YWG - BOS

$177 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 7/9. 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
$270
Typical prices: $480-$323
Air Canada
Sat 9/5Sat 9/12
YWG - BOS • 1 stop
Cheapest one-way
$177
Typical prices: $180-$351
Air Canada
Thu 7/9
YWG - BOS • 1 stop
Top airlines
Air Canada
Cheapest • from $270 (round-trip)
Air Canada
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
Ottawa (YOW)
Cheapest • Avg $304 (round-trip)
Minneapolis (MSP)
Shortest trip • 5h 26m (one-way)
Insights
Insights
Insights
Insights
When to travel
June
Cheapest • 44% price drop
May
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 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

Sat, Sep 5 - Sat, Sep 12
Air Canada Logo
7:55 am - 2:41 pm
YWG
-
BOS
5h 46m
1 stop
Air Canada Logo
3:35 pm - 9:14 pm
BOS
-
YWG
6h 39m
1 stop
$270Air Canada
Tue, Sep 1 - Sat, Sep 5
Porter Airlines Logo
12:15 pm - 7:15 pm
YWG
-
BOS
6h 00m
1 stop
Porter Airlines Logo
10:05 am - 3:19 pm
BOS
-
YWG
6h 14m
1 stop
$302Porter Airlines
Sat, Sep 5 - Sat, Sep 12
Porter Airlines Logo
12:15 pm - 7:15 pm
YWG
-
BOS
6h 00m
1 stop
Porter Airlines Logo
7:10 am - 5:58 pm
BOS
-
YWG
11h 48m
2 stops
$305Porter Airlines
Fri, Oct 2 - Mon, Oct 5
Porter Airlines Logo
9:20 am - 7:15 pm
YWG
-
BOS
8h 55m
1 stop
Porter Airlines Logo
10:05 am - 3:19 pm
BOS
-
YWG
6h 14m
1 stop
$310Porter Airlines
Fri, Oct 2 - Mon, Oct 5
Porter Airlines Logo
9:20 am - 7:15 pm
YWG
-
BOS
8h 55m
1 stop
Porter Airlines Logo
10:05 am - 3:19 pm
BOS
-
YWG
6h 14m
1 stop
$311Porter Airlines
Fri, Oct 2 - Mon, Oct 5
Porter Airlines Logo
9:20 am - 7:15 pm
YWG
-
BOS
8h 55m
1 stop
Porter Airlines Logo
10:05 am - 5:58 pm
BOS
-
YWG
8h 53m
2 stops
$313Porter Airlines
Fri, Oct 2 - Mon, Oct 5
Porter Airlines Logo
9:20 am - 7:15 pm
YWG
-
BOS
8h 55m
1 stop
Porter Airlines Logo
10:05 am - 5:58 pm
BOS
-
YWG
8h 53m
2 stops
$314Porter Airlines
Wed, Aug 26 - Wed, Sep 9
Porter Airlines Logo
12:15 pm - 7:15 pm
YWG
-
BOS
6h 00m
1 stop
Porter Airlines Logo
10:05 am - 3:19 pm
BOS
-
YWG
6h 14m
1 stop
$317Porter Airlines
Fri, Jun 26 - Fri, Jul 3
Air Canada Logo
8:00 am - 2:41 pm
YWG
-
BOS
5h 41m
1 stop
Air Canada Logo
3:35 pm - 11:20 pm
BOS
-
YWG
8h 45m
2 stops
$318Air Canada
Fri, Jun 26 - Fri, Jul 3
Air Canada Logo
8:00 am - 2:41 pm
YWG
-
BOS
5h 41m
1 stop
Air Canada Logo
6:00 am - 11:15 am
BOS
-
YWG
6h 15m
1 stop
$319Air Canada
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 September.

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 January and April, where the average cost of round-trip tickets is $782 and $705 respectively.

Find deals

Good to know

Low seasonJanuary
Cheapest flight$177
Best time to beat the crowds but there is an average 52% increase in price.
Most popular time to fly with an average 10% 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 7 days, the lowest price for a flight from Winnipeg to Boston was $177 for a one-way ticket and $270 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 11075 reviews
7.3Boarding
6.8Entertainment
6.3Food
7.1Comfort
7.8Crew
Airline reviews

Never flown with Air Canada before, but it's now a top choice! Loved it!

10.0 ExcellentAnonymous, May 2026
YVR - PHX
Read more Air Canada reviews

Never flown with Air Canada before, but it's now a top choice! Loved it!

Horrible crew, horrible seats configuration, ridiculous space in the toilets, Air Canada is no longer a option.

Crew at gate and onboard were just very OK, not very friendly and honestly seemed bothered to be there. I will give a shout out to still selling headphones for those who forgot.

Flight Boarded and departed on time. The Flight crew was very friendly and accommodating. The aircraft was clean and free from clutter and debris. I will be happy to recommend Air Canada to my friends and relatives for their flight needs. They were very attentive and responsive to our needs as Senior citizens.

Another good flight experience with Air Canada. The business section did not feature the full length sleeping arrangement, but this was a shorter trip. The food was excellent. But the flight crew was truly top tier: friendly, cheerful, helpful at all the right times. Air Canada truly outshines all U.S. carriers.

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.

Everything. The crew was so friendly, helpful & smiled. We had an excellent flight getting in earlier.

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.

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

Information on your arrival and departure airports

Winnipeg (YWG)
Boston (BOS)