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Cheap flights from Winnipeg to Boston from C$ 215

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 30/8. Fares are subject to change and may not be available on all flights or dates of travel.
YWG — BOS
3 Aug — 10 Aug1
1 adult

Cheapflights Tip: The best prices from Winnipeg to Boston Logan Intl are usually found in October or September, booked 55 days in advance, depart on a Tuesday or Thursday and return on a Tuesday

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 29 July 2025.

Round-trip from

C$ 412

One-way from

C$ 215

Popular in

December

Cheapest in

October

Average price

C$ 484
United Airlines
  • United Airlines
  • 12/11-17/11
  • 2 total stops
  • 22h 56m total
  • Winnipeg to Boston
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WestJet
  • WestJet
  • 30/8
  • 1 total stop
  • 10h 10m total
  • Winnipeg to Boston
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Highest demand for flights based on searches. 22% potential increase in price (C$ 223 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 5% potential price decrease (C$ 41 potential savings vs. average RT price).
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Average for round-trip flights in July 2025
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Find flight deals from Winnipeg to Boston

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 29 July 2025.

Wed 12/112:20 p.m.YWG - BOS
1 stop6h 29mUnited Airlines
Mon 17/118:30 p.m.BOS - YWG
1 stop16h 27mUnited Airlines
Deal found 27/7C$ 412
Fri 22/89:00 a.m.YWG - BOS
2 stops12h 34mMultiple Airlines
Mon 8/96:30 p.m.BOS - YWG
1 stop15h 31mMultiple Airlines
Deal found 27/7C$ 424
Thu 25/96:30 a.m.YWG - BOS
1 stop10h 10mWestJet
Mon 29/97:00 p.m.BOS - YWG
1 stop20h 13mWestJet
Deal found 28/7C$ 431
Sat 13/911:40 a.m.YWG - BOS
1 stop5h 15mAir Canada
Mon 15/96:00 a.m.BOS - YWG
2 stops13h 15mAir Canada
Deal found 28/7C$ 541
Fri 15/811:45 a.m.YWG - BOS
1 stop5h 43mPorter Airlines
Sun 17/83:50 p.m.BOS - YWG
1 stop7h 56mPorter Airlines
Deal found 27/7C$ 657
Sat 2/88:35 a.m.YWG - BOS
1 stop9h 44mDelta
Tue 5/83:15 p.m.BOS - YWG
1 stop9h 10mDelta
Deal found 29/7C$ 1,176

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 29 July 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 12/11

2:20 p.m.-9:49 p.m.

1 stop6h 29m

Boston Logan Intl

Mon 17/11

8:30 p.m.-11:57 a.m.

1 stop16h 27m

C$ 412

WinnipegBoston

YWG - BOS

YWGBOS

Winnipeg

Fri 22/8

9:00 a.m.-10:34 p.m.

2 stops12h 34m

Boston Logan Intl

Mon 8/9

6:30 p.m.-9:01 a.m.

1 stop15h 31m

C$ 424

WinnipegBoston

YWG - BOS

YWGBOS

Winnipeg

Thu 25/9

6:30 a.m.-5:40 p.m.

1 stop10h 10m

Boston Logan Intl

Mon 29/9

7:00 p.m.-2:13 p.m.

1 stop20h 13m

C$ 431

WinnipegBoston

YWG - BOS

YWGBOS

Winnipeg

Sat 13/9

11:40 a.m.-5:55 p.m.

1 stop5h 15m

Boston Logan Intl

Mon 15/9

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

2 stops13h 15m

C$ 541

WinnipegBoston

YWG - BOS

YWGBOS

Winnipeg

Fri 15/8

11:45 a.m.-6:28 p.m.

1 stop5h 43m

Boston Logan Intl

Sun 17/8

3:50 p.m.-10:46 p.m.

1 stop7h 56m

C$ 657

WinnipegBoston

YWG - BOS

YWGBOS

Winnipeg

Sat 30/8

6:30 a.m.-5:40 p.m.

1 stop10h 10m

C$ 215

WinnipegBoston

YWG - BOS

YWGBOS

Winnipeg

Wed 27/8

5:00 a.m.-11:28 a.m.

1 stop5h 28m

C$ 239

WinnipegBoston

YWG - BOS

YWGBOS

Winnipeg

Tue 26/8

7:00 a.m.-4:43 p.m.

1 stop8h 43m

C$ 243

WinnipegBoston

YWG - BOS

YWGBOS

Winnipeg

Tue 26/8

9:05 p.m.-10:34 p.m.

3 stops24h 29m

C$ 246

WinnipegBoston

YWG - BOS

YWGBOS

Winnipeg

Mon 25/8

11:45 a.m.-6:28 p.m.

1 stop5h 43m

C$ 364

Flights are sorted by cheapest round-trip flights first.

Deals found on 27/7

Showing 1-10 of 11 results
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

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 25 July 2025.

To ensure you get the cheapest price possible for a flight from Winnipeg to Boston, you should look to book at least 55 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$ 291). Flying from Winnipeg to Boston in April is currently the most expensive (average of C$ 350). 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 29 July 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 afternoon tend to be the most expensive. A flight in the morning could potentially save you up to 18% on airfare.

What’s the top layover airport for flights from Winnipeg to Boston?

Share of one-stop round-trip flights from Winnipeg to Boston chosen by Cheapflights users in the past 12 months, using the same layover each way.

Montreal (YUL) – chosen by Cheapflights users on 34% of one-stop itineraries from Winnipeg to Boston on Cheapflights.

What’s the cheapest layover airport for flights from Winnipeg to Boston?

Average round-trip fare for 1-stop flights from Winnipeg to Boston, chosen by Cheapflights users in the past 12 months, with the same layover each way.

