YWG - BOS

C$ 179 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 17/5. 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.
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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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Cheap Flight Deals 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.

Recent round-trip flight deals from Winnipeg to Boston

KAYAK's recommended round-trip deals from the most popular airlines that fly from Winnipeg to Boston.
Discover the best prices for you by selecting your travel dates on KAYAK.
Choose your dates
United Airlines Logo
4:25 p.m. - 6:01 a.m.YWG-BOS
12h 36m1 stop
United Airlines Logo
6:05 a.m. - 6:02 p.m.BOS-YWG
12h 57m2 stops
C$ 324United Airlines
Find Deal
Sat, 7 Jun - Sat, 14 Jun
United Airlines Logo
5:00 a.m. - 4:19 p.m.YWG-BOS
10h 19m2 stops
United Airlines Logo
6:05 a.m. - 6:02 p.m.BOS-YWG
12h 57m2 stops
C$ 332United Airlines
Find Deal
Sat, 7 Jun - Sat, 14 Jun
Delta Logo
8:35 a.m. - 7:12 p.m.YWG-BOS
9h 37m1 stop
Delta Logo
7:10 a.m. - 4:51 p.m.BOS-YWG
10h 41m1 stop
C$ 334Delta
Find Deal
Thu, 3 Jul - Sat, 23 Aug
Delta Logo
12:40 p.m. - 10:25 p.m.YWG-BOS
8h 45m1 stop
Delta Logo
12:55 p.m. - 11:22 p.m.BOS-YWG
11h 27m2 stops
C$ 339Delta
Find Deal
Thu, 10 Jul - Wed, 6 Aug
 Logo
11:45 a.m. - 9:09 a.m.YWG-BOS
20h 24m2 stops
 Logo
8:14 p.m. - 12:31 a.m.BOS-YWG
29h 17m3 stops
C$ 564
Find Deal
Sat, 7 Jun - Sat, 14 Jun
 Logo
6:30 a.m. - 7:03 a.m.YWG-BOS
23h 33m3 stops
 Logo
8:14 p.m. - 12:31 a.m.BOS-YWG
29h 17m3 stops
C$ 597
Find Deal
Sat, 7 Jun - Sat, 14 Jun
Porter Airlines Logo
11:25 a.m. - 6:08 p.m.YWG-BOS
5h 43m1 stop
Porter Airlines Logo
8:45 a.m. - 6:00 p.m.BOS-YWG
10h 15m2 stops
C$ 625Porter Airlines
Find Deal
Fri, 16 May - Mon, 19 May
Air Canada Logo
5:00 a.m. - 6:00 p.m.YWG-BOS
12h 00m2 stops
Air Canada Logo
5:50 a.m. - 4:13 p.m.BOS-YWG
11h 23m2 stops
C$ 665Air Canada
Find Deal
Thu, 10 Jul - Wed, 6 Aug
Air Canada Logo
5:00 a.m. - 6:00 p.m.YWG-BOS
12h 00m2 stops
Air Canada Logo
5:50 a.m. - 4:13 p.m.BOS-YWG
11h 23m2 stops
C$ 666Air Canada
Find Deal
Thu, 10 Jul - Wed, 6 Aug
Porter Airlines Logo
11:25 a.m. - 6:08 p.m.YWG-BOS
5h 43m1 stop
Porter Airlines Logo
8:20 p.m. - 10:26 a.m.BOS-YWG
15h 06m2 stops
C$ 706Porter Airlines
Find Deal
Fri, 16 May - Tue, 20 May

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 October, where tickets cost C$ 404 (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$ 871 and C$ 744 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 5 weeks before departure. For the absolute cheapest price, our data suggests you should book 20 weeks before departure.

Good to know

Low season

March

High season

October

Cheapest flight

C$ 179
Best time to beat the crowds but there is an average 3% increase in price.
Most popular time to fly and prices are also 30% 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$ 129 for a one-way ticket and C$ 234 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, and SkyTeam are the airline alliances operating flights between Winnipeg and Boston, with Star Alliance being the most commonly used for this route.

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

    The two airlines most popular with KAYAK users for flights from Winnipeg to Boston are Porter Airlines and Delta. With an average price for the route of C$ 521 and an overall rating of 8.0, Porter Airlines is the most popular choice. Delta is also a great choice for the route, with an average price of C$ 499 and an overall rating of 8.0.

  • 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.

See more FAQs

Top 3 airlines serving 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 285 reviews
7.0Entertainment
8.1Comfort
7.6Food
8.2Boarding
8.8Crew
Airline reviews

I love the 2 seats per row. More room. The crew were excellent.

10.0 ExcellentAnonymous, Apr 2025YHZ - YOW
Read more Porter Airlines reviews

I love the 2 seats per row. More room. The crew were excellent.

