YWG - BOS

$158 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 3/10. 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
Travelers love KAYAK
41.299.237 searches in the past 7 days on KAYAK

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Everything you should know

Cheapest round-trip
$332
Overall average: $323
United Airlines
Sat 4/4Sat 4/11
YWG - BOS • 1 stop
Cheapest one-way
$158
Typical prices: $249-$651
Delta
Tue 3/10
YWG - BOS • 1 stop
Top airlines
United Airlines
Cheapest • from $332 (round-trip)
Delta
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
Toronto (YYZ)
Cheapest • Avg $259 (round-trip)
Ottawa (YOW)
Shortest trip • 5h 33m (one-way)
Insights
Insights
Insights
Insights
When to book
3 weeks
in advance
Our data shows that travelers who book at least 3 weeks in advance save around 58% compared to booking last minute.
Insights
Insights
Insights
Insights
When to travel
June
Cheapest • 36% 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

Sat, Apr 4 - Sat, Apr 11
United Airlines Logo
2:00 pm - 12:59 am
YWG
-
BOS
9h 59m
1 stop
United Airlines Logo
6:15 am - 12:33 pm
BOS
-
YWG
7h 18m
1 stop
$332United Airlines
Sun, Apr 5 - Sun, Apr 12
Air Canada Logo
8:15 am - 2:52 pm
YWG
-
BOS
5h 37m
1 stop
Air Canada Logo
5:30 am - 10:09 am
BOS
-
YWG
5h 39m
1 stop
$335Air Canada
Sat, Apr 4 - Sat, Apr 11
United Airlines Logo
7:05 am - 9:59 pm
YWG
-
BOS
13h 54m
2 stops
United Airlines Logo
7:05 am - 5:18 pm
BOS
-
YWG
11h 13m
2 stops
$340United Airlines
Sun, Apr 5 - Sun, Apr 12
Multiple Airlines Logo
6:00 am - 2:52 pm
YWG
-
BOS
7h 52m
2 stops
Multiple Airlines Logo
6:40 pm - 9:35 am
BOS
-
YWG
15h 55m
2 stops
$373Multiple Airlines
Thu, Apr 9 - Wed, Apr 15
Multiple Airlines Logo
8:05 pm - 9:35 am
YWG
-
BOS
12h 30m
1 stop
Multiple Airlines Logo
6:00 am - 3:09 pm
BOS
-
YWG
10h 09m
1 stop
$395Multiple Airlines
Mon, Mar 2 - Wed, Mar 4
Air Canada Logo
5:30 am - 7:12 pm
YWG
-
BOS
12h 42m
2 stops
Air Canada Logo
5:30 am - 10:15 am
BOS
-
YWG
5h 45m
1 stop
$397Air Canada
Thu, Apr 16 - Sun, Apr 19
Air Canada Logo
8:15 am - 2:52 pm
YWG
-
BOS
5h 37m
1 stop
Air Canada Logo
5:30 am - 10:09 am
BOS
-
YWG
5h 39m
1 stop
$415Air Canada
Thu, Apr 9 - Wed, Apr 15
Air Canada Logo
5:30 am - 2:52 pm
YWG
-
BOS
8h 22m
2 stops
Air Canada Logo
5:30 am - 10:09 am
BOS
-
YWG
5h 39m
1 stop
$416Air Canada
Thu, Jul 23 - Tue, Jul 28
Porter Airlines Logo
9:20 am - 5:35 pm
YWG
-
BOS
7h 15m
1 stop
Porter Airlines Logo
7:15 am - 5:58 pm
BOS
-
YWG
11h 43m
2 stops
$420Porter Airlines
Thu, Jul 23 - Tue, Jul 28
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
$421Porter 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 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 January and March, where the average cost of round-trip tickets is $782 and $554 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 58% 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$158
Best time to beat the crowds but there is an average 67% increase in price.
Most popular time to fly with an average 1% 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 $158 for a one-way ticket and $332 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 8215 reviews
8.1Boarding
7.8Entertainment
8.5Crew
7.9Comfort
7.2Food
Airline reviews

Boarding and crew were fantastic, but I paid for a window seat with no window. Seat 11D on a CRJ-900 apparently does not have a window. Lesson learned.

