C$ 250 Find Cheap Flights from Winnipeg to Massachusetts – Compare and Save

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 9/9. 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, 0 bags

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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

Mon, 7 Sep - Thu, 17 Sep
Porter Airlines Logo
12:15 p.m. - 6:35 p.m.-
5h 20m
Porter Airlines Logo
10:05 a.m. - 3:19 p.m.-
6h 14m
C$ 455Porter Airlines
Thu, 3 Sep - Tue, 8 Sep
Porter Airlines Logo
12:15 p.m. - 6:35 p.m.-
5h 20m
Porter Airlines Logo
10:05 a.m. - 3:19 p.m.-
6h 14m
C$ 455Porter Airlines
Thu, 3 Dec - Tue, 8 Dec
Porter Airlines Logo
11:35 a.m. - 10:17 p.m.-
9h 42m
Porter Airlines Logo
1:15 p.m. - 6:10 p.m.-
5h 55m
C$ 463Porter Airlines
Wed, 16 Sep - Wed, 23 Sep
Multiple Airlines Logo
7:45 a.m. - 6:35 p.m.-
9h 50m
Multiple Airlines Logo
10:05 a.m. - 5:15 p.m.-
8h 10m
C$ 466Multiple Airlines
Wed, 16 Sep - Wed, 23 Sep
Multiple Airlines Logo
6:15 a.m. - 6:35 p.m.-
11h 20m
Multiple Airlines Logo
2:20 p.m. - 9:45 a.m.-
20h 25m
C$ 474Multiple Airlines
Fri, 16 Oct - Fri, 23 Oct
WestJet Logo
9:05 p.m. - 5:40 p.m.-
19h 35m
WestJet Logo
6:30 p.m. - 2:05 p.m.-
20h 35m
C$ 476WestJet
Wed, 16 Sep - Wed, 23 Sep
Air Canada Logo
5:00 a.m. - 2:41 p.m.-
8h 41m
Air Canada Logo
5:50 a.m. - 4:27 p.m.-
11h 37m
C$ 490Air Canada
Thu, 17 Sep - Sat, 19 Sep
United Airlines Logo
2:00 p.m. - 1:10 a.m.-
10h 10m
United Airlines Logo
8:21 p.m. - 11:52 a.m.-
16h 31m
C$ 494United Airlines
Thu, 3 Dec - Tue, 8 Dec
United Airlines Logo
8:30 a.m. - 7:59 p.m.-
10h 29m
United Airlines Logo
6:00 a.m. - 11:39 a.m.-
6h 39m
C$ 494United Airlines
Fri, 16 Oct - Fri, 23 Oct
Air Canada Logo
1:25 p.m. - 9:26 p.m.-
7h 01m
Air Canada Logo
5:50 a.m. - 12:29 p.m.-
7h 39m
C$ 496Air Canada
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.

How much is a round-trip flight from Winnipeg to Massachusetts?

This analysis is based on the cheapest round-trip price found on KAYAK in the last 12 months by searching for a flight from Winnipeg to Massachusetts departing in September.

Flight prices are below average for this route right now.

Flights to Massachusetts from Winnipeg usually cost between C$ 465 and C$ 616 in September.
The lowest price found in the past 5 days was C$ 455 on Porter Airlines (3 Sep–8 Sep).

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 August, when tickets cost C$ 483 (return) on average. On the other hand, the most expensive months are April and January, when the average cost of round-trip tickets is C$ 1,284 and C$ 1,098 respectively.

Good to know

Low season

January

Cheapest flight

C$ 250
Best time to beat the crowds but there is an average 43% increase in price.
Most popular time to fly and prices are also 37% 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.

Reviews of the top 3 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 450 reviews
7.5Food
6.9Entertainment
8.2Boarding
8.6Crew
8.0Comfort
Airline reviews

A very comfortable flight, an additional wash room could have made it almost perfect.

10.0 ExcellentAnonymous, Aug 2026
Read more Porter Airlines reviews

A very comfortable flight, an additional wash room could have made it almost perfect.

