$176 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 8/25. 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$311
Albany
Albany2 stops$432
Boston
Boston1 stop$311
Albany
Albany2 stops$432

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, Jul 21 - Tue, Jul 28
Porter Airlines Logo
12:15 pm - 6:35 pm
YWG
-
BOS
5h 20m
1 stop
Porter Airlines Logo
10:05 am - 3:19 pm
BOS
-
YWG
6h 14m
1 stop
$311Porter Airlines
Thu, Jul 9 - Mon, Jul 13
Air Canada Logo
2:05 pm - 10:38 pm
YWG
-
BOS
7h 33m
1 stop
Air Canada Logo
6:00 am - 11:15 am
BOS
-
YWG
6h 15m
1 stop
$313Air Canada
Tue, Jul 21 - Thu, Jul 23
Air Canada Logo
5:00 am - 11:52 am
YWG
-
BOS
5h 52m
1 stop
Air Canada Logo
6:00 am - 11:15 am
BOS
-
YWG
6h 15m
1 stop
$314Air Canada
Fri, Jul 24 - Mon, Jul 27
Porter Airlines Logo
12:15 pm - 6:35 pm
YWG
-
BOS
5h 20m
1 stop
Porter Airlines Logo
10:05 am - 3:19 pm
BOS
-
YWG
6h 14m
1 stop
$318Porter Airlines
Sat, Jul 4 - Sat, Jul 11
Air Canada Logo
7:55 am - 2:41 pm
YWG
-
BOS
5h 46m
1 stop
Air Canada Logo
10:50 am - 4:20 pm
BOS
-
YWG
6h 30m
1 stop
$319Air Canada
Fri, Jul 3 - Mon, Jul 13
Porter Airlines Logo
12:15 pm - 6:35 pm
YWG
-
BOS
5h 20m
1 stop
Porter Airlines Logo
10:05 am - 3:19 pm
BOS
-
YWG
6h 14m
1 stop
$325Porter Airlines
Sat, Jul 4 - Sat, Jul 11
Air Canada Logo
5:00 am - 2:41 pm
YWG
-
BOS
8h 41m
2 stops
Air Canada Logo
3:35 pm - 11:45 pm
BOS
-
YWG
9h 10m
2 stops
$326Air Canada
Tue, Sep 22 - Sat, Sep 26
Delta Logo
12:46 pm - 11:55 pm
YWG
-
ALB
10h 09m
2 stops
Delta Logo
12:45 pm - 11:30 pm
ALB
-
YWG
11h 45m
2 stops
$432Delta
Sat, Jul 11 - Fri, Sep 4
WestJet Logo
6:15 am - 11:22 am
YWG
-
ALB
28h 07m
2 stops
WestJet Logo
6:00 am - 8:30 pm
ALB
-
YWG
15h 30m
2 stops
$464WestJet
Sat, Jul 11 - Fri, Sep 4
WestJet Logo
6:15 am - 5:59 pm
YWG
-
ALB
34h 44m
2 stops
WestJet Logo
6:00 am - 8:30 pm
ALB
-
YWG
15h 30m
2 stops
$465WestJet
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 July.

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 $116 (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 $411 respectively.

Find deals

Good to know

Low seasonJanuary
Cheapest flight$176
Best time to beat the crowds but there is an average 51% increase in price.
Most popular time to fly and prices are also 16% 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.

Reviews of the top airline 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.
7.1
Air CanadaOverall score based on 11160 reviews
7.8Crew
7.1Comfort
7.3Boarding
6.8Entertainment
6.3Food
Airline reviews

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

10.0 ExcellentAnonymous, Jun 2026
YEG - SFO
Read more Air Canada reviews

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!!

Never flown with Air Canada before, but it's now a top choice! Loved it!

Horrible crew, horrible seats configuration, ridiculous space in the toilets, Air Canada is no longer a option.

Crew at gate and onboard were just very OK, not very friendly and honestly seemed bothered to be there. I will give a shout out to still selling headphones for those who forgot.

Flight Boarded and departed on time. The Flight crew was very friendly and accommodating. The aircraft was clean and free from clutter and debris. I will be happy to recommend Air Canada to my friends and relatives for their flight needs. They were very attentive and responsive to our needs as Senior citizens.

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

Information on your arrival and departure airports

Winnipeg (YWG)