C$ 234 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 11/9. 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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Best Massachusetts Flight Deals from Winnipeg

Cheapest round-trip prices found by our users on KAYAK in the last 72 hours
Boston
Boston1 stopC$ 406
Boston
Boston1 stopC$ 406

Cheap Flights from Winnipeg to Massachusetts

 
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

Sat, 11 Oct - Wed, 15 Oct
Air Canada Logo
5:00 a.m. - 11:29 a.m.YWG-BOS
5h 29m1 stop
Air Canada Logo
10:40 a.m. - 5:45 p.m.BOS-YWG
8h 05m1 stop
C$ 406Air Canada
Find Deal
Sat, 11 Oct - Wed, 15 Oct
Air Canada Logo
5:00 a.m. - 11:29 a.m.YWG-BOS
5h 29m1 stop
Air Canada Logo
6:00 a.m. - 5:50 p.m.BOS-YWG
12h 50m2 stops
C$ 443Air Canada
Find Deal
Sun, 12 Oct - Mon, 13 Oct
WestJet Logo
6:30 a.m. - 5:40 p.m.YWG-BOS
10h 10m1 stop
WestJet Logo
7:00 p.m. - 11:41 a.m.BOS-YWG
17h 41m2 stops
C$ 447WestJet
Find Deal
Sat, 11 Oct - Tue, 14 Oct
Delta Logo
6:40 a.m. - 5:12 p.m.YWG-BOS
9h 32m1 stop
Delta Logo
5:45 a.m. - 11:30 a.m.BOS-YWG
6h 45m1 stop
C$ 452Delta
Find Deal
Sat, 11 Oct - Mon, 13 Oct
WestJet Logo
6:30 a.m. - 5:40 p.m.YWG-BOS
10h 10m1 stop
WestJet Logo
7:00 p.m. - 2:13 p.m.BOS-YWG
20h 13m1 stop
C$ 476WestJet
Find Deal
Sat, 20 Sep - Sat, 27 Sep
United Airlines Logo
4:25 p.m. - 8:09 a.m.YWG-BOS
14h 44m2 stops
United Airlines Logo
5:30 a.m. - 10:33 p.m.BOS-YWG
18h 03m2 stops
C$ 490United Airlines
Find Deal
Fri, 10 Oct - Wed, 15 Oct
United Airlines Logo
2:20 p.m. - 12:50 a.m.YWG-BOS
9h 30m1 stop
United Airlines Logo
9:53 a.m. - 3:31 p.m.BOS-YWG
6h 38m1 stop
C$ 492United Airlines
Find Deal
Sat, 11 Oct - Tue, 14 Oct
Delta Logo
6:40 a.m. - 5:52 p.m.YWG-BOS
10h 12m2 stops
Delta Logo
1:05 p.m. - 11:27 p.m.BOS-YWG
11h 22m2 stops
C$ 494Delta
Find Deal
Fri, 22 Aug - Thu, 28 Aug
Porter Airlines Logo
11:45 a.m. - 6:28 p.m.YWG-BOS
5h 43m1 stop
Porter Airlines Logo
3:30 p.m. - 10:46 p.m.BOS-YWG
8h 16m1 stop
C$ 632Porter Airlines
Find Deal
Fri, 10 Oct - Tue, 14 Oct
Porter Airlines Logo
11:20 a.m. - 6:28 p.m.YWG-BOS
6h 08m1 stop
Porter Airlines Logo
7:15 p.m. - 10:25 a.m.BOS-YWG
16h 10m2 stops
C$ 781Porter 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 C$ 407 (return) on average. On the other hand, the most expensive months are December and January, when the average cost of round-trip tickets is C$ 868 and C$ 741 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.

When flying from Winnipeg to Massachusetts, you should consider leaving on a Tuesday and avoid Sundays if you are looking for the best rates. For your return to Winnipeg, you’ll find the best rates on Wednesdays and the most expensive ones on Thursdays.

