BOS - YWG

C$ 220 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 11/5. 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.
1 adult
0 bags

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 41,299,237 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.

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
8:57 p.m. - 1:03 p.m.BOS-YWG
17h 06m1 stop
2:50 p.m. - 10:38 p.m.YWG-BOS
6h 48m1 stop
C$ 509United Airlines
Find Deal
Sun, 11 May - Sat, 17 May
6:00 a.m. - 5:37 p.m.BOS-YWG
12h 37m2 stops
5:00 a.m. - 11:28 a.m.YWG-BOS
5h 28m1 stop
C$ 523United Airlines
Find Deal
Sun, 11 May - Sat, 17 May
6:00 a.m. - 5:37 p.m.BOS-YWG
12h 37m2 stops
2:15 p.m. - 11:55 p.m.YWG-BOS
8h 40m2 stops
C$ 543United Airlines
Find Deal
Sun, 11 May - Sat, 17 May
5:10 a.m. - 3:08 p.m.BOS-YWG
10h 58m1 stop
11:35 a.m. - 6:15 p.m.YWG-BOS
5h 40m1 stop
C$ 683
Find Deal
Fri, 14 Mar - Sat, 22 Mar
7:05 a.m. - 6:04 p.m.BOS-YWG
11h 59m2 stops
11:35 a.m. - 6:15 p.m.YWG-BOS
5h 40m1 stop
C$ 759
Find Deal
Fri, 14 Mar - Sat, 22 Mar
7:05 a.m. - 6:04 p.m.BOS-YWG
11h 59m2 stops
11:35 a.m. - 6:15 p.m.YWG-BOS
5h 40m1 stop
C$ 856Porter Airlines
Find Deal
Tue, 4 Mar - Sun, 9 Mar
7:05 a.m. - 6:04 p.m.BOS-YWG
11h 59m2 stops
11:35 a.m. - 8:15 p.m.YWG-BOS
7h 40m2 stops
C$ 869Porter Airlines
Find Deal
Tue, 4 Mar - Sun, 9 Mar
6:35 p.m. - 6:04 p.m.BOS-YWG
24h 29m2 stops
11:35 a.m. - 1:15 p.m.YWG-BOS
24h 40m2 stops
C$ 935Porter Airlines
Find Deal
Fri, 14 Mar - Sat, 22 Mar
5:35 a.m. - 11:51 a.m.BOS-YWG
7h 16m1 stop
11:35 a.m. - 6:15 p.m.YWG-BOS
5h 40m1 stop
C$ 944
Find Deal
Tue, 4 Mar - Sun, 9 Mar
10:50 a.m. - 4:28 p.m.BOS-YWG
6h 38m1 stop
7:45 a.m. - 4:53 p.m.YWG-BOS
8h 08m1 stop
C$ 1,007Air Canada
Find Deal
Tue, 4 Mar - Sat, 8 Mar

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 Monday 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$ 501 (return) on average. On the other hand, the most expensive months are December and March, where the average cost of round-trip tickets is C$ 1,134 and C$ 922 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 7 weeks before departure. For the absolute cheapest price, our data suggests you should book 11 weeks before departure.

Good to know

Low season

January

High season

December

Cheapest flight

C$ 220
Best time to beat the crowds (28% less expensive on average)
Most popular time to fly (43% 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$ 153 for a one-way ticket and C$ 354 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?

    SkyTeam, and Star Alliance 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 8413 reviews
6.8Entertainment
7.8Crew
6.3Food
7.3Boarding
7.0Comfort
Airline reviews

I had a disappointing experience at the San Diego airport with one of your gate agents. Despite being in Zone 4 and traveling with a standard carry-on bag that has never been an issue (30 flights in Q4 alone), the tall, blonde gentleman forced me to gate-check my bag. When I politely asked if we could verify the bag’s size, he became confrontational, even threatening to deny me boarding twice. His behavior appeared erratic and unprofessional, projecting a negative attitude onto passengers, as if he was going through something mentally. Notably, there was ample overhead space once all passengers had boarded. In contrast, the tall, older Asian agent handled the situation with professionalism and calmness, making a clear effort to de-escalate. As an avid traveler, this unnecessary inconvenience set a frustrating tone for my trip to Asia.

2.0 MediocreAnonymous, Dec 2024SAN - YVR
Read more Air Canada reviews

I had a disappointing experience at the San Diego airport with one of your gate agents. Despite being in Zone 4 and traveling with a standard carry-on bag that has never been an issue (30 flights in Q4 alone), the tall, blonde gentleman forced me to gate-check my bag. When I politely asked if we could verify the bag’s size, he became confrontational, even threatening to deny me boarding twice. His behavior appeared erratic and unprofessional, projecting a negative attitude onto passengers, as if he was going through something mentally. Notably, there was ample overhead space once all passengers had boarded. In contrast, the tall, older Asian agent handled the situation with professionalism and calmness, making a clear effort to de-escalate. As an avid traveler, this unnecessary inconvenience set a frustrating tone for my trip to Asia.

The seats are soooooooo small in economy. I was offered no tea or coffee in the am. When I asked was told that it was too late. The plane was 2 hours late leaving.

Very good. Very efficient. Entertainment was not functioning both ways which was disappointing.

Lots of announcements that no wheeled carry on bags were allowed on the flight, yet the overhead bins were totally full and made it uncomfortable trying to get through and significantly held up departure. Why were they allowed on when they said that they weren't? Trash only came by soon after service and I wasn't ready to dispose of it. I had to first hold on to it and after flagging and attendant was told to stuff it in the seat back! I have never run into the need to walk outside in northern winter weather at an international airport and wasn't dressed to do so in the cold pouring rain! I'm not thinking that I'll be back unless I hear things have changed.

My first flight left so late we knew I would miss my connection. Rather than redirecting me then, they made me take a flight to Montreal, then Toronto (there was a flight leaving for Toronto when I was in NYC, no need for me to also go to montreal). Then they gave me a food voucher that did not work (4 places would not accept it). At least they gave me a hotel automatically, even though it was a cheap crappy one. I'm still not home, and it's been over 24 hours. I'm exhausted.

Liked the size of seats. Not much food offered given length of flight.

The boarding was at a dual gate hallway and there was only one spoken explanation about which way to turn to board the correct plane. It wasn't marked visually at the split in the gate. The phone charger did not work at my seat. The temperature was quite chilly throughout the flight and the recorded announcements were extremely loud for a small plane.

The Air Canada staff at the gate in Newark were fantastic and so very helpful!!!

Flight was delayed 1.5 hours as crew was stuck in traffic...that is absurd that the airline would be transfering a crew by car through NYC during rush hour. I missed my shuttle bus and got stuck in Vancouver for the night. Airline did not offer a voucher

Flight was great, no plug in for charging and no inflight entertainment.

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.
11/5Sun
1 stopDelta
10h 03mBOS-YWG
C$ 220
11/5Sun
2 stopsUnited Airlines
18h 52mBOS-YWG
C$ 266
14/2Fri
3 stops
25h 46mBOS-YWG
C$ 399
14/2Fri
2 stops
24h 34mBOS-YWG
C$ 456
14/2Fri
1 stopAir Canada
9h 48mBOS-YWG
C$ 509
27/12Fri
1 stopWestJet
7h 17mBOS-YWG
C$ 855
27/12Fri
2 stopsWestJet
11h 09mBOS-YWG
C$ 862

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

Information on your arrival and departure airports

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