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BOS - YWG

Find cheap flights from Boston to Winnipeg from C$ 244

This is the cheapest one-way flight price found by a KAYAK user in the last 72 hours by searching for a flight from Boston to Winnipeg departing on 21/6. 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
0 bags
lör 25/5
lör 1/6

Search hundreds of travel sites at once for deals on flights to Winnipeg

 
These are the airlines KAYAK users have selected most often from within our search results in flight searches from Boston to Winnipeg, 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 Boston to Winnipeg, as well as popular online travel agencies
In the last 7 days, travellers have searched 44,979,812 times on KAYAK, and here is why:

Save 22% or moreCompare multiple travel sites with one search.

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Cheap flight deals from Boston to Winnipeg (BOS-YWG)

Here are some of the best deals found on KAYAK recently from the most popular airlines for round-trip flights from Boston to Winnipeg 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 and deals for you by selecting your travel dates.
Choose your dates
8:15 a.m. - 3:15 p.m.BOS-YWG
8h 00m1 stop
12:00 p.m. - 6:05 p.m.YWG-BOS
5h 05m1 stop
C$ 589
Find Deal
tors, 23 maj - tors, 30 maj
3:55 p.m. - 9:15 a.m.BOS-YWG
18h 20m2 stops
12:00 p.m. - 6:05 p.m.YWG-BOS
5h 05m1 stop
C$ 595
Find Deal
tors, 23 maj - tors, 30 maj
8:15 a.m. - 5:47 p.m.BOS-YWG
10h 32m2 stops
8:00 a.m. - 9:50 a.m.YWG-BOS
24h 50m2 stops
C$ 604
Find Deal
ons, 22 maj - ons, 29 maj
8:15 a.m. - 5:47 p.m.BOS-YWG
10h 32m2 stops
12:25 p.m. - 9:17 p.m.YWG-BOS
7h 52m2 stops
C$ 613Porter Airlines
Find Deal
fre, 17 maj - mån, 20 maj
8:15 a.m. - 5:47 p.m.BOS-YWG
10h 32m2 stops
11:50 a.m. - 6:05 p.m.YWG-BOS
5h 15m1 stop
C$ 615Porter Airlines
Find Deal
mån, 3 jun - tis, 11 jun
10:20 a.m. - 3:11 p.m.BOS-YWG
5h 51m1 stop
7:30 a.m. - 3:09 p.m.YWG-BOS
6h 39m1 stop
C$ 642Air Canada
Find Deal
tis, 9 jul - tis, 16 jul
6:00 a.m. - 11:01 a.m.BOS-YWG
6h 01m1 stop
5:00 a.m. - 2:38 p.m.YWG-BOS
8h 38m2 stops
C$ 649Air Canada
Find Deal
tis, 9 jul - tis, 16 jul
1:07 p.m. - 11:29 p.m.BOS-YWG
11h 22m2 stops
12:26 p.m. - 10:33 p.m.YWG-BOS
9h 07m1 stop
C$ 725Delta
Find Deal
tors, 4 jul - sön, 7 jul
6:05 a.m. - 9:00 p.m.BOS-YWG
15h 55m1 stop
7:30 a.m. - 3:08 p.m.YWG-BOS
6h 38m1 stop
C$ 739United Airlines
Find Deal
sön, 2 jun - ons, 12 jun
5:35 a.m. - 4:45 p.m.BOS-YWG
12h 10m2 stops
12:26 p.m. - 1:31 a.m.YWG-BOS
12h 05m2 stops
C$ 854Delta
Find Deal
sön, 2 jun - mån, 10 jun

Flights from Boston to Winnipeg - Travel Insights & Trends

Get data-powered insights and trends into flights from Boston to Winnipeg 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 Boston to Winnipeg?

The average price of all flights from Boston to Winnipeg clicked on KAYAK for each day over the last 12 months.
If your flying dates are flexible, you should consider flying to Winnipeg on a Monday, as we generally find the cheapest rates on that day for this route. On the other hand, Saturday is the most expensive day to fly from Boston to Winnipeg. For your return ticket, we recommend flying on a Sunday and avoiding Mondays for the best deals.

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

To calculate monthly average prices, KAYAK takes all prices for each month over the last year for flights from Boston to Winnipeg, 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 Boston to Winnipeg is August, where tickets cost C$ 732 on average. On the other hand, the most expensive months are April and June, where the average cost of tickets is C$ 1,161 and C$ 950 respectively.

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

To calculate daily average prices, KAYAK takes all prices for each day before departure over the last year for flights from Boston to Winnipeg, removes the top 0.1% to account for outliers, and then takes the average of all the values for each month.
To get a below average price on the flight from Boston to Winnipeg, you should book around 1 week before departure. For the absolute cheapest price, our data suggests you should book 55 days before departure.

Which airlines provide the cheapest flights from Boston to Winnipeg?

The cheapest price for the route for each airline clicked by KAYAK users in the last 72 hours.
In the last 72 hours, the cheapest one-way ticket from Boston to Winnipeg found on KAYAK was with Porter Airlines for C$ 293. Porter Airlines proposed a round-trip connection from C$ 613 and Air Canada from C$ 642.

Good to know

Low season

February

High season

July

Cheapest flight

C$ 244
Best time to beat the crowds (8% less expensive on average)
Most popular time to fly and prices are also 7% lower on average.
Flight from Boston to Winnipeg

When to book flights from Boston to Winnipeg

Are your dates flexible? Find out the best times to travel from Boston to Winnipeg 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 Boston to Winnipeg

  • What is the cheapest flight from Boston to Winnipeg?

