$123 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 12/10. 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$343
Albany
Albany1 stop$314
Boston
Boston1 stop$343
Albany
Albany1 stop$314

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 21 - Sun, Jan 25
United Airlines Logo
2:20 pm - 9:22 pmYWG-ALB
6h 02m1 stop
United Airlines Logo
6:00 am - 11:57 amALB-YWG
6h 57m1 stop
$314United Airlines
Find Deal
Wed, Jan 21 - Sun, Jan 25
United Airlines Logo
2:20 pm - 9:22 pmYWG-ALB
6h 02m1 stop
United Airlines Logo
6:00 am - 11:57 amALB-YWG
6h 57m1 stop
$315United Airlines
Find Deal
Wed, Jan 21 - Sun, Jan 25
United Airlines Logo
2:20 pm - 11:41 pmYWG-ALB
8h 21m2 stops
United Airlines Logo
6:00 am - 11:57 amALB-YWG
6h 57m1 stop
$316United Airlines
Find Deal
Thu, Mar 12 - Mon, Mar 16
Multiple Airlines Logo
5:00 am - 2:45 pmYWG-BOS
8h 45m1 stop
Multiple Airlines Logo
10:20 am - 7:09 pmBOS-YWG
9h 49m1 stop
$343Multiple Airlines
Find Deal
Thu, Mar 12 - Mon, Mar 16
Multiple Airlines Logo
5:00 am - 6:10 pmYWG-BOS
12h 10m2 stops
Multiple Airlines Logo
10:20 am - 7:09 pmBOS-YWG
9h 49m1 stop
$360Multiple Airlines
Find Deal
Sun, Jan 11 - Wed, Jan 14
Air Canada Logo
7:05 am - 7:42 pmYWG-BOS
11h 37m2 stops
Air Canada Logo
5:30 am - 10:16 amBOS-YWG
5h 46m1 stop
$373Air Canada
Find Deal
Thu, Mar 12 - Mon, Mar 16
Air Canada Logo
8:15 am - 2:52 pmYWG-BOS
5h 37m1 stop
Air Canada Logo
10:15 am - 4:35 pmBOS-YWG
7h 20m1 stop
$377Air Canada
Find Deal
Thu, Mar 12 - Mon, Mar 16
Air Canada Logo
5:30 am - 2:52 pmYWG-BOS
8h 22m2 stops
Air Canada Logo
5:30 am - 10:15 amBOS-YWG
5h 45m1 stop
$379Air Canada
Find Deal
Thu, Mar 12 - Mon, Mar 16
Air Canada Logo
5:30 am - 7:12 pmYWG-BOS
12h 42m2 stops
Air Canada Logo
10:15 am - 9:44 pmBOS-YWG
12h 29m2 stops
$390Air Canada
Find Deal
Sun, Jan 11 - Wed, Jan 14
Air Canada Logo
7:05 pm - 12:12 pmYWG-BOS
16h 07m1 stop
Air Canada Logo
5:30 am - 10:16 amBOS-YWG
5h 46m1 stop
$408Air Canada
Find Deal
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 $618 and $537 respectively.

What’s the cheapest day of the week to fly from Winnipeg to Massachusetts?

The average price of all round-trip flights from Winnipeg to Massachusetts clicked on KAYAK for each day over the last 12 months.

If you are looking for a flight deal from Winnipeg to Massachusetts, look for departures on Saturdays and avoid leaving on a Monday, as it's usually the priciest day. When flying back from Massachusetts, Sunday is the cheapest day to fly and Monday is the most expensive.

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 66% 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$123
Best time to beat the crowds but there is an average 1% 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.

  • What is the cheapest time of day to fly to Massachusetts?

    The cheapest time of day to fly to Massachusetts is generally in the morning, when round-trip flights cost $493 on average. The most expensive time of day to fly to Massachusetts is generally in the afternoon, which is peak travel time and where the average cost of a ticket is $618.

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 8009 reviews
7.9Comfort
7.3Food
8.5Crew
7.9Entertainment
8.1Boarding
Airline reviews

Very smooth, on-time, and pleasantly uneventful flight. The team at the gate and on board were professional and genuinely courteous. The pilot kept us well updated throughout, and both takeoff and landing were steady and enjoyable without any drama. Just a good, solid flight. Thank you! 💗

10.0 ExcellentHartaj, Nov 2025LGA - RDU
Read more Delta reviews

Very smooth, on-time, and pleasantly uneventful flight. The team at the gate and on board were professional and genuinely courteous. The pilot kept us well updated throughout, and both takeoff and landing were steady and enjoyable without any drama. Just a good, solid flight. Thank you! 💗

Staff was exceptional! Everyone was kind, professional and friendly making the trip very pleasant. Thank you!

