$156 Find Cheap Flights from Winnipeg to Massachusetts

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 Massachusetts departing on 9/26. 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
1 adult, Economy

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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 Massachusetts, 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 Massachusetts, as well as popular online travel agencies
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Cheap Flights from Winnipeg to Massachusetts

Cheapest round-trip prices found by our users on KAYAK in the last 72 hours
Boston
Boston1 stop$299
Boston
Boston1 stop$299

Book Cheap Winnipeg to Massachusetts Plane Tickets

 
Here are some of the best deals found on KAYAK recently from the most popular airlines for round-trip flights from Winnipeg to Massachusetts 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 for you by selecting your travel dates on KAYAK.

Recent round-trip flight deals from Winnipeg to Massachusetts

Fri, Oct 3 - Mon, Oct 6
WestJet Logo
6:30 am - 5:40 pmYWG-BOS
10h 10m1 stop
WestJet Logo
7:00 pm - 2:13 pmBOS-YWG
20h 13m1 stop
$299WestJet
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Thu, Sep 18 - Mon, Sep 22
WestJet Logo
8:15 pm - 6:10 pmYWG-BOS
20h 55m1 stop
WestJet Logo
7:00 pm - 2:13 pmBOS-YWG
20h 13m1 stop
$309WestJet
Find Deal
Thu, Nov 20 - Sun, Nov 23
Air Canada Logo
8:15 am - 2:52 pmYWG-BOS
5h 37m1 stop
Air Canada Logo
5:30 am - 10:16 amBOS-YWG
5h 46m1 stop
$313Air Canada
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Thu, Sep 18 - Mon, Sep 22
 Logo
9:15 pm - 6:10 pmYWG-BOS
19h 55m1 stop
 Logo
7:00 pm - 11:41 amBOS-YWG
17h 41m2 stops
Tue, Oct 7 - Wed, Oct 15
Air Canada Logo
5:00 am - 11:29 amYWG-BOS
5h 29m1 stop
Air Canada Logo
10:40 am - 4:15 pmBOS-YWG
6h 35m1 stop
$326Air Canada
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Fri, Sep 19 - Mon, Sep 22
 Logo
9:00 am - 10:47 pmYWG-BOS
12h 47m2 stops
 Logo
7:00 pm - 2:13 pmBOS-YWG
20h 13m1 stop
Tue, Oct 7 - Wed, Oct 15
Delta Logo
5:40 pm - 11:59 pmYWG-BOS
5h 19m1 stop
Delta Logo
9:00 am - 8:10 pmBOS-YWG
12h 10m2 stops
$355Delta
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Fri, Sep 19 - Mon, Sep 22
United Airlines Logo
2:20 pm - 10:35 amYWG-BOS
19h 15m2 stops
United Airlines Logo
5:30 am - 10:33 pmBOS-YWG
18h 03m2 stops
$358United Airlines
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Fri, Oct 10 - Fri, Oct 17
Delta Logo
12:20 pm - 10:04 pmYWG-BOS
8h 44m1 stop
Delta Logo
7:10 am - 4:50 pmBOS-YWG
10h 40m1 stop
$402Delta
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Thu, Sep 18 - Mon, Sep 22
United Airlines Logo
7:00 am - 5:34 pmYWG-BOS
9h 34m2 stops
United Airlines Logo
1:00 pm - 10:33 pmBOS-YWG
10h 33m2 stops
$432United Airlines
Find Deal
Booking Insights

KAYAK's insights & trends for Winnipeg to Massachusetts flights

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

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

To calculate monthly average prices, KAYAK takes all prices for each month over the last year for round-trip flights from Winnipeg to Massachusetts, 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 Massachusetts is October, when tickets cost $305 (return) on average. On the other hand, the most expensive months are December and January, when the average cost of round-trip tickets is $629 and $537 respectively.

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

The average price of all round-trip flights from Winnipeg to Massachusetts clicked on KAYAK for each day over the last 12 months.

If you are looking for a flight deal from Winnipeg to Massachusetts, look for departures on Saturdays and avoid leaving on a Monday, as it's usually the priciest day. When flying back from Massachusetts, Sunday is the cheapest day to fly and Monday is the most expensive.

