HomeSearch by dateVacation packagesHotelsFlight dealsCar rentalTravel tips & news
Massachusetts

$147+ Cheap flights from Winnipeg (YWG) to Massachusetts

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 5/1. Fares are subject to change and may not be available on all flights or dates of travel.
YWG — BOS
Apr 6 — Apr 131
Sun 4/6
Sun 4/13
1 adult, Economy
We work with more than 300 partners to bring you better travel deals

Find cheap flights from Winnipeg to Massachusetts with Cheapflights

1. Tell us where you want to go
Enter your travel information like dates, passengers, trip type (one-way or round trip), and preferred cabin class then click “Find deals”
2. Select your favorite providers
We find the providers serving your travel needs. Choose up to four travel providers to compare side-by-side for flights, hotels, or car rentals.
3. Compare prices and book
Review each provider’s pricing and select the best option for you! Book through your favorite provider’s website for a seamless experience.

Cheap flight deals from Winnipeg to Massachusetts

Keep the following information in mind while searching for Winnipeg to Massachusetts flight deals. Data was last updated April 1, 2025.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$281
(United)

One-way from

$147
(Air Canada)

Popular in

December

Cheapest in

October

Average price

$377
Provider with most accurate pricing for Winnipeg-Boston Logan Intl flight deals.
Search Deals
Provider most trusted by Cheapflights users for Winnipeg-Boston Logan Intl flights.
Search Deals
From Winnipeg to Massachusetts
Search Deals
One-way flight from Winnipeg to Massachusetts
Search Deals
Highest demand for flights based on searches. 18% potential increase in price ($97 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 4% potential price decrease ($19 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in April 2025
Search Deals

Find flight deals from Winnipeg to Massachusetts

Cheapest flights from Winnipeg to Massachusetts
Explore the most affordable flight options available from Winnipeg to Massachusetts. Find the lowest fares from popular airlines and budget airlines, with prices last updated on April 1, 2025.

This United deal was found by Cheapflights users on 3/29. 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 is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 5/152:20 pmYWG - BOS
1 stop9h 25mMultiple Airlines
Sat 5/3110:20 amBOS - YWG
2 stops8h 30mMultiple Airlines
Deal found 3/29$281
This Air Canada deal was found by Cheapflights users on 3/31. 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.
Thu 7/105:00 amYWG - BOS
1 stop5h 28mAir Canada
Wed 8/610:40 amBOS - YWG
1 stop7h 58mAir Canada
Deal found 3/31$282
This Delta deal was found by Cheapflights users on 3/30. 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.
Thu 5/1512:52 pmYWG - BOS
1 stop10h 04mDelta
Sat 5/178:25 amBOS - YWG
2 stops12h 43mDelta
Deal found 3/30$300
This United Airlines deal was found by Cheapflights users on 3/31. 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 7/102:20 pmYWG - BOS
1 stop9h 39mUnited Airlines
Wed 8/65:30 amBOS - YWG
2 stops18h 03mUnited Airlines
Deal found 3/31$309
This FlightHub deal was found by Cheapflights users on 3/30. 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.
Fri 8/2211:45 amYWG - BOS
1 stop5h 23mPorter Airlines
Sun 9/73:50 pmBOS - YWG
1 stop5h 56mPorter Airlines
Deal found 3/30$339

Cheapflights Fare Finder

Customize your flight search to find flights from Winnipeg to Massachusetts 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 April 1, 2025.
Use the filters below to find and compare flights from Winnipeg to Massachusetts that are best for you.

