HomeSearch by dateVacation packagesHotelsFlight dealsCar rentalTravel tips & news
Winnipeg

$108+ Cheap flights from Boston (BOS) to Winnipeg (YWG)

This is the cheapest one-way flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 11/28. Fares are subject to change and may not be available on all flights or dates of travel.
BOS — YWG
nov. 22 — nov. 291
sáb. 11/22
sáb. 11/29
1 adult, Economy
We work with more than 300 partners to bring you better travel deals

Find cheap flights from Boston to Winnipeg with Cheapflights

1. Tell us where you want to go

Enter your travel information like dates, passengers, trip type (one-way or round trip), and preferred cabin class then click “Find deals”

2. Select your favorite providers

We find the providers serving your travel needs. Choose up to four travel providers to compare side-by-side for flights, hotels, or car rentals.

3. Compare prices and book

Review each provider’s pricing and select the best option for you! Book through your favorite provider’s website for a seamless experience.

Cheapflights Tip: The best prices from Boston Logan Intl to Winnipeg are usually found in July or January, booked 63 days in advance, depart on a Sunday or Friday and return on a Saturday

Cheap flight deals from Boston to Winnipeg

Discover tips and strategies to find the most affordable flight options for your journey from Boston (BOS) to Winnipeg (YWG). Learn about various techniques such as flexible date searches, comparing prices across and setting up price alerts. Use these methods to find the cheapest flights available for your travel needs. Data last updated octubre 23, 2025.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$267
(Kiwi.com)

One-way from

$108
(Kiwi.com)

Popular in

February

Cheapest in

July

Average price

$417
Provider with most accurate pricing for Boston Logan Intl-Winnipeg flight deals.
Search Deals
Provider most trusted by Cheapflights users for Boston Logan Intl-Winnipeg flights.
Search Deals
From Boston Logan Intl to Winnipeg
Search Deals
One-way flight from Boston Logan Intl to Winnipeg
Search Deals
Highest demand for flights based on searches. 5% potential increase in price ($23 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 2% potential price decrease ($12 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in October 2025
Search Deals

Find flight deals from Boston to Winnipeg

Cheapest flights from Boston to Winnipeg
Explore the most affordable flight options available from Boston to Winnipeg. Find the lowest fares from popular airlines and budget airlines, with prices last updated on octubre 23, 2025.

This Kiwi.com deal was found by Cheapflights users on 10/22. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
jue. 11/209:54 pmBOS - YWG
1 stop18h 13mMultiple Airlines
vie. 11/287:30 amYWG - BOS
1 stop12h 19mMultiple Airlines
Deal found 10/22$267
This Kiwi.com deal was found by Cheapflights users on 10/21. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
jue. 11/612:20 pmBOS - YWG
2 stops27h 47mMultiple Airlines
mié. 11/127:30 amYWG - BOS
1 stop24h 30mMultiple Airlines
Deal found 10/21$312
This Kiwi.com deal was found by Cheapflights users on 10/22. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
vie. 12/511:19 amBOS - YWG
2 stops14h 22mMultiple Airlines
lun. 12/88:00 amYWG - BOS
1 stop14h 57mMultiple Airlines
Deal found 10/22$326
This Kiwi.com deal was found by Cheapflights users on 10/21. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mar. 11/46:16 amBOS - YWG
2 stops33h 51mMultiple Airlines
mié. 11/125:00 amYWG - BOS
1 stop8h 55mMultiple Airlines
Deal found 10/21$347
This Kiwi.com deal was found by Cheapflights users on 10/21. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mar. 11/46:16 amBOS - YWG
2 stops33h 51mMultiple Airlines
mar. 11/115:00 amYWG - BOS
1 stop8h 55mMultiple Airlines
Deal found 10/21$356
This Kiwi.com deal was found by Cheapflights users on 10/21. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mar. 11/46:16 amBOS - YWG
2 stops33h 51mMultiple Airlines
lun. 11/108:05 pmYWG - BOS
1 stop12h 30mMultiple Airlines
Deal found 10/21$375
This Air Canada deal was found by Cheapflights users on 10/22. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Air Canada is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mié. 11/125:30 amBOS - YWG
1 stop5h 46mAir Canada
sáb. 11/228:15 amYWG - BOS
1 stop5h 37mAir Canada
Deal found 10/22$380
This Kiwi.com deal was found by Cheapflights users on 10/23. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
dom. 12/73:40 pmBOS - YWG
2 stops10h 02mMultiple Airlines
dom. 12/147:30 amYWG - BOS
1 stop25h 52mMultiple Airlines
Deal found 10/23$387

