Find flights
Deals
Insights
When to book
FAQs & Tips
Airlines

BOS - YWG

Find cheap flights from Boston to Winnipeg from C$ 290

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 3/6. 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
Fri 7/6
Fri 14/6

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 43,707,506 times on KAYAK, and here is why:

Save 21% or moreCompare multiple travel sites with one search.

Track pricesNot ready to book? Create a price alert for when prices drop.

Free to useThere are no hidden charges or fees.

Filter your dealsChoose cabin class, free Wi-Fi and more.

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. - 5:52 p.m.BOS-YWG
10h 37m2 stops
6:00 a.m. - 7:27 p.m.YWG-BOS
12h 27m2 stops
C$ 471Porter Airlines
Find Deal
Fri, 27 Sep - Mon, 30 Sep
1:20 p.m. - 6:07 p.m.BOS-YWG
5h 47m1 stop
8:00 a.m. - 11:01 a.m.YWG-BOS
26h 01m2 stops
C$ 488
Find Deal
Sat, 1 Jun - Fri, 7 Jun
1:20 p.m. - 6:07 p.m.BOS-YWG
5h 47m1 stop
8:50 p.m. - 12:15 a.m.YWG-BOS
26h 25m3 stops
C$ 500
Find Deal
Sat, 1 Jun - Fri, 7 Jun
6:00 a.m. - 11:00 a.m.BOS-YWG
6h 00m1 stop
8:15 a.m. - 2:37 p.m.YWG-BOS
5h 22m1 stop
C$ 529Air Canada
Find Deal
Tue, 1 Oct - Wed, 9 Oct
1:20 p.m. - 5:52 p.m.BOS-YWG
5h 32m1 stop
6:00 a.m. - 7:27 p.m.YWG-BOS
12h 27m2 stops
C$ 531Porter Airlines
Find Deal
Sat, 28 Sep - Mon, 30 Sep
8:15 a.m. - 5:47 p.m.BOS-YWG
10h 32m2 stops
12:25 p.m. - 6:30 p.m.YWG-BOS
5h 05m1 stop
C$ 535Porter Airlines
Find Deal
Thu, 23 May - Sun, 26 May
6:00 a.m. - 11:00 a.m.BOS-YWG
6h 00m1 stop
5:00 a.m. - 2:37 p.m.YWG-BOS
8h 37m2 stops
C$ 537Air Canada
Find Deal
Tue, 1 Oct - Wed, 9 Oct
8:15 a.m. - 6:07 p.m.BOS-YWG
10h 52m2 stops
11:50 a.m. - 9:17 p.m.YWG-BOS
8h 27m2 stops
C$ 549Porter Airlines
Find Deal
Tue, 11 Jun - Wed, 12 Jun
8:14 a.m. - 4:45 p.m.BOS-YWG
9h 31m1 stop
5:35 p.m. - 11:49 p.m.YWG-BOS
5h 14m1 stop
C$ 585Delta
Find Deal
Sun, 2 Jun - Thu, 6 Jun
11:00 a.m. - 11:29 p.m.BOS-YWG
13h 29m2 stops
5:30 p.m. - 11:55 p.m.YWG-BOS
5h 25m1 stop
C$ 588Delta
Find Deal
Sun, 30 Jun - Sun, 14 Jul

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 January, where tickets cost C$ 548 on average. On the other hand, the most expensive months are September and June, where the average cost of tickets is C$ 918 and C$ 898 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.

Good to know

Low season

January

High season

July

Cheapest flight

C$ 290
Best time to beat the crowds (31% less expensive on average)
Most popular time to fly (3% 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$ 212 for a one-way ticket and C$ 344 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 SkyTeam 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 6915 reviews
7.8Crew
6.2Food
6.8Entertainment
7.2Boarding
7.0Comfort
Airline reviews

Everything went smoothly and as expected. We were on time and one flight arrived early.

10.0 ExcellentAnonymous, May 2024SAN - YVR
Read more about Air Canada reviews

Everything went smoothly and as expected. We were on time and one flight arrived early.

First time flying Air Canada and the trip was very pleasant! They did a great job getting us out of Toronto and into Rome (early!) For an international flight it was very enjoyable.

This is not a Business Class equipped airplane and even the crew apologize before take over BUT BUT Air Canada charged full business class fare

All was good, except our baggage was lost for most of a day. We are thankful that it was found quickly and delivered to our hotel. Rouge was fine outside of that problem.

You do not have a space for flight cancelled. BUT!!! Air Canada handled it great. Was booked on another airline for the next day. The original flight was booked solid. But he precheck by the maintenance found a mechanical problem and the plane was not safe to fly. It was an inconvenience to have to wait until next day but I would rather arrive safely.

Very good other than we have to wait for one crew and we’re delayed and the pilot and his co- pilot has to make a difference to be right on time arrival. Disappointed about no food service also.

I had written all my complaints on my trip from Grand Junction to Denver so I will repeat it here! I was absolutely appalled that I had to pay for a regular seat that I choose 24 hrs before boarding! Also I checked my large bag which I had to pay for as well, and by the time I boarded all the room in the bins were gone so also had to check that one. I noticed people pulling out oversized suitcases, bigger than the measurements stated for carry on, and also large pack packs stuffed full! So these people were taking up 2 or 3 spaces that the rest of us should have been able to use but couldn’t! NoTV on the flight! Thankfully I had downloaded the United Airlines app and was able to watch movies on my phone. Don’t remember the last time I flew in a plane with no movie screens!

Easy boarding, roomy seats, plenty of good food, very helpful snd friendly staff. Very smooth flight! Only thing that could have been better was to have cranberry juice. Women like this as it helps avoid UTI’s and not as sweet as other juices.

The crew was friendly, the seats are too small. Air travel is barely tolerable anymore.

Food was icecold or frozen including breakfast. Hopeless service. Rude crew.

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.
3/6Mon
2 stopsPorter Airlines
13h 40mBOS-YWG
C$ 290
3/6Mon
1 stopPorter Airlines
17h 05mBOS-YWG
C$ 293
3/6Mon
3 stops
26h 26mBOS-YWG
C$ 331

Search by stops

Search by airline

Search by price

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.
12/5Sun
multi-stopAir Canada
6h 04mBOS-YWG
19/5Sun
multi-stopAir Canada
8h 06mYWG-BOS
C$ 615
12/5Sun
multi-stopAir Canada
6h 04mBOS-YWG
19/5Sun
multi-stopAir Canada
8h 51mYWG-BOS
C$ 630
12/5Sun
multi-stop
22h 47mBOS-YWG
19/5Sun
multi-stop
7h 52mYWG-BOS
C$ 796
12/5Sun
multi-stop
45h 07mBOS-YWG
19/5Sun
multi-stop
7h 52mYWG-BOS
C$ 894

Search by stops

Search by airline

Search by price

Boston - Winnipeg Flights

Departure:

Boston (undefined)United States

Destination:

Winnipeg (YWG)Canada

Return flight deals:

Winnipeg - Boston

Cabin classes:

Browse destinations: