BOS - YWG

C$ 183 Find Cheap Flights from Boston to Winnipeg

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 25/6. 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.
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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
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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.

Recent round-trip flight deals from Boston to Winnipeg

Recommended round-trip deals departing in the coming months from the most popular airlines that fly from Boston to Winnipeg.
Discover the best prices and deals for you by selecting your travel dates.
Choose your dates
6:00 a.m. - 4:28 p.m.BOS-YWG
11h 28m1 stop
6:30 a.m. - 10:12 p.m.YWG-BOS
14h 42m2 stops
C$ 332
Find Deal
Wed, 14 May - Tue, 20 May
6:00 a.m. - 4:28 p.m.BOS-YWG
11h 28m1 stop
9:00 a.m. - 5:34 p.m.YWG-BOS
7h 34m1 stop
C$ 335
Find Deal
Wed, 14 May - Tue, 20 May
12:15 p.m. - 5:38 p.m.BOS-YWG
6h 23m1 stop
5:00 a.m. - 11:28 a.m.YWG-BOS
5h 28m1 stop
C$ 434United Airlines
Find Deal
Thu, 17 Jul - Mon, 21 Jul
6:00 a.m. - 5:38 p.m.BOS-YWG
12h 38m2 stops
2:50 p.m. - 10:38 p.m.YWG-BOS
6h 48m1 stop
C$ 449United Airlines
Find Deal
Thu, 17 Jul - Mon, 21 Jul
2:00 p.m. - 10:45 a.m.BOS-YWG
21h 45m1 stop
5:00 a.m. - 3:30 p.m.YWG-BOS
9h 30m1 stop
C$ 615Porter Airlines
Find Deal
Sat, 15 Feb - Sat, 22 Feb
10:30 a.m. - 5:18 p.m.BOS-YWG
7h 48m1 stop
3:00 p.m. - 10:39 p.m.YWG-BOS
6h 39m1 stop
C$ 669Air Canada
Find Deal
Tue, 4 Mar - Sat, 8 Mar
6:10 a.m. - 1:58 p.m.BOS-YWG
8h 48m1 stop
7:45 a.m. - 2:58 p.m.YWG-BOS
6h 13m1 stop
C$ 690Air Canada
Find Deal
Tue, 4 Mar - Sun, 9 Mar
7:05 a.m. - 5:59 p.m.BOS-YWG
11h 54m2 stops
5:00 a.m. - 6:35 p.m.YWG-BOS
12h 35m2 stops
C$ 767Porter Airlines
Find Deal
Fri, 14 Feb - Fri, 21 Feb
5:02 p.m. - 11:38 p.m.BOS-YWG
7h 36m2 stops
5:43 p.m. - 11:50 p.m.YWG-BOS
5h 07m1 stop
C$ 783Delta
Find Deal
Tue, 4 Mar - Sun, 9 Mar
6:55 a.m. - 4:43 p.m.BOS-YWG
10h 48m2 stops
6:40 a.m. - 3:53 p.m.YWG-BOS
8h 13m2 stops
C$ 791Delta
Find Deal
Tue, 11 Feb - Thu, 20 Feb

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 round-trip flights from Boston to Winnipeg clicked on KAYAK for each day over the last 12 months.
When flying from Boston to Winnipeg, you should consider leaving on a Wednesday and avoid Thursdays if you are looking for the best rates. For your return to Boston, you’ll find the best rates on Tuesdays and the most expensive ones on Sundays.

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 round-trip 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 October, where tickets cost C$ 503 (return) on average. On the other hand, the most expensive months are March and August, where the average cost of round-trip tickets is C$ 902 and C$ 896 respectively.

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

To calculate weekly average prices, KAYAK takes all prices for each week before departure over the last year for round-trip 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 week.
To get a below average price on the flight from Boston to Winnipeg, you should book around 3 weeks before departure. For the absolute cheapest price, our data suggests you should book 11 weeks before departure.

Good to know

Low season

February

High season

December

Cheapest flight

C$ 183
Best time to beat the crowds but there is an average 7% increase in price.
Most popular time to fly (2% more expensive 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$ 127 for a one-way ticket and C$ 230 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 8640 reviews
6.2Food
7.3Boarding
6.8Entertainment
7.0Comfort
7.8Crew
Airline reviews

Plane was old, cabin was small, overhead bins were small, seats really uncomfortable, no seat-back entertainment

4.0 OkayAnonymous, Jan 2025SAN - YVR
Read more Air Canada reviews

Plane was old, cabin was small, overhead bins were small, seats really uncomfortable, no seat-back entertainment

Everything was good till we got to yyz...then we got to the gate and there was NO GATE AGENT. We waited 15 min before disembarking. No internet No IFE Old aircraft Second leg in two weeks NOT IMPRESSED

The flight was delayed at the last moment quoting an absurd weather reason. This delay led to an issue with my connecting flight. I was made to run (literary) from this flight to the next one ( as they preponed departure. I was still in my DCA to YYZ flight when the boarding started for the next connecting flight. After my sprint to get the connecting flight, found that no place for my carry on. Had to sit for 3 hours with my back-pack on my lap , it was the most uncomfortable and inconvenient journey with little to no empathy shown by cabin crew in both flights. Another poor show from Air Canada!! Cant help because of lack of options !!

Horrible I had a health emergency and couldn’t go Air Canada refused to allow me to reschedule

First, When I check in at Phx air Canada counter, I couldn’t make it myself, either at the check in counter, the lady told me that I need a Canada visa to take this plane, then I told her that I have a lots of friends go back to China and transfer in Canada, I’ve never heard they say they needed a visa to stay in the airport, also, I have US lawful green card, as I did research, I knew all U.S. green card holders don’t need a visa to go to Canada if stay a short time. And then they agent lady asked her workmates, spent over an hour then finally have the boarding passes for me. Secondly, my flight is from Phoenix to Hongkong, one stop at Vancouver, but I had to get my bag in Vancouver then re-check in again there. I asked them, they told me that because my layover time is too long (about 20 hours), so they can’t do bags check through. I understand this, just compared with other airlines I travel before, this isn’t a good experience to me.

Excellent crew, great food despite catering issues. We need more people like this.

Very good ! I would recommande it to my friend and family

Really poor travel experience. My first flight was cancelled, which cut my international trip short and threw off my schedule. I will not be flying Air Canada again if I can so help it. The crew and in-flight experience was pleasant and enjoyable but the consistent delays and cancellations are not worth it.

I was not even asked if I want some water. Joke. Steward gave me a biscuit cover in chocolate and did not even look at me.

Economy middle seat was so narrow that I could not sit back comfortably with passengers on either side of me. Over the 9-hour flight, with my body slightly twisted most of that time, my previously-healthy left knee became very painful, even though I got up to walk multiple times. The knee is still painful 3 weeks later. Otherwise, it was a nice flight, but I was crippled over my entire vacation.

Travelling to a place near Winnipeg?

Book flights to Winnipeg if you plan to visit one of these locations
Morden
Scanterbury

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

Information on your arrival and departure airports

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