No lunch on a x-country flight scheduled for 10:50 am departure, arrived 5+ hrs later. That requires a black box label before you pay for the tickets. Worst, when I checked in online, it's specifically said that lunch was served on his flight for economy Plus passengers.

We had a lot of really rough weather but that was not Delta's fault. Pilot was amazing.

One of the best airlines that I flew on, the flight attendants were very attentive and professional.

First, Delta needs more flights to/from Miami. Second, a 1000pm leaving at 1230pm is unacceptable from their biggest airport world hub. Another aircraft could have been used such as the aircraft scheduled to be used in the morning for that exact same route. Yes, I did get me there but the lack of sleep the next day didn't help me enjoy my entire trip since I was busy with activities during the weekend. This can be and is expected from Spirit (going bankrupt) and Frontier (despite they're nickel and dimers). But from Delta's World Hub? That's totally unacceptable!

This flight was straightforward and without difficulty. Service was OK, but I continue to be underwhelmed by level of attention given to Sky Priority passengers.

It would’ve been nice for all that money to have a more substantial snack for free. I remember once upon a time getting a very nice turkey sandwich with Swiss cheese on whole wheat bread for no charge along with a drink. I guess those days are gone. it’s a little insulting being given a cookie or a bag of baked chips Going forward I’ll just bring my own.

Our flight from SFO to MSP was right on time on 11/15/2025. No delays. As we approached MSP at about 8 pm, we circled in the air until 8:40 pm so I don't call that efficient for MSP. I think the captain should announce the delay and why. (as if we all don't know that we are just circling around the area, slowing down, speeding up, slowing down.) Thank you. Marilyn Fischer

Service in business class was not impressive. I ordered coffee with dinner and then watched other people get 2 refills before I got my 1 cup of coffee, and only after I pressed the attendant button overhead. Furthermore, the seats in the forward cabin need maintenance on this 737-800: the upholstery is detaching from the seat frame, at least on the backs of seats 1C, 1D.

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.

It was all good flight was on time, service was good I enjoyed a few movies and everything was smooth

Efficient, calm when things were delayed and kept us regularly informed of what was happening.

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.

The staff was great and made the long trip easy peasy!

Air Canada cancelled our flight and reschedule it 26 hours later that completely interrupted my family's long waited Japan trip, it wasn't due to natural reason such as weather but under the company's control. On the day we wasted 9 hours of our time from 6am to 3pm, including a few hours in the customer counter waiting for supervisor to handle our rescheduling. When we came to the counter for rebooking help there were at least 4 employees on the counter but we were told they were not trained to handle customer rebooking, we were also told the supervisor could come 10:30 to handle our rebooking, but she showed up more than one hour later, the end result was exactly the same so the few hours we spent waiting for her was completely wasted; We already prepaid hotel and all the tickets for the our stay in Tokyo so all of the cost for the first day is completed wasted; The $80 meal voucher issues was far less than our financial loss due to the financial cancellation, and it was not surprisingly invalid (as Your company screw up everything possible along the flight), the vouchers were supposed to last 72 hours, when we tried to used it at our lounge next day less than 24 hours from its issuing at a designated restaurant, the worker there couldn't scan the vouchers after multiple tries on all 4 vouchers issued, so we had to pay the food from our own money; For the two return flights they were also full of unfortunate events that caused bad experience and further delay and waste of our time, both flights departed late and the last leg had another significant delay of more than half an hour after touchdown, the gate was for some reason not available so we waited more than half an hour, when we got out of plane it was almost one hour later than the supposed arrival time; The gate you arranged is the farthest in Vancouver airport, also was the luggage pickup location in Seattle airport; We also called customer service for rescheduling help and after a long time wait (more than an hour) we got a call back but the CS representative was equally clueless and unhelpful. Other than a fatal crash, your company couldn't do anything right and provided the worst service possible among the tons of flights we have taken in our lives.

The free Wi-fi for Aeroplan members was a great touch. The time passed quickly. I found the seats seemed a little closer together than I remember. Not Air Canada's fault, but we were about 20 minutes late landing because the airport was too busy. We had to circle around for a while. The boarding and disembarking went very smoothly.

It was crazy, boarded over a hour late from scheduled departure. Then when arrived in BNA issued with getting off the plane…over 1/2 hour. Not looking forward to flying Air Canada, ever again.

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

Information on your arrival and departure airports