$154 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 3/4. 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$313
Albany
Albany1 stop$339
Boston
Boston1 stop$313
Albany
Albany1 stop$339

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, May 6 - Mon, May 11
WestJet Logo
6:30 am - 5:40 pm
YWG
-
BOS
10h 10m
1 stop
WestJet Logo
6:25 pm - 2:30 pm
BOS
-
YWG
21h 05m
1 stop
$313WestJet
Fri, May 1 - Wed, May 6
WestJet Logo
6:30 am - 5:40 pm
YWG
-
BOS
10h 10m
1 stop
WestJet Logo
6:25 pm - 12:30 am
BOS
-
YWG
31h 05m
1 stop
$325WestJet
Wed, May 6 - Sun, May 10
WestJet Logo
6:30 am - 5:40 pm
YWG
-
BOS
10h 10m
1 stop
WestJet Logo
6:25 pm - 5:40 pm
BOS
-
YWG
24h 15m
1 stop
$333WestJet
Tue, Feb 3 - Thu, Feb 5
United Airlines Logo
2:20 pm - 9:23 pm
YWG
-
ALB
6h 03m
1 stop
United Airlines Logo
6:00 am - 11:57 am
ALB
-
YWG
6h 57m
1 stop
$339United Airlines
Mon, Mar 2 - Fri, Mar 6
Multiple Airlines Logo
9:00 pm - 1:13 am
YWG
-
BOS
27h 13m
2 stops
Multiple Airlines Logo
6:00 am - 3:09 pm
BOS
-
YWG
10h 09m
1 stop
$389Multiple Airlines
Wed, May 6 - Mon, May 11
Multiple Airlines Logo
6:30 am - 5:40 pm
YWG
-
BOS
10h 10m
1 stop
Multiple Airlines Logo
12:15 pm - 10:46 pm
BOS
-
YWG
11h 31m
2 stops
$424Multiple Airlines
Mon, Mar 2 - Wed, Mar 4
United Airlines Logo
2:20 pm - 11:57 pm
YWG
-
BOS
8h 37m
2 stops
United Airlines Logo
6:00 am - 11:57 am
BOS
-
YWG
6h 57m
1 stop
$477United Airlines
Mon, Mar 2 - Wed, Mar 4
Air Canada Logo
6:00 am - 2:52 pm
YWG
-
BOS
7h 52m
2 stops
Air Canada Logo
5:30 am - 10:15 am
BOS
-
YWG
5h 45m
1 stop
$478Air Canada
Sat, Jul 11 - Fri, Sep 4
Air Canada Logo
5:10 am - 9:02 pm
YWG
-
ALB
14h 52m
2 stops
Air Canada Logo
4:30 pm - 10:24 pm
ALB
-
YWG
6h 54m
1 stop
$715Air Canada
Sat, Feb 14 - Sat, Feb 21
American Airlines Logo
6:00 am - 3:58 pm
YWG
-
ALB
8h 58m
2 stops
American Airlines Logo
5:05 pm - 11:35 pm
ALB
-
YWG
31h 30m
3 stops
$947American 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 January and December, when the average cost of round-trip tickets is $550 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 3 weeks before departure, which saves you about 51% 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$154
Best time to beat the crowds but there is an average 3% increase in price.
Most popular time to fly and prices are also 9% 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 8075 reviews
7.9Comfort
7.8Entertainment
7.2Food
8.5Crew
8.1Boarding
Airline reviews

Probably not the fault of Delta but there was delay after delay after delay and I ended up getting home 4 hours later then I should have at 1:30 in the morning

4.0 Okaybyron, Jan 2026
CWA - MSP
Read more Delta reviews

Probably not the fault of Delta but there was delay after delay after delay and I ended up getting home 4 hours later then I should have at 1:30 in the morning

My requested wheelchair never appeared. So many entertainment choices yet, I found little of interest and no internet option to search on my own. Both were minor issues.

No in flight service, no explanation - FC got service, C+ did not, unsure about Economy. No turbulence to speak of, so I guess another way to cut cost, or promote health and well being of Delta employees? Also, boarding in MEM combined zones, and with overhead space already full on both flights after Zone 2/ Diamond, presents a huge challenge to find a space for a bag. Delta, other than point A to B, is no longer reasonable to fly - very poor experiences, not even taking into account the chastising at the gate and rude crews, across the board.

It would have been better if the flight wasn't delayed by 2.5 hours

Delta’s staff is unmatched. From the gate agents, to the pilots, to the flight attendants… all top of the industry.

Delta flight Delay for ,more that two hours i.e original flight was 6.30 PM and it starts at 8.45 PM, When we connect Delta team for meal vouchers as it is late arrival in designation,But we did not get it as per delta policy , which is not good for mid night arrival,

Inexperienced boarding crew allowed too many bags on to a full flight and delayed takeoff causing a missed connection and unplanned overnight stay. There was a hotel at the airport but Delta would not pay for it offering only to shuttle me to an area hotel. Never even offerred so much as an apology by anyone working for Delta.

Staff was great! Kind and cordial! Middle seat row 28 seat B has a hump in it. Trays were getting stuck when putting down and up. Good flight

Departure was delayed resulting in me missing my connection. Delta did not autimatically find me another flight.

The seats weren’t reclining even though it wasn’t as exit seat

Reliable, nice crew, I fly often on that flight and I like it all.

l really enjoy very much the flight was very pleasant

I like flying first class, and United has a nice one

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

Air Canada’s problems are not staff related by and large, no. The problem is tiny jets between the U.S. and Canada - yes, believe it or not they are still “international” (just ask our own Mango Maniac in power in the U.S.). The little aisle is compounded by a design flaw of a “dog leg” starting at seat 12. Woe be unto you if you sit here as passengers and attendants do not have sufficient room to not hit you in the face with backpacks. One thing I will say very positively about Air Canada is you still provide pillows and blankets on transcontinental flights to all, not just the elites. Your tiny improperly designed jets are also a problem flying city to city within Canada also. One can only say you remind us of a “Jet Blue” or “Spirit” experience. Also your luggage space is downright Byzantine! We will endeavor to avoid you and use other U.S. carriers, albeit charging more.

Terrible canceled flight and lost my luggage. Flew me to Halifax. Tgat flight was delayed, had to spend night in airport chair.

Better entertainment & food options more may be adding chicken option or on vegetarian side good quality pasta

My seat was not comfortable. Flight was smooth. Regretfully we had two delays before takeoff

Amazing service, with enthusiastic crew members, and some breathtaking views of Vancouver. No IFE though, as it is only a 1 hour flight on a regional Turboprop jet.

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

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

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