Ottawa (YOW) is the most affordable 1-stop option, with an average round-trip price of C$ 438.

What’s the fastest layover option from Winnipeg to Boston?

Shortest average travel time for 1-stop one-way flights from Winnipeg to Boston, based on itineraries clicked by Cheapflights users over the past 12 months, grouped by layover airport.

Flights via Montreal (YUL) have the shortest average one-way travel time for 1-stop routes: 2h 49m.

Which airport typically offers the quickest layover for flights from Winnipeg to Boston?

Average layover duration for 1-stop one-way flights from Winnipeg to Boston, chosen by Cheapflights users in the last 12 months, grouped by stopover airport.

Flights via Montreal (YUL) offer the fastest connection on this route, with an average layover time of 1h 46m.

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 29 July 2025.
Read through reviews of airlines operating flights from Winnipeg to Boston, such as Porter Airlines,Delta, andUnited Airlines. Reviews also offer insight into each airline's entertainment options, comfort, food, crew/service, and boarding process.
Porter Airlines
8.0
Very good
317 reviews
Check prices

Comfort

8.0

Boarding

8.2

Crew

8.7

Entertainment

7.0

Food

7.6

Overall

8.0

Reviews

1 / 20
8.0
Excellent

Anonymous,Jul 2025

LIS - YYZ

Everything was on time and easy. Crew were nice on flights and helpful. International flight, so long and typically uncomfortable but not more than most. Food and drink service were below average but you get what you pay for. Overall, good experience
Porter Airlines
8.0
Very good
317 reviews
Porter Airlines
8.0
Very good
317 reviews
Check prices

Comfort

8.0

Boarding

8.2

Crew

8.7

Entertainment

7.0

Food

7.6

Overall

8.0

Reviews

1 / 20
8.0
Excellent

Anonymous,Jul 2025

LIS - YYZ

Everything was on time and easy. Crew were nice on flights and helpful. International flight, so long and typically uncomfortable but not more than most. Food and drink service were below average but you get what you pay for. Overall, good experience
Delta
8.0
Very good
7,977 reviews
Porter Airlines
8.0
Very good
317 reviews
Check prices

Comfort

8.0

Boarding

8.2

Crew

8.7

Entertainment

7.0

Food

7.6

Overall

8.0

Reviews

1 / 20
8.0
Excellent

Anonymous,Jul 2025

LIS - YYZ

Everything was on time and easy. Crew were nice on flights and helpful. International flight, so long and typically uncomfortable but not more than most. Food and drink service were below average but you get what you pay for. Overall, good experience
United Airlines
7.4
Good
8,899 reviews
Porter Airlines
8.0
Very good
317 reviews
Check prices

Comfort

8.0

Boarding

8.2

Crew

8.7

Entertainment

7.0

Food

7.6

Overall

8.0

Reviews

1 / 20
8.0
Excellent

Anonymous,Jul 2025

LIS - YYZ

Everything was on time and easy. Crew were nice on flights and helpful. International flight, so long and typically uncomfortable but not more than most. Food and drink service were below average but you get what you pay for. Overall, good experience
WestJet
7.2
Good
2,973 reviews
Porter Airlines
8.0
Very good
317 reviews
Check prices

Comfort

8.0

Boarding

8.2

Crew

8.7

Entertainment

7.0

Food

7.6

Overall

8.0

Reviews

1 / 20
8.0
Excellent

Anonymous,Jul 2025

LIS - YYZ

Everything was on time and easy. Crew were nice on flights and helpful. International flight, so long and typically uncomfortable but not more than most. Food and drink service were below average but you get what you pay for. Overall, good experience
Air Canada
7.1
Good
9,822 reviews
Porter Airlines
8.0
Very good
317 reviews
Check prices

Comfort

8.0

Boarding

8.2

Crew

8.7

Entertainment

7.0

Food

7.6

Overall

8.0

Reviews

1 / 20
8.0
Excellent

Anonymous,Jul 2025

LIS - YYZ

Everything was on time and easy. Crew were nice on flights and helpful. International flight, so long and typically uncomfortable but not more than most. Food and drink service were below average but you get what you pay for. Overall, good experience

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.

  • 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$ 412. Other airlines that can offer you cheap pricing are WestJet, from C$ 431, and Air Canada, from C$ 541. Users have found that United Airlines is 24% cheaper than the other options available to this destination.

  • What are the cheapest airlines to fly from Winnipeg to Boston one-way?

    C$ 215 is the cheapest one-way deal found within the past few days, from WestJet. You may also be able to find cheap deals on Air Canada and United Airlines, with prices starting from C$ 239 and C$ 243, respectively.

  • 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$ 291). Flying from Winnipeg to Boston in April is currently the most expensive (average of C$ 350). 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
Braintree
Waltham
Somerville
Rockland
Chelsea
Warwick
Milford
Plymouth
Quincy
Old Orchard Beach
Revere
Hampton
Lynn
Merrimack
Andover
Watertown
Kennebunk
Amherst
Seekonk

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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 5 airlines flying from Winnipeg to Boston

Discover the top 5 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 29 July 2025.
AirlineCheapestAverageFlexibilityOn-time
United AirlinesCheapestC$ 237AverageC$ 395FlexibilityNo cancel feeOn-time69%
Search United Airlines flights
Porter AirlinesCheapestC$ 317AverageC$ 510FlexibilityNo cancel feeOn-time52%
Search Porter Airlines flights
Air CanadaCheapestC$ 326AverageC$ 473FlexibilityNo cancel feeOn-time67%
Search Air Canada flights
DeltaCheapestC$ 364AverageC$ 452FlexibilityNo cancel feeOn-timeN/A
Search Delta flights
WestJetCheapestC$ 827AverageC$ 1,127FlexibilityNo 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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