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Cheap flights from Winnipeg to Boston from C$ 234

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 22/4. Fares are subject to change and may not be available on all flights or dates of travel.
YWG — BOS
26 Feb — 5 Mar1
1 adult
1 adult, Economy, 0 bags

Cheap flight deals from Winnipeg to Boston

Enter your travel dates to find the best prices.

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 27 January 2026.

Mon 16/28:00 a.m.
YWG
-
BOS
1 stop25h 26m
Multiple Airlines
Mon 23/26:00 a.m.
BOS
-
YWG
2 stops37h 05m
Multiple Airlines
Deal found 26/1C$ 393
Wed 11/37:30 a.m.
YWG
-
BOS
1 stop27h 11m
Multiple Airlines
Tue 24/312:36 p.m.
BOS
-
YWG
1 stop27h 33m
Multiple Airlines
Deal found 27/1C$ 437
Sat 25/46:55 p.m.
YWG
-
BOS
1 stop19h 55m
WestJet
Sun 3/54:45 p.m.
BOS
-
YWG
1 stop9h 10m
WestJet
Deal found 26/1C$ 445
Mon 16/28:00 a.m.
YWG
-
BOS
1 stop25h 26m
Multiple Airlines
Tue 24/26:55 p.m.
BOS
-
YWG
1 stop17h 37m
Multiple Airlines
Deal found 26/1C$ 477
Wed 11/37:30 a.m.
YWG
-
BOS
1 stop27h 11m
Multiple Airlines
Wed 25/35:49 p.m.
BOS
-
YWG
2 stops26h 20m
Multiple Airlines
Deal found 25/1C$ 479
Sun 15/28:05 p.m.
YWG
-
BOS
1 stop12h 30m
Multiple Airlines
Tue 24/26:00 a.m.
BOS
-
YWG
2 stops19h 40m
Multiple Airlines
Deal found 26/1C$ 492
Tue 17/28:05 p.m.
YWG
-
BOS
1 stop17h 40m
Multiple Airlines
Tue 24/26:00 a.m.
BOS
-
YWG
2 stops19h 40m
Multiple Airlines
Deal found 26/1C$ 496
Tue 17/212:10 p.m.
YWG
-
BOS
2 stops21h 16m
Multiple Airlines
Mon 23/26:55 p.m.
BOS
-
YWG
1 stop17h 37m
Multiple Airlines
Deal found 26/1C$ 523
Mon 16/28:00 a.m.
YWG
-
BOS
1 stop25h 26m
Multiple Airlines
Sun 22/26:55 p.m.
BOS
-
YWG
1 stop17h 37m
Multiple Airlines
Deal found 26/1C$ 526

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 27 January 2026.

Round-trip from

C$ 393

One-way from

C$ 234

Popular in

January

Cheapest in

June

Average price

C$ 753
16/2-24/2
  • 16/2-24/2
  • 3 total stops
  • 45h 06m total
  • Winnipeg to Boston
Search Deals
22/4
  • 22/4
  • 1 total stop
  • 16h 21m total
  • Winnipeg to Boston
Search Deals
Highest demand for flights based on searches. 17% potential increase in price (C$ 168 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 2% potential price decrease (C$ 22 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in January 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 629,999 searches. Data last updated 27 January 2026.
Use the filters below to find and compare flights from Winnipeg to Boston that are best for you.

Fly from

Winnipeg

Fly to

Boston

Route

Depart

Return

Price

WinnipegBoston

YWG - BOS

YWGBOS

Winnipeg

Mon 16/2

8:00 a.m.-10:26 a.m.

1 stop25h 26m

Boston Logan Intl

Mon 23/2

6:00 a.m.-6:05 p.m.

2 stops37h 05m

C$ 393

WinnipegBoston

YWG - BOS

YWGBOS

Winnipeg

Wed 11/3

7:30 a.m.-11:41 a.m.

1 stop27h 11m

Boston Logan Intl

Tue 24/3

12:36 p.m.-3:09 p.m.

1 stop27h 33m

C$ 437

WinnipegBoston

YWG - BOS

YWGBOS

Winnipeg

Mon 16/2

8:00 a.m.-10:26 a.m.

1 stop25h 26m

Boston Logan Intl

Tue 24/2

6:55 p.m.-11:32 a.m.

1 stop17h 37m

C$ 477

WinnipegBoston

YWG - BOS

YWGBOS

Winnipeg

Sat 25/4

6:45 a.m.-3:50 p.m.

2 stops32h 05m

Boston Logan Intl

Sun 3/5

4:45 p.m.-12:55 a.m.

1 stop9h 10m

C$ 505

WinnipegBoston

YWG - BOS

YWGBOS

Winnipeg

Mon 16/2

8:00 a.m.-10:26 a.m.

1 stop25h 26m

Boston Logan Intl

Sun 22/2

6:55 p.m.-11:32 a.m.

1 stop17h 37m

C$ 526

WinnipegBoston

YWG - BOS

YWGBOS

Winnipeg

Wed 11/3

7:30 a.m.-11:44 p.m.

2 stops15h 14m

Boston Logan Intl

Wed 25/3

5:40 a.m.-11:32 a.m.

2 stops30h 52m

C$ 572

WinnipegBoston

YWG - BOS

YWGBOS

Winnipeg

Sun 15/2

8:05 p.m.-9:35 a.m.

1 stop12h 30m

Boston Logan Intl

Mon 23/2

6:55 p.m.-11:32 a.m.

1 stop17h 37m

C$ 575

WinnipegBoston

YWG - BOS

YWGBOS

Winnipeg

Tue 17/2

8:05 p.m.-2:45 p.m.

1 stop17h 40m

Boston Logan Intl

Mon 23/2

6:55 p.m.-11:32 a.m.

1 stop17h 37m

C$ 579

WinnipegBoston

YWG - BOS

YWGBOS

Winnipeg

Wed 22/4

7:30 a.m.-12:51 a.m.

1 stop16h 21m

C$ 234

WinnipegBoston

YWG - BOS

YWGBOS

Winnipeg

Sun 12/4

7:30 a.m.-11:45 a.m.

1 stop27h 15m

C$ 251

Flights are sorted by cheapest round-trip flights first.

Deals found on 25/1

Showing 1-10 of 14 results
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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?

Use this chart to determine the optimal time to book a round-trip flight from Winnipeg to Boston. Price data was last updated on 23 January 2026.

To ensure you get the cheapest price possible for a flight from Winnipeg to Boston, you should look to book at least 24 days in advance of your intended travel date. The price of your flight may increase if you delay and leave booking until a week or so before departure.

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

Currently, May is the cheapest month in which you can book a flight from Winnipeg to Boston (average of C$ 231). Flying from Winnipeg to Boston in January is currently the most expensive (average of C$ 583). 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.

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 27 January 2026.
Read through reviews of airlines operating flights from Winnipeg to Boston, such as Porter Airlines,United Airlines, andWestJet. Reviews also offer insight into each airline's entertainment options, comfort, food, crew/service, and boarding process.
Porter Airlines
7.9
Good
412 reviews
Check prices

Food

7.5

Boarding

8.2

Entertainment

6.9

Comfort

7.9

Overall

7.9

Crew

8.6

Reviews

1 / 20
8.0
Excellent

Mohameed,Nov 2025

LAS - YYZ

It's good. Planes are new and fresh. WiFi is best and stands out
Porter Airlines
7.9
Good
412 reviews
Porter Airlines
7.9
Good
412 reviews
Check prices

Food

7.5

Boarding

8.2

Entertainment

6.9

Comfort

7.9

Overall

7.9

Crew

8.6

Reviews

1 / 20
8.0
Excellent

Mohameed,Nov 2025

LAS - YYZ

It's good. Planes are new and fresh. WiFi is best and stands out
United Airlines
7.4
Good
9,205 reviews
Porter Airlines
7.9
Good
412 reviews
Check prices

Food

7.5

Boarding

8.2

Entertainment

6.9

Comfort

7.9

Overall

7.9

Crew

8.6

Reviews

1 / 20
8.0
Excellent

Mohameed,Nov 2025

LAS - YYZ

It's good. Planes are new and fresh. WiFi is best and stands out
WestJet
7.2
Good
3,251 reviews
Porter Airlines
7.9
Good
412 reviews
Check prices

Food

7.5

Boarding

8.2

Entertainment

6.9

Comfort

7.9

Overall

7.9

Crew

8.6

Reviews

1 / 20
8.0
Excellent

Mohameed,Nov 2025

LAS - YYZ

It's good. Planes are new and fresh. WiFi is best and stands out
Air Canada
7.1
Good
10,660 reviews
Porter Airlines
7.9
Good
412 reviews
Check prices

Food

7.5

Boarding

8.2

Entertainment

6.9

Comfort

7.9

Overall

7.9

Crew

8.6

Reviews

1 / 20
8.0
Excellent

Mohameed,Nov 2025

LAS - YYZ

It's good. Planes are new and fresh. WiFi is best and stands out

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?

    A quick flight from Winnipeg to Boston can take about 32h 05m. WestJet provides one of the quickest options available for as low as C$ 505. The distance from Winnipeg to Boston is about 2173 km.

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

    Cheapflights users have booked flights from Winnipeg to Boston round-trip from C$ 174. Other airlines that can offer you cheap pricing are Air Canada, from C$ 315, and Porter Airlines, from C$ 419. Users have found that United Airlines is 70% cheaper than the other options available 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, May is the cheapest month in which you can book a flight from Winnipeg to Boston (average of C$ 231). Flying from Winnipeg to Boston in January is currently the most expensive (average of C$ 583). 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

Travelling to a place near Boston?

Book flights to Boston if you plan to visit one of these locations
Medford
Merrimack
Chelsea
Milford
Braintree
Hampton
Old Orchard Beach
Revere
Waltham
Kennebunk
Watertown
Warwick
Lawrence
Seekonk
Nashua

Browse thousands of different options on Cheapflights for your next trip

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Alternative routes for Winnipeg to Boston

See prices for flight routes from nearby airports that may be better suited for you.
Winnipeg to Albany flights

Top 4 airlines flying from Winnipeg to Boston

Discover the top 4 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 629,999 searches. Data last updated 27 January 2026.
AirlineCheapestAverageFlexibilityOn-time
United AirlinesCheapestC$ 174AverageC$ 395FlexibilityNo cancel feeOn-time69%
Search United Airlines flights
Air CanadaCheapestC$ 315AverageC$ 491FlexibilityNo cancel feeOn-time67%
Search Air Canada flights
Porter AirlinesCheapestC$ 419AverageC$ 629FlexibilityNo cancel feeOn-time52%
Search Porter Airlines flights
WestJetCheapestC$ 469AverageC$ 1,125FlexibilityNo cancel feeOn-time60%
Search WestJet flights

Fly with Cheapflights

Find the best flight deals on Cheapflights, where travelers can enjoy low prices and a wide availability of flights to their desired destinations.

How does Cheapflights help users find flights from Winnipeg to Boston?

Cheapflights goes through 900+ travel sites to look for the best flight deals for flights from Winnipeg to Boston. Too many options? Cheapflights also provides filters for things like airlines, price ranges, and number of stops to help you make a decision easily.

Why should you use Cheapflights to find cheap flight tickets from Winnipeg to Boston?

By finding flights from multiple airlines and providers at completely no cost, Cheapflights helps millions of users like you annually find the best flights to Boston from Winnipeg.

Can Cheapflights find flights from Winnipeg to Boston with no change fees?

Certainly. Search results for flights to Boston from Winnipeg shown to you on Cheapflights can be narrowed down with different useful search filters, which includes flexible booking options.

Can Cheapflights notify me if prices for flights from Winnipeg to Boston become cheaper?

Yes, Cheapflights has a feature called Price Alert, which notifies users when flight prices change. Track prices for your flight to Boston from Winnipeg today and book when prices fit your budget.

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