Cheapflights Fare Finder

 
Customize your flight search to find flights from Boston to Winnipeg that fit within your specific budget. Explore options based on user searches and filter the results based on your desired price range. Find flights that match your budget for a cost-effective journey. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated octubre 23, 2025.
Use the filters below to find and compare flights from Boston to Winnipeg that are best for you.

Fly from

Boston

Fly to

Winnipeg

Route

Depart

Return

Price

BostonWinnipeg

BOS - YWG

BOSYWG

Boston Logan Intl

jue. 11/20

9:54 pm-3:07 pm

1 stop18h 13m

Winnipeg

vie. 11/28

7:30 am-8:49 pm

1 stop12h 19m

$267

BostonWinnipeg

BOS - YWG

BOSYWG

Boston Logan Intl

vie. 12/5

11:19 am-12:41 am

2 stops14h 22m

Winnipeg

lun. 12/8

8:00 am-11:57 pm

1 stop14h 57m

$326

BostonWinnipeg

BOS - YWG

BOSYWG

Boston Logan Intl

mar. 11/4

6:16 am-3:07 pm

2 stops33h 51m

Winnipeg

mié. 11/12

5:00 am-2:55 pm

1 stop8h 55m

$347

BostonWinnipeg

BOS - YWG

BOSYWG

Boston Logan Intl

mié. 11/12

5:30 am-10:16 am

1 stop5h 46m

Winnipeg

sáb. 11/22

8:15 am-2:52 pm

1 stop5h 37m

$380

BostonWinnipeg

BOS - YWG

BOSYWG

Boston Logan Intl

mié. 11/12

1:25 pm-3:21 pm

2 stops26h 56m

Winnipeg

sáb. 11/22

5:00 am-2:55 pm

1 stop8h 55m

$432

BostonWinnipeg

BOS - YWG

BOSYWG

Boston Logan Intl

sáb. 11/15

11:43 am-3:07 pm

1 stop28h 24m

Winnipeg

sáb. 11/22

5:00 am-2:55 pm

1 stop8h 55m

$449

BostonWinnipeg

BOS - YWG

BOSYWG

Boston Logan Intl

vie. 11/28

6:00 am-3:07 pm

1 stop10h 07m

$108

BostonWinnipeg

BOS - YWG

BOSYWG

Boston Logan Intl

dom. 11/30

5:30 am-10:16 am

1 stop5h 46m

$226

BostonWinnipeg

BOS - YWG

BOSYWG

Boston Logan Intl

jue. 11/27

10:15 am-4:35 pm

1 stop7h 20m

$252

BostonWinnipeg

BOS - YWG

BOSYWG

Boston Logan Intl

dom. 12/7

6:00 am-11:57 am

1 stop6h 57m

$257

Flights are sorted by cheapest round-trip flights first.

Deals found on 10/22

Showing 1-10 of 12 results
1
2

Compare providers for flights from Boston to Winnipeg

Provider information is updated monthly. Please note that these providers often have deals for this flight, but the availability may vary on a day-by-day basis on Cheapflights.
Use the table below to compare price accuracy, trust ratings, and cancellation policies for each provider offering flight deals from Boston to Winnipeg in October.
ProviderPrice AccuracyTrust Score*
ExpediaPrice Accuracy2 starsTrust Score*3 stars
FlightHubPrice Accuracy3 starsTrust Score*3 stars
eDreamsPrice Accuracy3 starsTrust Score*3 stars
Kiwi.comPrice Accuracy3 starsTrust Score*3 stars

*The Trust Score is based on feedback from users after their booking experience. It measures overall satisfaction, helping us identify issues like hidden fees, problems during the ticketing process, and the quality of customer service. This score is our best indicator of the provider's quality and reliability.

