$243 Find Cheap Flights from Winnipeg to Massachusetts

This is the cheapest round-trip flight price found by a KAYAK user in the last 72 hours by searching for a flight from Winnipeg to Massachusetts departing on 1/28. 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

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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
Boston2 stops$243
Albany
Albany1 stop$512
Boston
Boston2 stops$243
Albany
Albany1 stop$512

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

Wed, Jan 28 - Wed, Feb 4
Multiple Airlines Logo
12:55 pm - 1:13 am
YWG
-
BOS
35h 18m2 stops
Multiple Airlines Logo
6:00 am - 3:09 pm
BOS
-
YWG
10h 09m1 stop
$243Multiple Airlines
Wed, Apr 8 - Wed, Apr 22
Multiple Airlines Logo
7:30 am - 1:04 am
YWG
-
BOS
16h 34m1 stop
Multiple Airlines Logo
7:55 pm - 7:09 pm
BOS
-
YWG
24h 14m2 stops
$282Multiple Airlines
Wed, Jan 28 - Wed, Feb 4
Multiple Airlines Logo
6:00 am - 8:30 pm
YWG
-
BOS
13h 30m1 stop
Multiple Airlines Logo
6:00 am - 3:09 pm
BOS
-
YWG
10h 09m1 stop
$301Multiple Airlines
Wed, Jan 28 - Wed, Feb 4
Multiple Airlines Logo
12:55 pm - 4:19 pm
YWG
-
BOS
26h 24m3 stops
Multiple Airlines Logo
5:53 pm - 12:40 am
BOS
-
YWG
31h 47m3 stops
$334Multiple Airlines
Wed, Apr 8 - Wed, Apr 22
Air Canada Logo
8:15 am - 2:52 pm
YWG
-
BOS
5h 37m1 stop
Air Canada Logo
5:30 am - 10:07 am
BOS
-
YWG
5h 37m1 stop
$406Air Canada
Mon, Mar 2 - Wed, Mar 4
Delta Logo
5:19 pm - 11:50 pm
YWG
-
BOS
5h 31m1 stop
Delta Logo
6:25 pm - 11:36 pm
BOS
-
YWG
6h 11m1 stop
$408Delta
Mon, Mar 2 - Wed, Mar 4
Air Canada Logo
6:00 am - 2:52 pm
YWG
-
BOS
7h 52m2 stops
Air Canada Logo
10:15 am - 8:28 pm
BOS
-
YWG
11h 13m2 stops
$409Air Canada
Fri, Jan 23 - Sun, Jan 25
United Airlines Logo
2:20 pm - 9:22 pm
YWG
-
ALB
6h 02m1 stop
United Airlines Logo
6:00 am - 11:57 am
ALB
-
YWG
6h 57m1 stop
$512United Airlines
Sun, Jan 18 - Thu, Jan 22
Delta Logo
6:40 am - 10:55 pm
YWG
-
ALB
15h 15m2 stops
Delta Logo
12:29 pm - 12:42 am
ALB
-
YWG
13h 13m2 stops
$537Delta
Sun, Jan 18 - Thu, Jan 22
United Airlines Logo
7:05 am - 11:41 pm
YWG
-
ALB
15h 36m2 stops
United Airlines Logo
6:00 am - 11:57 am
ALB
-
YWG
6h 57m1 stop
$630United 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.

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 $300 (return) on average. On the other hand, the most expensive months are December and January, when the average cost of round-trip tickets is $583 and $550 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 4 weeks before departure, which saves you about 68% compared to booking last minute. For the absolute cheapest price, our data suggests you should book 20 weeks before departure.

Good to know

Low seasonMarch
Cheapest flight$243
Best time to beat the crowds but there is an average 3% increase in price.
Most popular time to fly and prices are also 13% 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 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 8017 reviews
7.2Food
7.9Comfort
8.5Crew
8.1Boarding
7.8Entertainment
Airline reviews

This flight was no comparison to our prior flight. I'm thinking it all has to do with the age of the aircraft.

