C$ 260 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 9/7. 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

KAYAK searches hundreds of travel sites at once for deals on flights to Massachusetts

 
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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Flight Deals

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

Thu, 6 Aug - Wed, 12 Aug
Porter Airlines Logo
12:15 p.m. - 7:15 p.m.
YWG
-
BOS
6h 00m
1 stop
Porter Airlines Logo
10:05 a.m. - 3:19 p.m.
BOS
-
YWG
6h 14m
1 stop
C$ 450Porter Airlines
Thu, 2 Jul - Sat, 11 Jul
Air Canada Logo
5:00 a.m. - 11:52 a.m.
YWG
-
BOS
5h 52m
1 stop
Air Canada Logo
6:00 a.m. - 11:15 a.m.
BOS
-
YWG
6h 15m
1 stop
C$ 456Air Canada
Thu, 2 Jul - Wed, 8 Jul
Air Canada Logo
5:00 a.m. - 11:52 a.m.
YWG
-
BOS
5h 52m
1 stop
Air Canada Logo
10:50 a.m. - 6:15 p.m.
BOS
-
YWG
8h 25m
1 stop
C$ 459Air Canada
Thu, 2 Jul - Wed, 8 Jul
Air Canada Logo
5:00 a.m. - 11:52 a.m.
YWG
-
BOS
5h 52m
1 stop
Air Canada Logo
5:45 a.m. - 2:25 p.m.
BOS
-
YWG
9h 40m
2 stops
C$ 460Air Canada
Thu, 6 Aug - Wed, 12 Aug
Porter Airlines Logo
9:20 a.m. - 8:55 p.m.
YWG
-
BOS
10h 35m
2 stops
Porter Airlines Logo
10:05 a.m. - 3:19 p.m.
BOS
-
YWG
6h 14m
1 stop
C$ 461Porter Airlines
Thu, 2 Jul - Sat, 11 Jul
Air Canada Logo
5:00 a.m. - 11:52 a.m.
YWG
-
BOS
5h 52m
1 stop
Air Canada Logo
5:45 a.m. - 4:20 p.m.
BOS
-
YWG
11h 35m
2 stops
C$ 463Air Canada
Fri, 7 Aug - Wed, 12 Aug
Air Canada Logo
2:05 p.m. - 10:38 p.m.
YWG
-
BOS
7h 33m
1 stop
Air Canada Logo
6:00 a.m. - 11:15 a.m.
BOS
-
YWG
6h 15m
1 stop
C$ 466Air Canada
Mon, 21 Sep - Wed, 23 Sep
Delta Logo
3:58 p.m. - 11:59 p.m.
YWG
-
BOS
7h 01m
1 stop
Delta Logo
5:55 a.m. - 11:56 a.m.
BOS
-
YWG
7h 01m
1 stop
C$ 478Delta
Tue, 7 Jul - Tue, 21 Jul
United Airlines Logo
7:00 a.m. - 11:47 p.m.
YWG
-
ALB
15h 47m
2 stops
United Airlines Logo
6:00 a.m. - 10:38 p.m.
ALB
-
YWG
17h 38m
2 stops
C$ 705United Airlines
Tue, 7 Jul - Tue, 21 Jul
United Airlines Logo
7:00 a.m. - 3:17 p.m.
YWG
-
ALB
7h 17m
1 stop
United Airlines Logo
4:23 p.m. - 10:38 p.m.
ALB
-
YWG
7h 15m
1 stop
C$ 706United Airlines
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 August.

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 February, when tickets cost C$ 164 (return) on average. On the other hand, the most expensive months are January and March, when the average cost of round-trip tickets is C$ 1,107 and C$ 582 respectively.

Good to know

Low seasonJanuary
Cheapest flightC$ 260
Best time to beat the crowds but there is an average 45% increase in price.
Most popular time to fly and prices are also 19% 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 438 reviews
8.2Boarding
7.6Food
6.9Entertainment
8.0Comfort
8.6Crew
Airline reviews

The staff was amazing. Best service I’ve had on an aircraft in a long time. Was not particularly happy with the food. Flight was at 10:50 and left home too early for breakfast and wasn’t able to purchase food at airport and felt for sure I could get some breakfast to buy on airplane. Nope as food was served around 11:30 and only one choice left (I was at 22C) so ordered the chicken dish thinking I’m getting a hot meal but cold chicken with rice and carrots etc. I was looking forward to a croissant sandwich and a hot cup of tea. The FA was kind to explain they were serving dinner at that time. She was lovely Other than the disappointment with the food the staff was amazing. On my return flight I will make sure to eat and take some food with me so I’m not hungry or disappointed. This was my second time ever flying Porter and will consider checking them when I next come to visit my daughter. Have to say it again best crew I’ve ever experienced on a flight and I travel quite a bit. Thanks.

10.0 ExcellentAngela, May 2026
YYZ - YVR
Read more Porter Airlines reviews

The staff was amazing. Best service I’ve had on an aircraft in a long time. Was not particularly happy with the food. Flight was at 10:50 and left home too early for breakfast and wasn’t able to purchase food at airport and felt for sure I could get some breakfast to buy on airplane. Nope as food was served around 11:30 and only one choice left (I was at 22C) so ordered the chicken dish thinking I’m getting a hot meal but cold chicken with rice and carrots etc. I was looking forward to a croissant sandwich and a hot cup of tea. The FA was kind to explain they were serving dinner at that time. She was lovely Other than the disappointment with the food the staff was amazing. On my return flight I will make sure to eat and take some food with me so I’m not hungry or disappointed. This was my second time ever flying Porter and will consider checking them when I next come to visit my daughter. Have to say it again best crew I’ve ever experienced on a flight and I travel quite a bit. Thanks.

I didn’t receive any help when they messed up and wasn’t honest and the supervisor did absolutely nothing to help me so I had to buy another ticket at $537

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

The Flight took off 2hrs late because there was no pilot showing up when the flight was ready to board.. Though the cabin crew was present and had prepared the plane, the FO turned around after 15 min and went away. A crew to fly the plane finally arrived over an hour later and we were able to board 1h30 min later than planned time... until everything was loaded, we left 2h late from the gate. This was a small plane, so don't expect any Entertainment... Wi-Fi access on board would work, but took an awful amount of time to figure out and get it work (I'm an IT person). Flying as VIPorter customer, I was expecting at least some warm meal, but everything served was just cold.. except the coffee maybe. Even in so-called VIPorter seats, space is cramped and trays are so tiny, you can barely setup your food. Flight caught up during the coast-to-coast crossing and was able to recoup about 45 min from the delay.. still arrived very late in Vancouver and had to wait a long time to get our registered bags. Let's see how the return flight will be in a few days..

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.

Due to a known technical error that Porter has not fixed in over a year, I was unable to check in the children on my reservation online and had to do it at the airport. Upon check in, there were no seats together, which was an issue as we had young children. The gate agent did manage to seat us together by moving other passengers, which was appreciated, but the other passengers were never informed, leading to confusion and delay upon boarding. The flight was over an hour late; no explanation or apology was ever issued. The bags on Porter take a long time to arrive--over half an hour at Hamilton on my inbound flight, and not much better on my return to Edmonton.

On my e-boarding pass it shows free wifi, yet the plane I was on didn’t have wifi. Please remove false advertising from your website and boarding passes

3.5 hr delay for a 1 hr work flight. No information as to why the delay until 20 mins before boarding.

Organization and the adjusted times but the snacks could be of a bigger portion

Smaller plane. Food and bar service for free is amazing. Drinks were in glass not plastic cups.

Prefer not to have an almost 3 hour delay with useless communication that wasn't accurate.

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

Boarding was smooth and efficient. The only food was some pretzels, but it was a short flight. Not much to order if you were hungry.

Crew were welcoming, accommodating and they worked hard to find places for all carry on.

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.

Seats very comfortable; service efficient and pleasant; flight was on-time; boarding organized.

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

Starlink is great Crew was polite Business class didn’t get a welcome drink just water and snacks were ok

very average service no complimentary alcoholics drinks unlike other airlines such as Porter airlines No decent seats available during check-in time the day before

Good but airlines getting smaller. I didn't like the meal but the service was fine. Flight was fine and luggage arrived. So good.

Aircraft is designed with all 3 washrooms at the back of the plane, meaning that when there is service underway, there are no washrooms available and it gets very crowded at the back of the plane.

Multiple delays and gate changes resulting in arrival with a 5 hour delay.

One crew member, Brandy was very helpful with recovering phone lost in customs. The plane was ancient and poorly maintained. Checked baggage did not arrive with flight. Almost missed flight because if insanely short layover time. Air Canada is worst flight I have ever booked with Kayak. Wanted to charge for headsets for on flight media.

The flight was good. My luggage didn’t land with me when I arrived in Columbus. So grateful I was able to get my luggage back within the 2 hours😍👍.

gave me complimentary food as the flight was not full and was attentive to my needs

It was a nice and smooth trip. Gave a friendly environment throughout the journey.

Meal and drink service was good. Old plane with old business class seats were quite disappointing

The flight was smooth, the plane was spacious and clean, the staff was kind and the food was decent.

Pretzels were a bit dry and dusty, however it is nice to have a choice between sweet and savory snacks.

Flight crew was great, and even the crew for checking bags! I had a question for a friend of mine flying tomorrow and the man I talked to was awesome and answered my questions and looked up things for me when he didn’t have to! I was able to give her current & accurate info for her flight and she was so appreciative too!!

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

Information on your arrival and departure airports