YWG - BOS

$161 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 6/22. 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
$269
Overall average: $323
Delta
Thu 4/2Wed 4/8
YWG - BOS • 1 stop
Cheapest one-way
$161
Typical prices: $158-$260
Air Canada
Mon 6/22
YWG - BOS • 1 stop
Top airlines
Delta
Cheapest • from $269 (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 • 35% 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

Thu, Apr 2 - Wed, Apr 8
Delta Logo
6:40 am - 5:28 pm
YWG
-
BOS
9h 48m
1 stop
Delta Logo
5:50 am - 11:01 am
BOS
-
YWG
6h 11m
1 stop
$269Delta
Thu, May 28 - Fri, May 29
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
$287Porter Airlines
Thu, May 28 - Fri, May 29
Porter Airlines Logo
9:20 am - 8:55 pm
YWG
-
BOS
10h 35m
2 stops
Porter Airlines Logo
10:05 am - 3:19 pm
BOS
-
YWG
6h 14m
1 stop
$290Porter Airlines
Thu, May 28 - Fri, May 29
Air Canada Logo
5:10 am - 2:47 pm
YWG
-
BOS
8h 37m
2 stops
Air Canada Logo
5:10 am - 11:08 am
BOS
-
YWG
6h 58m
1 stop
$291Air Canada
Tue, Mar 17 - Tue, Mar 24
Delta Logo
6:40 am - 5:04 pm
YWG
-
BOS
9h 24m
1 stop
Delta Logo
3:10 pm - 11:35 pm
BOS
-
YWG
9h 25m
1 stop
$316Delta
Thu, Apr 2 - Wed, Apr 8
Multiple Airlines Logo
5:30 pm - 2:52 pm
YWG
-
BOS
20h 22m
2 stops
Multiple Airlines Logo
6:15 am - 12:40 am
BOS
-
YWG
19h 25m
2 stops
$339Multiple Airlines
Thu, Apr 9 - Mon, Apr 13
Delta Logo
6:40 am - 5:28 pm
YWG
-
BOS
9h 48m
1 stop
Delta Logo
3:10 pm - 11:30 pm
BOS
-
YWG
9h 20m
1 stop
$340Delta
Thu, Apr 9 - Mon, Apr 13
United Airlines Logo
5:30 am - 11:59 pm
YWG
-
BOS
17h 29m
2 stops
United Airlines Logo
6:25 pm - 11:52 am
BOS
-
YWG
18h 27m
2 stops
$346United Airlines
Sat, Apr 11 - Sat, Apr 18
Multiple Airlines Logo
12:20 pm - 9:35 am
YWG
-
BOS
20h 15m
1 stop
Multiple Airlines Logo
7:00 am - 12:39 am
BOS
-
YWG
18h 39m
1 stop
$360Multiple Airlines
Thu, Apr 9 - Mon, Apr 13
United Airlines Logo
8:45 am - 8:13 pm
YWG
-
BOS
10h 28m
1 stop
United Airlines Logo
6:25 pm - 11:52 am
BOS
-
YWG
18h 27m
2 stops
$370United 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 December, where the average cost of round-trip tickets is $782 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 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$161
Best time to beat the crowds but there is an average 69% increase in price.
Most popular time to fly with an average 2% 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 $161 for a one-way ticket and $269 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 8249 reviews
7.9Comfort
8.5Crew
8.1Boarding
7.8Entertainment
7.2Food
Airline reviews

The whole experience was excellent. As it most often is with Delta

10.0 ExcellentRay, Mar 2026
LGA - MCO
Read more Delta reviews

The whole experience was excellent. As it most often is with Delta

Cabin was not pressurized properly. Several passengers had respiratory difficulties.

I was happy that I was able to get a last minute flight but unfortunately my seat was a middle seat. Even with Delta Comfort I wasn't comfortable

There’s not much to say about a one hour flight. This is a connection from LA to RNO that I missed the previous night due to a mechanical check delay on my originating flight from JFK to LAX. The short flight itself was fine. Instructions from the pilot and crew were per usual. The coffee was barely lukewarm, which possibly was purposeful so we would down it quickly. Bags were already on carousel upon reaching baggage claim, which was excellent.

Flight was warm for first few hours and quite rough

Seat was extremely hard which made even a short 1 hour 20 minute flight fairly uncomfortable.

Improve boarding- the zone assignment and boarding is always a mess- there is not clear instructions of what is going on at the gate. As a meme bet there is no more selection of a good seats when booking. Only offers middle seats to choose or pay extra. There is not more benefit with Amex no benefits at all.

alike schedule and times it’s very good for me, I will stay wad delta for ever

Everything was good except wifi and a leaking drink chiller. The floor was all wet and my bag was soaked. Did not notice until debarking. Have not heard back from Delta. Even though this was leg one of an international flight in first class, they denied access to their Sky Club - very disappointing!

The staff was fine. The plane was extremely tight, and I paid for the wifi and it did not work at all. I was actually going to ask for a refund.

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

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

The plane was delayed an hour. Heard from other passengers that the Vancouver connection to SFO was never on-time.

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

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

Information on your arrival and departure airports