  • Most accurate provider: When it comes to deals on Boston-Winnipeg flights, users find the pricing of FlightHub to be most consistent on Cheapflights vs. FlightHub Users can find the same prices on Boston-Winnipeg flight deals on Cheapflights vs. FlightHub >95% of the time. Price accuracy is based on data collected from Boston-Winnipeg flight searches over the past month and is updated monthly.
  • Most trusted provider: When it comes to deals on Boston-Winnipeg flights, Cheapflights users trust FlightHub the most. FlightHub has received a user feedback score of 3 out of 3 stars (3 being the best), meaning they have been trusted the most by Cheapflights users looking for Boston-Winnipeg flight deals. Provider user feedback score is based on Cheapflights searches over the past month and is updated monthly.

Best time to book a flight from Boston to Winnipeg

Have a flexible travel schedule? Discover the best time to fly to Winnipeg from Boston with our price prediction graph.
Estimated round-trip price
Rates are based on past data. Find the cheapest month and day to book your flight based on your travel requirements, then search for cheap deals.

Cheapflights Insights

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

How far ahead should I book a flight from Boston to Winnipeg?

Use this chart to determine the optimal time to book a round-trip flight from Boston to Winnipeg. Price data was last updated on October 17, 2025.

Booking 63 days in advance of your planned departure date is, on average, the best time to get cheap flights from Boston to Winnipeg. The general trend is that the closer you book to the departure date, the more expensive your flight will be.

What is the cheapest month to book a flight from Boston to Winnipeg?

Currently, July is the cheapest month in which you can book a flight from Boston to Winnipeg (average of $128). Flying from Boston to Winnipeg in April is currently the most expensive (average of $432). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

What is the cheapest time of day to fly from BOS to YWG?

Find hourly flight availability from Boston to Winnipeg. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated octubre 23, 2025.

It’s typically best to fly out from Boston to Winnipeg at noon. Doing so could potentially save you 26% on the flight price compared to flying in the afternoon, which is usually more expensive.

Reviews of airlines servicing Winnipeg

Get insights into the airlines that provide service to Winnipeg. Read reviews, discover amenities, and learn about the overall travel experience offered by airlines. Use this information to make informed decisions when choosing an airline for your flight to Winnipeg. Reviews last updated octubre 23, 2025.
Peruse reviews from past customers who have flown with Porter Airlines, Delta, and United Airlines from Boston to Winnipeg to help guide your decision. You can also see how each airline stacks up in terms of entertainment options, comfort, food, crew/service, and boarding process.
Porter Airlines
8.0
Very good
383 reviews

Food

7.6

Entertainment

7.0

Boarding

8.2

Crew

8.6

Comfort

8.0

Overall

8.0

Reviews

1 / 20
2.0
Mediocre

Anonymous,Sep 2025

YYZ - OPO

Very disappointing, booked with Porter airlines and changed to Air Transit last minute. Old plane, cramped seating, even the aisle was the narrowest I’ve ever seen. Very uncomfortable flight. Full meal at 130 am and only a small piece of banana bread in the morning… should be opposite.
Porter Airlines
8.0
Very good
383 reviews
Porter Airlines
8.0
Very good
383 reviews

Food

7.6

Entertainment

7.0

Boarding

8.2

Crew

8.6

Comfort

8.0

Overall

8.0

Reviews

1 / 20
2.0
Mediocre

Anonymous,Sep 2025

YYZ - OPO

Very disappointing, booked with Porter airlines and changed to Air Transit last minute. Old plane, cramped seating, even the aisle was the narrowest I’ve ever seen. Very uncomfortable flight. Full meal at 130 am and only a small piece of banana bread in the morning… should be opposite.
Delta
7.9
Good
7,981 reviews
Porter Airlines
8.0
Very good
383 reviews

