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Winnipeg

$150+ 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 6/11. Fares are subject to change and may not be available on all flights or dates of travel.
BOS — YWG
Jun 9 — Jun 161
Tue 6/9
Tue 6/16
1 adult, Economy
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1. Tell us where you want to go

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Cheap 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 May 10, 2026.

This Gotogate deal was found by Cheapflights users on 5/6. 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 Gotogate is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 7/810:05 am
BOS
-
YWG
1 stop6h 14m
Porter Airlines
Wed 7/159:20 am
YWG
-
BOS
1 stop7h 15m
Porter Airlines
Deal found 5/6$324
This Booking.com deal was found by Cheapflights users on 5/9. 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 Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/1710:05 am
BOS
-
YWG
1 stop6h 14m
Porter Airlines
Tue 9/299:20 am
YWG
-
BOS
1 stop7h 15m
Porter Airlines
Deal found 5/9$330
This Justfly.com deal was found by Cheapflights users on 5/6. 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 Justfly.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/1310:05 am
BOS
-
YWG
1 stop6h 14m
Porter Airlines
Wed 10/219:20 am
YWG
-
BOS
1 stop7h 15m
Porter Airlines
Deal found 5/6$336
This Booking.com deal was found by Cheapflights users on 5/9. 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 Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 6/107:10 am
BOS
-
YWG
2 stops11h 48m
Porter Airlines
Tue 6/239:20 am
YWG
-
BOS
1 stop7h 15m
Porter Airlines
Deal found 5/9$338
This Booking.com deal was found by Cheapflights users on 5/7. 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 Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 6/67:10 am
BOS
-
YWG
2 stops11h 53m
Porter Airlines
Sun 6/79:20 am
YWG
-
BOS
1 stop7h 15m
Porter Airlines
Deal found 5/7$339
This FlightHub deal was found by Cheapflights users on 5/8. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 7/1010:05 am
BOS
-
YWG
1 stop6h 14m
Porter Airlines
Wed 7/159:20 am
YWG
-
BOS
1 stop7h 15m
Porter Airlines
Deal found 5/8$344
This FlightHub deal was found by Cheapflights users on 5/8. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 7/97:10 am
BOS
-
YWG
2 stops11h 48m
Porter Airlines
Wed 7/159:20 am
YWG
-
BOS
1 stop7h 15m
Porter Airlines
Deal found 5/8$346

Find 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 May 10, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$324
(Gotogate)

One-way from

$150
(Mytrip)

Popular in

January

Cheapest in

August

Average price

$431
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. 22% potential increase in price ($150 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 4% potential price decrease ($22 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in May 2026
Search Deals

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 May 10, 2026.
Use the filters below to find and compare flights from Boston to Winnipeg that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip

BostonWinnipeg

BOS - YWG

BOSYWG

Boston Logan Intl

Thu 9/17

10:05 am-3:19 pm

1 stop6h 14m

Winnipeg

Tue 9/29

9:20 am-5:35 pm

1 stop7h 15m

$330

BostonWinnipeg

BOS - YWG

BOSYWG

Boston Logan Intl

Mon 8/17

10:05 am-3:19 pm

1 stop6h 14m

Winnipeg

Fri 8/21

9:20 am-5:35 pm

1 stop7h 15m

$338
Quickest round-trip

BostonWinnipeg

BOS - YWG

BOSYWG

Boston Logan Intl

Thu 10/22

10:40 am-3:09 pm

1 stop5h 29m

Winnipeg

Sat 10/24

8:10 am-2:41 pm

1 stop5h 31m

$356

BostonWinnipeg

BOS - YWG

BOSYWG

Boston Logan Intl

Sat 6/6

7:10 am-6:03 pm

2 stops11h 53m

Winnipeg

Sun 6/7

9:20 am-5:35 pm

1 stop7h 15m

$361

BostonWinnipeg

BOS - YWG

BOSYWG

Boston Logan Intl

Wed 10/14

10:05 am-5:58 pm

2 stops8h 53m

Winnipeg

Wed 10/21

9:20 am-5:35 pm

1 stop7h 15m

$372

BostonWinnipeg

BOS - YWG

BOSYWG

Boston Logan Intl

Wed 7/8

7:10 am-5:58 pm

2 stops11h 48m

Winnipeg

Thu 7/16

9:20 am-5:35 pm

1 stop7h 15m

$383

BostonWinnipeg

BOS - YWG

BOSYWG

Boston Logan Intl

Wed 7/8

7:10 am-5:58 pm

2 stops11h 48m

Winnipeg

Wed 7/15

9:20 am-5:35 pm

1 stop7h 15m

$383

BostonWinnipeg

BOS - YWG

BOSYWG

Boston Logan Intl

Wed 7/8

7:10 am-5:58 pm

2 stops11h 48m

Winnipeg

Fri 7/17

9:20 am-5:35 pm

1 stop7h 15m

$383
Cheapest one-way

BostonWinnipeg

BOS - YWG

BOSYWG

Boston Logan Intl

Thu 6/11

7:10 am-5:58 pm

2 stops11h 48m

$150

BostonWinnipeg

BOS - YWG

BOSYWG

Boston Logan Intl

Sun 9/27

7:10 am-4:54 pm

1 stop10h 44m

$155

Flights are sorted by cheapest round-trip flights first.

Deals found on 5/6

Showing 1-10 of 20 resultsSorted by cheapest first
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 May.
ProviderPrice AccuracyTrust Score*
ExpediaPrice Accuracy1 starTrust Score*3 stars
FlightHubPrice 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

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

Currently, August is the cheapest month in which you can book a flight from Boston to Winnipeg (average of $420). Flying from Boston to Winnipeg in January is currently the most expensive (average of $774). 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.

How much does it cost to fly round-trip from Boston to Winnipeg?

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 May 10, 2026.
Peruse reviews from past customers who have flown with Porter Airlines,Delta, andUnited 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
437 reviews

Overall

8.0

Boarding

8.2

Crew

8.6

Food

7.6

Entertainment

7.0

Comfort

8.0

Reviews

1 / 20
10.0
Excellent

John,Mar 2026

YYZ - PVR

I'm 6ft 4in. The seats don't have enough room. But was a good flight.
Porter Airlines
8.0
Very good
437 reviews
Porter Airlines
8.0
Very good
437 reviews

Overall

8.0

Boarding

8.2

Crew

8.6

Food

7.6

Entertainment

7.0

Comfort

8.0

Reviews

1 / 20
10.0
Excellent

John,Mar 2026

YYZ - PVR

I'm 6ft 4in. The seats don't have enough room. But was a good flight.
Delta
7.9
Good
8,453 reviews
Porter Airlines
8.0
Very good
437 reviews

Overall

8.0

Boarding

8.2

Crew

8.6

Food

7.6

Entertainment

7.0

Comfort

8.0

Reviews

1 / 20
10.0
Excellent

John,Mar 2026

YYZ - PVR

I'm 6ft 4in. The seats don't have enough room. But was a good flight.
United Airlines
7.4
Good
9,694 reviews
Porter Airlines
8.0
Very good
437 reviews

Overall

8.0

Boarding

8.2

Crew

8.6

Food

7.6

Entertainment

7.0

Comfort

8.0

Reviews

1 / 20
10.0
Excellent

John,Mar 2026

YYZ - PVR

I'm 6ft 4in. The seats don't have enough room. But was a good flight.
Air Canada
7.1
Good
11,013 reviews
Porter Airlines
8.0
Very good
437 reviews

Overall

8.0

Boarding

8.2

Crew

8.6

Food

7.6

Entertainment

7.0

Comfort

8.0

Reviews

1 / 20
10.0
Excellent

John,Mar 2026

YYZ - PVR

I'm 6ft 4in. The seats don't have enough room. But was a good flight.

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.

  • How long is the flight from Boston to Winnipeg?

    Departing from Boston to Winnipeg will take you 5h 29m. The distance between Boston and Winnipeg is about 1350 mi. When browsing for deals, the options you’ll see will be for both nonstop flights and flights with stops.

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

    Currently priced at $143, Delta will fly you from Boston to Winnipeg and back. In addition to Delta, many other airlines offer competitively priced options for your trip. Search Cheapflights for deals from United Airlines and Air Canada - these airlines can fly you to your destination from $149 and $194, respectively. Delta is currently priced 73% 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, August is the cheapest month in which you can book a flight from Boston to Winnipeg (average of $420). Flying from Boston to Winnipeg in January is currently the most expensive (average of $774). 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 May 10, 2026.
AirlineCheapestAverageFlexibilityOn-time
DeltaCheapest$143Average$420FlexibilityNo cancel feeOn-timeN/A
United AirlinesCheapest$149Average$644FlexibilityNo cancel feeOn-time69%
Air CanadaCheapest$194Average$508FlexibilityNo cancel feeOn-time67%
Porter AirlinesCheapest$409Average$493FlexibilityNo cancel feeOn-time52%

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