YWG - BOS

$137 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 1/29. 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

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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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, Nov 15 - Sat, Nov 22
United Airlines Logo
8:40 am - 6:48 pmYWG-BOS
9h 08m2 stops
United Airlines Logo
6:00 am - 11:57 amBOS-YWG
6h 57m1 stop
$290United Airlines
Find Deal
Fri, Dec 5 - Sun, Dec 7
Multiple Airlines Logo
7:30 am - 12:44 amYWG-BOS
16h 14m1 stop
Multiple Airlines Logo
6:00 am - 3:07 pmBOS-YWG
10h 07m1 stop
$292Multiple Airlines
Find Deal
Fri, Oct 31 - Mon, Nov 3
Multiple Airlines Logo
7:30 am - 10:48 amYWG-BOS
26h 18m1 stop
Multiple Airlines Logo
12:59 pm - 5:26 pmBOS-YWG
29h 27m1 stop
$301Multiple Airlines
Find Deal
Fri, Dec 5 - Sun, Dec 7
United Airlines Logo
8:40 am - 9:33 pmYWG-BOS
11h 53m2 stops
United Airlines Logo
6:00 am - 11:57 amBOS-YWG
6h 57m1 stop
$305United Airlines
Find Deal
Fri, Dec 5 - Sun, Dec 7
Multiple Airlines Logo
2:20 pm - 11:41 pmYWG-BOS
8h 21m2 stops
Multiple Airlines Logo
5:30 am - 5:19 pmBOS-YWG
12h 49m2 stops
$311Multiple Airlines
Find Deal
Thu, Nov 20 - Mon, Nov 24
Air Canada Logo
5:30 am - 12:12 pmYWG-BOS
5h 42m1 stop
Air Canada Logo
5:30 am - 10:16 amBOS-YWG
5h 46m1 stop
$315Air Canada
Find Deal
Sat, Oct 25 - Wed, Oct 29
Air Canada Logo
5:00 am - 6:10 pmYWG-BOS
12h 10m1 stop
Air Canada Logo
5:30 am - 10:16 amBOS-YWG
5h 46m1 stop
$335Air Canada
Find Deal
Fri, Oct 31 - Mon, Nov 3
Multiple Airlines Logo
7:30 am - 10:48 amYWG-BOS
26h 18m1 stop
Multiple Airlines Logo
3:55 pm - 5:26 pmBOS-YWG
26h 31m2 stops
$337Multiple Airlines
Find Deal
Fri, Oct 24 - Tue, Oct 28
Delta Logo
5:40 pm - 11:59 pmYWG-BOS
5h 19m1 stop
Delta Logo
3:00 pm - 11:27 pmBOS-YWG
9h 27m1 stop
$348Delta
Find Deal
Fri, Oct 24 - Tue, Oct 28
Delta Logo
12:20 pm - 10:04 pmYWG-BOS
8h 44m1 stop
Delta Logo
3:00 pm - 11:27 pmBOS-YWG
9h 27m1 stop
$371Delta
Find Deal

Everything you should know

Top airlines
United Airlines
Cheapest • from $290 (round-trip)
Delta
Best reviews • 7.9 score
Airline reviews
Airline reviews
+1
+1
Airline reviews
Airline reviews
+1
When to book
4 weeks
in advance
Our data shows that travelers who book at least 4 weeks in advance save around 63% compared to booking last minute.
Insights
Insights
Insights
Insights
When to travel
October
Cheapest • 24% price drop
May
Most popular
Good to know
Good to know
+1
+1
Good to know
Good to know
+1
Cheapest round-trip
$290
Typical prices: $353-$490
United Airlines
Sat 11/15Sat 11/22
YWG - BOS • 2 stops
Cheapest one-way
$137
Typical prices: $264-$502
Multiple Airlines
Thu 1/29
YWG - BOS • 2 stops
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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!
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 November.

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 October, where tickets cost $305 (return) on average. On the other hand, the most expensive months are December and January, where the average cost of round-trip tickets is $646 and $537 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 63% 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$137
Best time to beat the crowds but there is an average 5% increase in price.
Most popular time to fly and prices are also 11% 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 $137 for a one-way ticket and $290 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 Porter Airlines?

    The two airlines most popular with KAYAK users for flights from Winnipeg to Boston are Delta and Porter Airlines. With an average price for the route of $464 and an overall rating of 7.9, Delta is the most popular choice. Porter Airlines is also a great choice for the route, with an average price of $355 and an overall rating of 7.9.

  • 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 4 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 7971 reviews
8.5Crew
7.9Comfort
7.3Food
8.2Boarding
7.9Entertainment
Airline reviews

The crew was not very visible. This might be a good thing for people who wanted to sleep but seemed odd when compared to the Atlantic crossing where they are more present in the cabin. The Food (beef) was not good. Tough and tasteless. Would love to see more choices on a long flight like that.

8.0 ExcellentKathrin, Oct 2025SYD - LAX
Read more Delta reviews

The crew was not very visible. This might be a good thing for people who wanted to sleep but seemed odd when compared to the Atlantic crossing where they are more present in the cabin. The Food (beef) was not good. Tough and tasteless. Would love to see more choices on a long flight like that.

The flight was great. The gate location was way to far away!!!

This was our second flight using the Delta One class of service. Overall, it’s a good product but for me the POD configuration is a bit constrictive. I am an average size male at 5’ 10” height weighing 190 lbs so it’s not a size thing for me. I’d rather have extra wide seats without the POD walls to be honest.

