YWG - BOS

C$ 182 Find Cheap Flights from Winnipeg to Boston

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 Boston 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 Boston

 
These are the airlines KAYAK users have selected most often from within our search results in flight searches from Winnipeg to Boston, 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 Boston, as well as popular online travel agencies
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Flight Deals

Cheap Flights from Winnipeg to Boston (YWG-BOS)

 
Here are some of the best deals found on KAYAK recently from the most popular airlines for round-trip flights from Winnipeg to Boston 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 Boston

Wed, 26 Nov - Wed, 3 Dec
Multiple Airlines Logo
7:30 a.m. - 8:49 p.m.YWG-BOS
12h 19m1 stop
Multiple Airlines Logo
9:54 p.m. - 12:41 a.m.BOS-YWG
27h 47m2 stops
C$ 404Multiple Airlines
Find Deal
Tue, 25 Nov - Tue, 2 Dec
Air Canada Logo
8:15 a.m. - 2:52 p.m.YWG-BOS
5h 37m1 stop
Air Canada Logo
5:30 a.m. - 10:16 a.m.BOS-YWG
5h 46m1 stop
C$ 428Air Canada
Find Deal
Wed, 26 Nov - Wed, 3 Dec
Air Canada Logo
5:30 a.m. - 12:12 p.m.YWG-BOS
5h 42m1 stop
Air Canada Logo
5:30 a.m. - 10:16 a.m.BOS-YWG
5h 46m1 stop
C$ 437Air Canada
Find Deal
Wed, 26 Nov - Wed, 3 Dec
Multiple Airlines Logo
7:30 a.m. - 11:53 p.m.YWG-BOS
15h 23m2 stops
Multiple Airlines Logo
9:54 p.m. - 8:06 p.m.BOS-YWG
23h 12m3 stops
C$ 442Multiple Airlines
Find Deal
Tue, 25 Nov - Tue, 2 Dec
Multiple Airlines Logo
5:00 a.m. - 2:55 p.m.YWG-BOS
8h 55m1 stop
Multiple Airlines Logo
9:54 p.m. - 3:07 p.m.BOS-YWG
18h 13m2 stops
C$ 444Multiple Airlines
Find Deal
Tue, 25 Nov - Tue, 2 Dec
United Airlines Logo
8:40 a.m. - 11:42 p.m.YWG-BOS
14h 02m2 stops
United Airlines Logo
6:00 a.m. - 11:57 a.m.BOS-YWG
6h 57m1 stop
C$ 703United Airlines
Find Deal
Sat, 21 Feb - Mon, 23 Feb
United Airlines Logo
7:15 a.m. - 3:57 p.m.YWG-BOS
7h 42m1 stop
United Airlines Logo
10:30 a.m. - 9:44 p.m.BOS-YWG
12h 14m2 stops
C$ 739United Airlines
Find Deal
Fri, 19 Dec - Mon, 22 Dec
Delta Logo
5:45 p.m. - 12:06 a.m.YWG-BOS
5h 21m1 stop
Delta Logo
3:15 p.m. - 11:44 p.m.BOS-YWG
9h 29m1 stop
C$ 764Delta
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Mon, 24 Nov - Tue, 2 Dec
American Airlines Logo
12:10 p.m. - 10:43 p.m.YWG-BOS
9h 33m2 stops
American Airlines Logo
9:13 p.m. - 11:35 p.m.BOS-YWG
27h 22m3 stops
C$ 865American Airlines
Find Deal
Sat, 20 Dec - Sun, 21 Dec
American Airlines Logo
12:10 p.m. - 10:55 p.m.YWG-BOS
9h 45m2 stops
American Airlines Logo
7:50 a.m. - 11:35 p.m.BOS-YWG
16h 45m2 stops
C$ 876American Airlines
Find Deal