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 a flight from Winnipeg to Massachusetts, you should book around 5 weeks before departure, which saves you about 48% 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 flightC$ 234
Best time to beat the crowds but there is an average 7% increase in price.
Most popular time to fly and prices are also 27% 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 travellers 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 C$ 389 on average. Morning departures are around 17% cheaper than evening flights, on average. The most expensive time of day to fly to Massachusetts is generally in the evening, which is peak travel time and where the average cost of a ticket is C$ 470.

Reviews of the top 5 airlines flying 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.
8.0
Porter AirlinesOverall score based on 318 reviews
8.0Comfort
8.2Boarding
7.6Food
8.7Crew
7.0Entertainment
Airline reviews

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

10.0 ExcellentAnonymous, Jul 2025YYZ - RSW
Read more Porter Airlines reviews

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!

The whole experience from check in to deboarding was fantastic.

Just an evening before they canceled my ticket and offered me ticket costing 3 x times more than. I will not fall prey to these scams,Will never book through kayak now. Such a bad experience.

was okay except.. 1)the porter check in webpage doesn't let you print your boarding pass from home 2)that there was a 90 min cut off for checking in on the kiosk in general, and to print a boarding pass, even tho i checked in online already....

Great! Personable crew. I love that they pour complimentary beer and wine.

I love the 2 seats per row. More room. The crew were excellent.

My experience on any Delta flight is always overshadowed by the time Delta removed me from a flight for no apparent reason.

Check in process was terrible. Lady at counter didn’t know what she was doing

Delayed and took off even later than the scheduled delay time

For a 69 year old with health problems I had the worse experience, no wheelchair when I entered a lady told me to sit and wait while a gentleman told me I had to walk to the Delta station, which I did. I had a carry on and a bag, and I was traveling with my service dog, which was on his carrier and the lady charged me for my carry on luggage, beside all the waiting cause of the delay, I had to walk to get my luggage cause no wheelchair showed up, I am so disappointed. I will get in touch with the company. I got home at 3:00 am, not good for my health situation.

Great experience on Delta. Staff from baggage check to flight attendants were very courteous and professional. My only issue was a personal preference for pretzels instead of the chips and cookies that were offered.

The crew was amazing; Von, Vera and Guadalupe were very friendly and attentive throughout the entire flight. They were friendly and welcoming to everyone. A solid and dedicated team for sure!

Terrible. I was bumped off of my original flight and spent the next six days fighting to get back on it. I lost hours of my vacation trying to get this situation corrected.

There was no problems, just a little uncomfortable with seats that do not lay back a little

Always good but we must do something about people in rows ahead of you that don't put their seats back up when they are suppose to. And It's rough to not be able to even lean over to get something out of my purse.

Flight was delayed, 30+ bags had to be gate checked. Crew were very friendly!

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.

Michael, our FA was very attentive, even finding me a chocolate brownie from economy class when the dessert selections were all dairy based. ( intolerant, not allergic so don’t usually need to order dairy free)

We tried to upgrade to economy premium but were told this was not possible as we had booked through United Airlines (and Air Canada was operating the flight). This seemed silly given there was ample space in economy premium. Additionally, we had to wait almost 1.5 hours upon arrival to taxi to the gate. Otherwise, the crew were very pleasant and passengers were friendly.

Staff were courteous and helpful. The only negative was the flight delays (which are usually unavoidable) and the high baggage price.

Absolutely terrible, from the customer service to boarding the plane. On the phone, there was some mishaps with getting in my correct date and they did not help me retrieve a refund or any assistance. I’m gonna be reporting to all my followers and family around the region of Los Angeles to New York.

Could not fly out of Canada. Called airlines on Monday, July 14th. Tried to cancel the flight 7 days away, but they said I could not cancel and there would be no refund.

A little disorganized but overall good. The Delta flights were great though

Price was good. Entertainment and food could have been better

Staff was nice, helpful, and did all they could. I understand economy seats are bottom of the barrel, but we're crammed in there with others in our row.

