$183 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 5/12. 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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Cheap Flights from Winnipeg to Massachusetts

Cheapest round-trip prices found by our users on KAYAK in the last 72 hours
Boston
Boston1 stop$235
Albany
Albany1 stop$313
Boston
Boston1 stop$235
Albany
Albany1 stop$313

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

Tue, Jun 2 - Wed, Jun 10
Porter Airlines Logo
9:20 am - 5:35 pm
YWG
-
BOS
7h 15m
1 stop
Porter Airlines Logo
10:05 am - 3:19 pm
BOS
-
YWG
6h 14m
1 stop
$235Porter Airlines
Tue, Jun 2 - Wed, Jun 10
Porter Airlines Logo
9:20 am - 5:35 pm
YWG
-
BOS
7h 15m
1 stop
Porter Airlines Logo
7:10 am - 5:58 pm
BOS
-
YWG
11h 48m
2 stops
$238Porter Airlines
Tue, Jun 2 - Tue, Jun 9
Porter Airlines Logo
9:20 am - 8:55 pm
YWG
-
BOS
10h 35m
2 stops
Porter Airlines Logo
10:05 am - 3:19 pm
BOS
-
YWG
6h 14m
1 stop
$242Porter Airlines
Fri, May 29 - Tue, Jun 2
United Airlines Logo
7:00 am - 12:59 am
YWG
-
BOS
16h 59m
1 stop
United Airlines Logo
8:15 am - 10:33 pm
BOS
-
YWG
15h 18m
1 stop
$252United Airlines
Mon, Jun 1 - Tue, Jun 9
Delta Logo
5:41 pm - 11:54 pm
YWG
-
BOS
5h 13m
1 stop
Delta Logo
5:55 am - 3:04 pm
BOS
-
YWG
10h 09m
1 stop
$253Delta
Tue, Jun 2 - Tue, Jun 9
Air Canada Logo
5:10 am - 11:46 am
YWG
-
BOS
5h 36m
1 stop
Air Canada Logo
5:10 am - 11:08 am
BOS
-
YWG
6h 58m
1 stop
$263Air Canada
Tue, Jun 2 - Tue, Jun 9
Air Canada Logo
5:10 am - 11:46 am
YWG
-
BOS
5h 36m
1 stop
Air Canada Logo
5:10 am - 11:08 am
BOS
-
YWG
6h 58m
1 stop
$264Air Canada
Tue, May 5 - Wed, May 6
United Airlines Logo
8:45 am - 11:30 pm
YWG
-
ALB
13h 45m
1 stop
United Airlines Logo
6:00 am - 11:52 am
ALB
-
YWG
6h 52m
1 stop
$313United Airlines
Thu, Jun 25 - Sat, Jun 27
WestJet Logo
10:45 am - 11:09 pm
YWG
-
ALB
11h 24m
2 stops
WestJet Logo
6:00 am - 2:25 pm
ALB
-
YWG
33h 25m
2 stops
$428WestJet
Sat, Jul 11 - Fri, Sep 4
WestJet Logo
6:15 am - 11:06 pm
YWG
-
ALB
15h 51m
2 stops
WestJet Logo
1:15 pm - 12:55 am
ALB
-
YWG
12h 40m
2 stops
$435WestJet
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 June.

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 June, when tickets cost $300 (return) on average. On the other hand, the most expensive months are January and March, when the average cost of round-trip tickets is $782 and $554 respectively.

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 3 weeks before departure, which saves you about 57% compared to booking last minute. For the absolute cheapest price, our data suggests you should book 20 weeks before departure.

Good to know

Low seasonJanuary
Cheapest flight$183
Best time to beat the crowds but there is an average 66% increase in price.
Most popular time to fly with an average 8% increase in price.
Flight from Winnipeg to Albany

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.

Reviews of the top 3 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 8358 reviews
7.9Comfort
7.2Food
8.1Boarding
8.5Crew
7.8Entertainment
Airline reviews

Delta is always a wonderful experience. A clean plane and the crew is really friendly.

10.0 ExcellentCharlean, Mar 2026
LAS - ATL
Read more Delta reviews

Delta is always a wonderful experience. A clean plane and the crew is really friendly.

Too many people are taking up space in the overhead bins with their extra piece of luggage. Since they cannot fit their backpacks or extra luggage piece under the seat in front of them, they store it in the overheads and thus taking up room for other passengers. It wasn’t only one or two persons; more like 12 or 13 passengers.

This was the worse experience. They delayed our flight twice and we still had to find another flight to get home sooner which was alos delayed. Also, the flight attendant named Ginny on DL9890 leaving at 4:13pm on 3/23/26 was extremely rude.

I love Delta the flight attendants were personable and the flight arrived 1/2 earlier thanks expected. All a plus. The gate agent was a bit flustered but even with that I still had a good experience. Her supervisor assisted me.

Wonderful crew, great movie selection and good food. I prefer Airbus to Boeing, much more comfortable

Got to fly my favorite plane, the Boeing 767-400ER, to Milan. The soft blush pink mood lighting during meal service was very beautiful and gorgeous. The service was top-notch, and our flights were on time. I highly recommend Delta.

I am still at the Airport! Delayed Delayed and Delyaed

I took seat 15A in anticipation of window seat, there is no window.

I lost my plane and spend 5 hours at the airport arriving at Buffalo at 1 am taxis are very expensive at that time.

The first class flight attendant was awful to everyone. Very rude; no customer service. She should not be working in first class.

Hopped on time for the flight only to get deplaned and delayed another 2.5 hours.

Given I (and I’m assuming most people) have both carry in and a personal item included in their fare, I find it very unfair that on neither of my flights I was able to use the overhead for my small backpack because they were completely rammed with luggage, people personal items, jackets, hats and other items. So the only item I brought in had to be stuffed under my seat while they had their leg room and sat comfortable with all of their items in the overhead. This has to stop because I was uncomfortable on both flights when I only had one smaller item that could not be checked due to its contents (medication etc). Plenty of people could have checked theirs but chose not to and then took up the space allotment for 2 people.

Flight attendants had a little attitude. Food tastes no good.

From pre boarding to flight attendant, crew and baggage handler, excellent. Didn’t lost my luggage like West jet.

Very poor. The flight was delayed from Toronto because some forget to do there job . I got to my connecting gate in San Francisco 10 minutes before the departure.but this didn’t let me board even though the flight was still there for an other 30 minutes. The the gentleman at the unite airline desk told me that they usually wait for passengers but air Canada called and told them not to we I been rerouted to Manila instead of Hong Kong . In San Francisco they mad me check in my carryon bag . I was told the it will directly go yo ho chi minn cuyt but I was told that by the Vietnams airline desk that’s not there I’m 10 hours behind my scheduled flight and looks like I I’m going without baggage. I don’t have a chance of catching ..

It was great. There were some issues prior to takeoff. The weather was poor so we had to go through deicing, and we were delayed a bit by the pilots' concern about one of the engines, but that's aviation. The pilots handled everything with aplomb, and kept us apprised

Reliable, nice crew, I fly often on that flight and I like it all.

l really enjoy very much the flight was very pleasant

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

Very disappointed with premier lounge. Food selection very poor, both coffee machines out of order. For the price you charge for an upgrade, the seats don’t fully recline, movie selection is old. Not very good value. Asian airlines are light years ahead at a more affordable price.

The seat design in the premium economy section leaves virtually no room under the seat to store a bag or purse. Other than that, it was a great flight. Arrived early.

The flight was delayed, but not for weather. We landed over 3hrs later than planned.

The stag were helpful, kind and liked the passengers. The plane was pristinely clean! Great flight!

My flight was delayed more than once, but Air Canada updated us regularly. Friends on other airlines had much worse experiences.

My ticket did not exist when I got to the airport. I had to book another flight and was still charged by Kayak

Got denied my flight was told on Google that Air Canada was supposed to book me a flight back home because I never was able to go to my destination. They did not help me whatsoever. I had to book a whole new flight for that reason I would write this is zero

The plane was delayed an hour. Heard from other passengers that the Vancouver connection to SFO was never on-time.

My experience was good with United too But only not so good thing was that at Calgary airport I was not given lounge access despite of flying business. Aspire lounge denied it to me, which was unfair I feel

We left over 2 hours late and they didn't even give us a complimentary snack, when getting to the desk I asked if I could be put in a row with only 1 other person or an empt y one I was told the flight was full when the last two rows were empty. All around over it

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

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