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Cheap flights from Winnipeg to Boston from C$ 284

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 14/8. Fares are subject to change and may not be available on all flights or dates of travel.
YWG — BOS
5 Aug — 12 Aug1
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 6 July 2026.

Sun 6/1211:35 a.m.
YWG
-
BOS
2 stops9h 42m
Porter Airlines
Thu 10/121:15 p.m.
BOS
-
YWG
1 stop5h 55m
Porter Airlines
Deal found 3/7C$ 458
Mon 27/712:15 p.m.
YWG
-
BOS
1 stop5h 35m
Porter Airlines
Mon 3/87:10 a.m.
BOS
-
YWG
2 stops11h 48m
Porter Airlines
Deal found 3/7C$ 462
Tue 21/712:15 p.m.
YWG
-
BOS
1 stop5h 35m
Porter Airlines
Thu 23/710:05 a.m.
BOS
-
YWG
1 stop6h 14m
Porter Airlines
Deal found 3/7C$ 466
Mon 14/93:58 p.m.
YWG
-
BOS
1 stop7h 01m
Delta
Fri 18/95:55 a.m.
BOS
-
YWG
1 stop7h 01m
Delta
Deal found 2/7C$ 468
Mon 14/95:00 a.m.
YWG
-
BOS
2 stops8h 41m
Air Canada
Fri 18/93:35 p.m.
BOS
-
YWG
1 stop6h 39m
Air Canada
Deal found 1/7C$ 479
Fri 2/103:58 p.m.
YWG
-
BOS
1 stop7h 01m
Delta
Mon 5/105:55 a.m.
BOS
-
YWG
1 stop10h 13m
Delta
Deal found 2/7C$ 482
Tue 25/83:20 p.m.
YWG
-
BOS
1 stop6h 18m
Air Canada
Thu 27/86:00 a.m.
BOS
-
YWG
1 stop6h 15m
Air Canada
Deal found 2/7C$ 486
Fri 28/812:15 p.m.
YWG
-
BOS
1 stop5h 35m
Porter Airlines
Mon 31/810:05 a.m.
BOS
-
YWG
1 stop6h 14m
Porter Airlines
Deal found 6/7C$ 492

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 6 July 2026.

Round-trip from

C$ 458

One-way from

C$ 284

Popular in

April

Cheapest in

July

Average price

C$ 523
Porter Airlines
  • Porter Airlines
  • 6/12-10/12
  • 3 total stops
  • 15h 37m total
  • Winnipeg to Boston
Search Deals
Air Canada
  • Air Canada
  • 14/8
  • 1 total stop
  • 6h 18m total
  • Winnipeg to Boston
Search Deals
Highest demand for flights based on searches. 17% potential increase in price (C$ 228 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 6% potential price decrease (C$ 71 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 629,999 searches. Data last updated 6 July 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

Mon 14/9

3:58 p.m.-11:59 p.m.

1 stop7h 01m

Boston Logan Intl

Fri 18/9

5:55 a.m.-11:56 a.m.

1 stop7h 01m

C$ 466

WinnipegBoston

YWG - BOS

YWGBOS

Winnipeg

Mon 14/9

5:00 a.m.-2:41 p.m.

2 stops8h 41m

Boston Logan Intl

Fri 18/9

3:35 p.m.-9:14 p.m.

1 stop6h 39m

C$ 479

WinnipegBoston

YWG - BOS

YWGBOS

Winnipeg

Fri 2/10

3:58 p.m.-11:59 p.m.

1 stop7h 01m

Boston Logan Intl

Mon 5/10

5:55 a.m.-3:08 p.m.

1 stop10h 13m

C$ 482

WinnipegBoston

YWG - BOS

YWGBOS

Winnipeg

Fri 28/8

5:42 p.m.-11:58 p.m.

1 stop5h 16m

Boston Logan Intl

Mon 31/8

7:10 a.m.-3:08 p.m.

1 stop8h 58m

C$ 519

WinnipegBoston

YWG - BOS

YWGBOS

Winnipeg

Fri 2/10

9:20 a.m.-6:35 p.m.

1 stop8h 15m

Boston Logan Intl

Mon 5/10

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

2 stops8h 53m

C$ 556
Cheapest one-way
Quickest one-way

WinnipegBoston

YWG - BOS

YWGBOS

Winnipeg

Fri 14/8

3:20 p.m.-10:38 p.m.

1 stop6h 18m

C$ 284

WinnipegBoston

YWG - BOS

YWGBOS

Winnipeg

Sat 15/8

8:00 a.m.-4:00 p.m.

1 stop7h 00m

C$ 321

WinnipegBoston

YWG - BOS

YWGBOS

Winnipeg

Fri 14/8

9:25 a.m.-8:55 p.m.

2 stops10h 30m

C$ 335

WinnipegBoston

YWG - BOS

YWGBOS

Winnipeg

Thu 16/7

9:25 a.m.-6:50 p.m.

1 stop8h 25m

C$ 451

WinnipegBoston

YWG - BOS

YWGBOS

Winnipeg

Thu 16/7

9:20 a.m.-8:55 p.m.

2 stops10h 35m

C$ 581

Flights are sorted by cheapest round-trip flights first.

Deals found on 2/7

Sorted by cheapest first

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, July is the cheapest month in which you can book a flight from Winnipeg to Boston (average of C$ 523). Flying from Winnipeg to Boston in April is currently the most expensive (average of C$ 1,301). 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 6 July 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
7.9
Good
442 reviews
Check prices

Entertainment

6.9

Comfort

7.9

Overall

7.9

Food

7.5

Boarding

8.2

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
7.9
Good
442 reviews
Porter Airlines
7.9
Good
442 reviews
Check prices

Entertainment

6.9

Comfort

7.9

Overall

7.9

Food

7.5

Boarding

8.2

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
9,940 reviews
Porter Airlines
7.9
Good
442 reviews
Check prices

Entertainment

6.9

Comfort

7.9

Overall

7.9

Food

7.5

Boarding

8.2

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
11,308 reviews
Porter Airlines
7.9
Good
442 reviews
Check prices

Entertainment

6.9

Comfort

7.9

Overall

7.9

Food

7.5

Boarding

8.2

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 7h 01m. Delta provides one of the quickest options available for as low as C$ 466. 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$ 222. Other airlines that can offer you cheap pricing are Porter Airlines, from C$ 333, and Air Canada, from C$ 403. Users have found that United Airlines is 71% 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, July is the cheapest month in which you can book a flight from Winnipeg to Boston (average of C$ 523). Flying from Winnipeg to Boston in April is currently the most expensive (average of C$ 1,301). 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
Hampton
Merrimack
Chelsea
Braintree
Milford
Old Orchard Beach
Revere
Waltham
Watertown
Ogunquit
Warwick
Lawrence
Pawtucket
Seekonk
Nashua
Kittery

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 6 July 2026.
AirlineCheapestAverageFlexibilityOn-time
United AirlinesCheapestC$ 222AverageC$ 628FlexibilityNo cancel feeOn-time69%
Search United Airlines flights
Porter AirlinesCheapestC$ 333AverageC$ 542FlexibilityNo cancel feeOn-time52%
Search Porter Airlines flights
Air CanadaCheapestC$ 403AverageC$ 637FlexibilityNo 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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