Boston

$240+ Cheap flights from Winnipeg (YWG) to Boston (BOS)

YWG — BOS
Dec 9 — Dec 161
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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

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Cheap flight deals from Winnipeg to Boston

Cheapest flights from Winnipeg to Boston

Mon 12/711:00 am -
1 stop8h 10m
Sun 12/131:15 pm -
1 stop7h 24m
Deal found 11/6$425
Sun 12/1312:40 pm -
2 stops8h 54m
Wed 1/61:15 pm -
1 stop6h 00m
Deal found 11/5$436
Thu 12/311:00 am -
1 stop22h 10m
Tue 12/81:15 pm -
1 stop5h 59m
Deal found 11/5$441
Thu 12/1012:40 pm -
2 stops8h 54m
Sun 12/131:15 pm -
1 stop7h 24m
Deal found 11/7$447
Sat 12/511:00 am -
1 stop8h 10m
Sat 12/121:15 pm -
1 stop5h 59m
Deal found 11/5$452
Wed 12/912:40 pm -
2 stops8h 54m
Sun 12/131:15 pm -
1 stop7h 24m
Deal found 11/7$465
Thu 12/1011:00 am -
1 stop8h 10m
Sun 12/139:50 am -
1 stop9h 20m
Deal found 11/7$493

Find flight deals from Winnipeg to Boston

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$425
(Kiwi.com)

One-way from

$240
(Kiwi.com)

Popular in

April

Cheapest in

August

Average price

$582
Provider with most accurate pricing for Winnipeg-Boston Logan Intl flight deals.
Provider most trusted by Cheapflights users for Winnipeg-Boston Logan Intl flights.
From Winnipeg to Boston Logan Intl
One-way flight from Winnipeg to Boston Logan Intl
Highest demand for flights based on searches. 15% potential increase in price ($96 potential increase over avg. RT price).
Cheapest flight prices on average. 6% potential price decrease ($35 potential savings vs. average RT price).
Average for round-trip flights in November 2026

Cheapflights Fare Finder

 
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 Winnipeg - BOS Boston Logan Intl

