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Cheap flights from Winnipeg to Boston from C$ 218

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 25/6. Fares are subject to change and may not be available on all flights or dates of travel.
YWG — BOS
18 Jun — 25 Jun1
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 13 June 2025.

Round-trip from

C$ 361

One-way from

C$ 218

Popular in

December

Cheapest in

October

Average price

C$ 459
United Airlines
  • United Airlines
  • 10/7-14/7
  • 3 total stops
  • 33h 22m total
  • Winnipeg to Boston
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United Airlines
  • United Airlines
  • 25/6
  • 2 total stops
  • 14h 46m total
  • Winnipeg to Boston
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Highest demand for flights based on searches. 22% potential increase in price (C$ 215 potential increase over avg. RT price).
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Cheapest flight prices on average. 5% potential price decrease (C$ 39 potential savings vs. average RT price).
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Average for round-trip flights in June 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 13 June 2025.

Thu 10/74:25 p.m.YWG - BOS
1 stop12h 36mUnited Airlines
Mon 14/78:48 p.m.BOS - YWG
1 stop17h 21mUnited Airlines
Deal found 11/6C$ 361
Thu 10/76:45 a.m.YWG - BOS
1 stop9h 07mDelta
Wed 6/81:00 p.m.BOS - YWG
2 stops11h 25mDelta
Deal found 12/6C$ 469
Thu 10/75:00 a.m.YWG - BOS
1 stop5h 28mAir Canada
Wed 6/810:40 a.m.BOS - YWG
1 stop6h 38mAir Canada
Deal found 11/6C$ 498
Thu 10/78:15 p.m.YWG - BOS
3 stops22h 19mMultiple Airlines
Mon 14/78:48 p.m.BOS - YWG
3 stops28h 43mMultiple Airlines
Deal found 11/6C$ 538
Thu 10/711:45 a.m.YWG - BOS
2 stops25h 56mPorter Airlines
Wed 6/812:15 p.m.BOS - YWG
2 stops11h 31mPorter Airlines
Deal found 12/6C$ 731

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 13 June 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

Thu 10/7

4:25 p.m.-6:01 a.m.

1 stop12h 36m

Boston Logan Intl

Mon 14/7

8:48 p.m.-1:09 p.m.

1 stop17h 21m

C$ 361

WinnipegBoston

YWG - BOS

YWGBOS

Winnipeg

Thu 10/7

6:45 a.m.-4:52 p.m.

1 stop9h 07m

Boston Logan Intl

Wed 6/8

1:00 p.m.-11:25 p.m.

2 stops11h 25m

C$ 469

WinnipegBoston

YWG - BOS

YWGBOS

Winnipeg

Thu 10/7

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

1 stop5h 28m

Boston Logan Intl

Wed 6/8

10:40 a.m.-4:18 p.m.

1 stop6h 38m

C$ 498

WinnipegBoston

YWG - BOS

YWGBOS

Winnipeg

Thu 10/7

8:15 p.m.-7:34 p.m.

3 stops22h 19m

Boston Logan Intl

Mon 14/7

8:48 p.m.-12:31 a.m.

3 stops28h 43m

C$ 538

WinnipegBoston

YWG - BOS

YWGBOS

Winnipeg

Thu 10/7

11:45 a.m.-2:41 p.m.

2 stops25h 56m

Boston Logan Intl

Wed 6/8

12:15 p.m.-10:46 p.m.

2 stops11h 31m

C$ 731

WinnipegBoston

YWG - BOS

YWGBOS

Winnipeg

Wed 25/6

4:25 p.m.-8:11 a.m.

2 stops14h 46m

C$ 218

WinnipegBoston

YWG - BOS

YWGBOS

Winnipeg

Mon 13/10

8:50 a.m.-10:24 p.m.

2 stops12h 34m

C$ 229

WinnipegBoston

YWG - BOS

YWGBOS

Winnipeg

Mon 30/6

6:45 p.m.-9:55 a.m.

1 stop14h 10m

C$ 244

WinnipegBoston

YWG - BOS

YWGBOS

Winnipeg

Tue 1/7

6:30 a.m.-8:39 a.m.

3 stops25h 09m

C$ 320

Flights are sorted by cheapest round-trip flights first.

Deals found on 11/6

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 9 June 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 13 June 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.

Rainfall in Boston by month

Plan your trip to Boston by taking into account the average rainfall totals by month.

In terms of precipitation, rainfall in Boston ranges from 78.0 - 101.0 mm per month. March is typically the wettest month, when rainfall can reach 101.0 mm. July is typically the driest time to visit Boston when rainfall is around 78.0 mm.

Temperature in Boston by month

Plan your trip to Boston by taking into account the average temperature totals by month.