6.0 GoodAnthony, Feb 2026
LGA - CMH
Read more Delta reviews

Boarding and crew were fantastic, but I paid for a window seat with no window. Seat 11D on a CRJ-900 apparently does not have a window. Lesson learned.

Terrible. Four hour delay because Delta could not find crew to man the aircraft. Terrible communication. Terrible insight into the delays. One of the worst flight experiences I’ve had.

The landing was the worst I’ve experienced with a flight.

The crew, and fellow passengers, were super gracious and kind. There seemed to be plenty of bin space even though the plane was full. It’s nice to get a glass of wine with dinner in Premiere seating, and there was a lot of food.

First flight out and was 85 minutes delayed. Notification came out way too late

Delta flights recently are always delayed AND at jfk tney get the gates further away (need To walk 20’ to get to them/all the way at the end of the terminal). Not sure whats happening but price doesnt match experience!

Boarding was efficient and smooth. Departure time was on time. Arrival to Detroit was early. Average food . Average crew service Very average cabin comfort. Nothing spectacular one way ir another, except for the excellent on time performance.

Everything I mentioned earlier - the airbus was more comfortable indeed and the experience was further enhanced.

Delta continues to set the benchmark for traveler-friendly service with minimal disruption and clear communication within the mainland US (coast to coast). I am consistently pleased to be a Delta customer, and this experience once again met my expectations. There was a brief delay departing from MIA due to a technical issue that required the aircraft to return to the gate. However, the situation was handled professionally and transparently. Fortunately, my planned layover allowed ample buffer time, so the adjustment caused no stress. Overall, another smooth and reassuring experience.

Good experience and the flight landed early. There was no food I had or entertainment.

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

I like flying first class, and United has a nice one

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. 🙂

My experience was good with United too But only not so good thing was that at Calgary airport I was not given lounge access despite of flying business. Aspire lounge denied it to me, which was unfair I feel

We left over 2 hours late and they didn't even give us a complimentary snack, when getting to the desk I asked if I could be put in a row with only 1 other person or an empt y one I was told the flight was full when the last two rows were empty. All around over it

they were super helpful. Agents at the desk got me on an earlier flight and I was able to get home several hours earlier.

This is a great non-stop YVR-MIA. Very comfortable plane, and no transfer through a city that gets major winter weather!

Terrible…. Reported missing luggage’s with injectable meds that needed refrigeration. Yet, delivery could not be expedited. Luggage’s were delivered 5 days after arrival. The meds were useless as ice pack had melted. So disappointed!!!

Air Canada’s problems are not staff related by and large, no. The problem is tiny jets between the U.S. and Canada - yes, believe it or not they are still “international” (just ask our own Mango Maniac in power in the U.S.). The little aisle is compounded by a design flaw of a “dog leg” starting at seat 12. Woe be unto you if you sit here as passengers and attendants do not have sufficient room to not hit you in the face with backpacks. One thing I will say very positively about Air Canada is you still provide pillows and blankets on transcontinental flights to all, not just the elites. Your tiny improperly designed jets are also a problem flying city to city within Canada also. One can only say you remind us of a “Jet Blue” or “Spirit” experience. Also your luggage space is downright Byzantine! We will endeavor to avoid you and use other U.S. carriers, albeit charging more.

Terrible canceled flight and lost my luggage. Flew me to Halifax. Tgat flight was delayed, had to spend night in airport chair.

Better entertainment & food options more may be adding chicken option or on vegetarian side good quality pasta

My seat was not comfortable. Flight was smooth. Regretfully we had two delays before takeoff

Amazing service, with enthusiastic crew members, and some breathtaking views of Vancouver. No IFE though, as it is only a 1 hour flight on a regional Turboprop jet.

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

Information on your arrival and departure airports