YWG - BOS

C$ 244 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 14/8. 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
1 adult, Economy

KAYAK searches hundreds of travel sites at once for deals on flights to Boston

 
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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Flights Deals

Cheap Flights 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.
Discover the best prices for you by selecting your travel dates on KAYAK.

Recent round-trip flight deals from Winnipeg to Boston

Sat, 12 Jul - Tue, 15 Jul
United Airlines Logo
2:20 p.m. - 11:40 p.m.YWG-BOS
8h 20m2 stops
United Airlines Logo
9:03 a.m. - 3:31 p.m.BOS-YWG
7h 28m1 stop
C$ 411United Airlines
Find Deal
Tue, 12 Aug - Tue, 19 Aug
Air Canada Logo
5:00 a.m. - 11:28 a.m.YWG-BOS
5h 28m1 stop
Air Canada Logo
5:50 a.m. - 5:40 p.m.BOS-YWG
12h 50m2 stops
C$ 412Air Canada
Find Deal
Tue, 12 Aug - Tue, 19 Aug
Delta Logo
5:41 p.m. - 12:17 a.m.YWG-BOS
5h 36m1 stop
Delta Logo
8:10 a.m. - 4:51 p.m.BOS-YWG
9h 41m1 stop
C$ 418Delta
Find Deal
Tue, 12 Aug - Tue, 19 Aug
Air Canada Logo
5:00 a.m. - 6:00 p.m.YWG-BOS
12h 00m2 stops
Air Canada Logo
5:50 a.m. - 5:40 p.m.BOS-YWG
12h 50m2 stops
C$ 419Air Canada
Find Deal
Mon, 25 Aug - Thu, 28 Aug
Air Canada Logo
5:00 a.m. - 11:28 a.m.YWG-BOS
5h 28m1 stop
Air Canada Logo
5:50 a.m. - 6:59 p.m.BOS-YWG
14h 09m1 stop
C$ 471Air Canada
Find Deal
Thu, 25 Dec - Sun, 4 Jan
United Airlines Logo
2:15 p.m. - 9:55 p.m.YWG-BOS
6h 40m1 stop
United Airlines Logo
7:30 p.m. - 11:39 a.m.BOS-YWG
17h 09m2 stops
C$ 526United Airlines
Find Deal
Sat, 12 Jul - Tue, 15 Jul
United Airlines Logo
2:20 p.m. - 11:40 p.m.YWG-BOS
8h 20m2 stops
United Airlines Logo
7:04 p.m. - 1:09 p.m.BOS-YWG
19h 05m3 stops
C$ 580United Airlines
Find Deal
Wed, 30 Jul - Wed, 6 Aug
Air Canada Logo
5:00 a.m. - 11:28 a.m.YWG-BOS
5h 28m1 stop
Air Canada Logo
5:50 a.m. - 6:59 p.m.BOS-YWG
14h 09m1 stop
C$ 583Air Canada
Find Deal
Thu, 25 Dec - Sat, 3 Jan
Air Canada Logo
8:15 a.m. - 2:52 p.m.YWG-BOS
5h 37m1 stop
Air Canada Logo
5:30 a.m. - 10:16 a.m.BOS-YWG
5h 46m1 stop
C$ 593Air Canada
Find Deal
Wed, 30 Jul - Wed, 6 Aug
Delta Logo
6:30 a.m. - 4:36 p.m.YWG-BOS
9h 06m2 stops
Delta Logo
5:30 a.m. - 11:31 a.m.BOS-YWG
7h 01m1 stop
C$ 726Delta
Find Deal
Useful Info

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$ 399 (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$ 859 and C$ 733 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 seasonMarch
High seasonJuly
Cheapest flightC$ 244
Best time to beat the crowds but there is an average 5% increase in price.
Most popular time to fly and prices are also 11% 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$ 179 for a one-way ticket and C$ 301 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$ 510 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$ 474 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.

Reviews of the top 5 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 296 reviews
8.7Crew
8.2Boarding
7.6Food
7.0Entertainment
8.1Comfort
Airline reviews

Great! Personable crew. I love that they pour complimentary beer and wine.

10.0 ExcellentSteve, Jun 2025LAS - YOW
Read more Porter Airlines reviews

Great! Personable crew. I love that they pour complimentary beer and wine.

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.

From Atlanta to Savannah - flight connection was way to short (we weren't even late landing ) and flight was already boarding when we landed - we were told we were the last on board and so we had to gate check our bags. Once we got on the plane, there were at least seven open bag spots so that was unnecessary delay. There should be better communication between the gate agent and the crew.

Crew was excellent. Comfort seats not as nice as other kinds of planes.

Not a "Delta" issue, but a JFK issue: We booked a connecting flight with 3 1/2 hours between to clearn immigration and customs. Our inbound flight (BCN to JFK) was on the taxiway 45 minutes which ate into our layover time. Immigtration was insanely quick with the CBP MPC app; however, clearing TSA (again, after we were ALREADY cleared in Spain on the inbound international flight) took over 95 minutes. This left us with 10 minutes before boarding the connecting flight (JFK to SAN) to walk to the far end of Terminal 4 and try to find food. We didn't find any food that could promise to serve us in under 10 minutes so we boarded the Delta flight after coming off a plance and an 8-hour flight knowing that we wouldn't be served any food on the next 5 1/2 hour flight. I feel like Delta needs to put pressure on the JFK TSA to open more screening stations (by our count, we saw only 5 scanners open and a line of - as we said - over 90 minutes. The insult is that we WERE ALREADY SCREENED through TSA, but as you come off one flight into the USA, you have to go through the whole process again. It seems like if you have a connecting flight, there should be a way to pass through immigration and customs without needing to return through TSA.

