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Cheap flights from Winnipeg to Boston from C$ 182

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 11/11. Fares are subject to change and may not be available on all flights or dates of travel.
YWG — BOS
27 Nov — 4 Dec1
1 adult
1 adult, Economy, 0 bags

Cheapflights Tip: The best prices from Winnipeg to Boston Logan Intl are usually found in June or August, booked 24 days in advance, depart on a Tuesday or Thursday and return on a Tuesday

Find 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 28 October 2025.

Wed 26/117:30 a.m.YWG - BOS
1 stop12h 19mMultiple Airlines
Wed 3/129:54 p.m.BOS - YWG
2 stops27h 47mMultiple Airlines
Deal found 27/10C$ 404
Wed 26/115:30 a.m.YWG - BOS
1 stop5h 42mAir Canada
Wed 3/125:30 a.m.BOS - YWG
1 stop5h 46mAir Canada
Deal found 27/10C$ 438
Tue 25/115:00 a.m.YWG - BOS
1 stop8h 55mMultiple Airlines
Tue 2/129:54 p.m.BOS - YWG
2 stops18h 13mMultiple Airlines
Deal found 26/10C$ 445
Mon 24/118:20 p.m.YWG - BOS
1 stop12h 15mMultiple Airlines
Tue 2/129:54 p.m.BOS - YWG
2 stops18h 13mMultiple Airlines
Deal found 26/10C$ 455
Mon 24/117:05 p.m.YWG - BOS
1 stop13h 52mAir Canada
Tue 2/125:30 a.m.BOS - YWG
1 stop5h 46mAir Canada
Deal found 27/10C$ 470

Cheap 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 28 October 2025.

Round-trip from

C$ 404

One-way from

C$ 182

Popular in

December

Cheapest in

June

Average price

C$ 497
26/11-3/12
  • 26/11-3/12
  • 3 total stops
  • 40h 06m total
  • Winnipeg to Boston
Search Deals
11/11
  • 11/11
  • 2 total stops
  • 35h 00m total
  • Winnipeg to Boston
Search Deals
Highest demand for flights based on searches. 22% potential increase in price (C$ 232 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 5% potential price decrease (C$ 40 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in October 2025
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 28 October 2025.
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

Wed 26/11

7:30 a.m.-8:49 p.m.

1 stop12h 19m

Boston Logan Intl

Wed 3/12

9:54 p.m.-12:41 a.m.

2 stops27h 47m

C$ 404

WinnipegBoston

YWG - BOS

YWGBOS

Winnipeg

Tue 25/11

5:00 a.m.-2:55 p.m.

1 stop8h 55m

Boston Logan Intl

Tue 2/12

9:54 p.m.-3:07 p.m.

2 stops18h 13m

C$ 445

WinnipegBoston

YWG - BOS

YWGBOS

Winnipeg

Mon 24/11

7:05 p.m.-9:57 a.m.

1 stop13h 52m

Boston Logan Intl

Tue 2/12

5:30 a.m.-10:16 a.m.

1 stop5h 46m

C$ 470

WinnipegBoston

YWG - BOS

YWGBOS

Winnipeg

Wed 10/12

7:30 a.m.-11:56 p.m.

2 stops15h 26m

Boston Logan Intl

Wed 17/12

5:45 a.m.-7:12 p.m.

2 stops14h 27m

C$ 552

WinnipegBoston

YWG - BOS

YWGBOS

Winnipeg

Tue 25/11

8:15 a.m.-2:52 p.m.

1 stop5h 37m

Boston Logan Intl

Sun 30/11

5:30 a.m.-10:16 a.m.

1 stop5h 46m

C$ 611

WinnipegBoston

YWG - BOS

YWGBOS

Winnipeg

Tue 25/11

5:30 a.m.-7:12 p.m.

2 stops12h 42m

Boston Logan Intl

Tue 2/12

5:30 a.m.-10:16 a.m.

1 stop5h 46m

C$ 625

WinnipegBoston

YWG - BOS

YWGBOS

Winnipeg

Tue 25/11

5:00 a.m.-10:05 p.m.

1 stop16h 05m

Boston Logan Intl

Sun 30/11

7:00 a.m.-11:27 a.m.

2 stops29h 27m

C$ 632

WinnipegBoston

YWG - BOS

YWGBOS

Winnipeg

Tue 11/11

9:00 p.m.-9:00 a.m.

2 stops35h 00m

C$ 182

WinnipegBoston

YWG - BOS

YWGBOS

Winnipeg

Tue 25/11

8:15 a.m.-2:52 p.m.

1 stop5h 37m

C$ 249

WinnipegBoston

YWG - BOS

YWGBOS

Winnipeg

Fri 12/12

7:30 a.m.-7:06 p.m.