The flight attendant in first class was beyond rude and didn't care at all about her job. AND the gate agent was even worse than the flight attendant for rudeness. She was awful.

Convient flight. Good experience. No complaints other than the food quality seems to have decreased.

Food tray looked like penitentiary food - little effort to make it look appealing (packaging colour and design)

Movie selection was meh. Food was great. Crew as always great. I paid for premium because that’s the only way not to feel like a sardine. That’s how economy should be imo. Sadly passengers have to pay an extra $1000 to get what they should at base price but that’s all airlines. The airline industry in general treats passengers as cargo.

Gate agent rushed to fill hot jetway with crowd so it took over 12 minutes to go from gate to plane. Just like a discount airline Pooly prepared cabin and third time that claim of rough air prevented any cabin service. Friends on a Southwest flight at similar time had service.

My only complaint on any flight is meals but your gnocchi was good. The worst is breakfast. I can’t understand why you don’t just serve something simple like yogurt, fruit and a muffin or cinnamon roll.

Cramped seating for me. Luckily it wasn’t a long flight

Smaller plane. Food and bar service for free is amazing. Drinks were in glass not plastic cups.

Poor landing as we overshot the runway and had to re land the plane. Lost both of my luggage not found as of yet. Had to pay extra money for my luggage in USD, now great my luggage is gone. Will not fly with Porter again.

This flight to St. Johns was really good. Boarding was a breeze. We left spot on time. Seats were actually pretty good. Recliner further than I expected. Three more flights to go we will see if this is the status quo for Porter.👍

I was not happy with AirfareAssist, the agency that kayak advised me would be handling my booking. I was advised by porter airlines that I had been overcharged for the Basic express , a option that I had asked airfare assist to help arrange after I realized that the basic fare I had chosen with porter did not include a carryon. At each checkin porter advised I had been overcharged for this . They advised that money would be refunded to my credit card, however, this is not likely to happen as it is not my name and credit card that appeared on the porter invoice, but that of another individual/agent. When airfare assist was arranging the basic express with porter on my behalf, they asked me to confirm that I agreed to pay $263 USD for this. I did agree, as I was advised this was needed to proceed. When I checked the invoice on the porter website and saw that it was not my name and credit card on the invoice, I was advised that this was how airfareassist processed the payment. The Porter invoice indicated a billed amount of $126USD I will not use Kayak or their designated AirfareAssist again

Our flight was delayed by a bit. I appreciated that we were kept informed on why periodically. Boarding was fine. I overheard one flight attendant sounding very rude to a passenger who was not paying attention to the safety demonstration. The snacks were minimal as it was a short flight. There was no entertainment. Overall the flight was good back to LGA.

The flight was fine see earlier note for the problem

All good the seats a little tight and no I pad screen

Everything was good except the fact you charge more for a carry on bag vs a check in bag and to top it off in US$ that was not impressive

Our flight was cancelled at the last minute for maintenance reasons and we were rebooked on a late flight when we purposefully booked our flight to be home early due to work.

Seemed like an old plane. Very noisy. The seat cushions were so old that the metal bracing of the seats were poking through. There was plenty of leg room though.

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.

It was all good flight was on time, service was good I enjoyed a few movies and everything was smooth

Efficient, calm when things were delayed and kept us regularly informed of what was happening.

Impressed with the service despite turbulence because of the weather. Both flights arrived before their scheduled times.

Airbus plane, nice and polite staff, entertainment even as it was a short flight.

Very nice and clean plane. Transit time between flights was tight though

Our flights got changed from United to Air Canada and our purchased seats did not get transferred so we had to pay for seats twice. I brought it up with Air Canada and they stated I had to go back and chase it with United. The united seats were $21 Canadian each and Air Canada were $56 each so we have paid $77 for each seat. Very unhappy

So far so good but food and entertainment are not available for this flight

First message when all on board was that we didnt have a pilot, then they found one, then it was something about the bridge something not working, they will either fix or do manually. Flight of course was leaving late with all the cruise guests worrying about making it to their ship in time. Then only some luggage made it off the ship. Around 15 to 20 people waiting. 45 min later arrived except mine. I asked the rep at the luggage conveyor, he asked me my name. Then said it was not picked up with the first batch so they put it in a room. I was going to take public transport but now worried about time so took a taxi that cost me $65 USD

The flight was very smooth and good. Boarding was fast, but the staff was just decently friendly.

Air Canada flight staff are in contact negotiations and they are less than happy and it show. The process of self checking baggage is less than desirable with lack of support staff to help

A sandwich and a drink would have been better thank a snack bar...

I liked the behaviour of the crew members.The flight was good.

1 hour late No hot drinks No restroom in the back of the plane

I swear airplane seats keep getting smaller and smaller but everything else was great. Smooth sailing and we got in early.

No food to provide, they forgot that, in some cases, people stay at the airport for hours without food. Now, to provide them with food, they have to ask them to pay, because some don't have money. That way, they can't eat.

After a long flight from Tokyo, our connecting flight home was canceled due to “maintenance” while we were on our layover in Toronto. Very frustrating to close out our honeymoon, although I’m sure others had it even worse during last week’s strike. Air Canada staff at Pearson Airport are the one thing that kept me remotely at peace during this — they were very helpful and deserve a lot of props. But I would not fly Air Canada again.

I had wonderful wheelchair assistance through the Montreal airport onto the flight. Air Canada was excellent in this both at the Fredericton airport and the Montreal one where an attendant helped us through customs as well as transport and baggage security.

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

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