$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 9/13. 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$272
Albany
Albany2 stops$326
Boston
Boston1 stop$272
Albany
Albany2 stops$326

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 12 - Tue, Sep 15
Delta Logo
5:38 pm - 11:52 pm
YWG
-
BOS
5h 14m
1 stop
Delta Logo
3:05 pm - 11:27 pm
BOS
-
YWG
9h 22m
1 stop
$272Delta
Sat, Sep 12 - Tue, Sep 15
Air Canada Logo
12:20 pm - 9:27 pm
YWG
-
BOS
8h 07m
2 stops
Air Canada Logo
5:00 pm - 11:07 pm
BOS
-
YWG
7h 07m
1 stop
$286Air Canada
Fri, Aug 28 - Mon, Aug 31
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
$294Porter Airlines
Fri, Aug 28 - Mon, Aug 31
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
$295Porter Airlines
Fri, Sep 25 - Wed, Sep 30
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
$299Porter Airlines
Tue, Sep 29 - Sun, Oct 4
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
$300Porter Airlines
Fri, May 8 - Sun, May 10
Delta Logo
5:41 pm - 11:54 pm
YWG
-
BOS
5h 13m
1 stop
Delta Logo
5:51 am - 10:54 am
BOS
-
YWG
6h 03m
1 stop
$314Delta
Tue, Jul 7 - Tue, Jul 21
United Airlines Logo
7:00 am - 9:27 pm
YWG
-
ALB
13h 27m
1 stop
United Airlines Logo
5:05 pm - 10:33 pm
ALB
-
YWG
6h 28m
1 stop
$346United Airlines
Tue, Jul 7 - Tue, Jul 21
United Airlines Logo
7:00 am - 11:47 pm
YWG
-
ALB
15h 47m
2 stops
United Airlines Logo
5:05 pm - 10:33 pm
ALB
-
YWG
6h 28m
1 stop
$347United Airlines
Tue, Jun 9 - Sat, Jun 13
Air Canada Logo
7:00 am - 3:26 pm
YWG
-
ALB
7h 26m
1 stop
Air Canada Logo
4:43 pm - 10:33 pm
ALB
-
YWG
6h 50m
1 stop
$379Air Canada
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 June, when tickets cost $290 (return) on average. On the other hand, the most expensive months are April and January, when the average cost of round-trip tickets is $788 and $782 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$176
Best time to beat the crowds but there is an average 54% increase in price.
Most popular time to fly with an average 4% 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 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 8444 reviews
8.1Boarding
7.2Food
7.8Entertainment
7.9Comfort
8.5Crew
Airline reviews

WiFi didn’t work. Flight delayed 3 hours Crew members were illiterate Seat lean back did not work.

2.0 MediocreNicholas, Apr 2026
LGA - CLT
Read more Delta reviews

WiFi didn’t work. Flight delayed 3 hours Crew members were illiterate Seat lean back did not work.

Flight was delayed, we could have been notified earlier and in a consistent manner. App was not refreshing for another passenger to get the latest flight status. We could have stayed and waited at the hotel instead of waiting at the airport had we known the flight was going to delayed for more than 5 hours. The toilet is too tight, and needs to be cleaned more frequently (every hour). The entertainment screen froze, the touch screen not responding to touch. We were upgraded to comfort, it is more comfortable than regular economy seats.

This wasn't my experience with Delta. It was just the Pegasus flight. Seats were very hard. Staff was kinda rough. Not very nice. Charged me for snacks. For a 4 hour flight I would've expected more.

Crew was nice, meal was good. Entertainment had to be rebooted 3 times and still did not work. Turns out there was residue on screen, it needed to be cleaned to prevent the touchscreen buttons from continuously activating. I had entertainment for the last 45 minutes of a 5 hour 45 minute flight. Really unacceptable for first class. Flight attendent indicated your cleaning solution creates this problem. Seems as if this is widely known, you should be using a different product or cleaning better. Really really disappointing which simply added to the wi fi on your planes with reliably never ever works.

The baggage belt was not updated on the Delta App and was displayed on the wrong belt board. Was not expecting this to happen.

The plan was delayed and left DC 90 minutes late. However, it showed a 20 minute delay on the delta app, then a 12 min delay. It turned out to be an hour delay. I found out where the plane was with flightaware. Stop keeping customers in the dark about what is going on.

Everything went smoothly, although the usual gripes about airline travel were still present: the boarding process is inefficient, the snack selection is limited, and so on. Since there was extra space on the flight, the gate agent rearranged many people's seats to put people on the aisles and windows, leaving the middle seats empty, as much as possible, which was pretty great.

Landed without a gate ready. Plane is extremely old and dirty.

All the amenities was wonderful, if they could keep their prices that low. I'd fly with them all the time.

Very old plane with no inflight entertainment. I purchased the internet pass and it was nearly unusable.

very average service no complimentary alcoholics drinks unlike other airlines such as Porter airlines No decent seats available during check-in time the day before

Good but airlines getting smaller. I didn't like the meal but the service was fine. Flight was fine and luggage arrived. So good.

They were fast and I like how they used to entertainment system to play video about the safety.

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.

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

After 3 hours of delays, they ended up cancelling my flight. And although I could purchase one-way tickets to get to my destination, they would not offer me these flights as compensation for the cancelled flight, and I didn't end up making it home until 13 hours after I was originally supposed to arrive. It made for an extremely strenuous end to an otherwise good trip.

Be careful about the bad policy and when purchasing seats

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

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

Information on your arrival and departure airports