If weather is an important factor for your trip to Boston, use this chart to help with planning. For those seeking warmer temperatures, July is the ideal time of year to visit, when temperatures reach an average of 23.0 C. Travellers hoping to avoid the cold should look outside of January, when temperatures are typically at their lowest (around -1.0 C).

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 13 June 2025.
Porter Airlines
8.0
Very good
288 reviews
Check prices

Boarding

8.2

Overall

8.0

Entertainment

7.0

Comfort

8.1

Food

7.6

Crew

8.7

Reviews

1 / 20
4.0
Okay

Mary,Jun 2025

FLL - YYZ

Fort Lauderdale staff was not helpful at all to try to accommodate my husband and myself to sit together. Also very surprised to get charged USD53 for each of our checked luggage, as when we booked the tickets online, the website indicated that our first checked luggage will be charged CAD50!! Very misleading!!!
Porter Airlines
8.0
Very good
288 reviews
Porter Airlines
8.0
Very good
288 reviews
Check prices

Boarding

8.2

Overall

8.0

Entertainment

7.0

Comfort

8.1

Food

7.6

Crew

8.7

Reviews

1 / 20
4.0
Okay

Mary,Jun 2025

FLL - YYZ

Fort Lauderdale staff was not helpful at all to try to accommodate my husband and myself to sit together. Also very surprised to get charged USD53 for each of our checked luggage, as when we booked the tickets online, the website indicated that our first checked luggage will be charged CAD50!! Very misleading!!!
Delta
8.0
Very good
7,946 reviews
Porter Airlines
8.0
Very good
288 reviews
Check prices

Boarding

8.2

Overall

8.0

Entertainment

7.0

Comfort

8.1

Food

7.6

Crew

8.7

Reviews

1 / 20
4.0
Okay

Mary,Jun 2025

FLL - YYZ

Fort Lauderdale staff was not helpful at all to try to accommodate my husband and myself to sit together. Also very surprised to get charged USD53 for each of our checked luggage, as when we booked the tickets online, the website indicated that our first checked luggage will be charged CAD50!! Very misleading!!!
United Airlines
7.4
Good
8,790 reviews
Porter Airlines
8.0
Very good
288 reviews
Check prices

Boarding

8.2

Overall

8.0

Entertainment

7.0

Comfort

8.1

Food

7.6

Crew

8.7

Reviews

1 / 20
4.0
Okay

Mary,Jun 2025

FLL - YYZ

Fort Lauderdale staff was not helpful at all to try to accommodate my husband and myself to sit together. Also very surprised to get charged USD53 for each of our checked luggage, as when we booked the tickets online, the website indicated that our first checked luggage will be charged CAD50!! Very misleading!!!
Air Canada
7.1
Good
9,537 reviews
Porter Airlines
8.0
Very good
288 reviews
Check prices

Boarding

8.2

Overall

8.0

Entertainment

7.0

Comfort

8.1

Food

7.6

Crew

8.7

Reviews

1 / 20
4.0
Okay

Mary,Jun 2025

FLL - YYZ

Fort Lauderdale staff was not helpful at all to try to accommodate my husband and myself to sit together. Also very surprised to get charged USD53 for each of our checked luggage, as when we booked the tickets online, the website indicated that our first checked luggage will be charged CAD50!! Very misleading!!!

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$ 361. Other airlines that can offer you cheap pricing are Delta, from C$ 469, and Air Canada, from C$ 498. Users have found that United Airlines is 34% cheaper than the other options available to this destination.

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

    C$ 218 is the cheapest one-way deal found within the past few days, from United Airlines. You may also be able to find cheap deals on Delta and Air Canada, with prices starting from C$ 239 and C$ 244, 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 Winnipeg?

Book flights to Winnipeg if you plan to visit one of these locations
Seekonk
Waltham
Medford
Braintree
Somerville
Dedham
Rockland
Chelsea
Warwick
Milford
Plymouth
Quincy
Old Orchard Beach
Revere
Hampton
Lynn
Merrimack
Andover
Watertown
Kennebunk

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 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 13 June 2025.
AirlineCheapestAverageFlexibilityOn-time
United AirlinesCheapestC$ 235AverageC$ 392FlexibilityNo cancel feeOn-time69%
Search United Airlines flights
Porter AirlinesCheapestC$ 323AverageC$ 513FlexibilityNo cancel feeOn-time52%
Search Porter Airlines flights
Air CanadaCheapestC$ 332AverageC$ 493FlexibilityNo cancel feeOn-time67%
Search Air Canada flights
DeltaCheapestC$ 362AverageC$ 473FlexibilityNo cancel feeOn-timeN/A
Search Delta flights
WestJetCheapestC$ 822AverageC$ 1,120FlexibilityNo 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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