Everything you should know

Top airlines
Air Canada
Cheapest • from C$ 428 (round-trip)
Porter Airlines
Best reviews • 8.0 score
Airline reviews
Airline reviews
+1
+1
Airline reviews
Airline reviews
+1
When to book
4 weeks
in advance
Our data shows that travellers who book at least 4 weeks in advance save around 62% compared to booking last minute.
Insights
Insights
Insights
Insights
When to travel
June
Cheapest • 22% price drop
May
Most popular
Good to know
Good to know
+1
+1
Good to know
Good to know
+1
Cheapest round-trip
C$ 404
Overall average: C$ 587
Multiple Airlines
Wed 26/11Wed 3/12
YWG - BOS • 1 stop
Cheapest one-way flights
C$ 182
Typical prices: C$ 299-C$ 735
Multiple Airlines
Tue 11/11
YWG - BOS • 2 stops
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KAYAK searches hundreds of sites at once to find you the best travel deals.
We hope you love your trip to Boston!
Booking Insights

KAYAK's insights & trends for Winnipeg to Boston flights

Get data-powered insights and trends into flights from Winnipeg to Boston to help you find the cheapest flights, the best time to fly and much more.

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

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

If your flying dates are flexible, you should consider flying to Boston on a Tuesday, as we generally find the cheapest rates on that day for this route. On the other hand, Sunday is the most expensive day to fly from Winnipeg to Boston. For your return ticket, we recommend flying on a Wednesday and avoiding Thursdays for the best deals.

What is the cheapest month to fly from Winnipeg to Boston?

To calculate monthly average prices, KAYAK takes all prices for each month over the last year for round-trip flights from Winnipeg to Boston, 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 Boston is June, where tickets cost C$ 444 (return) on average. On the other hand, the most expensive months are December and January, where the average cost of round-trip tickets is C$ 864 and C$ 750 respectively.

How far in advance should I book a flight from Winnipeg to Boston?

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 Boston, 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 Boston, 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 flightC$ 182
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

When to book flights from Winnipeg to Boston

Are your dates flexible? Find out the best times to travel from Winnipeg to Boston based on our flight data from the last year. Discover the cheapest month and even day to fly.
Estimated round-trip price
KAYAK looks at all historical flight data for each date to provide a predicted price for one-way trips or round-trips with a duration up to 40 days. While we try to provide actual minimum prices for each date, some prices are predictions and actual prices may differ.

FAQs for booking flights from Winnipeg to Boston

  • What is the cheapest flight from Winnipeg to Boston?

    In the last 3 days, the lowest price for a flight from Winnipeg to Boston was C$ 182 for a one-way ticket and C$ 404 for a round-trip.

  • Which airports will I be using when flying from Winnipeg to Boston?

    Winnipeg airport is called Winnipeg and the only airport in Boston is Boston Logan Intl.

  • Which aircraft models fly most regularly from Winnipeg to Boston?

    We unfortunately don’t have that data for this specific route.

  • Which airline alliances offer flights from Winnipeg to Boston?

    Star Alliance is the only airline alliance operating flights between Winnipeg and Boston.

  • Which is the best airline for flights from Winnipeg to Boston, Porter Airlines or United Airlines?

    The two airlines most popular with KAYAK users for flights from Winnipeg to Boston are Porter Airlines and United Airlines. With an average price for the route of C$ 641 and an overall rating of 8.0, Porter Airlines is the most popular choice. United Airlines is also a great choice for the route, with an average price of C$ 405 and an overall rating of 7.4.

  • How does KAYAK find such low prices on flights from Winnipeg to Boston?

    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 Boston.

  • How does KAYAK's flight Price Forecast tool help me choose the right time to buy my flight ticket from Winnipeg to Boston?

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight to Boston from Winnipeg 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 Boston?

    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 to Boston with an airline and back to Winnipeg with another airline.

  • What is KAYAK's "flexible dates" feature and why should I care when looking for a flight from Winnipeg to Boston?

    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 to Boston from Winnipeg up to 3 days before/after your preferred dates. You can then pick the flights that suit you best.

Reviews of the top 4 airlines flying from Winnipeg to Boston

 
See real verified KAYAK customer reviews for airlines flying from Winnipeg to Boston. 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 Boston? 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.
8.0
Porter AirlinesOverall score based on 384 reviews
7.6Food
8.6Crew
7.0Entertainment
8.2Boarding
8.0Comfort
Airline reviews

Smaller plane. Food and bar service for free is amazing. Drinks were in glass not plastic cups.