    In the last 3 days, the lowest price for a flight from Boston to Winnipeg was C$ 178 for a one-way ticket and C$ 430 for a round-trip.

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

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

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

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

  • Which airline alliances offer flights from Boston to Winnipeg?

    Star Alliance, and SkyTeam are the airline alliances operating flights between Boston and Winnipeg, with Star Alliance being the most commonly used for this route.

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

    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 Boston to Winnipeg.

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

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

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

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

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

See more FAQs

Top airline flying from Boston to Winnipeg

 
See real verified KAYAK customer reviews for airlines flying from Boston to Winnipeg. 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 Boston to Winnipeg? 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.
7.0
Air CanadaOverall score based on 6857 reviews
7.2boarding
6.2food
6.8entertainment
7.8crew
7.0comfort
Airline reviews

Due to a strike taking place with the airline, it negatively impacted my flight in multiple ways. My flight was delayed over 2 hours and the food served was mediocre at best.

4.0 OkayJarrett, Apr. 2024LAX - YYZ
Read more about Air Canada reviews

Due to a strike taking place with the airline, it negatively impacted my flight in multiple ways. My flight was delayed over 2 hours and the food served was mediocre at best.

Cabin crew were great. Seats are criminal for tall people

Flight was delayed 1.5 hrs due to problem with a previous flight to mine; I was informed appropriately via Text & Email, however, website did not keep up with messages sent by nearly an hour. When checking-in warm & friendly reception at check-in desk until female Air Canada Rep noticed my flight number and instantly pivoted to a condescending & sarcastic comments about getting my bag checked in since I’m running so late; then tone instantly changed again few minutes later when she muttered, “Oh, they’ve delayed it” another sign systems & worse front line staff, not fully informed or simply not reading their flight status updates. Flight crew were very friendly & did a great job trying to make up lost time due to the delay.

It was great, love the experience and will definitely recommend 👌. Communication was great

My flight was great! Gate attendants and crew were great… pleasant and in good spirits. Flight delayed several hours and we were well informed of the status while on plane. Thank you!

The fact that I got to Toronto alive and well and safe is a huge plus. I thank the captain and crew for a safe flight The comfort of the aircraft leaves much to be desired. Human beings should not have to be that cramped and squashed on a flight that we pay a lot for and even have to pay for lousy food choices The cabin crew were pleasant and helpful Kudos to them as the flight was packed to capacity and there was a lot of work for them in a short space of time All in all a good experience, but too cramped

It was great to check carryon luggage at no charge when there was no room for ours. A hidden benefit of having low-tier tickets. Also great to stay off plane as long as possible. Airline gave us seats we wanted on this last leg, again at no charge.

The late departure Of two hours waitresses, immature, and gossiping

We had a good flight, service was good and lots of leg room. Service was good and the staff were friendly.

Overall I will say it was a very good experience. It was as comfortable as can be expected for such a long flight - 12 hours from Toronto to Tokyo. Everyone was very pleasant and polite. Even the passengers were cooperative and trying to be nice to each other. Of course the space is limited on such a long flight. The bathrooms were actually very clean. The food was very good. I liked how there was a variety of food options. The in flight entertainment system was also very impressive! There were some children on the flight but they were well behaved and hardly ever crying. Great Job Canada Air! I will definitely fly with Air Canada again!

Book cheap flights from Boston to Winnipeg

Recent one-way flight deals

 
Only flying one-way? Below are some of the best one-way flight deals from Boston to Winnipeg found on KAYAK in the last 72 hours.
21/6fre
1 stop
9h 15mBOS-YWG
C$ 244
21/6fre
2 stopsPorter Airlines
22h 52mBOS-YWG
C$ 293
31/8lör
1 stopAir Canada
14h 12mBOS-YWG
C$ 355
2/6sön
2 stops
31h 56mBOS-YWG
C$ 381
2/6sön
1 stopAir Canada
6h 20mBOS-YWG
C$ 390
21/6fre
3 stops
24h 20mBOS-YWG
C$ 413
2/6sön
3 stops
27h 52mBOS-YWG
C$ 426
31/8lör
2 stops
13h 04mBOS-YWG
C$ 444
31/8lör
3 stops
24h 53mBOS-YWG
C$ 501

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Last minute flights from Boston to Winnipeg

Last minute flight, train and bus deals

 
These last-minute flight deals are the cheapest flights found on KAYAK in the last 72 hours for flights from Boston to Winnipeg that are departing in the next 10 days.
27/4lör
multi-stopWestJet
6h 34mBOS-YWG
29/4mån
multi-stopWestJet
7h 52mYWG-BOS
C$ 1,849
27/4lör
multi-stop
32h 21mBOS-YWG
29/4mån
multi-stop
27h 43mYWG-BOS
C$ 1,855
27/4lör
multi-stopWestJet
13h 20mBOS-YWG
29/4mån
multi-stopWestJet
5h 50mYWG-BOS
C$ 1,856
27/4lör
multi-stopWestJet
13h 20mBOS-YWG
29/4mån
multi-stopWestJet
15h 41mYWG-BOS
C$ 1,863

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Boston - Winnipeg Flights

Departure:

Boston (BOS)United States

Destination:

Winnipeg (YWG)Canada

Return flight deals:

Winnipeg - Boston

Cabin classes:

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