$177 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
Travelers love KAYAK
41,299,237 searches in the past 7 days on KAYAK

Save 24% or moreCompare multiple travel sites with one search.

Track pricesNot ready to book? Create a price alert for when prices drop.

Bundle and saveSave money when you bundle your flight + hotel.

Filter your dealsChoose cabin class, free Wi-Fi and more.

Flight Deals
Booking Insights
Flight Deals

Cheap Flights from Winnipeg to Massachusetts

Cheapest round-trip prices found by our users on KAYAK in the last 72 hours
Boston
Boston1 stop$270
Albany
Albany1 stop$390
Boston
Boston1 stop$270
Albany
Albany1 stop$390

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

Sat, Sep 5 - Sat, Sep 12
Air Canada Logo
7:55 am - 2:41 pm
YWG
-
BOS
5h 46m
1 stop
Air Canada Logo
3:35 pm - 9:14 pm
BOS
-
YWG
6h 39m
1 stop
$270Air Canada
Sat, Sep 5 - Sat, Sep 12
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
$305Porter Airlines
Tue, Jul 21 - Sat, Jul 25
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
$346Porter Airlines
Tue, Jul 21 - Sat, Jul 25
Air Canada Logo
12:20 pm - 9:27 pm
YWG
-
BOS
8h 07m
2 stops
Air Canada Logo
6:00 am - 11:15 am
BOS
-
YWG
6h 15m
1 stop
$350Air Canada
Sat, Sep 5 - Sat, Sep 12
United Airlines Logo
5:00 am - 4:47 pm
YWG
-
BOS
10h 47m
2 stops
United Airlines Logo
8:00 am - 8:57 pm
BOS
-
YWG
13h 57m
2 stops
$390United Airlines
Sat, Oct 24 - Tue, Oct 27
United Airlines Logo
7:00 am - 2:54 pm
YWG
-
ALB
6h 54m
1 stop
United Airlines Logo
6:15 am - 11:39 am
ALB
-
YWG
6h 24m
1 stop
$390United Airlines
Fri, Oct 2 - Mon, Oct 5
WestJet Logo
7:00 am - 5:40 pm
YWG
-
BOS
9h 40m
1 stop
WestJet Logo
6:30 pm - 11:10 am
BOS
-
YWG
17h 40m
1 stop
$410WestJet
Sat, Jul 11 - Fri, Sep 4
WestJet Logo
10:45 am - 11:21 pm
YWG
-
ALB
11h 36m
2 stops
WestJet Logo
12:55 pm - 8:20 pm
ALB
-
YWG
32h 25m
2 stops
$451WestJet
Tue, Jul 7 - Tue, Jul 21
Delta Logo
7:45 am - 11:21 pm
YWG
-
ALB
14h 36m
2 stops
Delta Logo
6:05 am - 5:15 pm
ALB
-
YWG
12h 10m
2 stops
$468Delta
Tue, Jul 7 - Tue, Jul 21
Delta Logo
6:40 am - 11:17 pm
YWG
-
ALB
15h 37m
2 stops
Delta Logo
1:27 pm - 11:29 pm
ALB
-
YWG
11h 02m
2 stops
$480Delta
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 September.

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 58% compared to booking last minute. For the absolute cheapest price, our data suggests you should book 17 weeks before departure.

Find deals

Good to know

Low seasonJanuary
Cheapest flight$177
Best time to beat the crowds but there is an average 53% increase in price.
Most popular time to fly with an average 10% 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 11077 reviews
7.8Crew
6.3Food
7.1Comfort
6.8Entertainment
7.3Boarding
Airline reviews

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!!

10.0 ExcellentCourtney, May 2026
YUL - LAX
Read more Air Canada reviews

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. The crew was so friendly, helpful & smiled. We had an excellent flight getting in earlier.

Flight itself was not bad at all. However: my checked bag (checked in Calgary) did not make it onto this flight as I found out after I landed at EWR. I still don't have it but it appears that it is on its way to me.

Flight and attendance were very good we had 2 hour delay that took the shine of it

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

Information on your arrival and departure airports

Winnipeg (YWG)