BOS - YWG

$133 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 8/22. 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 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
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Everything you should know

Cheapest round-trip
$285
Typical prices: $568-$423
Porter Airlines
Thu 9/17Tue 9/29
BOS - YWG • 1 stop
Cheapest one-way
$133
Typical prices: $156-$255
Air Canada
Sat 8/22
BOS - YWG • 1 stop
Top airlines
Cheapest • from $285 (round-trip)
Best reviews • 8.0 score
Airline reviews
Airline reviews
+1
+1
Airline reviews
Airline reviews
+1
Nonstop flights
Not available
There are currently no direct flights between Boston and Winnipeg. You'll need at least 1 connection.
Insights
Insights
Insights
Insights
Top layover airports
Cheapest • Avg $441 (round-trip)
Shortest trip • 5h 58m (one-way)
Insights
Insights
Insights
Insights
When to travel
Cheapest • 26% price drop
Most popular
Good to know
Good to know
+1
+1
Good to know
Good to know
+1
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KAYAK searches 100s of sites at once to find you the best travel deals.
We hope you love your trip to Winnipeg!
Flight Deals
Booking Insights
Flight Deals

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

Recent round-trip flight deals from Boston to Winnipeg

Thu, Sep 17 - Tue, Sep 29
Porter Airlines Logo
10:05 am - 3:19 pm
BOS
-
YWG
6h 14m
1 stop
Porter Airlines Logo
9:20 am - 5:35 pm
YWG
-
BOS
7h 15m
1 stop
$285Porter Airlines
Thu, Sep 17 - Tue, Sep 29
Porter Airlines Logo
7:10 am - 5:58 pm
BOS
-
YWG
11h 48m
2 stops
Porter Airlines Logo
9:20 am - 5:35 pm
YWG
-
BOS
7h 15m
1 stop
$290Porter Airlines
Thu, Sep 17 - Tue, Sep 29
Porter Airlines Logo
10:05 am - 3:19 pm
BOS
-
YWG
6h 14m
1 stop
Porter Airlines Logo
9:20 am - 5:35 pm
YWG
-
BOS
7h 15m
1 stop
$292Porter Airlines
Thu, Jul 16 - Tue, Jul 21
Porter Airlines Logo
10:05 am - 3:19 pm
BOS
-
YWG
6h 14m
1 stop
Porter Airlines Logo
9:20 am - 5:35 pm
YWG
-
BOS
7h 15m
1 stop
$293Porter Airlines
Thu, Sep 17 - Tue, Sep 29
Porter Airlines Logo
7:10 am - 5:58 pm
BOS
-
YWG
11h 48m
2 stops
Porter Airlines Logo
9:20 am - 8:55 pm
YWG
-
BOS
10h 35m
2 stops
$298Porter Airlines
Wed, Jul 22 - Mon, Jul 27
Porter Airlines Logo
10:05 am - 3:19 pm
BOS
-
YWG
6h 14m
1 stop
Porter Airlines Logo
9:20 am - 5:35 pm
YWG
-
BOS
7h 15m
1 stop
$300Porter Airlines
Thu, Jul 16 - Tue, Jul 21
Porter Airlines Logo
10:05 am - 3:19 pm
BOS
-
YWG
6h 14m
1 stop
Porter Airlines Logo
9:20 am - 5:35 pm
YWG
-
BOS
7h 15m
1 stop
$308Porter Airlines
Wed, Sep 9 - Sat, Sep 12
Air Canada Logo
6:00 am - 11:12 am
BOS
-
YWG
6h 12m
1 stop
Air Canada Logo
8:10 am - 2:41 pm
YWG
-
BOS
5h 31m
1 stop
$312Air Canada
Wed, Sep 9 - Sat, Sep 12
United Airlines Logo
7:45 am - 8:48 pm
BOS
-
YWG
14h 03m
1 stop
United Airlines Logo
7:00 am - 7:19 pm
YWG
-
BOS
11h 19m
1 stop
$315United Airlines
Sat, Aug 22 - Wed, Aug 26
Air Canada Logo
10:40 am - 3:14 pm
BOS
-
YWG
5h 34m
1 stop
Air Canada Logo
8:15 am - 4:08 pm
YWG
-
BOS
6h 53m
1 stop
$320Air Canada
Booking Insights

KAYAK's insights & trends for Boston to Winnipeg flights

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.

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

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

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 May, where tickets cost $391 (return) on average. On the other hand, the most expensive months are January and February, where the average cost of round-trip tickets is $774 and $649 respectively.