Fly from

Winnipeg

Fly to

Massachusetts

Route

Depart

Return

Price

WinnipegBoston

YWG - BOS

YWGBOS

Winnipeg

Thu 5/15

2:20 pm-12:45 am

1 stop9h 25m

Boston Logan Intl

Sat 5/31

10:20 am-5:50 pm

2 stops8h 30m

$281

WinnipegBoston

YWG - BOS

YWGBOS

Winnipeg

Thu 7/10

5:00 am-11:28 am

1 stop5h 28m

Boston Logan Intl

Wed 8/6

10:40 am-5:38 pm

1 stop7h 58m

$282

WinnipegBoston

YWG - BOS

YWGBOS

Winnipeg

Thu 5/15

12:52 pm-11:56 pm

1 stop10h 04m

Boston Logan Intl

Sat 5/17

5:45 am-11:57 am

1 stop7h 12m

$300

WinnipegBoston

YWG - BOS

YWGBOS

Winnipeg

Thu 7/10

2:20 pm-12:59 am

1 stop9h 39m

Boston Logan Intl

Wed 8/6

5:30 am-10:33 pm

2 stops18h 03m

$309

WinnipegBoston

YWG - BOS

YWGBOS

Winnipeg

Fri 8/22

11:45 am-6:08 pm

1 stop5h 23m

Boston Logan Intl

Sun 9/7

3:50 pm-8:46 pm

1 stop5h 56m

$339

WinnipegBoston

YWG - BOS

YWGBOS

Winnipeg

Thu 5/1

5:00 am-11:28 am

1 stop5h 28m

$147

WinnipegBoston

YWG - BOS

YWGBOS

Winnipeg

Wed 5/28

12:52 pm-11:46 pm

2 stops9h 54m

$153

WinnipegBoston

YWG - BOS

YWGBOS

Winnipeg

Thu 5/1

9:05 pm-3:21 pm

2 stops17h 16m

$170

WinnipegBoston

YWG - BOS

YWGBOS

Winnipeg

Fri 7/25

11:45 am-10:01 pm

2 stops9h 16m

$212

WinnipegAlbany

YWG - ALB

YWGALB

Winnipeg

Fri 5/16

4:25 pm-2:16 pm

2 stops20h 51m

$330

Flights are sorted by cheapest round-trip flights first.

Deals found on 3/29

Showing 1-10 of 11 results
1
2

Best time to book a flight from Winnipeg to Massachusetts

Have a flexible travel schedule? Discover the best time to fly to Massachusetts 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 Massachusetts

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

Currently, January is the cheapest month in which you can book a flight from Winnipeg to Massachusetts (average of $218). Flying from Winnipeg to Massachusetts in July is currently the most expensive (average of $311). 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 MA?

Find hourly flight availability from Winnipeg to Massachusetts. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated April 1, 2025.

Regardless of the time of day you decide to fly, the ticket price will remain around the same. Book flights from Winnipeg to Massachusetts as you normally would.

Rainfall in Massachusetts by month

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

In terms of precipitation, rainfall in Massachusetts ranges from 3.1 - 4.0 inches per month. March is typically the wettest month, when rainfall can reach 4.0 in. July is typically the driest time to visit Massachusetts when rainfall is around 3.1 in.

Temperature in Massachusetts by month

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

If weather is an important factor for your trip to Massachusetts, 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 73.4 F. Travelers looking to avoid the cold should look outside of January, when temperatures are typically at their lowest (around 30.2 F).

Reviews of airlines servicing Massachusetts

Get insights into the airlines that provide service to Massachusetts. 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 Massachusetts. Reviews last updated April 1, 2025.
Delta
8.0
Very good
7,899 reviews

Crew

8.5

Food

7.3

Entertainment

7.9

Boarding

8.2

Overall

8.0

Comfort

8.0

Reviews

1 / 20
10.0
Excellent

Aaron,Oct 2024

TUS - LAX

Delta has consistently been the best U.S. airline for my travels and this flight was no exception
Delta
8.0
Very good
7,899 reviews
Delta
8.0
Very good
7,899 reviews

Crew

8.5

Food

7.3

Entertainment

7.9

Boarding

8.2

Overall

8.0

Comfort

8.0

Reviews

1 / 20
10.0
Excellent

Aaron,Oct 2024

TUS - LAX

Delta has consistently been the best U.S. airline for my travels and this flight was no exception
Porter Airlines
7.9
Good
277 reviews
Delta
8.0
Very good
7,899 reviews

Crew

8.5

Food

7.3

Entertainment

7.9

Boarding

8.2

Overall

8.0

Comfort

8.0

Reviews

1 / 20
10.0
Excellent

Aaron,Oct 2024

TUS - LAX

Delta has consistently been the best U.S. airline for my travels and this flight was no exception
United Airlines
7.4
Good
8,614 reviews
Delta
8.0
Very good
7,899 reviews

Crew

8.5

Food

7.3

Entertainment

7.9

Boarding

8.2

Overall

8.0

Comfort

8.0

Reviews

1 / 20
10.0
Excellent

Aaron,Oct 2024

TUS - LAX

Delta has consistently been the best U.S. airline for my travels and this flight was no exception
WestJet
7.2
Good
2,789 reviews
Delta
8.0
Very good
7,899 reviews

Crew

8.5

Food

7.3

Entertainment

7.9

Boarding

8.2

Overall

8.0

Comfort

8.0

Reviews

1 / 20
10.0
Excellent

Aaron,Oct 2024

TUS - LAX

Delta has consistently been the best U.S. airline for my travels and this flight was no exception
Air Canada
7.0
Good
9,013 reviews
Delta
8.0
Very good
7,899 reviews

Crew

8.5

Food

7.3

Entertainment

7.9

Boarding

8.2

Overall

8.0

Comfort

8.0

Reviews

1 / 20
10.0
Excellent

Aaron,Oct 2024

TUS - LAX

Delta has consistently been the best U.S. airline for my travels and this flight was no exception

Related info for your journey

Find useful and relevant information for your journey from Winnipeg to Massachusetts. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.