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

To calculate weekly average prices, KAYAK takes all prices for each week before departure over the last year for round-trip flights from Winnipeg to Massachusetts, removes the top 0.1% to account for outliers, and then takes the average of all the values for each week.

To get a below average price on the flight from Winnipeg to Massachusetts, you should book around 5 weeks before departure, which saves you about 49% compared to booking last minute. For the absolute cheapest price, our data suggests you should book 20 weeks before departure.

Good to know

Low seasonMarch
Cheapest flight$156
Best time to beat the crowds but there is an average 6% increase in price.
Most popular time to fly and prices are also 25% lower on average.
Flight from Winnipeg to Boston

FAQs - booking Massachusetts flights

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

    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 Massachusetts.

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

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

    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 from Winnipeg to Massachusetts with an airline and back with another airline.

  • What is KAYAK's "flexible dates" feature and why should I care when looking for a flight from Winnipeg to Massachusetts?

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

  • What is the cheapest time of day to fly to Massachusetts?

    The cheapest time of day to fly to Massachusetts is generally in the morning, when round-trip flights cost $493 on average. The most expensive time of day to fly to Massachusetts is generally in the afternoon, which is peak travel time and where the average cost of a ticket is $618.

Reviews of the top 4 airlines serving from Winnipeg to Massachusetts

 
See real verified KAYAK customer reviews for airlines flying from Winnipeg to Massachusetts. 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 Massachusetts? 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.
7.9
DeltaOverall score based on 7979 reviews
8.2Boarding
8.5Crew
7.3Food
7.9Comfort
7.9Entertainment
Airline reviews

This route with Delta always has delays or is cancelled. Aircrafts seem smaller and older. I fly Delta quite a bit - haven’t had issues with the international flights. But this route has always been the troublesome one

4.0 Okaypuravi, Aug 2025LGA - STL
Read more Delta reviews

This route with Delta always has delays or is cancelled. Aircrafts seem smaller and older. I fly Delta quite a bit - haven’t had issues with the international flights. But this route has always been the troublesome one

The flight crew was friendly. I tried to adjust my seat online ahead of time but no option existed without additional fees. My friend asked at the gate about a seat change and was able to make it happen. That was great! The flight crew moved a very tall gentleman and his companion which allowed us to have more space which was nice. Overall, good experience. Appreciated the blanket and pillow.

Three seats in first class were broken and while they were able to still acommodate us it was looking very touch and go and they had others they could not acommodate

Mechanic delay in addition to a 2 hour change in takeoff time was frustrating.

Delayed due to thunderstorms and no in-flight service due to rough weather — both of which are out of Delta’s control. Flight was good overall.

The flight attendants in SLC were rude. I arrived 40 minutes early to gate. Ticket said I needed check in for seat assignments and tried check in and attendants said they weren’t doing it. And proceeded to never call me to give me a ticket so when time to board I received the very last seat. Please relay to employees to do their job better..,

On this flight I felt the food offering was not as complete as on previous flights. The tomato salad was a bit off and there was nothing additional such a bread or butter. The breakfast was only one option, so you either ate what they had or ate nothing. The crew was efficient, but most seemed frustrated throughout the flight. The flight arrived early and was obstacle-free, so I’m overall quite happy, but the shine in the rest of the experience just wasn’t there.

Our seats were comfortable with adequate room to stretch out and recline. The food was tasty and served it just the right intervals. Our flight attendant was extra attentive and friendly. Flight arrived early. And the most turbulence. Overall that’s good and experience for an 11 hour flight as can be hoped for

The seats got pretty uncomfortable pretty fast. The armrests are bigger than on other planes, so I had less room in the actual seat. My butt hurt by the end of the flight. :/ comfort was the primary issue. The crew were fantastic!

I believe that a four-hour trip should have a meal. Delta had none.

