BOS - YWG

$174 Find Cheap Flights from Boston to Winnipeg - 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 Boston to Winnipeg departing on 9/6. 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
$339
Typical prices: $438-$611
Multiple Airlines
Sat 9/12Sat 9/19
BOS - YWG • 1 stop
Cheapest one-way
$174
Typical prices: $273-$316
Porter Airlines
Sun 9/6
BOS - YWG • 1 stop
Top airlines
Cheapest • from $343 (round-trip)
Best reviews • 8.0 score
Airline reviews
Airline reviews
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Airline reviews
Airline reviews
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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 $594 (round-trip)
Shortest trip • 5h 58m (one-way)
Insights
Insights
Insights
Insights
When to travel
Cheapest • 18% price drop
Most popular
Good to know
Good to know
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Good to know
Good to know
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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

Sat, Sep 12 - Sat, Sep 19
Multiple Airlines Logo
10:05 am - 8:20 pm-
11h 15m
Multiple Airlines Logo
11:15 am - 10:30 am-
22h 15m
$339Multiple Airlines
Fri, Sep 18 - Mon, Sep 21
Multiple Airlines Logo
7:00 am - 5:15 pm-
11h 15m
Multiple Airlines Logo
6:15 am - 4:46 pm-
9h 31m
$340Multiple Airlines
Thu, Sep 10 - Mon, Sep 14
Porter Airlines Logo
10:05 am - 3:19 pm-
6h 14m
Porter Airlines Logo
11:15 am - 10:30 am-
22h 15m
$343Porter Airlines
Sat, Nov 7 - Fri, Nov 13
Porter Airlines Logo
1:15 pm - 6:10 pm-
5h 55m
Porter Airlines Logo
11:35 am - 10:17 pm-
9h 42m
$361Porter Airlines
Fri, Nov 6 - Fri, Nov 13
Air Canada Logo
10:35 am - 4:38 pm-
7h 03m
Air Canada Logo
8:05 am - 2:53 pm-
5h 48m
$428Air Canada
Sat, Nov 7 - Fri, Nov 13
Air Canada Logo
5:30 am - 10:05 am-
5h 35m
Air Canada Logo
8:05 am - 2:53 pm-
5h 48m
$428Air Canada
Thu, Aug 27 - Mon, Aug 31
United Airlines Logo
6:01 am - 11:52 am-
6h 51m
United Airlines Logo
2:00 pm - 1:10 am-
10h 10m
$436United Airlines
Fri, Aug 28 - Sun, Aug 30
United Airlines Logo
8:31 pm - 11:52 am-
16h 21m
United Airlines Logo
7:00 am - 2:07 pm-
6h 07m
$436United Airlines
Wed, Sep 23 - Sat, Sep 26
Delta Logo
5:40 am - 4:54 pm-
12h 14m
Delta Logo
10:45 am - 11:58 pm-
12h 13m
$2,277Delta
Thu, Sep 24 - Sun, Sep 27
Delta Logo
6:05 am - 4:54 pm-
11h 49m
Delta Logo
10:45 am - 11:58 pm-
12h 13m
$2,467Delta
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.

Flight prices are below average for this route right now.

Flights to Winnipeg from Boston usually cost between $411 and $684 in September.
The lowest price found in the past 5 days was $339 on Multiple Airlines (Sep 12-Sep 19).

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 August, where tickets cost $509 (return) on average. On the other hand, the most expensive months are February and January, where the average cost of round-trip tickets is $918 and $776 respectively.

Good to know

Low season

February

Cheapest flight

$174
Best time to beat the crowds but there is an average 48% 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 5 days, the lowest price for a flight from Boston to Winnipeg was $174 for a one-way ticket and $339 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 $517 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 $626 and an overall rating of 7.8.

  • 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 450 reviews
7.5Food
6.9Entertainment
8.0Comfort
8.6Crew
8.2Boarding
Airline reviews

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..

6.0 GoodHarsh, Apr 2026
Read more Porter Airlines reviews

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..

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!

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

As a first time flyer with Porter I was happy with the service and comfort of the airline.

