YWG - BOS

$177 Find Cheap Flights from Winnipeg to Boston - Compare and Save

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 9/9. 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, 0 bags

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Everything you should know

Cheapest round-trip
$329
Typical prices: $349-$480
Air Canada
Thu 9/24Wed 9/30
YWG - BOS • 1 stop
Cheapest one-way
$177
Typical prices: $191-$338
Porter Airlines
Wed 9/9
YWG - BOS • 2 stops
Top airlines
Cheapest • from $329 (round-trip)
Best reviews • 8.0 score
Airline reviews
Airline reviews
+1
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Airline reviews
Airline reviews
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Nonstop flights
Not available
There are currently no direct flights between Winnipeg and Boston. You'll need at least 1 connection.
Insights
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Insights
Insights
Top layover airports
Cheapest • Avg $449 (round-trip)
Shortest trip • 5h 41m (one-way)
Insights
Insights
Insights
Insights
When to travel
Cheapest • 36% price drop
Most popular
Good to know
Good to know
+1
+1
Good to know
Good to know
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We hope you love your trip to Boston!
Flight Deals
Booking Insights
Flight 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

Thu, Sep 24 - Wed, Sep 30
Air Canada Logo
3:20 pm - 10:40 pm
YWG
-
BOS
6h 20m
1 stop
Air Canada Logo
6:00 am - 11:12 am
BOS
-
YWG
6h 12m
1 stop
$329Air Canada
Fri, Sep 18 - Tue, Sep 22
United Airlines Logo
7:00 am - 11:30 pm
YWG
-
BOS
15h 30m
1 stop
United Airlines Logo
6:00 am - 11:52 am
BOS
-
YWG
6h 52m
1 stop
$330United Airlines
Thu, Sep 10 - Mon, Sep 14
Multiple Airlines Logo
7:45 am - 6:35 pm
YWG
-
BOS
9h 50m
1 stop
Multiple Airlines Logo
10:05 am - 5:15 pm
BOS
-
YWG
8h 10m
1 stop
$331Multiple Airlines
Fri, Oct 16 - Fri, Oct 23
WestJet Logo
9:05 pm - 5:40 pm
YWG
-
BOS
19h 35m
1 stop
WestJet Logo
6:30 pm - 2:05 pm
BOS
-
YWG
20h 35m
1 stop
$339WestJet
Mon, Sep 14 - Tue, Sep 15
Porter Airlines Logo
9:20 am - 6:35 pm
YWG
-
BOS
8h 15m
1 stop
Porter Airlines Logo
10:05 am - 3:19 pm
BOS
-
YWG
6h 14m
1 stop
$342Porter Airlines
Thu, Sep 10 - Mon, Sep 14
Multiple Airlines Logo
6:15 am - 6:35 pm
YWG
-
BOS
11h 20m
1 stop
Multiple Airlines Logo
7:30 pm - 12:55 am
BOS
-
YWG
6h 25m
1 stop
$342Multiple Airlines
Thu, Sep 10 - Mon, Sep 14
Multiple Airlines Logo
7:45 am - 6:35 pm
YWG
-
BOS
9h 50m
1 stop
Multiple Airlines Logo
10:05 am - 5:15 pm
BOS
-
YWG
8h 10m
1 stop
$342Multiple Airlines
Fri, Oct 2 - Mon, Oct 5
Porter Airlines Logo
9:20 am - 6:35 pm
YWG
-
BOS
8h 15m
1 stop
Porter Airlines Logo
10:05 am - 3:19 pm
BOS
-
YWG
6h 14m
1 stop
$344Porter Airlines
Thu, Sep 10 - Mon, Sep 14
Multiple Airlines Logo
6:05 pm - 9:05 am
YWG
-
BOS
14h 00m
1 stop
Multiple Airlines Logo
7:30 pm - 10:43 am
BOS
-
YWG
16h 13m
2 stops
$344Multiple Airlines
Fri, Oct 16 - Fri, Oct 23
Air Canada Logo
1:25 pm - 9:26 pm
YWG
-
BOS
7h 01m
2 stops
Air Canada Logo
5:50 am - 12:29 pm
BOS
-
YWG
7h 39m
1 stop
$353Air Canada
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.

How much is a round-trip flight from Winnipeg to Boston?

This analysis is based on the cheapest round-trip price found on KAYAK in the last 12 months by searching for a flight from Winnipeg to Boston departing in September.

Flight prices are below average for this route right now.

Flights to Boston from Winnipeg usually cost between $331 and $439 in September.
The lowest price found in the past 5 days was $329 on Air Canada (Sep 24-Sep 30).

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 August, where tickets cost $348 (return) on average. On the other hand, the most expensive months are April and January, where the average cost of round-trip tickets is $915 and $782 respectively.

Good to know

Low season

January

Cheapest flight

$177
Best time to beat the crowds but there is an average 43% increase in price.
Most popular time to fly and prices are also 37% 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 5 days, the lowest price for a flight from Winnipeg to Boston was $177 for a one-way ticket and $329 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 is the only airline alliance operating flights between Winnipeg and Boston.

