$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 7/7. 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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Cheap Flights from Winnipeg to Massachusetts

Cheapest round-trip prices found by our users on KAYAK in the last 72 hours
Boston
Boston1 stop$299
Albany
Albany2 stops$336
Boston
Boston1 stop$299
Albany
Albany2 stops$336

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

Fri, Aug 7 - Tue, Aug 11
Air Canada Logo
3:20 pm - 10:38 pm
YWG
-
BOS
6h 18m
1 stop
Air Canada Logo
10:40 am - 3:14 pm
BOS
-
YWG
5h 34m
1 stop
$299Air Canada
Tue, Jul 7 - Tue, Jul 14
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
$303Air Canada
Fri, Sep 25 - Wed, Sep 30
Air Canada Logo
3:20 pm - 10:40 pm
YWG
-
BOS
6h 20m
1 stop
Air Canada Logo
10:50 am - 4:17 pm
BOS
-
YWG
6h 27m
1 stop
$331Air Canada
Tue, Jul 7 - Tue, Jul 14
Porter Airlines Logo
12:15 pm - 7:15 pm
YWG
-
BOS
6h 00m
1 stop
Porter Airlines Logo
7:10 am - 5:58 pm
BOS
-
YWG
11h 48m
2 stops
$336Porter Airlines
Fri, Oct 9 - Mon, Oct 12
Delta Logo
6:35 am - 11:34 pm
YWG
-
ALB
15h 59m
2 stops
Delta Logo
9:50 am - 8:16 pm
ALB
-
YWG
11h 26m
2 stops
$336Delta
Tue, Jul 7 - Tue, Jul 14
Porter Airlines Logo
9:20 am - 8:55 pm
YWG
-
BOS
10h 35m
2 stops
Porter Airlines Logo
7:10 am - 5:58 pm
BOS
-
YWG
11h 48m
2 stops
$352Porter Airlines
Fri, Oct 2 - Mon, Oct 5
Delta Logo
3:58 pm - 10:13 pm
YWG
-
BOS
5h 15m
1 stop
Delta Logo
5:55 am - 3:08 pm
BOS
-
YWG
10h 13m
1 stop
$368Delta
Mon, Nov 2 - Wed, Nov 4
United Airlines Logo
5:15 am - 9:02 pm
YWG
-
ALB
14h 47m
2 stops
United Airlines Logo
6:15 am - 11:39 am
ALB
-
YWG
6h 24m
1 stop
$404United Airlines
Mon, Nov 2 - Wed, Nov 4
United Airlines Logo
5:15 am - 9:02 pm
YWG
-
ALB
14h 47m
2 stops
United Airlines Logo
6:15 am - 11:39 am
ALB
-
YWG
6h 24m
1 stop
$405United Airlines
Fri, Oct 9 - Mon, Oct 12
WestJet Logo
7:00 am - 11:10 pm
YWG
-
ALB
15h 10m
2 stops
WestJet Logo
12:55 pm - 2:25 pm
ALB
-
YWG
26h 30m
2 stops
$458WestJet
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 $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.

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.

Find deals

Good to know

Low seasonJanuary
Cheapest flight$176
Best time to beat the crowds but there is an average 52% increase in price.
Most popular time to fly with an average 15% increase in price.
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 11126 reviews
7.3Boarding
6.3Food
7.8Crew
6.8Entertainment
7.1Comfort
Airline reviews

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

8.0 ExcellentAnonymous, Jun 2026
YYZ - MCO
Read more Air Canada reviews

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.

Another good flight experience with Air Canada. The business section did not feature the full length sleeping arrangement, but this was a shorter trip. The food was excellent. But the flight crew was truly top tier: friendly, cheerful, helpful at all the right times. Air Canada truly outshines all U.S. carriers.

Flight operated by PAL. We boarded, and one engine started. The crew found some problem that could not be fixed. The flight was canceled. This run from yhz-bos is very unreliable.

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

Information on your arrival and departure airports

Winnipeg (YWG)