YWG - BOS

$141 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 2/8. 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
$263
Overall average: $459
Multiple Airlines
Tue 2/24Tue 3/10
YWG - BOS • 2 stops
Cheapest one-way
$141
Multiple Airlines
Sun 2/8
YWG - BOS • 3 stops
When to book
4 weeks
in advance
Our data shows that travelers who book at least 4 weeks in advance save around 68% compared to booking last minute.
Insights
Insights
Insights
Insights
When to travel
June
Cheapest • 29% price drop
May
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

Tue, Feb 24 - Tue, Mar 10
Multiple Airlines Logo
6:15 am - 1:13 am
YWG
-
BOS
17h 58m2 stops
Multiple Airlines Logo
12:35 pm - 3:09 pm
BOS
-
YWG
27h 34m1 stop
$263Multiple Airlines
Tue, Feb 24 - Tue, Mar 10
Multiple Airlines Logo
8:00 am - 1:28 pm
YWG
-
BOS
28h 28m1 stop
Multiple Airlines Logo
12:35 pm - 3:09 pm
BOS
-
YWG
27h 34m1 stop
$279Multiple Airlines
Fri, Jan 23 - Fri, Jan 30
Multiple Airlines Logo
7:30 am - 1:13 am
YWG
-
BOS
16h 43m1 stop
Multiple Airlines Logo
3:43 pm - 1:26 am
BOS
-
YWG
10h 43m1 stop
$281Multiple Airlines
Fri, Jan 23 - Fri, Jan 30
Multiple Airlines Logo
5:00 am - 4:28 pm
YWG
-
BOS
34h 28m2 stops
Multiple Airlines Logo
3:43 pm - 1:26 am
BOS
-
YWG
10h 43m1 stop
$292Multiple Airlines
Fri, Jan 23 - Fri, Jan 30
Multiple Airlines Logo
7:30 am - 1:13 am
YWG
-
BOS
16h 43m1 stop
Multiple Airlines Logo
3:43 pm - 1:26 am
BOS
-
YWG
10h 43m1 stop
$304Multiple Airlines
Fri, Jan 23 - Fri, Jan 30
Multiple Airlines Logo
7:30 am - 11:57 pm
YWG
-
BOS
15h 27m2 stops
Multiple Airlines Logo
3:43 pm - 1:26 am
BOS
-
YWG
10h 43m1 stop
$314Multiple Airlines
Thu, Feb 5 - Sun, Feb 8
Multiple Airlines Logo
6:00 am - 8:30 pm
YWG
-
BOS
13h 30m1 stop
Multiple Airlines Logo
6:00 am - 12:40 am
BOS
-
YWG
19h 40m2 stops
$335Multiple Airlines
Fri, Jan 23 - Fri, Jan 30
Multiple Airlines Logo
7:30 am - 2:38 pm
YWG
-
BOS
30h 08m3 stops
Multiple Airlines Logo
7:00 am - 1:26 am
BOS
-
YWG
19h 26m1 stop
$349Multiple Airlines
Tue, Feb 24 - Tue, Mar 10
Multiple Airlines Logo
5:00 am - 11:46 pm
YWG
-
BOS
17h 46m2 stops
Multiple Airlines Logo
5:50 pm - 3:09 pm
BOS
-
YWG
22h 19m2 stops
$365Multiple Airlines
Thu, Feb 5 - Sun, Feb 8
Multiple Airlines Logo
8:20 pm - 11:05 am
YWG
-
BOS
13h 45m1 stop
Multiple Airlines Logo
6:55 pm - 7:35 pm
BOS
-
YWG
25h 40m1 stop
$368Multiple 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.

What’s the cheapest day of the week to fly from Winnipeg to Boston?

The average price of all round-trip flights from Winnipeg to Boston clicked on KAYAK for each day over the last 12 months.

If you are looking for a flight deal from Winnipeg to Boston, look for departures on Saturdays and avoid leaving on a Monday, as it's usually the priciest day. When flying back from Boston, Sunday is the cheapest day to fly and Monday is the most expensive.