10.0 ExcellentMike, Oct 2025YYC - YYZ
Read more Porter Airlines reviews

Smaller plane. Food and bar service for free is amazing. Drinks were in glass not plastic cups.

Poor landing as we overshot the runway and had to re land the plane. Lost both of my luggage not found as of yet. Had to pay extra money for my luggage in USD, now great my luggage is gone. Will not fly with Porter again.

This flight to St. Johns was really good. Boarding was a breeze. We left spot on time. Seats were actually pretty good. Recliner further than I expected. Three more flights to go we will see if this is the status quo for Porter.👍

I was not happy with AirfareAssist, the agency that kayak advised me would be handling my booking. I was advised by porter airlines that I had been overcharged for the Basic express , a option that I had asked airfare assist to help arrange after I realized that the basic fare I had chosen with porter did not include a carryon. At each checkin porter advised I had been overcharged for this . They advised that money would be refunded to my credit card, however, this is not likely to happen as it is not my name and credit card that appeared on the porter invoice, but that of another individual/agent. When airfare assist was arranging the basic express with porter on my behalf, they asked me to confirm that I agreed to pay $263 USD for this. I did agree, as I was advised this was needed to proceed. When I checked the invoice on the porter website and saw that it was not my name and credit card on the invoice, I was advised that this was how airfareassist processed the payment. The Porter invoice indicated a billed amount of $126USD I will not use Kayak or their designated AirfareAssist again

Our flight was delayed by a bit. I appreciated that we were kept informed on why periodically. Boarding was fine. I overheard one flight attendant sounding very rude to a passenger who was not paying attention to the safety demonstration. The snacks were minimal as it was a short flight. There was no entertainment. Overall the flight was good back to LGA.

The flight was fine see earlier note for the problem

All good the seats a little tight and no I pad screen

Everything was good except the fact you charge more for a carry on bag vs a check in bag and to top it off in US$ that was not impressive

Our flight was cancelled at the last minute for maintenance reasons and we were rebooked on a late flight when we purposefully booked our flight to be home early due to work.

Seemed like an old plane. Very noisy. The seat cushions were so old that the metal bracing of the seats were poking through. There was plenty of leg room though.

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.

Do not fly on WestJet if you have a connection. It failed to integrate with my connecting Delta flight and I almost missed it.

No internet, not even westjet connect makes for a boring flight

Our first flight from LAX to Winnipeg was changed but you never informed us at all. It went from a nonstop flight to a stay at Calgary. This impacted our trip negatively as we arrived much later than we planned to. Our returning flight was horrible. The flight was delayed 6 hours!! And we were NOT going to wait that long. The only way we got on our original flight was running there. However all of our suitcases were now coming on the delayed flight. It was the worst experience we ever had flying. I want my money back.

There was a man who was very rude at boarding. On the other hand personal bag measuring box is too small compared to USA airlines,

A little better seat cushions would be appreciated. Crews were all good.

The process and flight were both smooth and trouble free

Flight delayed 3 hours, missed my connection in Atlanta. Instead of getting to Savannah at 6PM arrived after 10:00PM Middle seat, couldn't get isle or window, couldn't book my seats in advance, had to book at the gate. That's a 1st for me and I used to travel a lot

my carry-on bag was delayed and I did not receive it until the day of my return at the airport. This delay caused me significant inconvenience, as I did not have access to my personal belongings for the duration of my trip. I had expected to rely on my carry-on items, and being without them negatively impacted my travel experience.

Technology issues at the bag-check counter caused a delay, and we were unable to check out our bags, ultimately missing our flight. They offered no assistance other than telling us to book another flight out of Calgary. We arrived with plenty of time; if there hadn't been an issue with the kiosk and the length of the lines due to the technical issues, we could have made it home.

Worst check in and bag drop off experience. Staff were incredibly rude given that it’s the WestJet system that is faulty.

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 Boston

Information on your arrival and departure airports

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