$130 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 11/11. 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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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$306
Albany
Albany1 stop$450
Boston
Boston1 stop$306
Albany
Albany1 stop$450

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

Tue, Nov 25 - Tue, Dec 2
Air Canada Logo
8:15 am - 2:52 pmYWG-BOS
5h 37m1 stop
Air Canada Logo
5:30 am - 10:16 amBOS-YWG
5h 46m1 stop
$306Air Canada
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Mon, Nov 24 - Tue, Dec 2
Air Canada Logo
5:30 am - 3:57 pmYWG-BOS
9h 27m1 stop
Air Canada Logo
5:30 am - 10:16 amBOS-YWG
5h 46m1 stop
$338Air Canada
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Thu, Nov 27 - Tue, Dec 2
Multiple Airlines Logo
7:30 am - 12:44 amYWG-BOS
16h 14m2 stops
Multiple Airlines Logo
12:44 pm - 3:07 pmBOS-YWG
27h 23m1 stop
$383Multiple Airlines
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Thu, Nov 27 - Thu, Dec 4
Multiple Airlines Logo
8:20 pm - 9:35 amYWG-BOS
12h 15m1 stop
Multiple Airlines Logo
7:00 am - 7:35 pmBOS-YWG
13h 35m1 stop
$392Multiple Airlines
Find Deal
Wed, Mar 25 - Thu, Mar 26
United Airlines Logo
2:15 pm - 9:06 pmYWG-ALB
5h 51m1 stop
United Airlines Logo
6:15 am - 11:39 amALB-YWG
6h 24m1 stop
$450United Airlines
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Wed, Mar 25 - Thu, Mar 26
United Airlines Logo
2:15 pm - 12:16 amYWG-ALB
9h 01m1 stop
United Airlines Logo
6:15 am - 11:39 amALB-YWG
6h 24m1 stop
$451United Airlines
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Mon, Nov 24 - Tue, Dec 2
Delta Logo
6:40 am - 8:00 pmYWG-BOS
12h 20m2 stops
Delta Logo
5:45 am - 11:45 amBOS-YWG
7h 00m1 stop
$462Delta
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Mon, Nov 24 - Tue, Dec 2
American Airlines Logo
12:10 pm - 10:43 pmYWG-BOS
9h 33m2 stops
American Airlines Logo
9:13 pm - 11:35 pmBOS-YWG
27h 22m3 stops
$619American Airlines
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Mon, Dec 22 - Sun, Dec 28
Delta Logo
5:45 pm - 11:54 pmYWG-BOS
5h 09m1 stop
Delta Logo
5:30 am - 4:55 pmBOS-YWG
12h 25m2 stops
$624Delta
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Fri, Nov 21 - Mon, Dec 1
American Airlines Logo
12:10 pm - 10:43 pmYWG-BOS
9h 33m2 stops
American Airlines Logo
9:13 pm - 11:35 pmBOS-YWG
51h 22m3 stops
$731American Airlines
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 $318 (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 62% 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$130
Best time to beat the crowds but there is an average 5% increase in price.
Most popular time to fly and prices are also 10% 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 7993 reviews
7.9Comfort
7.9Entertainment
8.5Crew
8.2Boarding
7.3Food
Airline reviews

DELTA does a terrific job making sure you are well taken care of during the flight, gives you assurance before the flight through numerous email notifications about your upcoming flight & lastly good follow up after the flight making sure your needs were mat. It has been, is & will continue to be my carrier of choice in all my future travels. Good Job DELTA

10.0 ExcellentAnonymous, Oct 2025CDG - SEA
Read more Delta reviews

DELTA does a terrific job making sure you are well taken care of during the flight, gives you assurance before the flight through numerous email notifications about your upcoming flight & lastly good follow up after the flight making sure your needs were mat. It has been, is & will continue to be my carrier of choice in all my future travels. Good Job DELTA

Staff were friendly and happy. Delta could make sure passengers that don't have the app know of changes. Without Kayak I would not have known about the change of gate or the delay. Kayak was faster to notify me.

They ended up paying for the bag twice, but the counter wouldn't take my baggage receipt. Left it to me to resolve. Not sure how to resolve the issue.

The customer service before board was very rude and when I expressed my concerns about making the connecting flight she laughed and told me I bought the wrong ticket. I explained once it showed the flight was delayed it no longer let me change seats or anything. I was trying to upgrade to make sure I would get to the next gate on time.

Non stop on long haul is the way to go. Great experience

Seats comfortable, service and food very mediocre, staff not very attentive, worse than many other our flights with Delta.

Overall good experience; however, there was one flight attendant who was rather rough compared to everyone else. Everything else was good: entertainment, food. Delta keeps on delivering! Thank you!

The flight used a B767 with a very old interior from before 2014. The entertainment system did not work at all during the flight despite attempts to reset the system. It was like they flew this route just to be competitive.

Crew blocked exits to front of ship with galley carts. Also split five person family apart on international flight without fixing.

They changed planes and the new plane couldn’t carry enough fuel to fly across the country so we had to stop in Kansas City to refuel. Flight was delayed .

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.

Impressed with the service despite turbulence because of the weather. Both flights arrived before their scheduled times.

Airbus plane, nice and polite staff, entertainment even as it was a short flight.

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.

Extremely turbulent landing. Crew was friendly and plane comfortable. Airport and US pre clearance was understaffed

The airplane is way too tight, you can hardly enter into your row to sit.. more like kids seats than adults.

taking our carryon and forcing us to check it through

Wifi was great. Kind air crew and comfortable seating. Also liked the entertainment options.

Great flight. Only complaint is it took over an hour for my luggage to get to the carousel on the return to LAX That was irritating

I knew I was going to fall asleep unsettlingly from exhaustion so I warned the guy next to me in advance. The attendant took to checking on me frequently and even insisted I take my snack because I said no while sleep hazed and then absolutely wanted it about 5 minutes later. He was So caring and kind to my situation!!

First message when all on board was that we didnt have a pilot, then they found one, then it was something about the bridge something not working, they will either fix or do manually. Flight of course was leaving late with all the cruise guests worrying about making it to their ship in time. Then only some luggage made it off the ship. Around 15 to 20 people waiting. 45 min later arrived except mine. I asked the rep at the luggage conveyor, he asked me my name. Then said it was not picked up with the first batch so they put it in a room. I was going to take public transport but now worried about time so took a taxi that cost me $65 USD

The flight was very smooth and good. Boarding was fast, but the staff was just decently friendly.

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

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