10.0 ExcellentAnonymous, Dec 2025
DCA - SEA
Read more Delta reviews

This flight was no comparison to our prior flight. I'm thinking it all has to do with the age of the aircraft.

This flight was a first class choice and left much to be desired. Seat backs on seats were falling apart and torn. Seats actually didn't come to a "full & upright position". Pull out table was sprung. Not any significant leg room. All in all we were on an obviously older plane and felt overcharged for what we received as first class.

Flight was delayed several times. At one point, they "pulled back" 15 minutes from the delayed boarding and sent a text saying we would board sooner than previously advised. The flight then was delayed again. And when we boarded, there was an unspecified technical issue which had us waiting in the plane for about an hour.

Delta is a good airline. I've never had an issue with Delta. I'll continue to fly with them until they show me that I shouldn't.

The only thing nice I can say is the flight crew was really nice and apologetic about the situation. They shared as much information as they had and advised us on what we could do about missing connecting flights. The boarding process was so slow. The gate agent was working by herself and should have had someone working with her. It took almost an hour to board because she was trying to board a full flight of people and provide customer service to everyone who was flying standby and/or had questions. It was really chaotic. This didn't help the fact that we were delayed and folks were missing connections the longer it took.

The gate attendants and the crew were terrible. Because of high winds, they needed to carry more fuel, so they had to get volunteers to take the next flight at 6 am the next day. They did a terrible job of it - our flight ended up taking off just under 3 hours of the scheduled time. I hope to never fly Delta again.

Did not realize internet screen was hidden between seats and no info printed!!!!

I went to washroom twice and once there was no toilet seat cover and the other no toilet paper at all. I don't think it was ever replenished or checked before we boarded as it was very early on in the flight.

2 of the seats in row 31 the entertainment system was not working, and one seat the tray table did not go all the way down. Flight arrived early and departed on time which was great.

Very good flight crew and very nice people staff were incredible especially the gate agent

United airlines has the best customer experience from booking to arrival. I always fly United airlines. The mileage program is excellent

The Sears in the 800s are not too good perfect Airbus why cant the new 737 fix that

Quick and seamless boarding. No entertainment but fast Starlink wifi for this short trip and the staff was really friendly.

I dread trans-Pacific flights. They are very long. This was my first time on Universal, and it was my best crossing ever. The staff were professional, the hospitality was great, and the food was delicious. The entertainment system filled the long flight hours. I will seek out Universal flights from now onwards. 🙂

The food quality sucks. One must starve if they do not eat flesh Or wheat based products Some variety would be expected. The trivial amount of snacks and or food is inhumane

We Left Calgary 1/2 hour late and that made for a tight connection in Denver. After arriving everything was done to help us make our connection. That was a great effort. Thank You United

Efficient all round, very good crew. Short flight so the food, of course, was just snacks

Overall, it was good. I was seating next to a wonderful lady and did not notice how time flew. Thanks

My flight was delayed about 1 1/2 hours in Chicago, but other then that it was a good flight.

The experience was great, the crew was very polite and hospitable. I will definitely make if my go to airlines.

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

They are very proactive and made our boarding easy and always notified us about any changes well in advance.

My seat was covered in vomit and I will be reaching out to Air Canada

It's kindof ridiculous that your system is even asking me about this since my flight was canceled and I wasn't rescheduled.

3 hr delay at the gate while they were doing maintenance. Next time, do not board passengers while maintenance is being performed

Digital check in is very poor with air canada compaired to other airlines

Baggage delayed we had to catch our cruise without any clothes 😒

Air Canada Rouge is great. Toronto Airport is the usual nightmare

Good but need to be better with the flight times.

The staff could not have been any friendlier. Lots of usb ports on our aircraft.

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

Information on your arrival and departure airports