The way BCN airport handled boarding was a huge improvement over our trip to Spain from JFK. Instead of gate-mosquitos edging in before their zone was called, in BCN they had clearly marked lines for Zones 1-8 and people just lined up correctly. The flight itself was uneventful. The meal (curried chicken and rice) was one of the better meals we've had on Delta. Entertainment options were plentiful, power chargers were available in Main Cabin, and seats were decent. Flight staff were very friendly and positive throughout the 8 hour flight.

It was a great flight and the stewards and stewardess were all kind and accommodating!! The seats were comfortable and entertainment screen excellent!

The checkpoint hornets are always looking fhrough Americans' luggage keeping what they deem impassible! Grrrrr!

There are 4 flights in consecutive gates with about the same departure time. Two flights were boarding at the same time. One was delayed or boarding would be happening at the same time. I am not sure what Delta and LAX need to do to have a better layout at the end of Terminal 2

Flight was an hour late, who knows why. It was OK, nothing outstanding.

Only not having an assigned seat was an issue. Rest was great

There was a security issue at the airport and we were unable to land. We circled endlessly and then landed at another airfield for fuel. We then circled the airport again, almost landed but didn’t fully touch down before circling again. I am thankful to the crew for keeping us safe- the issue was the airline and staff at the airport getting us seats on our connecting flights. That part was hours of searching for someone and getting in double my steps.

It was all good flight was on time, service was good I enjoyed a few movies and everything was smooth

Efficient, calm when things were delayed and kept us regularly informed of what was happening.

Impressed with the service despite turbulence because of the weather. Both flights arrived before their scheduled times.

Airbus plane, nice and polite staff, entertainment even as it was a short flight.

Very nice and clean plane. Transit time between flights was tight though

Our flights got changed from United to Air Canada and our purchased seats did not get transferred so we had to pay for seats twice. I brought it up with Air Canada and they stated I had to go back and chase it with United. The united seats were $21 Canadian each and Air Canada were $56 each so we have paid $77 for each seat. Very unhappy

So far so good but food and entertainment are not available for this flight

Plane temperature was comfortable (not to hot) when boarding and waiting for takeoff.

Michael, our FA was very attentive, even finding me a chocolate brownie from economy class when the dessert selections were all dairy based. ( intolerant, not allergic so don’t usually need to order dairy free)

We tried to upgrade to economy premium but were told this was not possible as we had booked through United Airlines (and Air Canada was operating the flight). This seemed silly given there was ample space in economy premium. Additionally, we had to wait almost 1.5 hours upon arrival to taxi to the gate. Otherwise, the crew were very pleasant and passengers were friendly.

WestJet canceled my booking, replaced it with a booking that didn't work (departing from cruise ship), and didn't offer any flights that did work. Their only option was for me to cancel and go to another airline for more money. Which I did.

Nothing to like because my inbound flight was cancelled without notification by West Jet or third party, JustFly. I couldn’t take the inbound flight due to cancellation; therefore could not take the outbound flight back.

The seats are totally uncomfortable making the flight less than pleasant. The cookies & pretzels were terrible!!!

Lots of overhead storage and a good crew and service.

On time. Friendly and efficient staff at check in and flight crew.

Late departure, so I missed connection in Detroit. But Delta gave me a great hotel & breakfast. Just sorry I could not get anything from my checked baggage.

Crew was friendly. Lost our luggage and told us it’d be in later in the evening of the day we returned. It was not. Still after 5 days have not received it.

Internet on both flights was sketchy. Thus in flight entertainment was non- existent on MN - Balrimote leg.

It took 30 minutes to check in with the Westjet rep. They didn’t have enough seats and she needed to make a call… I am always “randomly” selected to be checked at security. Their “randomly “ selection system may need some updating. They treat people like criminals. It is not appropriate behavior.

Will never book through you again. Very disappointed in the notices and action taken or provided when planes are rescheduled, enough to cause missed connections

In a nutshell, my bag, the one I have to pay for, because now you can’t even bring a carry on, did not make it. I am still waiting for an update. The fact that not only were have to pay for it, but on top of that we are stuck without getting it, it’s ridiculous..

The plane was filthy!!!! There were empty food wrappers in the pockets and worst of all a wad of hair where someone had obviously brushed their hair, cleaned out the brush and left the wad of hair in the pocket. It was the most disgusting thing I’ve ever seen!! The seats are so crammed together with NO leg room. The AC vent controllers do not adjust. I will likely not book another AC flight from Florida to Montreal.

This was an excellent experience for a very short flight.

Registered my luggage at 5pm. Arrived at JFK at 1:00 am. Worst trip ever. Never again

Really good, super comfy flight and the stewardess was great.

Air Canada never runs on time. You’re lucky if your flight is not cancelled or diverted. Worst airline in the world for gas lighting its customers.

No space in overhead bin, one cookie, 2 oz of juice - is not customer service.

Good flight, friendly crew and overall - good service on United Airlines.

Received email saying that there won’t be a seat back entertainment screen and inflight WiFi would be available. But no WiFi both ways. Say it in the email.

Somebody either kayak or Air Canada booked my flight under my preferred name Betty instead of my legal name and I almost was denied boarding my flight

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

Information on your arrival and departure airports

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