YWG - BOS

C$ 171 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 25/2. 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

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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Everything you should know

Cheapest round-trip
C$ 344
Overall average: C$ 611
Delta
Mon 2/3Wed 4/3
YWG - BOS • 1 stop
Cheapest one-way flights
C$ 171
Multiple Airlines
Wed 25/2
YWG - BOS • 1 stop
Top airlines
Delta
Cheapest • from C$ 344 (round-trip)
Porter Airlines
Best reviews • 8.0 score
Airline reviews
Airline reviews
+1
+1
Airline reviews
Airline reviews
+1
When to book
3 weeks
in advance
Our data shows that travellers who book at least 3 weeks in advance save around 51% compared to booking last minute.
Insights
Insights
Insights
Insights
When to travel
June
Cheapest • 29% price drop
May
Most popular
Good to know
Good to know
+1
+1
Good to know
Good to know
+1
Start a new search
KAYAK searches hundreds of sites at once to find you the best travel deals.
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

Mon, 2 Mar - Wed, 4 Mar
Delta Logo
5:19 p.m. - 11:50 p.m.
YWG
-
BOS
5h 31m1 stop
Delta Logo
5:50 a.m. - 11:01 a.m.
BOS
-
YWG
6h 11m1 stop
C$ 344Delta
Mon, 2 Mar - Wed, 4 Mar
Air Canada Logo
5:30 a.m. - 2:52 p.m.
YWG
-
BOS
8h 22m2 stops
Air Canada Logo
5:30 a.m. - 10:15 a.m.
BOS
-
YWG
5h 45m1 stop
C$ 356Air Canada
Mon, 2 Mar - Wed, 4 Mar
Air Canada Logo
5:30 a.m. - 2:52 p.m.
YWG
-
BOS
8h 22m2 stops
Air Canada Logo
5:30 a.m. - 10:15 a.m.
BOS
-
YWG
5h 45m1 stop
C$ 358Air Canada
Mon, 2 Mar - Wed, 4 Mar
Air Canada Logo
5:30 a.m. - 10:37 p.m.
YWG
-
BOS
16h 07m1 stop
Air Canada Logo
5:30 a.m. - 10:15 a.m.
BOS
-
YWG
5h 45m1 stop
C$ 402Air Canada
Mon, 2 Mar - Wed, 4 Mar
Air Canada Logo
5:30 p.m. - 10:02 a.m.
YWG
-
BOS
15h 32m1 stop
Air Canada Logo
5:30 a.m. - 10:15 a.m.
BOS
-
YWG
5h 45m1 stop
C$ 403Air Canada
Thu, 4 Jun - Sun, 7 Jun
Air Canada Logo
5:10 a.m. - 4:08 p.m.
YWG
-
BOS
9h 58m1 stop
Air Canada Logo
5:25 a.m. - 11:08 a.m.
BOS
-
YWG
6h 43m1 stop
C$ 405Air Canada
Mon, 2 Mar - Wed, 4 Mar
Air Canada Logo
5:30 a.m. - 7:12 p.m.
YWG
-
BOS
12h 42m2 stops
Air Canada Logo
5:30 a.m. - 8:28 p.m.
BOS
-
YWG
15h 58m2 stops
C$ 413Air Canada
Sat, 21 Mar - Thu, 26 Mar
Air Canada Logo
5:30 p.m. - 9:32 a.m.
YWG
-
BOS
15h 02m2 stops
Air Canada Logo
10:15 a.m. - 4:35 p.m.
BOS
-
YWG
7h 20m1 stop
C$ 416Air Canada
Sun, 1 Mar - Fri, 6 Mar
Multiple Airlines Logo
7:30 a.m. - 1:12 a.m.
YWG
-
BOS
16h 42m1 stop
Multiple Airlines Logo
6:00 a.m. - 3:09 p.m.
BOS
-
YWG
10h 09m1 stop
C$ 427Multiple Airlines
Sun, 1 Mar - Fri, 6 Mar
Multiple Airlines Logo
8:05 p.m. - 11:44 p.m.
YWG
-
BOS
26h 39m2 stops
Multiple Airlines Logo
6:00 a.m. - 3:09 p.m.
BOS
-
YWG
10h 09m1 stop
C$ 485Multiple Airlines
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 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 June, where tickets cost C$ 417 (return) on average. On the other hand, the most expensive months are January and December, where the average cost of round-trip tickets is C$ 765 and C$ 765 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 3 weeks before departure, which saves you about 51% compared to booking last minute. For the absolute cheapest price, our data suggests you should book 20 weeks before departure.

