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Cheap flights from Winnipeg to Boston from C$ 216

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 12/6. Fares are subject to change and may not be available on all flights or dates of travel.
YWG — BOS
4 May — 11 May1
1 adult

Cheapflights Tip: The best prices from Winnipeg to Boston Logan Intl are usually found in October or May, 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 April 2025.

Round-trip from

C$ 388

One-way from

C$ 216

Popular in

December

Cheapest in

October

Average price

C$ 491
Delta
  • Delta
  • 10/7-6/8
  • 3 total stops
  • 17h 23m total
  • Winnipeg to Boston
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United Airlines
  • United Airlines
  • 12/6
  • 1 total stop
  • 9h 39m total
  • Winnipeg to Boston
Search Deals
Highest demand for flights based on searches. 20% potential increase in price (C$ 207 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 4% potential price decrease (C$ 38 potential savings vs. average RT price).
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Average for round-trip flights in April 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 April 2025.

Thu 10/712:26 p.m.YWG - BOS
2 stops10h 27mDelta
Wed 6/85:35 a.m.BOS - YWG
1 stop6h 56mDelta
Deal found 28/4C$ 388
Wed 21/52:20 p.m.YWG - BOS
2 stops8h 39mUnited Airlines
Tue 27/56:00 a.m.BOS - YWG
1 stop10h 31mUnited Airlines
Deal found 28/4C$ 399
Fri 25/711:45 a.m.YWG - BOS
2 stops9h 16mPorter Airlines
Fri 1/83:50 p.m.BOS - YWG
1 stop7h 56mPorter Airlines
Deal found 28/4C$ 492
Wed 6/85:00 a.m.YWG - BOS
1 stop5h 28mAir Canada
Sun 10/85:50 a.m.BOS - YWG
1 stop5h 29mAir Canada
Deal found 28/4C$ 525
Sat 7/611:45 a.m.YWG - BOS
2 stops20h 24mMultiple Airlines
Wed 11/63:50 p.m.BOS - YWG
1 stop7h 56mMultiple Airlines
Deal found 28/4C$ 534

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 April 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

12:26 p.m.-10:24 p.m.

1 stop8h 58m

Boston Logan Intl

Wed 6/8

5:35 a.m.-11:31 a.m.

1 stop6h 56m

C$ 388

WinnipegBoston

YWG - BOS

YWGBOS

Winnipeg

Wed 21/5

2:20 p.m.-11:59 p.m.

2 stops8h 39m

Boston Logan Intl

Tue 27/5

6:00 a.m.-3:31 p.m.

1 stop10h 31m

C$ 399

WinnipegBoston

YWG - BOS

YWGBOS

Winnipeg

Fri 25/7

11:45 a.m.-10:01 p.m.

2 stops9h 16m

Boston Logan Intl

Fri 1/8

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

1 stop7h 56m

C$ 492

WinnipegBoston

YWG - BOS

YWGBOS

Winnipeg

Wed 6/8

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

1 stop5h 28m

Boston Logan Intl

Sun 10/8

5:50 a.m.-10:19 a.m.

1 stop5h 29m

C$ 525

WinnipegBoston

YWG - BOS

YWGBOS

Winnipeg

Sat 7/6

11:45 a.m.-9:09 a.m.

2 stops20h 24m

Boston Logan Intl

Wed 11/6

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

1 stop7h 56m

C$ 534

WinnipegBoston

YWG - BOS

YWGBOS

Winnipeg

Thu 12/6

2:20 p.m.-12:59 a.m.

1 stop9h 39m

C$ 216

WinnipegBoston

YWG - BOS

YWGBOS

Winnipeg

Mon 1/9

8:00 a.m.-2:31 p.m.

1 stop5h 31m

C$ 237

WinnipegBoston

YWG - BOS

YWGBOS

Winnipeg

Mon 1/9

12:40 p.m.-1:06 a.m.

2 stops11h 26m

C$ 254

WinnipegBoston

YWG - BOS

YWGBOS

Winnipeg

Thu 11/9

9:00 a.m.-11:29 p.m.

2 stops13h 29m

C$ 281

Flights are sorted by cheapest round-trip flights first.

Deals found on 27/4

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 April 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, January is the cheapest month in which you can book a flight from Winnipeg to Boston (average of C$ 298). 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 April 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 29 April 2025.
Porter Airlines
8.0
Very good
285 reviews
Check prices

Boarding

8.2

Comfort

8.1

Crew

8.8

Entertainment

7.0

Food

7.6

Overall

8.0

Reviews

1 / 18
10.0
Excellent

Anonymous,Apr 2025

MCO - YHZ

A good flight and the crew was very nice. Thank you
Porter Airlines
8.0
Very good
285 reviews
Porter Airlines
8.0
Very good
285 reviews
Check prices

Boarding

8.2

Comfort

8.1

Crew

8.8

Entertainment

7.0

Food

7.6

Overall

8.0

Reviews

1 / 18
10.0
Excellent

Anonymous,Apr 2025

MCO - YHZ

A good flight and the crew was very nice. Thank you
Delta
8.0
Very good
7,929 reviews
Porter Airlines
8.0
Very good
285 reviews
Check prices

Boarding

8.2

Comfort

8.1

Crew

8.8

Entertainment

7.0

Food

7.6

Overall

8.0

Reviews

1 / 18
10.0
Excellent

Anonymous,Apr 2025

MCO - YHZ

A good flight and the crew was very nice. Thank you
United Airlines
7.4
Good
8,696 reviews
Porter Airlines
8.0
Very good
285 reviews
Check prices

Boarding

8.2

Comfort

8.1

Crew

8.8

Entertainment

7.0

Food

7.6

Overall

8.0

Reviews

1 / 18
10.0
Excellent

Anonymous,Apr 2025

MCO - YHZ

A good flight and the crew was very nice. Thank you
Air Canada
7.0
Good
9,242 reviews
Porter Airlines
8.0
Very good
285 reviews
Check prices

Boarding

8.2

Comfort

8.1

Crew

8.8

Entertainment

7.0

Food

7.6

Overall

8.0

Reviews

1 / 18
10.0
Excellent

Anonymous,Apr 2025

MCO - YHZ

A good flight and the crew was very nice. Thank you

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$ 388. Other airlines that can offer you cheap pricing are United Airlines, from C$ 399, and Porter Airlines, from C$ 492. Users have found that Delta is 32% cheaper than the other options available to this destination.

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

    C$ 216 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 Air Canada and Delta, with prices starting from C$ 237 and C$ 254, 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, January is the cheapest month in which you can book a flight from Winnipeg to Boston (average of C$ 298). 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
Warwick
Medford
Braintree
Somerville
Dedham
Rockland
Chelsea
Plymouth
Quincy
Old Orchard Beach
Revere
Hampton
Lynn
Andover
Watertown
Kennebunk
Amherst
Sturbridge

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 629,999 searches. Data last updated 29 April 2025.
AirlineCheapestAverageFlexibilityOn-time
United AirlinesCheapestC$ 309AverageC$ 380FlexibilityNo cancel feeOn-time69%
Search United Airlines flights
Porter AirlinesCheapestC$ 329AverageC$ 522FlexibilityNo cancel feeOn-time52%
Search Porter Airlines flights
Air CanadaCheapestC$ 345AverageC$ 543FlexibilityNo cancel feeOn-time67%
Search Air Canada flights
DeltaCheapestC$ 368AverageC$ 500FlexibilityNo cancel feeOn-timeN/A
Search Delta 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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