Look, I understand that Kayak doesn't know I cancelled my flight on Porter. So I didn't actually fly yesterday. My main disappointment is with Porter ticket fare policies, and maybe you can pass this on to them: At my employer's request, I had booked a full fare ticket with no change fees since my trip to Toronto would likely be extended. Indeed, when I went to change my flight home to a later date, I was told the Fare Difference would cost an additional $550. So much for no change fees lol! While I had the agent on the line, I hopped over to Kayak, searched for new flights on the date in question, and saw a one-way ticket that got me home for only $355. So I got reimbursed about $450for the unused half of my roundtrip and bought a new ticket for $355. What good is a full fare / no change fee ticket if they screw you with "fare difference" BS. I'm still flying home on Porter Airlines but they just lost a hundred bucks with their stupid shenanigans.

I flew with Porter yesterday and overall had a positive experience. The flight was delayed, but the airline did a good job keeping passengers informed with frequent updates throughout the process. My biggest challenge was actually in Terminal 3, where the speaker system wasn’t very clear. It was often difficult to hear the announcements, which made it harder to follow updates at the gate. On board, the experience improved significantly. The aircraft felt very new and well maintained, and the seats were surprisingly comfortable for a short-haul flight. One of the flight attendants seemed a little disengaged, but the other was excellent—friendly, professional, and a pleasure to interact with. Despite the delay, the comfortable aircraft, clear communication from Porter, and positive onboard service made for a good overall experience.

Even tho the flight was a bit delayed the team was apologetic. Everyone was friendly and efficient.

It was okay. Had a thing with the front desk, she had me repack my suitcases to have them be under the weight restrictions, but then the other one was overweight, she argued with me about it when there were tons of people in line. Wasn’t great.

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

The flight was delayed by more than one hour. The terminal was consequently overcrowded and hot. We lost our car reservation and hit rush hour traffic in Boston, which added two hours stuck in traffic to our trip.

Due to mechanical problems it was delayed causing problems the actual flight. Was fune

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.

Nothing to like about porter. Flight cancelled. No flight back to Boston for 2 days. No hotel accommodation. Terrible. Never again by porter.

I missed my flight and had to buy new tickets Rome- Boston

My service dog and I were asked to deplane just before they closed the door - clearly very last minute they couldn’t find the documentation that I have filled out many many times before that is for flying service animals. I purposely purchase 3seats (a whole row) since he is large and not all passengers want to sit next to a dog on a cross country flight. The plane departed with my husband on it!!! They made me fill out a hard copy of the same form and had to reschedule me on a later flight where they could find 3 seats together!! I’ve done this so many times before - clearly the error was on their part in a technology glitch - but really people - do better!! Very traumatic - and my husband had to wait for us when he landed ….so bad. Poor pup was confused and tired.

Super friendly with lots of drink options an entertainment. Friendly crew.

I like flying first class, and United has a nice one

United airlines has the best customer experience from booking to arrival. I always fly United airlines. The mileage program is excellent

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

Plenty of room for me and the cat in Premium Economy. Seat was comfortable. Boarding was a breeze. The lady at the special check-in desk was great, super helpful and professional.

It’s been awhile since I have traveled on United. I, along with my family who were on the flight noted how smoothly everything went . Boarding, flight crew and service was excellent.

I was forced to check my carry-on backpack despite there being space - but it came out on the baggage carousel so fast it didn't even delay my pickup. Otherwise a good flight. Boarding began early (which was disadvantageous for me) but fine.

The check-in and passport submission was complicated and repetitive, due to the poor communication between Air Canada and United. There should have been a single set of instructions and a single questionnaire that provided the data for both airlines.

I like the fact air Canada is on time The food you guys serve is not good

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

Very tight leg room and not a fan of the new policy on no free carry on luggage. Besides that, it was fine.

Flight delay, cancellation rescheduling and misdirected luggage which created some stress. It all worked out in the end.

The flight was delayed several times, however , they kept me well informed with enough advance warning that I had not left home yet

Sat on the tarmac with no ventilation for almost an hour, without a single word from the crew. Appalling. When Air Canada goes bankrupt, again, almost everyone in Canada will be cheering.

If you have checked the status of my booking you would have seen that it was cancelled. And the travelers insurance we purchased only covered $100 per ticket. So my overall experience with kayak and air canada is poor

The plane for my second flight was reassigned. We had to wait for them to get a different plane out of the hangar and call in a crew

Send me 20 dollars and i will do the survey. You survey people think we do things in life to do surveys.

It was swiss air flight and they were very helpful and kind

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

Information on your arrival and departure airports