Good to know

Low seasonMarch
Cheapest flightC$ 171
Best time to beat the crowds but there is an average 4% increase in price.
Most popular time to fly and prices are also 9% 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$ 171 for a one-way ticket and C$ 344 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 is the only airline alliance operating flights between Winnipeg and Boston.

  • Which is the best airline for flights from Winnipeg to Boston, Porter Airlines or United Airlines?

    The two airlines most popular with KAYAK users for flights from Winnipeg to Boston are Porter Airlines and United Airlines. With an average price for the route of C$ 639 and an overall rating of 8.0, Porter Airlines is the most popular choice. United Airlines is also a great choice for the route, with an average price of C$ 403 and an overall rating of 7.4.

  • 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 4 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 406 reviews
8.2Boarding
7.9Comfort
7.0Entertainment
7.6Food
8.6Crew
Airline reviews

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.

6.0 GoodJen, Jan 2026
YTZ - BOS
Read more Porter Airlines reviews

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.

Due to a known technical error that Porter has not fixed in over a year, I was unable to check in the children on my reservation online and had to do it at the airport. Upon check in, there were no seats together, which was an issue as we had young children. The gate agent did manage to seat us together by moving other passengers, which was appreciated, but the other passengers were never informed, leading to confusion and delay upon boarding. The flight was over an hour late; no explanation or apology was ever issued. The bags on Porter take a long time to arrive--over half an hour at Hamilton on my inbound flight, and not much better on my return to Edmonton.

On my e-boarding pass it shows free wifi, yet the plane I was on didn’t have wifi. Please remove false advertising from your website and boarding passes

3.5 hr delay for a 1 hr work flight. No information as to why the delay until 20 mins before boarding.

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

Smaller plane. Food and bar service for free is amazing. Drinks were in glass not plastic cups.

Poor landing as we overshot the runway and had to re land the plane. Lost both of my luggage not found as of yet. Had to pay extra money for my luggage in USD, now great my luggage is gone. Will not fly with Porter again.

This flight to St. Johns was really good. Boarding was a breeze. We left spot on time. Seats were actually pretty good. Recliner further than I expected. Three more flights to go we will see if this is the status quo for Porter.👍

I was not happy with AirfareAssist, the agency that kayak advised me would be handling my booking. I was advised by porter airlines that I had been overcharged for the Basic express , a option that I had asked airfare assist to help arrange after I realized that the basic fare I had chosen with porter did not include a carryon. At each checkin porter advised I had been overcharged for this . They advised that money would be refunded to my credit card, however, this is not likely to happen as it is not my name and credit card that appeared on the porter invoice, but that of another individual/agent. When airfare assist was arranging the basic express with porter on my behalf, they asked me to confirm that I agreed to pay $263 USD for this. I did agree, as I was advised this was needed to proceed. When I checked the invoice on the porter website and saw that it was not my name and credit card on the invoice, I was advised that this was how airfareassist processed the payment. The Porter invoice indicated a billed amount of $126USD I will not use Kayak or their designated AirfareAssist again

Our flight was delayed by a bit. I appreciated that we were kept informed on why periodically. Boarding was fine. I overheard one flight attendant sounding very rude to a passenger who was not paying attention to the safety demonstration. The snacks were minimal as it was a short flight. There was no entertainment. Overall the flight was good back to LGA.