  • 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 airlines flying 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 449 reviews
8.2Boarding
8.6Crew
7.5Food
6.9Entertainment
8.0Comfort
Airline reviews

Look, I understand that Kayak doesn't know I cancelled my flight on Porter. So I didn't actually fly yesterday. My main disappointment is with Porter ticket fare policies, and maybe you can pass this on to them: At my employer's request, I had booked a full fare ticket with no change fees since my trip to Toronto would likely be extended. Indeed, when I went to change my flight home to a later date, I was told the Fare Difference would cost an additional $550. So much for no change fees lol! While I had the agent on the line, I hopped over to Kayak, searched for new flights on the date in question, and saw a one-way ticket that got me home for only $355. So I got reimbursed about $450for the unused half of my roundtrip and bought a new ticket for $355. What good is a full fare / no change fee ticket if they screw you with "fare difference" BS. I'm still flying home on Porter Airlines but they just lost a hundred bucks with their stupid shenanigans.

4.0 OkayJeff, Jul 2026
YYZ - SFO
Read more Porter Airlines reviews

Look, I understand that Kayak doesn't know I cancelled my flight on Porter. So I didn't actually fly yesterday. My main disappointment is with Porter ticket fare policies, and maybe you can pass this on to them: At my employer's request, I had booked a full fare ticket with no change fees since my trip to Toronto would likely be extended. Indeed, when I went to change my flight home to a later date, I was told the Fare Difference would cost an additional $550. So much for no change fees lol! While I had the agent on the line, I hopped over to Kayak, searched for new flights on the date in question, and saw a one-way ticket that got me home for only $355. So I got reimbursed about $450for the unused half of my roundtrip and bought a new ticket for $355. What good is a full fare / no change fee ticket if they screw you with "fare difference" BS. I'm still flying home on Porter Airlines but they just lost a hundred bucks with their stupid shenanigans.

I flew with Porter yesterday and overall had a positive experience. The flight was delayed, but the airline did a good job keeping passengers informed with frequent updates throughout the process. My biggest challenge was actually in Terminal 3, where the speaker system wasn’t very clear. It was often difficult to hear the announcements, which made it harder to follow updates at the gate. On board, the experience improved significantly. The aircraft felt very new and well maintained, and the seats were surprisingly comfortable for a short-haul flight. One of the flight attendants seemed a little disengaged, but the other was excellent—friendly, professional, and a pleasure to interact with. Despite the delay, the comfortable aircraft, clear communication from Porter, and positive onboard service made for a good overall experience.

Even tho the flight was a bit delayed the team was apologetic. Everyone was friendly and efficient.

It was okay. Had a thing with the front desk, she had me repack my suitcases to have them be under the weight restrictions, but then the other one was overweight, she argued with me about it when there were tons of people in line. Wasn’t great.

Organization and the adjusted times but the snacks could be of a bigger portion

Everything was good except the fact you charge more for a carry on bag vs a check in bag and to top it off in US$ that was not impressive

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.

Due to mechanical problems it was delayed causing problems the actual flight. Was fune

The airline arrival at the downtown airport is a big plus.. Food and beverage was excellent. Their non weather related cancellation is horrible. Overall I gave the airline 7 over 10 Tips for people flying porter from Boston. The airline doesn’t have inflight entertainment No TV No WIFI. Bring your entertainment with you.

Nothing to like about porter. Flight cancelled. No flight back to Boston for 2 days. No hotel accommodation. Terrible. Never again by porter.

My original flight was canceled the day before due to mechanical issues. I had to rebook and spend $129 for a night at the airport Comfort Inn.

Flight operated by PAL. We boarded, and one engine started. The crew found some problem that could not be fixed. The flight was canceled. This run from yhz-bos is very unreliable.

My ticket did not exist when I got to the airport. I had to book another flight and was still charged by Kayak

My return flight experience was one of the worst times I have had traveling anywhere this year. Not because of the flight. It was because there was not enough time allocated to deplane, go through U.S. Customs and U.S. Security to get to the gate for the connecting flight to Boston which I missed, There was well less than an hour between my landing in Montreal from Prince Edward Island to my connecting gate. I even called Air Canada on the morning of my return and noted my concern over the short layover time, not more that 45 minutes. The initial flight was four minutes late. I was seated in the rear of the first aircraft, and it took at least 20 minutes to deplane. The U.S. Customs was a considerable distance from the gate at which we landed. The need for double security seemed unnecessary and redundant. The distance from the security to my gate was again fairly great, and the wrong gate number was listed on my boarding pass. The agent I approached at the flight that was going to Newark, New Jersey was too busy to answer my question as to what gate was for Boston. When I got to the right gate, they had just closed the door to the aircraft even though I arrived a minute late. If I knew the distance to Customs and from Security to the gate, I would have asked for a seat on the next available flight which was 4:30 pm. When I made my call at 6:00AM that morning. When I asked the agent at the Boston gate, he said that the 4:30 flight was already “OVERBOOKED!” I was put on an 8:30 PM flight and didn’t get home until MIDNIGHT. I then had to care for a barnful of hungry animals and didn’t get to bed until 2:00 AM.

I paid for a comfort class seat and was seated in economy.

Very smooth flight and the crew members were very welcoming.

Crew was friendly and helpful; cabin seemed roomy even in economy class.

The flight was delayed but at least they let us know early about it (the night before)! Everything after that was smooth!

Air Canada was on schedule, fast, and took care of me the whole flight. With affordable price, I 100% recommend you fly Air Canada if you are able to.

Excellent overall experience. Seats were comfortable and ample leg room.

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

Information on your arrival and departure airports