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$158+ Cheap flights from Winnipeg (YWG) to Boston (BOS)

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 8/12. Fares are subject to change and may not be available on all flights or dates of travel.
YWG — BOS
Jun 6 — Jun 131
Sat 6/6
Sat 6/13
1 adult, Economy
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Cheap flight deals from Winnipeg to Boston

Cheapest flights from Winnipeg to Boston
Explore the most affordable flight options available from Winnipeg to Boston. Find the lowest fares from popular airlines and budget airlines, with prices last updated on May 7, 2026.

This Kiwi.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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 6/311:40 am
YWG
-
BOS
1 stop6h 25m
Porter Airlines
Wed 6/1010:05 am
BOS
-
YWG
1 stop6h 14m
Porter Airlines
Deal found 5/6$276
This Delta deal was found by Cheapflights users on 5/3. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/1212:46 pm
YWG
-
BOS
1 stop10h 12m
Delta
Mon 8/175:51 am
BOS
-
YWG
1 stop10h 17m
Delta
Deal found 5/3$279
This Booking.com deal was found by Cheapflights users on 5/5. 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.
Fri 8/289:20 am
YWG
-
BOS
1 stop7h 15m
Porter Airlines
Tue 9/87:10 am
BOS
-
YWG
2 stops11h 48m
Porter Airlines
Deal found 5/5$310
This Air Canada deal was found by Cheapflights users on 5/4. 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.
Mon 10/1910:50 am
YWG
-
BOS
1 stop6h 17m
Air Canada
Fri 10/236:00 am
BOS
-
YWG
1 stop6h 12m
Air Canada
Deal found 5/4$314
This Delta deal was found by Cheapflights users on 5/3. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 10/198:00 am
YWG
-
BOS
1 stop10h 11m
Delta
Fri 10/233:00 pm
BOS
-
YWG
1 stop9h 34m
Delta
Deal found 5/3$318
This FlightHub deal was found by Cheapflights users on 5/3. 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.
Wed 8/129:20 am
YWG
-
BOS
1 stop7h 15m
Porter Airlines
Mon 8/1710:05 am
BOS
-
YWG
1 stop10h 44m
Porter Airlines
Deal found 5/3$320
This Air Canada deal was found by Cheapflights users on 5/5. 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.
Fri 8/283:20 pm
YWG
-
BOS
1 stop6h 18m
Air Canada
Tue 9/86:00 am
BOS
-
YWG
1 stop6h 12m
Air Canada
Deal found 5/5$323
This FlightHub deal was found by Cheapflights users on 5/4. 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.
Tue 5/269:20 am
YWG
-
BOS
1 stop7h 15m
Porter Airlines
Thu 6/410:05 am
BOS
-
YWG
1 stop6h 14m
Porter Airlines
Deal found 5/4$333

Find flight deals from Winnipeg to Boston

Discover tips and strategies to find the most affordable flight options for your journey from Winnipeg (YWG) to Boston (BOS). 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 7, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$276
(Kiwi.com)

One-way from

$158
(Air Canada)

Popular in

April

Cheapest in

June

Average price

$528
Provider with most accurate pricing for Winnipeg-Boston Logan Intl flight deals.
Search Deals
Provider most trusted by Cheapflights users for Winnipeg-Boston Logan Intl flights.
Search Deals
From Winnipeg to Boston Logan Intl
Search Deals
One-way flight from Winnipeg to Boston Logan Intl
Search Deals
Highest demand for flights based on searches. 18% potential increase in price ($113 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 5% potential price decrease ($26 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 Winnipeg to Boston 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 7, 2026.
Use the filters below to find and compare flights from Winnipeg to Boston that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip
Quickest round-trip

WinnipegBoston

YWG - BOS

YWGBOS

Winnipeg

Wed 6/3

11:40 am-7:05 pm

1 stop6h 25m

Boston Logan Intl

Wed 6/10

10:05 am-3:19 pm

1 stop6h 14m

$276

WinnipegBoston

YWG - BOS

YWGBOS

Winnipeg

Wed 8/12

12:46 pm-11:58 pm

1 stop10h 12m

Boston Logan Intl

Mon 8/17

5:51 am-3:08 pm

1 stop10h 17m

$279

WinnipegBoston

YWG - BOS

YWGBOS

Winnipeg

Mon 10/19

8:00 am-7:11 pm

1 stop10h 11m

Boston Logan Intl

Fri 10/23

3:00 pm-11:34 pm

1 stop9h 34m

$318

WinnipegBoston

YWG - BOS

YWGBOS

Winnipeg

Wed 8/12

9:20 am-5:35 pm

1 stop7h 15m

Boston Logan Intl

Mon 8/17

10:05 am-7:49 pm

1 stop10h 44m

$320

WinnipegBoston

YWG - BOS

YWGBOS

Winnipeg

Mon 10/19

5:10 am-6:07 pm

2 stops11h 57m

Boston Logan Intl

Fri 10/23

6:00 am-11:12 am

1 stop6h 12m

$322

WinnipegBoston

YWG - BOS

YWGBOS

Winnipeg

Thu 6/18

5:41 pm-11:57 pm

1 stop5h 16m

Boston Logan Intl

Thu 6/25

8:15 am-4:51 pm

1 stop9h 36m

$360

WinnipegBoston

YWG - BOS

YWGBOS

Winnipeg

Thu 5/28

9:20 am-5:35 pm

1 stop7h 15m

Boston Logan Intl

Fri 6/5

10:05 am-3:19 pm

1 stop6h 14m

$364

WinnipegBoston

YWG - BOS

YWGBOS

Winnipeg

Tue 5/26

9:20 am-8:55 pm

2 stops10h 35m

Boston Logan Intl

Fri 6/5

10:05 am-3:19 pm

1 stop6h 14m

$367
Cheapest one-way

WinnipegBoston

YWG - BOS

YWGBOS

Winnipeg

Mon 6/15

9:20 am-5:35 pm

1 stop7h 15m

$188

WinnipegBoston

YWG - BOS

YWGBOS

Winnipeg

Fri 6/26

3:20 pm-10:38 pm

1 stop6h 18m

$200

Flights are sorted by cheapest round-trip flights first.

Deals found on 5/7

Showing 1-10 of 18 resultsSorted by cheapest first
1
2

Compare providers for flights from Winnipeg to Boston

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 Winnipeg to Boston in May.
ProviderPrice AccuracyTrust Score*
ExpediaPrice Accuracy1 starTrust Score*3 stars
FlightHubPrice 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 Winnipeg-Boston flights, users find the pricing of FlightHub to be most consistent on Cheapflights vs. FlightHub Users can find the same prices on Winnipeg-Boston flight deals on Cheapflights vs. FlightHub >95% of the time. Price accuracy is based on data collected from Winnipeg-Boston flight searches over the past month and is updated monthly.
  • Most trusted provider: When it comes to deals on Winnipeg-Boston 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 Winnipeg-Boston 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 Winnipeg to Boston

Have a flexible travel schedule? Discover the best time to fly to Boston from Winnipeg 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 Winnipeg to Boston

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

The best time to book flights from Winnipeg to Boston is 15 days before your desired departure date. The cost of your flight will likely increase significantly if you book two weeks in advance of your flight.

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

Currently, June is the cheapest month in which you can book a flight from Winnipeg to Boston (average of $290). Flying from Winnipeg to Boston in April is currently the most expensive (average of $788). 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 Winnipeg to Boston?

Reviews of airlines servicing Boston

Get insights into the airlines that provide service to Boston. 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 Boston. Reviews last updated May 7, 2026.
Read reviews from past customers who have flown United Airlines and Air Canada from Winnipeg to Boston. Users can see the overall rating for each airline as well as how each is rated in terms of entertainment options, comfort, food, crew/service, and boarding process.
United Airlines
7.4
Good
9,690 reviews

Comfort

7.3

Boarding

7.7

Entertainment

7.1

Overall

7.4

Crew

8.1

Food

6.6

Reviews

1 / 20
8.0
Excellent

Anonymous,Apr 2026

DFW - EWR

The flight was on time. Crew was friendly. Will fly again. The seats was comfortable.
United Airlines
7.4
Good
9,690 reviews
United Airlines
7.4
Good
9,690 reviews

Comfort

7.3

Boarding

7.7

Entertainment

7.1

Overall

7.4

Crew

8.1

Food

6.6

Reviews

1 / 20
8.0
Excellent

Anonymous,Apr 2026

DFW - EWR

The flight was on time. Crew was friendly. Will fly again. The seats was comfortable.
Air Canada
7.1
Good
11,004 reviews
United Airlines
7.4
Good
9,690 reviews

Comfort

7.3

Boarding

7.7

Entertainment

7.1

Overall

7.4

Crew

8.1

Food

6.6

Reviews

1 / 20
8.0
Excellent

Anonymous,Apr 2026

DFW - EWR

The flight was on time. Crew was friendly. Will fly again. The seats was comfortable.

Related info for your journey

Find useful and relevant information for your journey from Winnipeg to Boston. 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 Winnipeg to Boston?

    For as low as $276, Porter Airlines can have you in Boston from Winnipeg in 6h 25m. Airlines will cover a distance of 1350 mi. This flight may include one or multiple stops.

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

    According to our current data, United Airlines ($168), and Air Canada ($215) offers the cheapest pricing from Winnipeg to Boston. United Airlines is 66% cheaper than the average price of flights available within the next 90 days to this destination.

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

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

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

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

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

    Yes. Cheapflights offers flight deals from Winnipeg to Boston 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 Winnipeg to Boston?

    Currently, June is the cheapest month in which you can book a flight from Winnipeg to Boston (average of $290). Flying from Winnipeg to Boston in April is currently the most expensive (average of $788). 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 Boston?

Book flights to Boston if you plan to visit one of these locations
Medford
Cambridge
Concord
Hampton Beach
Watertown
Brockton
Seekonk
Cranston
Chelsea
Warwick
Peabody
Seabrook
York Beach
Londonderry
Swansea
Old Orchard Beach
Quincy
Waltham
Lowell
Braintree

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.

Top 2 airlines flying from Winnipeg to Boston

Discover the top 2 airlines that operate flights from Winnipeg to Boston. 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 7, 2026.
AirlineCheapestAverageFlexibilityOn-time
United AirlinesCheapest$168Average$455FlexibilityNo cancel feeOn-time69%
Air CanadaCheapest$215Average$596FlexibilityNo cancel feeOn-time67%

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