United airlines has the best customer experience from booking to arrival. I always fly United airlines. The mileage program is excellent

The Sears in the 800s are not too good perfect Airbus why cant the new 737 fix that

Quick and seamless boarding. No entertainment but fast Starlink wifi for this short trip and the staff was really friendly.

I dread trans-Pacific flights. They are very long. This was my first time on Universal, and it was my best crossing ever. The staff were professional, the hospitality was great, and the food was delicious. The entertainment system filled the long flight hours. I will seek out Universal flights from now onwards. 🙂

The food quality sucks. One must starve if they do not eat flesh Or wheat based products Some variety would be expected. The trivial amount of snacks and or food is inhumane

We Left Calgary 1/2 hour late and that made for a tight connection in Denver. After arriving everything was done to help us make our connection. That was a great effort. Thank You United

Efficient all round, very good crew. Short flight so the food, of course, was just snacks

Overall, it was good. I was seating next to a wonderful lady and did not notice how time flew. Thanks

My flight was delayed about 1 1/2 hours in Chicago, but other then that it was a good flight.

The experience was great, the crew was very polite and hospitable. I will definitely make if my go to airlines.

Great flight, great landing, nice staff. Our seats were a little cramped.

I will not be flying with westjet again. I was uncomfortable in my seat. The position made my back hurt so bad. My wife was able to fit the seatbelt around her with out an extension but was unable to put the tray table down or fit in the seat for that matter. Our bag was smashed and I spent two hours trying to fill out the application for a damaged bag before I gave up. The 80 photos I took would not work and nothing telling me the format to upload them as.. I made the mistake of unpacking the bag before taking photos so no claim for me. Next trip to Canada I will have to use air Canada.

Overall good experience. The wait for baggage at our destination was quite long, but other than that everything was good as expected

Airplane is too small. Crew, especially the flight attendant who looked after our area, was not at all friendly and a touch authoratative. She may have been the most gruff flight attendant i've come across in 40 years of business travel

I selected "carry-on" for a round trip on Kayak, but my return flight on WestJet did not include a carry-on and they would not allow me to add one. My only option was to add a "checked bag" which I had to wait for on the luggage carousel after landing. Not a good experience.

My flight was cancelled due to weather but Westjet got me on a new flight in a timely and efficient manor.

I was seated near a "stinky" person. That's not the fault of Westjet🙁😶‍🌫️

Do not fly on WestJet if you have a connection. It failed to integrate with my connecting Delta flight and I almost missed it.

No internet, not even westjet connect makes for a boring flight

Our first flight from LAX to Winnipeg was changed but you never informed us at all. It went from a nonstop flight to a stay at Calgary. This impacted our trip negatively as we arrived much later than we planned to. Our returning flight was horrible. The flight was delayed 6 hours!! And we were NOT going to wait that long. The only way we got on our original flight was running there. However all of our suitcases were now coming on the delayed flight. It was the worst experience we ever had flying. I want my money back.

Better entertainment & food options more may be adding chicken option or on vegetarian side good quality pasta

My seat was not comfortable. Flight was smooth. Regretfully we had two delays before takeoff

Amazing service, with enthusiastic crew members, and some breathtaking views of Vancouver. No IFE though, as it is only a 1 hour flight on a regional Turboprop jet.

I like the fact air Canada is on time The food you guys serve is not good

They are very proactive and made our boarding easy and always notified us about any changes well in advance.

My seat was covered in vomit and I will be reaching out to Air Canada

It's kindof ridiculous that your system is even asking me about this since my flight was canceled and I wasn't rescheduled.

3 hr delay at the gate while they were doing maintenance. Next time, do not board passengers while maintenance is being performed

Digital check in is very poor with air canada compaired to other airlines

Baggage delayed we had to catch our cruise without any clothes 😒

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

Information on your arrival and departure airports