2 stops34h 36m

C$ 257

Flights are sorted by cheapest round-trip flights first.

Deals found on 28/10

Showing 1-10 of 16 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 24 October 2025.

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$ 229). Flying from Winnipeg to Boston in December is currently the most expensive (average of C$ 501). 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.

What is the cheapest time of day to fly from YWG to BOS?

Find hourly flight availability from Winnipeg to Boston. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated 28 October 2025.

One of the essential ways to save on airfare from Winnipeg to Boston is to remain as flexible as possible. Flights that are in the evening tend to be the most expensive. A flight in the morning could potentially save you up to 24% on airfare.

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 28 October 2025.
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
8.0
Very good
384 reviews
Check prices

Boarding

8.2

Overall

8.0

Comfort

8.0

Food

7.6

Entertainment

7.0

Crew

8.6

Reviews

1 / 20
2.0
Mediocre

Anonymous,Sep 2025

YYZ - OPO

Very disappointing, booked with Porter airlines and changed to Air Transit last minute. Old plane, cramped seating, even the aisle was the narrowest I’ve ever seen. Very uncomfortable flight. Full meal at 130 am and only a small piece of banana bread in the morning… should be opposite.
Porter Airlines
8.0
Very good
384 reviews
Porter Airlines
8.0
Very good
384 reviews
Check prices

Boarding

8.2

Overall

8.0

Comfort

8.0

Food

7.6

Entertainment

7.0

Crew

8.6

Reviews

1 / 20
2.0
Mediocre

Anonymous,Sep 2025

YYZ - OPO

Very disappointing, booked with Porter airlines and changed to Air Transit last minute. Old plane, cramped seating, even the aisle was the narrowest I’ve ever seen. Very uncomfortable flight. Full meal at 130 am and only a small piece of banana bread in the morning… should be opposite.
United Airlines
7.4
Good
8,996 reviews
Porter Airlines
8.0
Very good
384 reviews
Check prices

Boarding

8.2

Overall

8.0

Comfort

8.0

Food

7.6

Entertainment

7.0

Crew

8.6

Reviews

1 / 20
2.0
Mediocre

Anonymous,Sep 2025

YYZ - OPO

Very disappointing, booked with Porter airlines and changed to Air Transit last minute. Old plane, cramped seating, even the aisle was the narrowest I’ve ever seen. Very uncomfortable flight. Full meal at 130 am and only a small piece of banana bread in the morning… should be opposite.
WestJet
7.2
Good
3,148 reviews
Porter Airlines
8.0
Very good
384 reviews
Check prices

Boarding

8.2

Overall

8.0

Comfort

8.0

Food

7.6

Entertainment

7.0

Crew

8.6

Reviews

1 / 20
2.0
Mediocre

Anonymous,Sep 2025

YYZ - OPO

Very disappointing, booked with Porter airlines and changed to Air Transit last minute. Old plane, cramped seating, even the aisle was the narrowest I’ve ever seen. Very uncomfortable flight. Full meal at 130 am and only a small piece of banana bread in the morning… should be opposite.
Air Canada
7.1
Good
10,370 reviews
Porter Airlines
8.0
Very good
384 reviews
Check prices

Boarding

8.2

Overall

8.0

Comfort

8.0

Food

7.6

Entertainment

7.0

Crew

8.6

Reviews

1 / 20
2.0
Mediocre

Anonymous,Sep 2025

YYZ - OPO

Very disappointing, booked with Porter airlines and changed to Air Transit last minute. Old plane, cramped seating, even the aisle was the narrowest I’ve ever seen. Very uncomfortable flight. Full meal at 130 am and only a small piece of banana bread in the morning… should be opposite.

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 13h 52m. Air Canada provides one of the quickest options available for as low as C$ 470. 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$ 241. Other airlines that can offer you cheap pricing are Air Canada, from C$ 348, and Porter Airlines, from C$ 428. Users have found that United Airlines is 57% 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$ 229). Flying from Winnipeg to Boston in December is currently the most expensive (average of C$ 501). 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
Chelsea
Waltham
Warwick
Milford
Braintree
Plymouth
Hampton
Old Orchard Beach
Revere
Merrimack
Kennebunk
Watertown
Sturbridge
Lawrence
Seekonk
Nashua

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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 28 October 2025.
AirlineCheapestAverageFlexibilityOn-time
United AirlinesCheapestC$ 241AverageC$ 405FlexibilityNo cancel feeOn-time69%
Search United Airlines flights
Air CanadaCheapestC$ 348AverageC$ 502FlexibilityNo cancel feeOn-time67%
Search Air Canada flights
Porter AirlinesCheapestC$ 428AverageC$ 642FlexibilityNo cancel feeOn-time52%
Search Porter Airlines flights
WestJetCheapestC$ 479AverageC$ 1,149FlexibilityNo 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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