YWGBOS

Winnipeg

Fri 2/5

7:00 am-9:29 am

2 stops26h 29m

Boston Logan Intl

Wed 12/31

12:00 am-11:00 pm

Nonstop0h 00m

$240

WinnipegBoston

YWG Winnipeg - BOS Boston Logan Intl

YWGBOS

Winnipeg

Wed 12/9

9:35 pm-10:13 am

3 stops36h 38m

Boston Logan Intl

Wed 12/31

12:00 am-11:00 pm

Nonstop0h 00m

$243

WinnipegBoston

YWG Winnipeg - BOS Boston Logan Intl

YWGBOS

Winnipeg

Tue 12/8

9:35 pm-9:39 am

3 stops36h 04m

Boston Logan Intl

Wed 12/31

12:00 am-11:00 pm

Nonstop0h 00m

$245
Quickest round-trip

WinnipegBoston

YWG Winnipeg - BOS Boston Logan Intl

YWGBOS

Winnipeg

Wed 12/2

11:00 am-7:10 pm

1 stop8h 10m

Boston Logan Intl

Wed 12/31

12:00 am-11:00 pm

Nonstop0h 00m

$251

WinnipegBoston

YWG Winnipeg - BOS Boston Logan Intl

YWGBOS

Winnipeg

Tue 12/8

12:40 pm-9:34 pm

2 stops8h 54m

Boston Logan Intl

Wed 12/31

12:00 am-11:00 pm

Nonstop0h 00m

$259

WinnipegBoston

YWG Winnipeg - BOS Boston Logan Intl

YWGBOS

Winnipeg

Wed 12/9

12:40 pm-9:34 pm

2 stops8h 54m

Boston Logan Intl

Wed 12/31

12:00 am-11:00 pm

Nonstop0h 00m

$266

WinnipegBoston

YWG Winnipeg - BOS Boston Logan Intl

YWGBOS

Winnipeg

Thu 11/19

9:35 pm-7:41 am

2 stops34h 06m

Boston Logan Intl

Wed 12/31

12:00 am-11:00 pm

Nonstop0h 00m

$289

WinnipegBoston

YWG Winnipeg - BOS Boston Logan Intl

YWGBOS

Winnipeg

Thu 4/8

11:40 am-9:35 pm

2 stops8h 55m

Boston Logan Intl

Mon 4/12

8:00 am-6:11 pm

2 stops11h 11m

$427

WinnipegBoston

YWG Winnipeg - BOS Boston Logan Intl

YWGBOS

Winnipeg

Wed 3/3

12:40 pm-9:34 pm

2 stops8h 54m

Boston Logan Intl

Wed 3/10

1:15 pm-7:19 pm

1 stop6h 04m

$432

WinnipegBoston

YWG Winnipeg - BOS Boston Logan Intl

YWGBOS

Winnipeg

Wed 3/3

12:40 pm-9:34 pm

2 stops8h 54m

Boston Logan Intl

Mon 3/8

1:15 pm-7:19 pm

1 stop6h 04m

$432

Flights are sorted by cheapest round-trip flights first.

Deals found on 11/4

Showing 1-10 of 16 resultsSorted by cheapest first
1
2

Compare providers for flights from Winnipeg to Boston

Use the table below to compare price accuracy, trust ratings, and cancellation policies for each provider offering flight deals from Winnipeg to Boston in November.
ProviderPrice AccuracyTrust Score*
ExpediaPrice Accuracy1 starTrust Score*3 stars
FlightHubPrice Accuracy3 starsTrust Score*3 stars
eDreamsPrice Accuracy2 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

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?

Airfare is typical for this route at the moment.

Winnipeg to Boston flights typically cost between $380 and $591 in December.
The cheapest round-trip price found within the last 5 days was $425 on Multiple Airlines (Dec 7-Dec 13).

Reviews of airlines servicing Boston

Read reviews from past customers who have flown Porter 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.

Comfort

8.0

Overall

8.0

Boarding

8.2

Food

7.6

Entertainment

6.9

Crew

8.6

Reviews

1 / 20
8.0
Excellent

D,Sep 2026

YHM - YVR

The flight including check-in, checked baggage, boarding, flight and timing were great. My checked bag was delayed two days which was concerning. They did deliver it to my door though which was great.

Comfort

8.0

Overall

8.0

Boarding

8.2

Food

7.6

Entertainment

6.9

Crew

8.6

Reviews

1 / 20
8.0
Excellent

D,Sep 2026

YHM - YVR

The flight including check-in, checked baggage, boarding, flight and timing were great. My checked bag was delayed two days which was concerning. They did deliver it to my door though which was great.

Comfort

8.0

Overall

8.0

Boarding

8.2

Food

7.6

Entertainment

6.9

Crew

8.6

Reviews

1 / 20
8.0
Excellent

D,Sep 2026

YHM - YVR

The flight including check-in, checked baggage, boarding, flight and timing were great. My checked bag was delayed two days which was concerning. They did deliver it to my door though which was great.

Related info for your journey

  • How long is the flight from Winnipeg to Boston?

    For as low as $427, Porter Airlines can have you in Boston from Winnipeg in 8h 55m. Airlines will cover a distance of 1350 mi.

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

    According to our current data, Air Canada ($215), and Porter Airlines ($282) offers the cheapest pricing from Winnipeg to Boston. Air Canada is 59% 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, 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
Randolph
Concord
Cambridge
Brockton
Dedham
Cranston
Warwick
Pawtucket
Peabody
Revere
Fitchburg
Londonderry
York Beach
North Falmouth
Chelsea
Swansea
Braintree
Auburn
Sandwich

Browse thousands of different options on Cheapflights for your next trip

Top 2 airlines flying from Winnipeg to Boston

AirlineCheapestAverageFlexibilityOn-time
Air CanadaCheapest$215Average$582FlexibilityNo cancel feeOn-time67%
Porter AirlinesCheapest$282Average$380FlexibilityNo cancel feeOn-time52%

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