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 $300 (return) on average. On the other hand, the most expensive months are December and January, where the average cost of round-trip tickets is $583 and $550 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 4 weeks before departure, which saves you about 68% compared to booking last minute. For the absolute cheapest price, our data suggests you should book 20 weeks before departure.

Good to know

Low seasonMarch
Cheapest flight$141
Best time to beat the crowds but there is an average 3% increase in price.
Most popular time to fly and prices are also 13% 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 3 days, the lowest price for a flight from Winnipeg to Boston was $141 for a one-way ticket and $263 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 8012 reviews
7.9Comfort
8.1Boarding
7.9Entertainment
7.3Food
8.5Crew
Airline reviews

Very good flight crew and very nice people staff were incredible especially the gate agent

10.0 ExcellentAnonymous, Dec 2025
DTW - MSY
Read more Delta reviews

Very good flight crew and very nice people staff were incredible especially the gate agent

Waited at the usual crowded gate at DCA where one ends up standing up because there aren't enough seats.

The flight was delayed for about 2 hrs. Other than it, it was good.

Advertised fruit trays with cheese, but only snacks handed out!

The plant way delayed departing by 3 hours. It was an old airplane with broken seats and armrests. The bathroom made a hollering sound. A really crappy flight experience and travel day all around.

Premium economy is like the forgotten class. Aside from meal service never saw a flight attendant. Any additional beverages required going to the very back of the plane to request and there was rarely an attendant there. Seat leg / foot rest hardly elevates and not well suite for someone under 5’6. Bulky armrests

Flight delays both to Detroits and return flight . The flight to Detroit was associated with mechanical difficulty

Flight was operated by Virgin Atlantic and it was up to their usual high standard. Minor grips about some issues, but they are really first world issues and as a whole, was an excellent flight.

I am extremely disappointed that delta internal pilot manuals now refer to the Gulf of Mexico as the “gulf of America”. You can bow down to the Orange turd on your own. I will never fly delta again

Delta One upgrade it would have been great if my tray extended (it was jammed and wouldn’t pull out), seatbelt had too much slack & my little cabin door didn’t close properly

United airlines has the best customer experience from booking to arrival. I always fly United airlines. The mileage program is excellent

The Sears in the 800s are not too good perfect Airbus why cant the new 737 fix that

Quick and seamless boarding. No entertainment but fast Starlink wifi for this short trip and the staff was really friendly.

I dread trans-Pacific flights. They are very long. This was my first time on Universal, and it was my best crossing ever. The staff were professional, the hospitality was great, and the food was delicious. The entertainment system filled the long flight hours. I will seek out Universal flights from now onwards. 🙂

The food quality sucks. One must starve if they do not eat flesh Or wheat based products Some variety would be expected. The trivial amount of snacks and or food is inhumane

We Left Calgary 1/2 hour late and that made for a tight connection in Denver. After arriving everything was done to help us make our connection. That was a great effort. Thank You United

Efficient all round, very good crew. Short flight so the food, of course, was just snacks

Overall, it was good. I was seating next to a wonderful lady and did not notice how time flew. Thanks

My flight was delayed about 1 1/2 hours in Chicago, but other then that it was a good flight.

The experience was great, the crew was very polite and hospitable. I will definitely make if my go to airlines.

They are very proactive and made our boarding easy and always notified us about any changes well in advance.

My seat was covered in vomit and I will be reaching out to Air Canada

It's kindof ridiculous that your system is even asking me about this since my flight was canceled and I wasn't rescheduled.

3 hr delay at the gate while they were doing maintenance. Next time, do not board passengers while maintenance is being performed

Digital check in is very poor with air canada compaired to other airlines

Baggage delayed we had to catch our cruise without any clothes 😒

Air Canada Rouge is great. Toronto Airport is the usual nightmare

Good but need to be better with the flight times.

The staff could not have been any friendlier. Lots of usb ports on our aircraft.

The staff was great and made the long trip easy peasy!

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

Information on your arrival and departure airports