Other than wifi no on board entertainment. Will use them again, roomier seats than other airlines and snacks and beverages, better than average

I like it, but the food isn't good. They need to offer more simple things. This bowls that have so many things your don't know what your are eating. The milenials like it, no the rest. And last but not least, they allowed somebody have a huge dog, vey agressive and fidgety in the flight. That's horrible. No animals should be allowed inside the airplane, what about allergies, etc

The flight was half empty yet they charged me $50 for a basic carry on! I saw how passengers of different colors were treated differently.

There was a 5 hour delay. Missed connection and now an almost 21 hour lay over!

Porter was excellent. Boarding was a breeze. The seats were a little uncomfortably but the overall trip was excellent.

travelling in 14th of April and now we are in 17th , I have not received my lost/delayed bag... this is very bad and the worst part is their call center is not able to see where is it!!!!

Flight from Savannah arrived very late and we did not take off till 2 hours after scheduled departure!

Very good seat and service. No complaints about the food. Take off delayed due to airport traffic

It is usually very pleasant. Good service for the price, international flights are even better

Flight attendant was very poor in taking care or showing attention. I slept up front for a few and missed the snacks. She saw me many times, went by me many times and never once asked if I needed anything. The whole 2 hours flight. And this is to a Diamond member in first.

I thought the service was very nice and pleasant. There were no hiccups and no issues so overall a good experience.

It was a pleasant surprise to have complimentary Wi-Fi on the flight

Flight was delayed, we could have been notified earlier and in a consistent manner. App was not refreshing for another passenger to get the latest flight status. We could have stayed and waited at the hotel instead of waiting at the airport had we known the flight was going to delayed for more than 5 hours. The toilet is too tight, and needs to be cleaned more frequently (every hour). The entertainment screen froze, the touch screen not responding to touch. We were upgraded to comfort, it is more comfortable than regular economy seats.

The baggage belt was not updated on the Delta App and was displayed on the wrong belt board. Was not expecting this to happen.

The plan was delayed and left DC 90 minutes late. However, it showed a 20 minute delay on the delta app, then a 12 min delay. It turned out to be an hour delay. I found out where the plane was with flightaware. Stop keeping customers in the dark about what is going on.

Airline stewardess service is good. The check-in attendant had a bad attitude and was unprofessional. We did not complete the trip as originally planned. Very dissatisfied☹️ We didn't get on this flight

I would have preferred a flight voucher and to hop on a different flight. Delayed over 6 hours.

Boarding was great, and the crew were very friendly. The seats must have been a bit on the older side and you could feel some of the seat components through the padding. Also, the plugs did not work on the row's entertainment screen or charging ports. Checked bag was transferred for connecting flight, and we appreciated how early we had the connecting gate information.

It was Swiss. Our kosher meals were literally frozen solid and therefore inedible, and the crew didnt care.

Food was great. Staff was phenomenal. Seats were a bit hard and could use a lot more entertainment options as far as movies to choose from. WiFi was good. Overall great trip.

The flight was delayed, they didn’t even have water for the toilets or for drinks

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

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

Flight got cancelled and there was no communication to mention the rescheduled / alternative flight details.

I really don’t know if it ever happened. I never made it any further than the horrible Newark airport because of the snowstorm.

I was rescheduled when I missed my flight due to border clearance issue

Delays. Poor support booking a hotel after a diverted flight.

Because of a change in aircraft, I was unable to experience the business class I paid for and was disappointed.

Very clean plane, staff were courteous, complimentary wifi and beverages are nice, and it was nice to have a whole row to myself! I do miss having seatback entertainment, though. And the prices are getting ridiculous, especially with the different teared tickets. But the flight overall was great.

Nuts would be better than pretzels as the non sweet snack

Kind and accommodating staff. Comfy seats. Plenty of leg and luggage room.

Flight was great, no plug in for charging and no inflight entertainment.

Seat cushion had lost much of its give and the entertainment monitors on the old A320 fleet are small.

The flight was good, the inflight tv's are too old and hard to work

The aircraft was very spacious and comfortable. Loved that the rows were more spread out.

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

Information on your arrival and departure airports