$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 7/9. 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

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$292
Albany
Albany1 stop$505
Boston
Boston1 stop$292
Albany
Albany1 stop$505

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, Jul 10 - Thu, Jul 16
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
$292Porter Airlines
Mon, Sep 14 - Fri, Sep 18
Air Canada Logo
8:10 am - 2:41 pm
YWG
-
BOS
5h 31m
1 stop
Air Canada Logo
3:35 pm - 9:14 pm
BOS
-
YWG
6h 39m
1 stop
$308Air Canada
Fri, Jul 10 - Thu, Jul 16
Air Canada Logo
8:15 am - 4:03 pm
YWG
-
BOS
6h 48m
1 stop
Air Canada Logo
5:45 am - 2:25 pm
BOS
-
YWG
9h 40m
2 stops
$314Air Canada
Fri, Jul 10 - Thu, Jul 16
Air Canada Logo
5:00 am - 2:41 pm
YWG
-
BOS
8h 41m
2 stops
Air Canada Logo
5:45 am - 2:25 pm
BOS
-
YWG
9h 40m
2 stops
$316Air Canada
Fri, Aug 7 - Sat, Aug 15
Air Canada Logo
3:20 pm - 10:38 pm
YWG
-
BOS
6h 18m
1 stop
Air Canada Logo
6:00 am - 11:15 am
BOS
-
YWG
6h 15m
1 stop
$322Air Canada
Mon, Jul 13 - Tue, Jul 21
Air Canada Logo
3:20 pm - 10:38 pm
YWG
-
BOS
6h 18m
1 stop
Air Canada Logo
6:00 am - 11:15 am
BOS
-
YWG
6h 15m
1 stop
$327Air Canada
Mon, Sep 14 - Fri, Sep 18
Delta Logo
3:58 pm - 11:59 pm
YWG
-
BOS
7h 01m
1 stop
Delta Logo
5:55 am - 11:56 am
BOS
-
YWG
7h 01m
1 stop
$329Delta
Tue, Aug 11 - Tue, Aug 18
United Airlines Logo
7:00 am - 9:36 pm
YWG
-
ALB
13h 36m
1 stop
United Airlines Logo
6:00 am - 10:33 pm
ALB
-
YWG
17h 33m
2 stops
$505United Airlines
Sat, Jul 11 - Fri, Sep 4
United Airlines Logo
7:00 am - 9:27 pm
YWG
-
ALB
13h 27m
1 stop
United Airlines Logo
8:10 am - 10:33 pm
ALB
-
YWG
15h 23m
1 stop
$536United Airlines
Sat, Jul 11 - Fri, Sep 4
United Airlines Logo
7:00 am - 9:27 pm
YWG
-
ALB
13h 27m
1 stop
United Airlines Logo
8:10 am - 10:33 pm
ALB
-
YWG
15h 23m
1 stop
$537United 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 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 45% increase in price.
Most popular time to fly and prices are also 20% 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 11270 reviews
7.8Crew
7.3Boarding
6.3Food
6.8Entertainment
7.1Comfort
Airline reviews

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

6.0 Goodtapha, Dec 2025
YWG - YUL
Read more Air Canada reviews

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

Winnipeg (YWG)