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YWG - BOS

Find cheap flights from Winnipeg to Boston from C$ 239

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 26/5. 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
Fri 7/6
Fri 14/6

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

 
These are the airlines KAYAK users have selected most often from within our search results in flight searches from Winnipeg to Boston.
These are the airlines KAYAK users have selected most often from within our search results in flight searches from Winnipeg to Boston.
In the last 7 days, travellers have searched 43,968,530 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
6:00 a.m. - 7:27 p.m.YWG-BOS
12h 27m2 stops
9:15 a.m. - 5:52 p.m.BOS-YWG
9h 37m2 stops
C$ 425Porter Airlines
Find Deal
Tue, 1 Oct - Sat, 5 Oct
4:15 p.m. - 5:57 a.m.YWG-BOS
12h 42m1 stop
6:00 a.m. - 11:00 a.m.BOS-YWG
6h 00m1 stop
C$ 449
Find Deal
Tue, 1 Oct - Sat, 5 Oct
11:50 a.m. - 6:05 p.m.YWG-BOS
5h 15m1 stop
11:20 a.m. - 6:07 p.m.BOS-YWG
7h 47m2 stops
C$ 451Porter Airlines
Find Deal
Thu, 20 Jun - Mon, 24 Jun
11:50 a.m. - 6:05 p.m.YWG-BOS
5h 15m1 stop
8:15 a.m. - 6:07 p.m.BOS-YWG
10h 52m2 stops
C$ 456Porter Airlines
Find Deal
Thu, 6 Jun - Thu, 13 Jun
12:26 p.m. - 1:22 a.m.YWG-BOS
11h 56m2 stops
5:20 a.m. - 4:37 p.m.BOS-YWG
12h 17m2 stops
C$ 474Delta
Find Deal
Sat, 20 Jul - Thu, 25 Jul
5:00 a.m. - 2:37 p.m.YWG-BOS
8h 37m2 stops
7:40 p.m. - 8:54 a.m.BOS-YWG
14h 14m1 stop
C$ 507Air Canada
Find Deal
Wed, 4 Sep - Mon, 9 Sep
5:28 p.m. - 11:59 p.m.YWG-BOS
5h 31m1 stop
8:30 a.m. - 11:29 p.m.BOS-YWG
15h 59m2 stops
C$ 534Delta
Find Deal
Thu, 20 Jun - Wed, 26 Jun
6:40 p.m. - 9:29 a.m.YWG-BOS
13h 49m1 stop
6:00 a.m. - 11:01 a.m.BOS-YWG
6h 01m1 stop
C$ 616Air Canada
Find Deal
Mon, 15 Jul - Wed, 31 Jul
2:18 p.m. - 1:20 a.m.YWG-BOS
10h 02m1 stop
6:35 p.m. - 1:11 p.m.BOS-YWG
19h 36m2 stops
C$ 661United Airlines
Find Deal
Fri, 31 May - Mon, 3 Jun
7:30 a.m. - 10:06 p.m.YWG-BOS
13h 36m2 stops
8:55 p.m. - 11:25 p.m.BOS-YWG
27h 30m1 stop
C$ 727WestJet
Find Deal
Sat, 20 Jul - Thu, 25 Jul

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 your flying dates are flexible, you should consider flying to Boston on a Sunday, as we generally find the cheapest rates on that day for this route. On the other hand, Monday is the most expensive day to fly from Winnipeg to Boston. For your return ticket, we recommend flying on a Monday and avoiding Saturdays for the best deals.

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 C$ 530 on average. On the other hand, the most expensive months are August and December, where the average cost of tickets is C$ 818 and C$ 772 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.
In the last 72 hours, the best return deals on flights connecting Winnipeg to Boston were found on Porter Airlines (C$ 425) and Delta (C$ 474). Porter Airlines proposed the cheapest one-way flight at C$ 239.

Good to know

Low season

November

High season

June

Cheapest flight

C$ 239
Best time to beat the crowds (0% less expensive on average)
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 C$ 174 for a one-way ticket and C$ 309 for a round-trip.

  • Which airports will I be using when flying from Winnipeg to Boston?

    Winnipeg airport is called Winnipeg and the only airport in Boston is Boston Logan Intl.

  • 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 C$ 648 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 C$ 715 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.

  • 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 5 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 10789 reviews
7.4Food
7.9Comfort
8.6Crew
8.2Boarding
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.

The flight was excellent, I recommend people to fly with Delta

On time departure, smooth trip, flight attendant told through passengers the gate we would arrive at and the gate our outbound flight was departing from. Early arrival

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

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

First time with Porter and I can say this is best airline company in Canada. Great service, free WiFi, free snack and drinks (including beer and wine). Seats were super comfy on the Embraer jet and I appreciated the folding try table too. Staff were excellent both legs of the trip.

Crew is ok. They offered food n drinks. Had difficulty connecting to wifi on board.

Tight transfer in Montreal. (15 min) However, we made it, as did my luggage.

Check in was slow because of passenger ahead in Reserve line. Seats were somewhat uncomfortable.

First time with Porter. Amazing experience overall, will be my airline of choice in North America whenever possible. Liked the quality of food and how it was served but one suggestion- a hot meal on the longer flights, perhaps?

Delayed by 2.5 hours. This happened previously on my flight from YOW to YVR on Dec. 26.2023. This is a terrible airline. The reason was there was lack of ground crew. This is a known event. AVOID PORTER AIRLINES IF YOU CAN. There is a reason half the plane was empty.

The airline arrival at the downtown airport is a big plus.. Food and beverage was excellent. Their non weather related cancellation is horrible. Overall I gave the airline 7 over 10 Tips for people flying porter from Boston. The airline doesn’t have inflight entertainment No TV No WIFI. Bring your entertainment with you.

The airline arrival at the downtown airport is a big plus.. Food and beverage was excellent. Their non weather related cancellation is horrible. Overall I gave the airline 7 over 10

Wasn’t on the flight- again. Bad weather in Halifax and I was in an accident. What a poor experience to have to pay for all this flight and not be on it

I didn’t make my flight due to poor weather and I had an accident driving there. I tried to get my money back or even credit and nothing. I have an entire flight both to Florida and back that I paid for and no one will give me any money back. I know this isn’t just Porter and it’s 3rd party- however airlines should allow these companies to take money for things they don’t get. I’m so upset. Who can afford a full flight they never take?

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.

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.

This was the first AC flight in a long time that we experienced no delays or frustrations. The gate attendant was extremely polite and accommodating to my husband who has Parkinson’s disease which made boarding extremely stress free. Flight departed ON TIME and was a smooth ride. If only all my AC experiences could be like this.

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.
26/5Sun
1 stopPorter Airlines
5h 05mYWG-BOS
C$ 239
26/5Sun
1 stopAir Canada
8h 06mYWG-BOS
C$ 249
26/5Sun
2 stopsPorter Airlines
7h 52mYWG-BOS
C$ 261
1/6Sat
1 stopDelta
6h 30mYWG-BOS
C$ 262
26/5Sun
2 stopsAir Canada
8h 51mYWG-BOS
C$ 264
17/8Sat
2 stopsPorter Airlines
11h 52mYWG-BOS
C$ 341

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Winnipeg - Boston Flights

Departure:

Winnipeg (undefined)Canada

Destination:

Boston (BOS)United States

Return flight deals:

Boston - Winnipeg

Cabin classes: