YWG - BOS

$179 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 8/31. 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
$292
Typical prices: $267-$440
Porter Airlines
Fri 7/10Thu 7/16
YWG - BOS • 1 stop
Cheapest one-way
$179
Typical prices: $236-$365
Porter Airlines
Mon 8/31
YWG - BOS • 2 stops
Top airlines
Cheapest • from $292 (round-trip)
Best reviews • 7.1 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 28m (one-way)
Insights
Insights
Insights
Insights
When to travel
Cheapest • 37% 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, Jul 10 - Thu, Jul 16
Porter Airlines Logo
12:15 pm - 6:35 pm
YWG
-
BOS
5h 20m
1 stop
Porter Airlines Logo
10:05 am - 3:19 pm
BOS
-
YWG
6h 14m
1 stop
$292Porter Airlines
Wed, Aug 5 - Tue, Aug 11
Porter Airlines Logo
12:15 pm - 6:35 pm
YWG
-
BOS
5h 20m
1 stop
Porter Airlines Logo
10:05 am - 3:19 pm
BOS
-
YWG
6h 14m
1 stop
$308Porter Airlines
Fri, Jul 10 - Thu, Jul 16
Air Canada Logo
8:15 am - 4:03 pm
YWG
-
BOS
6h 48m
1 stop
Air Canada Logo
5:45 am - 2:25 pm
BOS
-
YWG
9h 40m
2 stops
$314Air Canada
Fri, Jul 10 - Thu, Jul 16
Air Canada Logo
5:00 am - 2:41 pm
YWG
-
BOS
8h 41m
2 stops
Air Canada Logo
5:45 am - 2:25 pm
BOS
-
YWG
9h 40m
2 stops
$316Air Canada
Fri, Aug 7 - Sat, Aug 15
Air Canada Logo
3:20 pm - 10:38 pm
YWG
-
BOS
6h 18m
1 stop
Air Canada Logo
6:00 am - 11:15 am
BOS
-
YWG
6h 15m
1 stop
$322Air Canada
Wed, Aug 19 - Mon, Aug 24
Porter Airlines Logo
12:15 pm - 6:35 pm
YWG
-
BOS
5h 20m
1 stop
Porter Airlines Logo
7:10 am - 5:58 pm
BOS
-
YWG
11h 48m
2 stops
$325Porter Airlines
Thu, Jul 23 - Thu, Jul 30
Porter Airlines Logo
12:15 pm - 6:35 pm
YWG
-
BOS
5h 20m
1 stop
Porter Airlines Logo
10:05 am - 3:19 pm
BOS
-
YWG
6h 14m
1 stop
$333Porter Airlines
Wed, Aug 19 - Mon, Aug 24
Delta Logo
5:42 pm - 11:58 pm
YWG
-
BOS
5h 16m
1 stop
Delta Logo
7:10 am - 11:54 am
BOS
-
YWG
5h 44m
1 stop
$335Delta
Mon, Sep 21 - Wed, Sep 23
Delta Logo
3:58 pm - 11:59 pm
YWG
-
BOS
7h 01m
1 stop
Delta Logo
5:55 am - 11:56 am
BOS
-
YWG
7h 01m
1 stop
$336Delta
Fri, Aug 7 - Thu, Aug 13
Porter Airlines Logo
12:15 pm - 6:35 pm
YWG
-
BOS
5h 20m
1 stop
Porter Airlines Logo
10:05 am - 3:19 pm
BOS
-
YWG
6h 14m
1 stop
$337Porter 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 July.

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 $332 (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 seasonJanuary
Cheapest flight$179
Best time to beat the crowds but there is an average 47% increase in price.
Most popular time to fly and prices are also 19% 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 $179 for a one-way ticket and $292 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 airline 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.
7.1
Air CanadaOverall score based on 11254 reviews
6.8Entertainment
6.3Food
7.1Comfort
7.3Boarding
7.8Crew
Airline reviews

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.

2.0 MediocreAnonymous, May 2026
YHZ - BOS
Read more Air Canada reviews

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.

Con: Travelers shouldn't have to pay a fee for first checked bag, in any fare class. Pro: Plane was new and comfortable, even for the seats that didn't cost extra.

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

Information on your arrival and departure airports