Good to know

Low seasonFebruary
Cheapest flight$133
Best time to beat the crowds but there is an average 22% increase in price.
Most popular time to fly and prices are also 8% lower 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 $133 for a one-way ticket and $285 for a round-trip.

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

    Yes

  • Which airports will I be using when flying from Boston to Winnipeg?

    When flying out of Boston you will be using Boston Logan Intl. You will be landing at Winnipeg, also known as 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 SkyTeam being the most commonly used for this route.

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

    The two airlines most popular with KAYAK users for flights from Boston to Winnipeg are Porter Airlines and Delta. With an average price for the route of $493 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 $438 and an overall rating of 7.9.

  • 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. Booking your flights between Boston and YWG 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 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.

Reviews of the top 4 airlines serving 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.
8.0
Porter AirlinesOverall score based on 437 reviews
8.0Comfort
7.0Entertainment
7.6Food
8.6Crew
8.2Boarding
Airline reviews

The staff was amazing. Best service I’ve had on an aircraft in a long time. Was not particularly happy with the food. Flight was at 10:50 and left home too early for breakfast and wasn’t able to purchase food at airport and felt for sure I could get some breakfast to buy on airplane. Nope as food was served around 11:30 and only one choice left (I was at 22C) so ordered the chicken dish thinking I’m getting a hot meal but cold chicken with rice and carrots etc. I was looking forward to a croissant sandwich and a hot cup of tea. The FA was kind to explain they were serving dinner at that time. She was lovely Other than the disappointment with the food the staff was amazing. On my return flight I will make sure to eat and take some food with me so I’m not hungry or disappointed. This was my second time ever flying Porter and will consider checking them when I next come to visit my daughter. Have to say it again best crew I’ve ever experienced on a flight and I travel quite a bit. Thanks.

10.0 ExcellentAngela, May 2026
YYZ - YVR
Read more Porter Airlines reviews

The staff was amazing. Best service I’ve had on an aircraft in a long time. Was not particularly happy with the food. Flight was at 10:50 and left home too early for breakfast and wasn’t able to purchase food at airport and felt for sure I could get some breakfast to buy on airplane. Nope as food was served around 11:30 and only one choice left (I was at 22C) so ordered the chicken dish thinking I’m getting a hot meal but cold chicken with rice and carrots etc. I was looking forward to a croissant sandwich and a hot cup of tea. The FA was kind to explain they were serving dinner at that time. She was lovely Other than the disappointment with the food the staff was amazing. On my return flight I will make sure to eat and take some food with me so I’m not hungry or disappointed. This was my second time ever flying Porter and will consider checking them when I next come to visit my daughter. Have to say it again best crew I’ve ever experienced on a flight and I travel quite a bit. Thanks.

A few improvements: 1. No signages at the airport that the porter airline was a codeshare and i could check-in at American counter. 2. Crew at the gate said they couldn't change my reward to Alaska - despite that being done previously 3. Despite there being many open seats, i was assigned a seat at the very back near lavatory, last row. Fortunately, the pilot wanted more people moved up so the flight attendants moved me up. It seemed very odd to have been stuck in last row with very few people nearby..

I didn’t receive any help when they messed up and wasn’t honest and the supervisor did absolutely nothing to help me so I had to buy another ticket at $537

There was No Flight. Both Kayak and Porter refused to honor my booking. I was asked for an additional 1,300 $ CAD to keep the flight. After several emails to both Kayak and Porter I was ignored. I had to cancel my March spring break plans, dog kennel and hotel. I had to re-book another vacation to Nassau in January w Expedia. I had to re-book a new vacation for spring break. Porter and Kayak both blamed each other and would not work together to fix this. Not cool.

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

The flight was a little delayed but check in was easy and boarding was quick. Luggage was quickly available and everything worked great.

The Flight took off 2hrs late because there was no pilot showing up when the flight was ready to board.. Though the cabin crew was present and had prepared the plane, the FO turned around after 15 min and went away. A crew to fly the plane finally arrived over an hour later and we were able to board 1h30 min later than planned time... until everything was loaded, we left 2h late from the gate. This was a small plane, so don't expect any Entertainment... Wi-Fi access on board would work, but took an awful amount of time to figure out and get it work (I'm an IT person). Flying as VIPorter customer, I was expecting at least some warm meal, but everything served was just cold.. except the coffee maybe. Even in so-called VIPorter seats, space is cramped and trays are so tiny, you can barely setup your food. Flight caught up during the coast-to-coast crossing and was able to recoup about 45 min from the delay.. still arrived very late in Vancouver and had to wait a long time to get our registered bags. Let's see how the return flight will be in a few days..