It was amazing although they did bump us up to the front which gave us more leg room and a meal. The service was great! The staff were friendly. :)

Overall very good... staff were friendly and helpful. boarding was good for the most part, but a little hard to get our carry-on bags on there.... I think people should be directed to keep their coats and small bags with them until all the carry-ons are loaded, and then, if there is space, they can put their small bags and coats up top.. makes it much easier to put baggage up. i loved the internet feature, but the entertainment was not there unless you have your own Netflix or similar platform. My chair did not recline, which was very annoying, and the arms won't go up near the isle, which makes it tough to get in and out of the seat.

Staff were excellant. Only snacks served. Some turbulence so we were offered Free beer or wine.

The staff is always great. Just the fact that our flight was the only one delayed from Halifax when all other carries were still flying. It happen a year ago out of Toronto as well. All others were flying but our flight got cancelled 1 hr before the time of departure.

The only issue had when i mentioned about comfort was the man beside me was on the larger side and took about 1/3 of my seat where i was pressed against the wall/window of the plane for the trip.

The check-in staff, boarding staff, and flight crew were all very friendly. Really miss the Porter lounge in Ottawa.

Thanks for giving a beer to everyone in the seat infront of me and then telling me that I can’t have one because they are going to land. I guess I need to pay for a seat and then pick one in the very front of the plane

The flight was delayed by more than one hour. The terminal was consequently overcrowded and hot. We lost our car reservation and hit rush hour traffic in Boston, which added two hours stuck in traffic to our trip.

Awesome, the whole way through. Thank you, this is the new Canadian Airline benchmark.

Delta flight was on time, seats were comfortable, and crew was nice.

This had nothing to do with Delta… The flights were on time and flawless. The service was excellent. We purchased seats in (aisle/middle) comfort plus since this was a cross country flight. Unfortunately, the woman seated at the window was 300+ pounds and, as might be expected, covered up about a third of the middle seat also. there was absolutely nothing that Delta could have done about that… I just don’t know what the answer should be. If you purchase a seat, you should should be able to use the entire seat and not just the portion that someone else is not sitting/oozing in. Disappointing…there should be something that could be done….I'm just not sure what solution could be.

Delayed take-off. Very small plane so very scary with lots of bumps during the flight. Would never fly Delta on short flights in small 80 seaters plane again! Felt relieved when landed.

Delta is a cut above the others in customer service.

The worst part was I was NOT allowed in the lounge even though I was holding a first class ticket and have a premium American Express card. I have flown Business or First Class with many airlines. Delta is the ONLY one who does not extend this courtesy to anyone except people who hold the very expensive American Express card. As a result, I won’t fly Delta if I have any other choice.

A little bumpy ride . No food was being provided due the the turbulence. That was ok it was a short flight to my standards.

Simply outstanding. Their new lounge for Delta One customers is a cut above the rest.

I love the free WiFi!! Crew was nice. Bathroom was decent. First time flying delta in a long time and I enjoyed it. Will definitely look into booking with Delta more but I think Delta is a little more expensive than the other airlines.

third trip overseas with delta recently where the TV did not work- not acceptable for a 8 hour flight! your food really has declined crew great and I am loyal to delta

Boarding in Amsterdam is always chaotic. KLM/ Delta has not streamlined or made it efficient as it was boarding in Detroit . The food was mediocre The crew was unfriendly and more focused on getting things done quickly rather than service with a smile .

Overall good experience. The flight from Toronto to Denver does not have entertainment - movies to watch.

There is not enough space between two chairs and raws.

Terrible. 3 missed flights and 24 hours delayed with lost bag and promised $100 compensation from United and absolutely nothing from them…

It was a lovely flight. Very attentive crew, comfortable seats, good food and entertainment. Highly recommended. Only difficulty was with their app.

Terrible. Flight was delayed for hours and we ended up arriving at our home at 4am after 20+ hours flying.

Flight was cancelled around 45 -1hr minutes before scheduled take off time due to mechanical issues we hadn’t even boarded yet. Had to reroute to Orlando so someone had to drive 2 1/2 to come and get me… the alternative was go through Toronto and get a later flight which didn’t work for my schedule. The flight attendants barely gave anyone a smile…not the same as flying when a client/passenger was important. Very disappointed. By the way I have never ever made a complaint online about any company with feedback…even when I probably should have. The only good experience was the boarding desk associates who were very professional and got me on another flight with my checked bags…very nice team.

Flight delay, cancellation rescheduling and misdirected luggage which created some stress. It all worked out in the end.

Actually as my experience with air Canada from Canada to Newark it was crazy for me because it was a lot of delays which for me it shouldn’t be like that, but I was able to coup with it so that was my experience I hope next time they will do good on that thanks.

Boarding was challenging as we had to use the stairs from the tarmac. Stairs are okay but a roller bag makes it challenging.

Ensure prepaid food arrangements are appropriately understood by flight crew of who purchased and who did not

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

Information on your arrival and departure airports

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