  • What airport do you fly from for flights from Winnipeg to Massachusetts?

    For a flight from Winnipeg to Massachusetts, you will be flying from Winnipeg. Winnipeg (YWG) is just 4.6 mi from the center of the city.

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

    $147 is the cheapest one-way deal found within the past few days, from Air Canada. You may also be able to find cheap deals on Delta and Porter Airlines, with prices starting from $153 and $212, respectively.

  • What are the most popular routes from Winnipeg to Massachusetts?

    The most popular route from Winnipeg to Massachusetts is Winnipeg - Boston Logan Intl. You may also consider Winnipeg - Albany Intl or Winnipeg - Provincetown.

  • Can I find deals for flights from Winnipeg to Massachusetts that include hotel bookings?

    Yes. In addition to deals on Winnipeg to Massachusetts flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from Winnipeg to Massachusetts?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Winnipeg to Massachusetts.

  • Can I find deals for business class flights from Winnipeg to Massachusetts?

    Yes. Cheapflights offers flight deals from Winnipeg to Massachusetts 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 Massachusetts?

    Currently, January is the cheapest month in which you can book a flight from Winnipeg to Massachusetts (average of $218). Flying from Winnipeg to Massachusetts in July is currently the most expensive (average of $311). 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

Browse thousands of different options on Cheapflights for your next trip

Toggle through the tabs below to find thousands of options on Cheapflights for your next trip.

Alternative routes for Winnipeg to Massachusetts

See prices for flight routes from nearby airports that may be better suited for you.
Winnipeg to Las Vegas flights
Winnipeg to Newark flights
Winnipeg to John F Kennedy Intl flights
Winnipeg to O'Hare Intl flights
Winnipeg to Los Angeles flights
Winnipeg to Minneapolis flights
Winnipeg to LaGuardia flights
Winnipeg to Nashville flights
Winnipeg to Orlando flights
Winnipeg to Sky Harbor Intl flights
Winnipeg to Atlanta flights
Winnipeg to Midway flights
Winnipeg to Fort Lauderdale flights
Winnipeg to Fort Myers flights
Winnipeg to Dulles Intl flights
Winnipeg to Ontario flights
Winnipeg to Miami flights
Winnipeg to Dallas/Fort Worth flights
Winnipeg to Baltimore flights
Winnipeg to Honolulu flights
Winnipeg to Tampa flights
Winnipeg to Denver flights
Winnipeg to Reagan-National flights
Winnipeg to San Francisco flights
Winnipeg to Philadelphia flights
Winnipeg to Hobby flights
Winnipeg to Palm Springs flights
Winnipeg to San Diego flights
Winnipeg to Anchorage flights
Winnipeg to Love Field flights
Winnipeg to Sarasota flights
Winnipeg to Boston flights
Winnipeg to Seattle flights
Winnipeg to Daytona Beach flights
Winnipeg to Santa Ana flights
Winnipeg to Portland flights
Winnipeg to Kansas City flights
Winnipeg to Memphis flights
Winnipeg to George Bush Intcntl flights
Winnipeg to New Orleans flights
Winnipeg to Pensacola flights
Winnipeg to Detroit flights
Winnipeg to San Jose flights
Winnipeg to Sacramento flights
Winnipeg to Tulsa flights
Winnipeg to Charlotte flights
Winnipeg to Traverse City flights
Winnipeg to Norfolk flights
Winnipeg to Myrtle Beach flights
Winnipeg to Des Moines flights

Top 2 airlines flying from Winnipeg to Massachusetts

Discover the top 2 airlines that operate flights from Winnipeg to Massachusetts. 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 April 1, 2025.
AirlineCheapestAverageFlexibilityOn-time
Air CanadaCheapest$254Average$493FlexibilityNo cancel feeOn-time67%
Porter AirlinesCheapest$267Average$355FlexibilityNo cancel feeOn-time52%
100% Free
Cheapflights is completely free to use, so you can start saving the moment you arrive.
Book with Flexibility
Our users can plan ahead with confidence and find flights with no change fees
Travel Smart
Millions of people come to us for their flight needs every year. We help make travel planning easy by providing useful insights and data-driven graphs that can inform your decisions.