The flight booking code given by Kayak was not the correct one used by the airline. I had to call to get the correct one. It was never sent to me. Totally unacceptable!

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.

Much roomer than air Canada! Great flight for the price. No complaints

Much better than Latam, the worse airline company ever. I hope I don't have the need to fly Latam ever in my life again.

Seats in Delta Main are unbelievably close to the seat in front of. Hard to get a backpack under the seat.

The flight was operated by Latam. The aircraft had a technical issue and the flight was delayed for the next day. They grounded other passengers to get their airplane assigned to my flight. Most of he ground staff don't speak English (Orlando Airport), but were very polite.The crew on the other hand could speak English and Portuguese. On board service was good.

The agent at check in and at the gate were less than thrilled to be at work. I'm not a fan of Kayak's placement on the plane. I got put in the middle seat and none of my preferences were used.

In ATL they have two sets of departure screens. Follow what is on your airline's departure board - the ATL Airport Authority departure board had completely incorrect details about the gate assignment for my flight, which would have made me miss boarding.

Flight was delayed it was hot while sitting on the plane, one engine was working on the plane until they had to do some jimmy rigging down the runway in order for the other engine to charge up. It was ridiculous

The flight was very good and the staff was very friendly and helpful!

The only thing I would say is we tried to get on a standby earlier flight, but with our fair we couldn’t. That seems senseless to leave with open seats..

Very easy to use and convenient, you can perform any action within the same portal

In a world of delays, Delta was on time both ways! Boarding was fast and efficient. Staff was friendly. AND wifi worked.

Some crew were unfriendly or in some cases just straight up rude.

Putting people that close to the bathroom, where you have to look into the bathroom as people are exiting and entering was not great and the smell was also not great. I know the airlines are desperate for more chairs, but that seat is a crime.

one staffer was frustrated (it happen); the flight was late and the pilot mentioned they'll make amend but the snacks were the same, other than that the aircraft was clean and everything went smooth, no complaints

ticket agent lady wás very helpful , she arranged wheel chair for my elderly mother

It’s always a great time flying with united airlines.

Entertainment kept turning itself off. Gave up on watching a movie.

Very old flight - time to retire it for newer airplanes

2+ hours delayed Outlet in row 12 did not work Tv monitors did not work Lights kept off the entire flight for at 5pm-7pm flight

Wifi took a while to kick in and we had a maintenance issue that took over 40 mins at the gate in Washington before pulling back

Seated dude next to me even though lots of empty rows. But main thing was we sat on the tarmac after landing for 30 minutes because of, in the words of the dude who sat next to me, “operational incompetence”. We got changing directions about where to pick up gate checked bags. Pilot and flight attendant were awesome though.

I was charge a baggage checking fee $68!! I volunteered to check my duffle bag which usually goes under my seat!

I did not like anything because the flight was cancelled yesterday and I did not get to arrive on time in Toronto as I was rebooked with another airline. This caused me to be really stressed out as I am an individual with back injury and to be forced to stay longer in an airport to accommodate a change of airline and the transfers associated with it Due to this I am probably not going to book through your website to eliminate this potentially chaos in the future

shittiest airline in the hemisphere. To improve - start thinking you're flying people, not cattle

Easy boarding, inflight refreshments came on time and comfortable seat

It was good that our flight left early. It was a nice smooth flight and landing.

All good……but luggage didn’t make it on the airplane. Had to wait 3 days. Was a bummer.

Small suitcase used for carryon the last time was refused by boarding crew this time. Appears to be at the discretion and mood of the person on the day. Flight was only half booked, there would have been no problem with space.

It was a problem because there was a delay where we sat before taking off from newark,then when landed in Toronto we sat on tarmac and they wouldn't let us out for a long period of time. When we finally were released to the airport in Toronto the attendant scanned our boarding pass that we were here for our connection to Brazil. We ran all the way to the gate and they said at the gate the door is shut so we can not let you on the plane. We explained that we were checked in by the attendant when we arrived at Toronto airport to go to Brazil and they should not have shut the door. We were ignored at the gate

I bought a ticket from Kayak. When I got to the airport, the was no ticket. I had to pay 5X to get to my destination. No response received from Kayak. I will NEVER use them again.

everything was fine. but paying for 1 piece of check-in luggage and denying passengers to board with carry-on luggage which by air line's standards does not fit is not acceptable. when one travels for a longer time one needs to have some essentials

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

Information on your arrival and departure airports