Food

7.6

Entertainment

7.0

Boarding

8.2

Crew

8.6

Comfort

8.0

Overall

8.0

Reviews

1 / 20
2.0
Mediocre

Anonymous,Sep 2025

YYZ - OPO

Very disappointing, booked with Porter airlines and changed to Air Transit last minute. Old plane, cramped seating, even the aisle was the narrowest I’ve ever seen. Very uncomfortable flight. Full meal at 130 am and only a small piece of banana bread in the morning… should be opposite.
United Airlines
7.4
Good
8,992 reviews
Porter Airlines
8.0
Very good
383 reviews

Food

7.6

Entertainment

7.0

Boarding

8.2

Crew

8.6

Comfort

8.0

Overall

8.0

Reviews

1 / 20
2.0
Mediocre

Anonymous,Sep 2025

YYZ - OPO

Very disappointing, booked with Porter airlines and changed to Air Transit last minute. Old plane, cramped seating, even the aisle was the narrowest I’ve ever seen. Very uncomfortable flight. Full meal at 130 am and only a small piece of banana bread in the morning… should be opposite.
Air Canada
7.1
Good
10,348 reviews
Porter Airlines
8.0
Very good
383 reviews

Food

7.6

Entertainment

7.0

Boarding

8.2

Crew

8.6

Comfort

8.0

Overall

8.0

Reviews

1 / 20
2.0
Mediocre

Anonymous,Sep 2025

YYZ - OPO

Very disappointing, booked with Porter airlines and changed to Air Transit last minute. Old plane, cramped seating, even the aisle was the narrowest I’ve ever seen. Very uncomfortable flight. Full meal at 130 am and only a small piece of banana bread in the morning… should be opposite.

Related info for your journey

Find useful and relevant information for your journey from Boston to Winnipeg. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.

  • What are the cheapest airlines flying from Boston to Winnipeg round-trip?

    Currently priced at $134, Air Canada will fly you from Boston to Winnipeg and back. In addition to Air Canada, many other airlines offer competitively priced options for your trip. Search Cheapflights for deals from United Airlines and Delta - these airlines can fly you to your destination from $172 and $228, respectively. Air Canada is currently priced 69% below the average price you’ll pay for this route.

  • Can I find deals for flights from Boston to Winnipeg that include hotel bookings?

    Yes. In addition to deals on Boston to Winnipeg flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from Boston to Winnipeg?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Boston to Winnipeg.

  • Can I find deals for business class flights from Boston to Winnipeg?

    Yes. Cheapflights offers flight deals from Boston to Winnipeg by cabin class. In addition to browsing deals, you can also filter by cabin class on the search results page after making a search.

  • What is the cheapest month to book a flight from Boston to Winnipeg?

    Currently, July is the cheapest month in which you can book a flight from Boston to Winnipeg (average of $128). Flying from Boston to Winnipeg in April is currently the most expensive (average of $432). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

See more FAQs

Traveling to a place near Winnipeg?

Book flights to Winnipeg if you plan to visit one of these locations
Portage la Prairie

Browse thousands of different options on Cheapflights for your next trip

Toggle through the tabs below to find thousands of options on Cheapflights for your next trip.

Complete your trip

Complete your trip to Winnipeg by adding a car rental and/or hotel reservation to your travel itinerary.
Winnipeg car rentals
Winnipeg Airport car rentals

Top 4 airlines flying from Boston to Winnipeg

Discover the top 4 airlines that operate flights from Boston to Winnipeg. Compare their services, reliability, and customer satisfaction ratings to choose the airline that best suits your travel preferences and needs. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated octubre 23, 2025.
AirlineCheapestAverageFlexibilityOn-time
Air CanadaCheapest$134Average$488FlexibilityNo cancel feeOn-time67%
United AirlinesCheapest$172Average$569FlexibilityNo cancel feeOn-time69%
DeltaCheapest$228Average$420FlexibilityNo cancel feeOn-timeN/A
Porter AirlinesCheapest$335Average$438FlexibilityNo cancel feeOn-time52%

100% Free

Cheapflights is completely free to use, so you can start saving the moment you arrive.

Book with Flexibility

Our users can plan ahead with confidence and find flights with no change fees

Travel Smart

Millions of people come to us for their flight needs every year. We help make travel planning easy by providing useful insights and data-driven graphs that can inform your decisions.