HomeSearch by dateVacation packagesHotelsFlight dealsCar rentalTravel tips & news
Boston

$175+ 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 8/5. Fares are subject to change and may not be available on all flights or dates of travel.
YWG — BOS
Aug 20 — Aug 271
Thu 8/20
Thu 8/27
1 adult, Economy
We work with more than 300 partners to bring you better travel deals

Find cheap flights from Winnipeg to Boston 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.

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 July 21, 2026.

This SmartFares deal was found by Cheapflights users on 7/18. 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 SmartFares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/17:55 am
YWG
-
BOS
1 stop5h 46m
Air Canada
Tue 9/810:50 am
BOS
-
YWG
1 stop8h 22m
Air Canada
Deal found 7/18$292
This Air Canada deal was found by Cheapflights users on 7/19. 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.
Sat 8/295:00 am
YWG
-
BOS
1 stop5h 52m
Air Canada
Sun 9/66:00 am
BOS
-
YWG
1 stop6h 15m
Air Canada
Deal found 7/19$301
This Air Canada deal was found by Cheapflights users on 7/18. 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.
Wed 8/52:05 pm
YWG
-
BOS
1 stop7h 33m
Air Canada
Sat 8/226:00 am
BOS
-
YWG
1 stop6h 15m
Air Canada
Deal found 7/18$302
This Air Canada deal was found by Cheapflights users on 7/19. 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 10/23:20 pm
YWG
-
BOS
1 stop6h 20m
Air Canada
Mon 10/56:00 am
BOS
-
YWG
1 stop6h 12m
Air Canada
Deal found 7/19$303
This FlightHub deal was found by Cheapflights users on 7/19. 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.
Sat 8/2912:15 pm
YWG
-
BOS
1 stop6h 00m
Porter Airlines
Sun 9/67:10 am
BOS
-
YWG
2 stops11h 48m
Porter Airlines
Deal found 7/19$304
This Justfly.com deal was found by Cheapflights users on 7/19. 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.
Mon 8/3112:15 pm
YWG
-
BOS
1 stop5h 35m
Porter Airlines
Fri 9/1110:05 am
BOS
-
YWG
1 stop6h 14m
Porter Airlines
Deal found 7/19$311
This Kiwi.com deal was found by Cheapflights users on 7/17. 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.
Tue 9/112:15 pm
YWG
-
BOS
1 stop5h 20m
Porter Airlines
Tue 9/810:05 am
BOS
-
YWG
1 stop6h 14m
Porter Airlines
Deal found 7/17$319
This Kiwi.com deal was found by Cheapflights users on 7/18. 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.
Sat 8/1512:15 pm
YWG
-
BOS
1 stop6h 00m
Porter Airlines
Sat 8/227:10 am
BOS
-
YWG
2 stops11h 48m
Porter Airlines
Deal found 7/18$324

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 July 21, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$292
(SmartFares)

One-way from

$175
(Air Canada)

Popular in

April

Cheapest in

August

Average price

$440
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. 16% potential increase in price ($109 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 6% potential price decrease ($34 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in July 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 July 21, 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

WinnipegBoston

YWG - BOS

YWGBOS

Winnipeg

Fri 10/2

3:20 pm-10:40 pm

1 stop6h 20m

Boston Logan Intl

Mon 10/5

6:00 am-11:12 am

1 stop6h 12m

$303
Quickest round-trip

WinnipegBoston

YWG - BOS

YWGBOS

Winnipeg

Tue 9/1

12:15 pm-6:35 pm

1 stop5h 20m

Boston Logan Intl

Tue 9/8

10:05 am-3:19 pm

1 stop6h 14m

$319

WinnipegBoston

YWG - BOS

YWGBOS

Winnipeg

Sat 8/29

9:20 am-8:55 pm

2 stops10h 35m

Boston Logan Intl

Sun 9/6

10:05 am-3:19 pm

1 stop6h 14m

$326

WinnipegBoston

YWG - BOS

YWGBOS

Winnipeg

Fri 9/18

12:46 pm-11:59 pm

1 stop10h 13m

Boston Logan Intl

Tue 9/22

7:05 am-3:08 pm

1 stop9h 03m

$331

WinnipegBoston

YWG - BOS

YWGBOS

Winnipeg

Thu 8/6

5:00 am-11:52 am

1 stop5h 52m

Boston Logan Intl

Sun 8/9

6:00 am-11:15 am

1 stop6h 15m

$355

WinnipegBoston

YWG - BOS

YWGBOS

Winnipeg

Thu 8/27

5:00 am-2:41 pm

2 stops8h 41m

Boston Logan Intl

Wed 9/2

5:45 am-4:30 pm

2 stops11h 45m

$368

WinnipegBoston

YWG - BOS

YWGBOS

Winnipeg

Fri 10/9

9:20 am-6:35 pm

1 stop8h 15m

Boston Logan Intl

Sun 10/11

10:05 am-3:19 pm

1 stop6h 14m

$372

WinnipegBoston

YWG - BOS

YWGBOS

Winnipeg

Sat 9/26

12:41 pm-11:59 pm

1 stop10h 18m

Boston Logan Intl

Tue 9/29

5:55 am-11:51 am

1 stop6h 56m

$394
Cheapest one-way

WinnipegBoston

YWG - BOS

YWGBOS

Winnipeg

Wed 8/5

2:05 pm-10:38 pm

1 stop7h 33m

$175

WinnipegBoston

YWG - BOS

YWGBOS

Winnipeg

Thu 8/13

2:00 pm-1:11 am

1 stop10h 11m

$194

Flights are sorted by cheapest round-trip flights first.

Deals found on 7/19

Showing 1-10 of 19 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 July.
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

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

Currently, August is the cheapest month in which you can book a flight from Winnipeg to Boston (average of $348). Flying from Winnipeg to Boston in April is currently the most expensive (average of $915). 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 July 21, 2026.
Read reviews from past customers who have flown 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.
Air Canada
7.1
Good
11,361 reviews

Boarding

7.3

Food

6.3

Entertainment

6.8

Overall

7.1

Crew

7.8

Comfort

7.1

Reviews

1 / 20
6.0
Good

Paula,Mar 2026

YVR - PSP

Everything was OK, but we waited on the tarmac for an hour and 20 minutes after landing because there was no available gate. This is a daily occurrence at the Palm Springs airport, and happens with Air Canada and WestJet constantly.
Air Canada
7.1
Good
11,361 reviews
Air Canada
7.1
Good
11,361 reviews

Boarding

7.3

Food

6.3

Entertainment

6.8

Overall

7.1

Crew

7.8

Comfort

7.1

Reviews

1 / 20
6.0
Good

Paula,Mar 2026

YVR - PSP

Everything was OK, but we waited on the tarmac for an hour and 20 minutes after landing because there was no available gate. This is a daily occurrence at the Palm Springs airport, and happens with Air Canada and WestJet constantly.

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 $302, Air Canada can have you in Boston from Winnipeg in 7h 33m. Airlines will cover a distance of 1350 mi. This flight may include one or multiple stops.

  • What is the cheapest airline to fly from Winnipeg to Boston round-trip?

    According to our current data, Air Canada ($215), offers the cheapest pricing from Winnipeg to Boston. Air Canada is 60% cheaper than the average price of flights available within the next 90 days to this destination.

  • What are the cheapest airlines to fly from Winnipeg to Boston one-way?

    The cheapest airlines for a one-way flight from Winnipeg to Boston are United Airlines ($171), Air Canada ($183), and Delta ($197).

  • 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, August is the cheapest month in which you can book a flight from Winnipeg to Boston (average of $348). Flying from Winnipeg to Boston in April is currently the most expensive (average of $915). 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
Waltham
Cambridge
Concord
Randolph
Brockton
Seekonk
Hampton Beach
Cranston
Dedham
Warwick
Peabody
Auburn
York Beach
Chelsea
Londonderry
Swansea
Fitchburg
North Falmouth
Braintree
Sandwich

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 airline flying from Winnipeg to Boston

Discover the top airline 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 July 21, 2026.
AirlineCheapestAverageFlexibilityOn-time
Air CanadaCheapest$215Average$642FlexibilityNo cancel feeOn-time67%

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.