YWG - BOS

$176 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 9/13. 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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41 299 237 searches in the past 7 days on KAYAK

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Everything you should know

Cheapest round-trip
$294
Typical prices: $435-$268
Porter Airlines
Fri 8/28Mon 8/31
YWG - BOS • 1 stop
Cheapest one-way
$176
Typical prices: $184-$329
Porter Airlines
Sun 9/13
YWG - BOS • 1 stop
Top airlines
Cheapest • from $294 (round-trip)
Best reviews • 7.9 score
Airline reviews
Airline reviews
+1
+1
Airline reviews
Airline reviews
+1
Nonstop flights
Not available
There are currently no direct flights between Winnipeg and Boston. You'll need at least 1 connection.
Insights
Insights
Insights
Insights
Top layover airports
Cheapest • Avg $307 (round-trip)
Shortest trip • 5h 33m (one-way)
Insights
Insights
Insights
Insights
When to book
in advance
Our data shows that travelers who book at least 3 weeks in advance save around 57% compared to booking last minute.
Insights
Insights
Insights
Insights
When to travel
Cheapest • 43% price drop
Most popular
Good to know
Good to know
+1
+1
Good to know
Good to know
+1
Start a new search
KAYAK searches 100s 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

Fri, Aug 28 - Mon, Aug 31
Porter Airlines Logo
9:20 am - 5:35 pm
YWG
-
BOS
7h 15m
1 stop
Porter Airlines Logo
10:05 am - 3:19 pm
BOS
-
YWG
6h 14m
1 stop
$294Porter Airlines
Fri, Aug 28 - Mon, Aug 31
Porter Airlines Logo
9:20 am - 5:35 pm
YWG
-
BOS
7h 15m
1 stop
Porter Airlines Logo
10:05 am - 3:19 pm
BOS
-
YWG
6h 14m
1 stop
$295Porter Airlines
Fri, Sep 25 - Wed, Sep 30
Porter Airlines Logo
9:20 am - 5:35 pm
YWG
-
BOS
7h 15m
1 stop
Porter Airlines Logo
10:05 am - 3:19 pm
BOS
-
YWG
6h 14m
1 stop
$299Porter Airlines
Tue, Sep 29 - Sun, Oct 4
Porter Airlines Logo
9:20 am - 5:35 pm
YWG
-
BOS
7h 15m
1 stop
Porter Airlines Logo
7:10 am - 5:58 pm
BOS
-
YWG
11h 48m
2 stops
$300Porter Airlines
Fri, Aug 28 - Mon, Aug 31
Porter Airlines Logo
9:20 am - 5:35 pm
YWG
-
BOS
7h 15m
1 stop
Porter Airlines Logo
10:05 am - 5:58 pm
BOS
-
YWG
8h 53m
2 stops
$305Porter Airlines
Thu, Oct 1 - Mon, Oct 5
Porter Airlines Logo
9:20 am - 5:35 pm
YWG
-
BOS
7h 15m
1 stop
Porter Airlines Logo
7:10 am - 5:58 pm
BOS
-
YWG
11h 48m
2 stops
$307Porter Airlines
Fri, Sep 25 - Wed, Sep 30
Porter Airlines Logo
9:20 am - 5:35 pm
YWG
-
BOS
7h 15m
1 stop
Porter Airlines Logo
7:10 am - 5:58 pm
BOS
-
YWG
11h 48m
2 stops
$314Porter Airlines
Tue, Jun 2 - Tue, Jun 9
Porter Airlines Logo
9:20 am - 5:35 pm
YWG
-
BOS
7h 15m
1 stop
Porter Airlines Logo
10:05 am - 3:19 pm
BOS
-
YWG
6h 14m
1 stop
$317Porter Airlines
Mon, Jun 1 - Wed, Jun 10
Porter Airlines Logo
9:20 am - 5:35 pm
YWG
-
BOS
7h 15m
1 stop
Porter Airlines Logo
10:05 am - 3:19 pm
BOS
-
YWG
6h 14m
1 stop
$318Porter Airlines
Mon, Jun 1 - Wed, Jun 10
Porter Airlines Logo
9:20 am - 5:35 pm
YWG
-
BOS
7h 15m
1 stop
Porter Airlines Logo
10:05 am - 3:19 pm
BOS
-
YWG
6h 14m
1 stop
$319Porter 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.

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 August.

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 $290 (return) on average. On the other hand, the most expensive months are April and January, where the average cost of round-trip tickets is $788 and $782 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 57% compared to booking last minute. For the absolute cheapest price, our data suggests you should book 20 weeks before departure.

Good to know

Low seasonJanuary
Cheapest flight$176
Best time to beat the crowds but there is an average 54% increase in price.
Most popular time to fly with an average 4% increase in price.
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 $176 for a one-way ticket and $294 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?

    SkyTeam, and Star Alliance are the airline alliances operating flights between Winnipeg and Boston, with SkyTeam being the most commonly used for this route.

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

    The two airlines most popular with KAYAK users for flights from Winnipeg to Boston are Delta and United Airlines. With an average price for the route of $605 and an overall rating of 7.9, Delta is the most popular choice. United Airlines is also a great choice for the route, with an average price of $423 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. 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 3 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.
7.9
DeltaOverall score based on 8437 reviews
7.9Comfort
7.8Entertainment
8.1Boarding
8.5Crew
7.2Food
Airline reviews

This wasn't my experience with Delta. It was just the Pegasus flight. Seats were very hard. Staff was kinda rough. Not very nice. Charged me for snacks. For a 4 hour flight I would've expected more.

4.0 OkayAnonymous, Apr 2026
MYR - ATL
Read more Delta reviews

This wasn't my experience with Delta. It was just the Pegasus flight. Seats were very hard. Staff was kinda rough. Not very nice. Charged me for snacks. For a 4 hour flight I would've expected more.

Crew was nice, meal was good. Entertainment had to be rebooted 3 times and still did not work. Turns out there was residue on screen, it needed to be cleaned to prevent the touchscreen buttons from continuously activating. I had entertainment for the last 45 minutes of a 5 hour 45 minute flight. Really unacceptable for first class. Flight attendent indicated your cleaning solution creates this problem. Seems as if this is widely known, you should be using a different product or cleaning better. Really really disappointing which simply added to the wi fi on your planes with reliably never ever works.

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.

Everything went smoothly, although the usual gripes about airline travel were still present: the boarding process is inefficient, the snack selection is limited, and so on. Since there was extra space on the flight, the gate agent rearranged many people's seats to put people on the aisles and windows, leaving the middle seats empty, as much as possible, which was pretty great.

Landed without a gate ready. Plane is extremely old and dirty.

All the amenities was wonderful, if they could keep their prices that low. I'd fly with them all the time.

Very old plane with no inflight entertainment. I purchased the internet pass and it was nearly unusable.

My tray was broken so i had no place to work or eat except my lap. Flight attendant said I would get an email with some credit or miles, it was a complete waste of time as I could only function at about 20% of normal. I have not received anything yet.

Short trip, no food and therefore no expectation for much interaction with staff who were pleasant and professional. My critique is on comfort of the seats. Exit rows and comfort seats do not provide enough personal space for 3 side-by-side seats, especially when in the middle row. Some passengers are not considerate of the middle seat and there should be signs that state something to the effect of: "please consider giving middle seats use of the armrests."

Good but airlines getting smaller. I didn't like the meal but the service was fine. Flight was fine and luggage arrived. So good.

They were fast and I like how they used to entertainment system to play video about the safety.

Hopped on time for the flight only to get deplaned and delayed another 2.5 hours.

Given I (and I’m assuming most people) have both carry in and a personal item included in their fare, I find it very unfair that on neither of my flights I was able to use the overhead for my small backpack because they were completely rammed with luggage, people personal items, jackets, hats and other items. So the only item I brought in had to be stuffed under my seat while they had their leg room and sat comfortable with all of their items in the overhead. This has to stop because I was uncomfortable on both flights when I only had one smaller item that could not be checked due to its contents (medication etc). Plenty of people could have checked theirs but chose not to and then took up the space allotment for 2 people.

Flight attendants had a little attitude. Food tastes no good.

From pre boarding to flight attendant, crew and baggage handler, excellent. Didn’t lost my luggage like West jet.

Very poor. The flight was delayed from Toronto because some forget to do there job . I got to my connecting gate in San Francisco 10 minutes before the departure.but this didn’t let me board even though the flight was still there for an other 30 minutes. The the gentleman at the unite airline desk told me that they usually wait for passengers but air Canada called and told them not to we I been rerouted to Manila instead of Hong Kong . In San Francisco they mad me check in my carryon bag . I was told the it will directly go yo ho chi minn cuyt but I was told that by the Vietnams airline desk that’s not there I’m 10 hours behind my scheduled flight and looks like I I’m going without baggage. I don’t have a chance of catching ..

It was great. There were some issues prior to takeoff. The weather was poor so we had to go through deicing, and we were delayed a bit by the pilots' concern about one of the engines, but that's aviation. The pilots handled everything with aplomb, and kept us apprised

Reliable, nice crew, I fly often on that flight and I like it all.

l really enjoy very much the flight was very pleasant

Flight itself was not bad at all. However: my checked bag (checked in Calgary) did not make it onto this flight as I found out after I landed at EWR. I still don't have it but it appears that it is on its way to me.

Flight and attendance were very good we had 2 hour delay that took the shine of it

After 3 hours of delays, they ended up cancelling my flight. And although I could purchase one-way tickets to get to my destination, they would not offer me these flights as compensation for the cancelled flight, and I didn't end up making it home until 13 hours after I was originally supposed to arrive. It made for an extremely strenuous end to an otherwise good trip.

Be careful about the bad policy and when purchasing seats

Very disappointed with premier lounge. Food selection very poor, both coffee machines out of order. For the price you charge for an upgrade, the seats don’t fully recline, movie selection is old. Not very good value. Asian airlines are light years ahead at a more affordable price.

The seat design in the premium economy section leaves virtually no room under the seat to store a bag or purse. Other than that, it was a great flight. Arrived early.

The flight was delayed, but not for weather. We landed over 3hrs later than planned.

The stag were helpful, kind and liked the passengers. The plane was pristinely clean! Great flight!

My flight was delayed more than once, but Air Canada updated us regularly. Friends on other airlines had much worse experiences.

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

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

Information on your arrival and departure airports