I was not happy with AirfareAssist, the agency that kayak advised me would be handling my booking. I was advised by porter airlines that I had been overcharged for the Basic express , a option that I had asked airfare assist to help arrange after I realized that the basic fare I had chosen with porter did not include a carryon. At each checkin porter advised I had been overcharged for this . They advised that money would be refunded to my credit card, however, this is not likely to happen as it is not my name and credit card that appeared on the porter invoice, but that of another individual/agent. When airfare assist was arranging the basic express with porter on my behalf, they asked me to confirm that I agreed to pay $263 USD for this. I did agree, as I was advised this was needed to proceed. When I checked the invoice on the porter website and saw that it was not my name and credit card on the invoice, I was advised that this was how airfareassist processed the payment. The Porter invoice indicated a billed amount of $126USD I will not use Kayak or their designated AirfareAssist again

Our flight was delayed by a bit. I appreciated that we were kept informed on why periodically. Boarding was fine. I overheard one flight attendant sounding very rude to a passenger who was not paying attention to the safety demonstration. The snacks were minimal as it was a short flight. There was no entertainment. Overall the flight was good back to LGA.

There was a 5 hour delay. Missed connection and now an almost 21 hour lay over!

The flight was fine see earlier note for the problem

Three hours on the tarmac with almost zero communication from the cockpit. Not when offered a water in the interim. In my 67 years of flying all over the world the worst experience ever. The plane was half empty, however had to pay for seats to sit next to my girlfriend. Extra to take a carry on. I would never fly Porter again even for free.

All good the seats a little tight and no I pad screen

Everything was good except the fact you charge more for a carry on bag vs a check in bag and to top it off in US$ that was not impressive

Our flight was cancelled at the last minute for maintenance reasons and we were rebooked on a late flight when we purposefully booked our flight to be home early due to work.

Seemed like an old plane. Very noisy. The seat cushions were so old that the metal bracing of the seats were poking through. There was plenty of leg room though.

Flight was delayed over 2 hours, then landed at a different airport!

My flight was delayed about 1 1/2 hours in Chicago, but other then that it was a good flight.

The experience was great, the crew was very polite and hospitable. I will definitely make if my go to airlines.

It was all good flight was on time, service was good I enjoyed a few movies and everything was smooth

Efficient, calm when things were delayed and kept us regularly informed of what was happening.

Impressed with the service despite turbulence because of the weather. Both flights arrived before their scheduled times.

Airbus plane, nice and polite staff, entertainment even as it was a short flight.

Very nice and clean plane. Transit time between flights was tight though

Our flights got changed from United to Air Canada and our purchased seats did not get transferred so we had to pay for seats twice. I brought it up with Air Canada and they stated I had to go back and chase it with United. The united seats were $21 Canadian each and Air Canada were $56 each so we have paid $77 for each seat. Very unhappy

So far so good but food and entertainment are not available for this flight

Plane temperature was comfortable (not to hot) when boarding and waiting for takeoff.

I had wonderful wheelchair assistance through the Montreal airport onto the flight. Air Canada was excellent in this both at the Fredericton airport and the Montreal one where an attendant helped us through customs as well as transport and baggage security.

Horrible flight cancelled had to buy another very expensive ticket

Flight was cancelled last minute due to Air Canada strike leaving us stranded and having to stressfully find a way home that cost hundreds of dollars in excess cost added to the trip. Having just experienced our mother's funeral service, this was not a good way to end our trip.

Air Canada marooned me in Canada with no way back home during my summer vacation. I had to buy a last minute flight ticket for over $500 to make it back home. I have their credit card and have flown them for years. Never again.

Flight was cancelled last minute. Had to scramble and purchase a $2000 flight through a separate airlines. Stuck in Toronto two extra days. Missed my first two days on a new job. Had to rent a car for an additional two days. Scrambled to fins a place to live those extra two days. Spent a ton of extra money and lost a lot of money, as well as made a poor impression at work. Difficult difficult difficult

Terrible, return flight was cancelled a night before the flight was scheduled to depart and I was notified by an email and an automated message on their phone line. I’ll never book Air Canada again

Could not understand what the attendant was saying during his announcements.

Biggest problem for me is that I am Star Alliance Gold and they were not able to give me access to to Maple Lounge because of some computer glitch . It was management by information system. She could clearly see my status and still would not give me access because the computer woudl not let her. She should have override that be attentive to a customer and figure rhat out later

Economy seats always cramped, no meal on international flight, no plugs for electronics, but we got there and cabin crew was excellent.

Horrible, experience, 5 hours delay, they changed gates 3 times, the last one we had to wait for 1::30 hre for the door to open to get to that gate. 0 apologies from Air Canada, they don’t care at all about their passengers

Everything you need to know for your flight from Winnipeg to Massachusetts

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