong. We waited in line to go through the security line, just like other citizens. No wheelchair, disability, seniority etc were important for her. They treat us like she is in her twenties.  On several occasions they forced her to stand up. She was like "I swear to God that I can not walk, my son I wish I could walk, but I can not". They did not seem like they cared. Then finally they realized that she is legit disabled. They let her pass on a wheelchair. At the gate, Carlos showed up to make sure that I am going through the secondary check. They pulled me to the secondary check. And started asking me about my luggage. My response was "I only have one carry-on bag, to make everyone's (including my life) life easier". They asked the same question over again "Sir, do you just have only one bag?" I replied saying "Yes". She did not believe me and said "Just only one". So, I thought she did not believe me and I said "Yes, Si, Si, solo uno". She looked at me and then turned to the agent (Carlos) and stared at him like "did you not ask him about his bags, did you not know that he only had one carry on?". I am sorry to say that but they just looked like a bunch of idiots who do not know what they are doing. Finally they released me after a minute of secondary check. Meanwhile everyone is boarding and my grandma is waiting on her wheelchair. Then we approached the gate agent and I asked her if I could sit next to my family, if they had any seats available. She replied that "I can not change any seat at the gate, I do not have any authority". I replied "I understood". We got on the plane last and I asked our flight attendant if I could change my seat to be next to my family. FYI, their seats were 10 B and C, mine was the 35 D. Meanwhile there were empty seats on 10 D and F. Even flight attendants surprisingly said that "why did she put you all the way back, while we had 1/2 full flight. I will go and ask her". Our flight attendant was great and he made sure that I am next to my family. He went above and beyond and he gave the closest seat to the. Flight was good. Delta Airlines failed to bring the wheelchair when we arrived. Excuse was "Gate changed, that is why". I walked outside and grabbed an empty wheelchair. I put my grandma and brought her to the Customs. Then a Delta Airline worker approaches me and says that you can not move this wheelchair, it belongs to the gate. We will bring you a new one. A CBP officer heard our conversation and jumped in and said, "wait a minute you want her (pointed my grandma) to wait here while you bring her wheelchair?". He (delta worker) responded "yes sir". But when he talks to me, no sir, nothing. The CBP officer goes "Nope, she is not waiting here and I will make sure to pull her wheelchair". If that officer was not there we probably would have had to wait and be forced to change the wheelchair. The CBP officer, again the CBP officer, not the Delta employee, pushed our wheelchairs to the gate. Sincerely,

Airport monitors did not give the gate for our flight returning Detroit to Vancouver Juice served from glass storage containers are a far more healthy alternative for people. And would also minimize the need for recycling plastic or aluminum containers

Nothing to like about flying in the Dash 8s. With very small seats, little legroom, and a very noisy plane, nothing about such trips is enjoyable.

I wish that seats closer to the front of the plan were available, but when I booked the flight the seats were VERY expensive so I did not book seats at that time. The day before flying only seats at the back of the plane were available. It takes so long to board the plane and empty the plane on arrival due to SO many roller bags.

Difficult to say. Over crowded but that is the fault of the airplane not WestJet

Good flight. No I’m seat entertainment. But my phone worked just fine on the west jet app.

Check in was seamless , crew very polite , arrived on time!

Flight arrived early even after leaving late. Bag drop was a zoo, very slow even after using pre-checkin and airport kiosk.

I had planned to watch the Westjet entertainment for the entire flight however, because the seat mounted outlets in our row did not work.

Not a bad flight but our priority tagged luggage was the very last to come down the carousel.

Westjet delayed then rebooked us on flights for economy class when we paid for business class and now need a refund for fare difference and they aren't getting back to us

It was good! Appreciated that it was very on schedule so it made the connecting flight less stressful

Two flights,both poor. No entertainment. Cramped and uncomfortable seats, little space, the rest was OK. Staff were acceptable good.

The crew was doing their best on an old plane needing updating. Chairs that creaked and wouldn’t stay in position. My tray table was unusable as was on-board entertainment due the audio needing usb earphones (that were not provided). Prior to boarding in Toronto and despite being scheduled for a wheelchair and assistance, we were dropped off by clubcar without a wheelchair which I found myself by a gate. Due to no boarding gate assigned at that time we waited and when it was, it subsequently was moved from 64 to 95. No help could be found so I pushed my husband’s chair to that furthest gate in the airport at the highest speed possible for a 73 year old. And by that I mean I ran. It was a very stressful experience.

Crew was great and did their best to make us comfortable and captain came out at the beginning to announce why the flight was delayed, weather situation up ahead, and kept us updated throughout the flight.

Wifi wasn't working on one of the UA flights after boarding.

Leg room was lacking. Legs crammed into seat in front.

T hey did a great job. Flight was on time .

the plane was old. the wifi didn’t work. the entertainment was boring and dated. the charging ports were impossible to find. i was mostly ignored by flight attendants that had no problem speaking to the man beside me. i got two drinks the entire time i was on the plane.

Crew was not very helpful. They forgot to serve me coffee and had to wait for a long time.It looked as if they were not very happy with what they were doing.

The flight I was connecting with waited for me even though my 1st flight was late. I really appreciated that.

Everything was great. I really like how they had their safety film set up showing you the beauty of the country.

This time my experience was superior! Much better and improved from after the COVID-19. I hope they maintain the same. Earlier, service (specially crew attitude) was awful and sometime rude, but this time, crew was very welcoming, respectful and ready to serve. I will definitely repeat :-)

I liked the early check in. Flight was a bit bumpy due yo weather. Overall, everything went well.

Limited snack options cause the snack vendor was on strike

The experience was generally above average. The only downside was the absence of WiFi during my flight from Vancouver to San Francisco.

on demand entertainment in seat back awesome Check in Kiosk too demanding with endless demand for more information information then says go to counter. Counter agent unfriendly. Do it yourself check in luggage procedure not intuitive, upset employees frustrated the whole procedure.

It was an excellent experience, traveling from Toronto to Denver with United.

Ontime boarding. Almost 1 hour take off delay. We could have boarded slightly later since the pilots were in traffic

Flight was delayed, I had to put my luggage all the way in the back! They served only a beverage no snack on the way in Air Canada, definitely not a good first impression.

Headphones for the movies have too much bass and can't be adjusted. Almost impossible to hear. Great movie selections but can't really watch them because you can't hear them. Also the system is very slow.

Book cheap flights from Winnipeg to Boston

Recent one-way flight deals

 
Only flying one-way? Below are some of the best one-way flight deals from Winnipeg to Boston found on KAYAK in the last 72 hours.
5/26søn.
1 stopAir Canada
8h 06mYWG-BOS
$181
6/1lør.
2 stopsDelta
11h 43mYWG-BOS
$190
8/17lør.
1 stopAir Canada
7h 54mYWG-BOS
$191
5/26søn.
2 stopsAir Canada
8h 51mYWG-BOS
$192
6/1lør.
1 stopDelta
6h 30mYWG-BOS
$213
8/17lør.
2 stopsPorter Airlines
8h 07mYWG-BOS
$247
8/28ons.
2 stopsPorter Airlines
8h 07mYWG-BOS
$275
8/28ons.
1 stopPorter Airlines
8h 22mYWG-BOS
$310
6/1lør.
3 stopsUnited Airlines
14h 24mYWG-BOS
$525

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Winnipeg - Boston Flights

Departure:

Winnipeg (undefined)Canada

Destination:

Boston (BOS)United States

Return flight deals:

Boston - Winnipeg

Cabin classes: