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Cheap flights from Winnipeg to Boston from C$ 245

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 25/8. Fares are subject to change and may not be available on all flights or dates of travel.
YWG — BOS
11 Jul — 18 Jul1
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 11 June 2026.

Tue 21/712:15 p.m.
YWG
-
BOS
1 stop5h 20m
Porter Airlines
Tue 28/710:05 a.m.
BOS
-
YWG
1 stop6h 14m
Porter Airlines
Deal found 10/6C$ 433
Thu 9/72:05 p.m.
YWG
-
BOS
1 stop7h 33m
Air Canada
Mon 13/76:00 a.m.
BOS
-
YWG
1 stop6h 15m
Air Canada
Deal found 7/6C$ 436
Tue 21/75:00 a.m.
YWG
-
BOS
1 stop5h 52m
Air Canada
Thu 23/76:00 a.m.
BOS
-
YWG
1 stop6h 15m
Air Canada
Deal found 6/6C$ 438
Fri 24/712:15 p.m.
YWG
-
BOS
1 stop5h 20m
Porter Airlines
Mon 27/710:05 a.m.
BOS
-
YWG
1 stop6h 14m
Porter Airlines
Deal found 10/6C$ 443
Sat 4/77:55 a.m.
YWG
-
BOS
1 stop5h 46m
Air Canada
Sat 11/710:50 a.m.
BOS
-
YWG
1 stop6h 30m
Air Canada
Deal found 10/6C$ 445
Fri 3/712:15 p.m.
YWG
-
BOS
1 stop5h 20m
Porter Airlines
Mon 13/710:05 a.m.
BOS
-
YWG
1 stop6h 14m
Porter Airlines
Deal found 7/6C$ 453
Wed 24/69:20 a.m.
YWG
-
BOS
1 stop7h 15m
Porter Airlines
Mon 29/610:05 a.m.
BOS
-
YWG
1 stop6h 14m
Porter Airlines
Deal found 10/6C$ 456
Thu 6/812:15 p.m.
YWG
-
BOS
1 stop6h 00m
Porter Airlines
Tue 11/810:05 a.m.
BOS
-
YWG
1 stop6h 14m
Porter Airlines
Deal found 10/6C$ 457
Wed 24/62:05 p.m.
YWG
-
BOS
1 stop7h 33m
Air Canada
Fri 3/73:35 p.m.
BOS
-
YWG
1 stop6h 44m
Air Canada
Deal found 10/6C$ 467

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 11 June 2026.

Round-trip from

C$ 433

One-way from

C$ 245

Popular in

January

Cheapest in

June

Average price

C$ 498
Porter Airlines
  • Porter Airlines
  • 21/7-28/7
  • 2 total stops
  • 11h 34m total
  • Winnipeg to Boston
Search Deals
Air Canada
  • Air Canada
  • 25/8
  • 1 total stop
  • 5h 46m total
  • Winnipeg to Boston
Search Deals
Highest demand for flights based on searches. 15% potential increase in price (C$ 185 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 4% potential price decrease (C$ 48 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in June 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 11 June 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

Tue 21/7

5:00 a.m.-11:52 a.m.

1 stop5h 52m

Boston Logan Intl

Thu 23/7

6:00 a.m.-11:15 a.m.

1 stop6h 15m

C$ 438
Quickest round-trip

WinnipegBoston

YWG - BOS

YWGBOS

Winnipeg

Fri 3/7

12:15 p.m.-6:35 p.m.

1 stop5h 20m

Boston Logan Intl

Mon 13/7

10:05 a.m.-3:19 p.m.

1 stop6h 14m

C$ 453

WinnipegBoston

YWG - BOS

YWGBOS

Winnipeg

Sat 25/7

12:15 p.m.-7:15 p.m.

1 stop6h 00m

Boston Logan Intl

Mon 27/7

10:05 a.m.-5:58 p.m.

2 stops8h 53m

C$ 470

WinnipegBoston

YWG - BOS

YWGBOS

Winnipeg

Thu 25/6

12:56 p.m.-1:14 a.m.

1 stop11h 18m

Boston Logan Intl

Wed 1/7

8:15 a.m.-10:38 p.m.

1 stop15h 23m

C$ 471

WinnipegBoston

YWG - BOS

YWGBOS

Winnipeg

Sat 3/10

7:00 a.m.-12:59 a.m.

1 stop16h 59m

Boston Logan Intl

Wed 7/10

7:01 a.m.-10:33 p.m.

1 stop16h 32m

C$ 479

WinnipegBoston

YWG - BOS

YWGBOS

Winnipeg

Sat 25/7

5:00 a.m.-11:52 a.m.

1 stop5h 52m

Boston Logan Intl

Mon 27/7

6:00 a.m.-11:15 a.m.

1 stop6h 15m

C$ 488

WinnipegBoston

YWG - BOS

YWGBOS

Winnipeg

Fri 11/9

5:10 a.m.-5:52 p.m.

2 stops11h 42m

Boston Logan Intl

Fri 18/9

8:31 p.m.-11:52 a.m.

1 stop16h 21m

C$ 489

WinnipegBoston

YWG - BOS

YWGBOS

Winnipeg

Sat 3/10

12:20 p.m.-9:26 p.m.

2 stops8h 06m

Boston Logan Intl

Wed 7/10

6:00 a.m.-11:12 a.m.

1 stop6h 12m

C$ 498

WinnipegBoston

YWG - BOS

YWGBOS

Winnipeg

Thu 9/7

12:15 p.m.-6:35 p.m.

1 stop5h 20m

Boston Logan Intl

Sat 11/7

7:10 a.m.-5:58 p.m.

2 stops11h 48m

C$ 499
Cheapest one-way

WinnipegBoston

YWG - BOS

YWGBOS

Winnipeg

Mon 24/8

11:15 a.m.-10:30 a.m.

2 stops22h 15m

C$ 259

Flights are sorted by cheapest round-trip flights first.

Deals found on 11/6

Showing 1-10 of 20 resultsSorted by cheapest first
1
2

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, June is the cheapest month in which you can book a flight from Winnipeg to Boston (average of C$ 498). Flying from Winnipeg to Boston in January is currently the most expensive (average of C$ 1,090). 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 11 June 2026.
Read through reviews of airlines operating flights from Winnipeg to Boston, such as Porter Airlines,United Airlines, andAir Canada. Reviews also offer insight into each airline's entertainment options, comfort, food, crew/service, and boarding process.
Porter Airlines
8.0
Very good
438 reviews
Check prices

Comfort

8.0

Food

7.6

Overall

8.0

Boarding

8.2

Entertainment

6.9

Crew

8.6

Reviews

1 / 20
6.0
Good

Justin,May 2026

YYZ - MCO

Staff very nice. Seats were uncomfortable. Complimentary snacks leave much to be desired.
Porter Airlines
8.0
Very good
438 reviews
Porter Airlines
8.0
Very good
438 reviews
Check prices

Comfort

8.0

Food

7.6

Overall

8.0

Boarding

8.2

Entertainment

6.9

Crew

8.6

Reviews

1 / 20
6.0
Good

Justin,May 2026

YYZ - MCO

Staff very nice. Seats were uncomfortable. Complimentary snacks leave much to be desired.
United Airlines
7.4
Good
9,805 reviews
Porter Airlines
8.0
Very good
438 reviews
Check prices

Comfort

8.0

Food

7.6

Overall

8.0

Boarding

8.2

Entertainment

6.9

Crew

8.6

Reviews

1 / 20
6.0
Good

Justin,May 2026

YYZ - MCO

Staff very nice. Seats were uncomfortable. Complimentary snacks leave much to be desired.
Air Canada
7.1
Good
11,160 reviews
Porter Airlines
8.0
Very good
438 reviews
Check prices

Comfort

8.0

Food

7.6

Overall

8.0

Boarding

8.2

Entertainment

6.9

Crew

8.6

Reviews

1 / 20
6.0
Good

Justin,May 2026

YYZ - MCO

Staff very nice. Seats were uncomfortable. Complimentary snacks leave much to be desired.

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 5h 20m. Porter Airlines provides one of the quickest options available for as low as C$ 433. The distance from Winnipeg to Boston is about 2173 km. When browsing for deals, the options you’ll see will be for both direct flights and flights with stops.

  • 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$ 177. Other airlines that can offer you cheap pricing are Porter Airlines, from C$ 326, and Air Canada, from C$ 395. Users have found that United Airlines is 75% 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, June is the cheapest month in which you can book a flight from Winnipeg to Boston (average of C$ 498). Flying from Winnipeg to Boston in January is currently the most expensive (average of C$ 1,090). 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
Braintree
Milford
Seekonk
Hampton
Old Orchard Beach
Revere
Waltham
Watertown
Warwick
Ogunquit
Lawrence
Pawtucket
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 3 airlines flying from Winnipeg to Boston

Discover the top 3 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 11 June 2026.
AirlineCheapestAverageFlexibilityOn-time
United AirlinesCheapestC$ 177AverageC$ 592FlexibilityNo cancel feeOn-time69%
Search United Airlines flights
Porter AirlinesCheapestC$ 326AverageC$ 600FlexibilityNo cancel feeOn-time52%
Search Porter Airlines flights
Air CanadaCheapestC$ 395AverageC$ 625FlexibilityNo cancel feeOn-time67%
Search Air Canada 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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