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$152+ Cheap flights from Winnipeg (YWG) to Boston (BOS)

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 9/15. Fares are subject to change and may not be available on all flights or dates of travel.
YWG — BOS
Jul 8 — Jul 151
Tue 7/8
Tue 7/15
1 adult, Economy
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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 Saturday or Wednesday and return on a Sunday

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 July 3, 2025.

Round-trip from

$298
(United Airlines)

One-way from

$152
(Kiwi.com)

Popular in

December

Cheapest in

October

Average price

$361
From Winnipeg to Boston Logan Intl
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One-way flight from Winnipeg to Boston Logan Intl
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Highest demand for flights based on searches. 22% potential increase in price ($114 potential increase over avg. RT price).
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Cheapest flight prices on average. 5% potential price decrease ($21 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 July 3, 2025.

This United Airlines deal was found by Cheapflights users on 7/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 7/172:20 pmYWG - BOS
1 stop9h 39mUnited Airlines
Wed 7/238:48 pmBOS - YWG
1 stop17h 21mUnited Airlines
Deal found 7/1$298
This Air Canada deal was found by Cheapflights users on 7/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Air Canada is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 8/125:00 amYWG - BOS
1 stop5h 28mAir Canada
Tue 8/195:50 amBOS - YWG
2 stops12h 50mAir Canada
Deal found 7/3$303
This Delta deal was found by Cheapflights users on 7/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 7/166:45 amYWG - BOS
2 stops14h 23mDelta
Tue 7/225:15 amBOS - YWG
2 stops12h 43mDelta
Deal found 7/1$362
This Mytrip deal was found by Cheapflights users on 7/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 7/1611:45 amYWG - BOS
2 stops20h 13mMultiple Airlines
Tue 7/226:10 amBOS - YWG
3 stops19h 21mMultiple Airlines
Deal found 7/1$402
This FlightHub deal was found by Cheapflights users on 7/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 7/1011:45 amYWG - BOS
1 stop5h 43mPorter Airlines
Wed 8/612:15 pmBOS - YWG
2 stops11h 31mPorter Airlines
Deal found 7/1$579
This FlightHub deal was found by Cheapflights users on 7/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 7/1012:30 pmYWG - BOS
2 stops10h 27mWestJet
Wed 8/65:30 amBOS - YWG
2 stops12h 28mWestJet
Deal found 7/1$744

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 2,558,603 searches. Data last updated July 3, 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 7/17

2:20 pm-12:59 am

1 stop9h 39m

Boston Logan Intl

Wed 7/23

8:48 pm-1:09 pm

1 stop17h 21m

$298

WinnipegBoston

YWG - BOS

YWGBOS

Winnipeg

Tue 8/12

5:00 am-11:28 am

1 stop5h 28m

Boston Logan Intl

Tue 8/19

5:50 am-5:40 pm

2 stops12h 50m

$303

WinnipegBoston

YWG - BOS

YWGBOS

Winnipeg

Wed 7/16

6:45 am-10:08 pm

2 stops14h 23m

Boston Logan Intl

Tue 7/22

5:15 am-4:58 pm

2 stops12h 43m

$362

WinnipegBoston

YWG - BOS

YWGBOS

Winnipeg

Wed 7/16

11:45 am-8:58 am

2 stops20h 13m

Boston Logan Intl

Tue 7/22

6:10 am-12:31 am

3 stops19h 21m

$402

WinnipegBoston

YWG - BOS

YWGBOS

Winnipeg

Mon 9/15

6:30 pm-6:28 pm

2 stops22h 58m

$152

WinnipegBoston

YWG - BOS

YWGBOS

Winnipeg

Mon 8/25

5:00 am-11:28 am

1 stop5h 28m

$174

WinnipegBoston

YWG - BOS

YWGBOS

Winnipeg

Thu 9/4

11:25 am-6:28 pm

1 stop6h 03m

$178

WinnipegBoston

YWG - BOS

YWGBOS

Winnipeg

Fri 8/15

8:35 am-7:19 pm

1 stop9h 44m

$179

WinnipegBoston

YWG - BOS

YWGBOS

Winnipeg

Thu 9/4

7:00 am-5:34 pm

2 stops9h 34m

$184

Flights are sorted by cheapest round-trip flights first.

Deals found on 7/3

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 June 27, 2025.

The best time to book flights from Winnipeg to Boston is 55 days before your desired departure date. The cost of your flight will likely increase significantly if you book two weeks in advance of your flight.

What is the cheapest month to book a flight from Winnipeg to Boston?

Currently, January is the cheapest month in which you can book a flight from Winnipeg to Boston (average of $218). Flying from Winnipeg to Boston in June is currently the most expensive (average of $306). 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 July 3, 2025.

It’s typically best to fly out from Winnipeg to Boston in the morning. Doing so could potentially save you 21% on the flight price compared to flying at noon, which is usually more expensive.

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 July 3, 2025.
Read reviews from past customers who have flown Porter Airlines, Delta, and United Airlines from Winnipeg to Boston. Users can see the overall rating for each airline as well as how each is rated in terms of entertainment options, comfort, food, crew/service, and boarding process.
Porter Airlines
8.0
Very good
298 reviews

Entertainment

7.0

Crew

8.7

Food

7.7

Comfort

8.1

Boarding

8.2

Overall

8.0

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
298 reviews
Porter Airlines
8.0
Very good
298 reviews

Entertainment

7.0

Crew

8.7

Food

7.7

Comfort

8.1

Boarding

8.2

Overall

8.0

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
7,982 reviews
Porter Airlines
8.0
Very good
298 reviews

Entertainment

7.0

Crew

8.7

Food

7.7

Comfort

8.1

Boarding

8.2

Overall

8.0

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
8,861 reviews
Porter Airlines
8.0
Very good
298 reviews

Entertainment

7.0

Crew

8.7

Food

7.7

Comfort

8.1

Boarding

8.2

Overall

8.0

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
9,681 reviews
Porter Airlines
8.0
Very good
298 reviews

Entertainment

7.0

Crew

8.7

Food

7.7

Comfort

8.1

Boarding

8.2

Overall

8.0

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?

    According to our current data, United Airlines ($298), Air Canada ($303), and Delta ($362) offers the cheapest pricing from Winnipeg to Boston. United Airlines is 26% cheaper than the average price of flights available within the next 90 days to this destination.

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

    The cheapest airlines for a one-way flight from Winnipeg to Boston are Air Canada ($174), Porter Airlines ($178), and Delta ($179).

  • 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, January is the cheapest month in which you can book a flight from Winnipeg to Boston (average of $218). Flying from Winnipeg to Boston in June is currently the most expensive (average of $306). 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

Traveling to a place near Winnipeg?

Book flights to Winnipeg if you plan to visit one of these locations
Cambridge
Medford
Watertown
Warwick
Seabrook
Waltham
Framingham
Cranston
Randolph
Chestnut Hill
Chelsea
Brockton
York Beach
Saco
Burlington
West Yarmouth
Smithfield
Swansea
Lincoln
Quincy

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 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 2,558,603 searches. Data last updated July 3, 2025.
AirlineCheapestAverageFlexibilityOn-time
United AirlinesCheapest$100Average$369FlexibilityNo cancel feeOn-time69%
DeltaCheapest$241Average$388FlexibilityNo cancel feeOn-timeN/A
Air CanadaCheapest$254Average$356FlexibilityNo cancel feeOn-time67%
Porter AirlinesCheapest$267Average$353FlexibilityNo cancel feeOn-time52%

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