YWG - BOS

$201 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 8/29. 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

Wed, Aug 13 - Sun, Aug 24
Air Canada Logo
5:00 am - 11:28 amYWG-BOS
5h 28m1 stop
Air Canada Logo
5:50 am - 10:19 amBOS-YWG
5h 29m1 stop
$311Air Canada
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Fri, Aug 29 - Fri, Sep 5
 Logo
8:55 pm - 10:38 pmYWG-BOS
24h 43m2 stops
 Logo
6:55 pm - 2:30 pmBOS-YWG
20h 35m2 stops
Wed, Aug 13 - Sun, Aug 24
United Airlines Logo
2:20 pm - 11:32 pmYWG-BOS
8h 12m1 stop
United Airlines Logo
1:50 pm - 1:09 pmBOS-YWG
24h 19m2 stops
$415United Airlines
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Fri, Oct 10 - Mon, Oct 13
Delta Logo
12:40 pm - 11:55 pmYWG-BOS
10h 15m1 stop
Delta Logo
9:10 am - 8:15 pmBOS-YWG
12h 05m2 stops
$431Delta
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Fri, Oct 10 - Mon, Oct 13
Delta Logo
8:50 am - 10:24 pmYWG-BOS
12h 34m2 stops
Delta Logo
9:10 am - 8:15 pmBOS-YWG
12h 05m2 stops
$470Delta
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Wed, Aug 6 - Sat, Aug 9
United Airlines Logo
5:00 am - 11:32 pmYWG-BOS
17h 32m2 stops
United Airlines Logo
5:30 am - 4:18 pmBOS-YWG
11h 48m2 stops
$534United Airlines
Find Deal
Mon, Jul 28 - Tue, Jul 29
Porter Airlines Logo
11:45 am - 6:28 pmYWG-BOS
5h 43m1 stop
Porter Airlines Logo
3:30 pm - 10:46 pmBOS-YWG
8h 16m1 stop
$572Porter Airlines
Find Deal
Tue, Jul 29 - Sat, Aug 2
Porter Airlines Logo
11:45 am - 6:28 pmYWG-BOS
5h 43m1 stop
Porter Airlines Logo
3:50 pm - 10:46 pmBOS-YWG
7h 56m1 stop
$576Porter Airlines
Find Deal
Wed, Jul 30 - Wed, Jul 30
WestJet Logo
6:30 am - 4:36 pmYWG-BOS
9h 06m2 stops
WestJet Logo
8:50 pm - 1:43 pmBOS-YWG
17h 53m2 stops
$790WestJet
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Tue, Jul 29 - Tue, Jul 29
WestJet Logo
6:30 am - 4:36 pmYWG-BOS
9h 06m2 stops
WestJet Logo
7:00 pm - 9:43 amBOS-YWG
15h 43m2 stops
$820WestJet
Find Deal
Booking Insights

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 you are looking for a flight deal from Winnipeg to Boston, look for departures on Saturdays and avoid leaving on a Monday, as it's usually the priciest day. When flying back from Boston, Sunday is the cheapest day to fly and Monday is the most expensive.

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 $293 (return) on average. On the other hand, the most expensive months are December and January, where the average cost of round-trip tickets is $629 and $537 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 seasonOctober
Cheapest flight$201
Best time to beat the crowds but there is an average 7% increase in price.
Most popular time to fly and prices are also 27% 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 $201 for a one-way ticket and $311 for a round-trip.

  • Do I need a passport to fly between Winnipeg and Boston?

    Yes

  • 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 $369 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 $388 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. Booking your flights between Winnipeg and BOS can sometimes prove cheaper using this method.

  • 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 4 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 311 reviews
7.6Food
8.7Crew
8.1Comfort
8.2Boarding
7.0Entertainment
Airline reviews

Seemed like an old plane. Very noisy. The seat cushions were so old that the metal bracing of the seats were poking through. There was plenty of leg room though.

6.0 GoodRobert, Jul 2025YQB - YTZ
Read more Porter Airlines reviews

Seemed like an old plane. Very noisy. The seat cushions were so old that the metal bracing of the seats were poking through. There was plenty of leg room though.

Flight was delayed over 2 hours, then landed at a different airport!

The whole experience from check in to deboarding was fantastic.

Just an evening before they canceled my ticket and offered me ticket costing 3 x times more than. I will not fall prey to these scams,Will never book through kayak now. Such a bad experience.

was okay except.. 1)the porter check in webpage doesn't let you print your boarding pass from home 2)that there was a 90 min cut off for checking in on the kiosk in general, and to print a boarding pass, even tho i checked in online already....

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.

Terrible. I was bumped off of my original flight and spent the next six days fighting to get back on it. I lost hours of my vacation trying to get this situation corrected.

There was no problems, just a little uncomfortable with seats that do not lay back a little

Always good but we must do something about people in rows ahead of you that don't put their seats back up when they are suppose to. And It's rough to not be able to even lean over to get something out of my purse.

Flight was delayed, 30+ bags had to be gate checked. Crew were very friendly!

Everything was good until we were boarding our connection flight in Atlanta, we were told to gate check our carry-on, but when we got inside the plane, there was plenty of room in the overhead.

Did not know my son and I had different seating arrangements. He was fine, but it was disappointing.

Flight was canceled, and no effort was made to help with rebooking, no hotel vouchers, no car transportation and minimal food voucher and most places for food were closed by the time the voucher was given. Waited for 3 hours for bags. Simply the worst travel experience I have ever had

Our flight was canceled after several delays. No hotel vouchers offered, minimal help for resolution leave me ultimately to cancel and book on an other airline. Then waited to get bags for more than 3 hours This whole experience has been awful!!!

Food was surprisingly good but the WiFi was not great

this crew didn't care much. bumping carts into seats more times than i care to remember

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.

Orlando to Canada, despite being close and an international flight, the plane was not at all comfortable. It felt like the chair was being pushed forward, in addition to not having a TV and having to choose from a tiny glass of drink, for example, water or soda. I couldn't have both. When I asked the flight attendant for an extra glass of water, she looked at me with an ugly face. This is ridiculous. They don't want to give water to passengers. I will never fly with this airline again in my life.

Flight got canceled last minute and rescheduled 3 days later, as if we do not have jobs and children to return to. 5+ hours on hold with customer support with no answer. We booked a different airline and spent 3x as much to escape Montreal bc of Air Canada. Still haven’t heard from them. Boooo

Everything was good. Except Broken looking escape/exit doors over the wings need tending,

Pros: The airplane was new and had in-flight entertainment (tablet behind seats) with new movies instead of watching on personal devices. Cons: the flight time was changed without informing us. When I booked the flight, the time was 13:30pm (also in the email confirmation). However, when I reached the airport, the time was conveniently changed to 14:55pm. When I asked at the counter, they said the flight always took off at this time. The booking was made by Air Canada, but the flight was operated by United.

Took off on-time and staff was very nice. Got stuck on tarmac at ATL due to storms, but staff was still wonderful even though they were working and not getting paid.

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.

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

Information on your arrival and departure airports

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