$178 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 2/6. 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$281
Albany
Albany2 stops$370
Boston
Boston1 stop$281
Albany
Albany2 stops$370

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

Fri, Jan 23 - Fri, Jan 30
Multiple Airlines Logo
7:30 am - 1:13 am
YWG
-
BOS
16h 43m1 stop
Multiple Airlines Logo
3:43 pm - 1:26 am
BOS
-
YWG
10h 43m1 stop
$281Multiple Airlines
Fri, Jan 23 - Fri, Jan 30
Multiple Airlines Logo
7:30 am - 11:57 pm
YWG
-
BOS
15h 27m2 stops
Multiple Airlines Logo
3:43 pm - 1:26 am
BOS
-
YWG
10h 43m1 stop
$314Multiple Airlines
Wed, Jan 28 - Tue, Feb 3
Air Canada Logo
8:15 am - 2:52 pm
YWG
-
BOS
5h 37m1 stop
Air Canada Logo
10:15 am - 4:35 pm
BOS
-
YWG
7h 20m1 stop
$336Air Canada
Mon, Mar 9 - Wed, Mar 11
United Airlines Logo
7:05 pm - 2:53 pm
YWG
-
ALB
18h 48m2 stops
United Airlines Logo
7:24 pm - 11:57 am
ALB
-
YWG
17h 33m2 stops
$370United Airlines
Thu, May 7 - Mon, May 11
Porter Airlines Logo
11:45 am - 6:28 pm
YWG
-
BOS
5h 43m1 stop
Porter Airlines Logo
3:30 pm - 10:46 pm
BOS
-
YWG
8h 16m1 stop
$374Porter Airlines
Fri, Feb 13 - Sun, Feb 15
Air Canada Logo
7:20 pm - 10:02 am
YWG
-
BOS
13h 42m1 stop
Air Canada Logo
5:30 am - 10:15 am
BOS
-
YWG
5h 45m1 stop
$377Air Canada
Wed, Jan 28 - Tue, Feb 3
Multiple Airlines Logo
7:30 am - 1:03 am
YWG
-
BOS
16h 33m1 stop
Multiple Airlines Logo
5:23 pm - 3:09 pm
BOS
-
YWG
22h 46m2 stops
$387Multiple Airlines
Wed, Jan 21 - Thu, Jan 22
United Airlines Logo
2:20 pm - 9:38 pm
YWG
-
BOS
6h 18m1 stop
United Airlines Logo
6:00 am - 11:57 am
BOS
-
YWG
6h 57m1 stop
$408United Airlines
Mon, Mar 9 - Wed, Mar 11
Delta Logo
12:50 pm - 11:10 pm
YWG
-
ALB
9h 20m2 stops
Delta Logo
6:00 am - 3:09 pm
ALB
-
YWG
10h 09m2 stops
$422Delta
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
$608Delta
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.

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 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$178
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.

  • 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 8012 reviews
7.3Food
8.5Crew
8.1Boarding
7.9Entertainment
7.9Comfort
Airline reviews

The flight was delayed for about 2 hrs. Other than it, it was good.

8.0 ExcellentWen, Dec 2025
LAX - MSY
Read more Delta reviews

The flight was delayed for about 2 hrs. Other than it, it was good.

Advertised fruit trays with cheese, but only snacks handed out!

The plant way delayed departing by 3 hours. It was an old airplane with broken seats and armrests. The bathroom made a hollering sound. A really crappy flight experience and travel day all around.

Premium economy is like the forgotten class. Aside from meal service never saw a flight attendant. Any additional beverages required going to the very back of the plane to request and there was rarely an attendant there. Seat leg / foot rest hardly elevates and not well suite for someone under 5’6. Bulky armrests

Flight delays both to Detroits and return flight . The flight to Detroit was associated with mechanical difficulty

Flight was operated by Virgin Atlantic and it was up to their usual high standard. Minor grips about some issues, but they are really first world issues and as a whole, was an excellent flight.

I am extremely disappointed that delta internal pilot manuals now refer to the Gulf of Mexico as the “gulf of America”. You can bow down to the Orange turd on your own. I will never fly delta again

Delta One upgrade it would have been great if my tray extended (it was jammed and wouldn’t pull out), seatbelt had too much slack & my little cabin door didn’t close properly

I paid for a business class ticket on Delta. It was sourced to Virgin Atlantic. They changed out the aircraft which had fewer upper class tickets. Even though I'd checked into the lounge, was receiving alerts via kayak about the delay and changes; no one informed me that the seat would be changed - until I attempted to board and was told that I would have an economy seat or they could search to put me on another airline. Even the flight crew were informed of this change (10 passengers were bumped out of Upper Class) around 2 pm (1400) time. Hours would have helped to consider alternatives instead of making a last minute change. There needs to be compensation from both Delta and Virgin given this change in service/experience.

Wasn't a Delta issue I don't think, but seems there was a Delta flight at each of the 2 Dallas airports at the same exact time, both to Atlanta. I was evidently booked on the one at Love Airport, but the Carey transport shuttle took me to DFW instead and I ended up missing the flight by just a few minutes. Was able to book a Southwest flight from Love Airport, but was a big loss of time and an inconvenience.

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.

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.

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

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

Information on your arrival and departure airports