Our flight info was lost as the original booking was with westjet... almost missed our outbound flight trying to get it corrected. Inbound we had to reschedule completely as they didn't have our information and resold our seats ending up getting home much later than planned. The confirmation numbers we received from justfly for westjet didn't help anything with delta as they said we needed a delta confirmation which we never received. I talked with justfly and they said it's the airlines problem and with westjet and they said it is the 3rd party bookers issue.... so, not fun

They kept making changes to the itinerary. I actually wasn't able to go and i tried to get flight credit in exchange for the ticket, but the customer service chat was taking way too much time.

WestJet canceled my booking, replaced it with a booking that didn't work (departing from cruise ship), and didn't offer any flights that did work. Their only option was for me to cancel and go to another airline for more money. Which I did.

Nothing to like because my inbound flight was cancelled without notification by West Jet or third party, JustFly. I couldn’t take the inbound flight due to cancellation; therefore could not take the outbound flight back.

I did not noticed baggage was separate - I had assumed international flights included luggage, so it surprised me I had to pay to check a bag.

Flight got delayed for no reason. And Air Canada was doing 3 boardings via the same gate. It was chaotic!

My return flight experience was one of the worst times I have had traveling anywhere this year. Not because of the flight. It was because there was not enough time allocated to deplane, go through U.S. Customs and U.S. Security to get to the gate for the connecting flight to Boston which I missed, There was well less than an hour between my landing in Montreal from Prince Edward Island to my connecting gate. I even called Air Canada on the morning of my return and noted my concern over the short layover time, not more that 45 minutes. The initial flight was four minutes late. I was seated in the rear of the first aircraft, and it took at least 20 minutes to deplane. The U.S. Customs was a considerable distance from the gate at which we landed. The need for double security seemed unnecessary and redundant. The distance from the security to my gate was again fairly great, and the wrong gate number was listed on my boarding pass. The agent I approached at the flight that was going to Newark, New Jersey was too busy to answer my question as to what gate was for Boston. When I got to the right gate, they had just closed the door to the aircraft even though I arrived a minute late. If I knew the distance to Customs and from Security to the gate, I would have asked for a seat on the next available flight which was 4:30 pm. When I made my call at 6:00AM that morning. When I asked the agent at the Boston gate, he said that the 4:30 flight was already “OVERBOOKED!” I was put on an 8:30 PM flight and didn’t get home until MIDNIGHT. I then had to care for a barnful of hungry animals and didn’t get to bed until 2:00 AM.

From Montreal to Cincinnati the flight was perfect! Flight free and everyone was perfect and a pleasure to travel with. But from Casablanca to Montreal the flight crew were quite cold, unhelpful, also seemed to scold many passengers instead of simply educating or instructing them. There were a couple for sure I could describe but not name… i was really shocked bc my experience w air Canada is typically a good one at the very least. It seemed something was very much so I’m the air w the crew. The two older lady crew members and the male were amazing but the younger lady crew members w the exception of one were very clique-y and snarky, sassy

Seating wasn’t too cramped; I don’t understand how luggage bins get full if there are enough for each person. Shouldn’t there be room for the designated carry-on and personal item for each passenger at their seat? THEN, IF for some reason extra room is available for someone who prefers it, then shifts can occur. I’m simply saying it seems that I should have primary access to the storage bin at my seat and underneath in front of me. It was suggested that I go to the back of the plane to store my carry-on when I paid to have access to the first seat after 1st class. The additional stress and inconvenience could be avoided and I think all passengers and flight crew are interested in guidelines that are fair, clear, and reduce tension.

Upgraded to sit at the exit door so good leg room.

Wonderful airline. All staff were pleasant and helpful. What is sad is that it wasn’t grand gestures just everyday pleasantness and friendliness that are missing from the other airlines I have flown recently.

Friendly efficient crew, but plane had no way to charge phone. That is a near necessity with today’s travel where we carry out travel documents on our phones.

The flight was delayed for 2 hrs. We were changed to a smaller plane, which was shaking a lot.

Bad service as well. Another 3hr delayed flight from chicago to Charlotte.

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