HomeSearch by dateVacation packagesHotelsFlight dealsCar rentalTravel tips & news
Massachusetts

$160+ 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 6/25. Fares are subject to change and may not be available on all flights or dates of travel.
YWG — BOS
Jun 17 — Jun 241
Tue 6/17
Tue 6/24
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 June 12, 2025.

Round-trip from

$265
(United Airlines)

One-way from

$160
(United Airlines)

Popular in

December

Cheapest in

October

Average price

$337
From Winnipeg to Massachusetts
Search Deals
One-way flight from Winnipeg to Massachusetts
Search Deals
Highest demand for flights based on searches. 22% potential increase in price ($115 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 5% potential price decrease ($21 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in June 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 June 12, 2025.

This United Airlines deal was found by Cheapflights users on 6/11. 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 7/104:25 pmYWG - BOS
1 stop12h 36mUnited Airlines
Mon 7/148:48 pmBOS - YWG
1 stop17h 21mUnited Airlines
Deal found 6/11$265
This Delta deal was found by Cheapflights users on 6/12. 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 7/106:45 amYWG - BOS
1 stop9h 07mDelta
Wed 8/61:00 pmBOS - YWG
2 stops11h 25mDelta
Deal found 6/12$344
This Mytrip deal was found by Cheapflights users on 6/10. 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.
Thu 7/109:00 amYWG - BOS
2 stops25h 31mMultiple Airlines
Sun 7/1312:26 pmBOS - YWG
3 stops37h 05mMultiple Airlines
Deal found 6/10$359
This Air Canada deal was found by Cheapflights users on 6/11. 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 stop6h 38mAir Canada
Deal found 6/11$365
This FlightHub deal was found by Cheapflights users on 6/12. 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
2 stops25h 56mPorter Airlines
Wed 8/612:15 pmBOS - YWG
2 stops11h 31mPorter Airlines
Deal found 6/12$536
This Mytrip deal was found by Cheapflights users on 6/10. 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.
Sat 7/269:10 amYWG - ALB
2 stops27h 02mMultiple Airlines
Sat 8/26:30 pmALB - YWG
3 stops29h 16mMultiple Airlines
Deal found 6/10$677
This United Airlines deal was found by Cheapflights users on 6/11. 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.
Sat 7/265:00 amYWG - ALB
2 stops17h 58mUnited Airlines
Sat 8/26:00 amALB - YWG
2 stops18h 28mUnited Airlines
Deal found 6/11$826
This Air Canada deal was found by Cheapflights users on 6/10. 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.
Wed 7/307:00 amYWG - ALB
1 stop7h 09mAir Canada
Sat 8/26:00 amALB - YWG
1 stop10h 31mAir Canada
Deal found 6/10$1,333

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 June 12, 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 7/10

4:25 pm-9:26 am

2 stops16h 01m

Boston Logan Intl

Mon 7/14

8:48 pm-1:09 pm

1 stop17h 21m

$265

WinnipegBoston

YWG - BOS

YWGBOS

Winnipeg

Thu 7/10

6:45 am-4:52 pm

1 stop9h 07m

Boston Logan Intl

Wed 8/6

1:00 pm-11:25 pm

2 stops11h 25m

$344

WinnipegBoston

YWG - BOS

YWGBOS

Winnipeg

Thu 7/10

9:00 am-11:31 am

2 stops25h 31m

Boston Logan Intl

Sun 7/13

12:26 pm-12:31 am

3 stops37h 05m

$359

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-4:18 pm

1 stop6h 38m

$365

WinnipegBoston

YWG - BOS

YWGBOS

Winnipeg

Thu 7/10

11:45 am-2:41 pm

2 stops25h 56m

Boston Logan Intl

Wed 8/6

12:15 pm-10:46 pm

2 stops11h 31m

$536

WinnipegAlbany

YWG - ALB

YWGALB

Winnipeg

Sat 7/26

9:10 am-1:12 pm

2 stops27h 02m

Albany Intl

Sat 8/2

6:30 pm-10:46 pm

3 stops29h 16m

$677

WinnipegAlbany

YWG - ALB

YWGALB

Winnipeg

Thu 6/26

4:25 pm-12:11 pm

2 stops18h 46m

Albany Intl

Thu 8/28

1:22 pm-10:33 pm

1 stop10h 11m

$728

WinnipegAlbany

YWG - ALB

YWGALB

Winnipeg

Wed 7/30

7:00 am-3:09 pm

1 stop7h 09m

Albany Intl

Sat 8/2

6:00 am-3:31 pm

1 stop10h 31m

$1,333

WinnipegBoston

YWG - BOS

YWGBOS

Winnipeg

Wed 6/25

4:25 pm-8:11 am

2 stops14h 46m

$160

WinnipegBoston

YWG - BOS

YWGBOS

Winnipeg

Mon 10/13

8:50 am-10:24 pm

2 stops12h 34m

$168

Flights are sorted by cheapest round-trip flights first.

Deals found on 6/11

Showing 1-10 of 12 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 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 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 June 12, 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 June 12, 2025.
Read reviews from past customers who have flown Porter Airlines, Delta and United Airlines from Winnipeg to Massachusetts. In addition to providing an overall rating, users have also rated airlines in terms of entertainment options, comfort, food, crew/service, and boarding process.
Porter Airlines
8.0
Very good
288 reviews

Boarding

8.2

Food

7.6

Crew

8.7

Comfort

8.1

Overall

8.0

Entertainment

7.0

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
288 reviews
Porter Airlines
8.0
Very good
288 reviews

Boarding

8.2

Food

7.6

Crew

8.7

Comfort

8.1

Overall

8.0

Entertainment

7.0

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
7,950 reviews
Porter Airlines
8.0
Very good
288 reviews

Boarding

8.2

Food

7.6

Crew

8.7

Comfort

8.1

Overall

8.0

Entertainment

7.0

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
8,790 reviews
Porter Airlines
8.0
Very good
288 reviews

Boarding

8.2

Food

7.6

Crew

8.7

Comfort

8.1

Overall

8.0

Entertainment

7.0

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
9,531 reviews
Porter Airlines
8.0
Very good
288 reviews

Boarding

8.2

Food

7.6

Crew

8.7

Comfort

8.1

Overall

8.0

Entertainment

7.0

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 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?

    $160 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 $168 and $179, 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 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

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 O'Hare Intl flights
Winnipeg to Las Vegas flights
Winnipeg to Los Angeles flights
Winnipeg to Minneapolis flights
Winnipeg to Newark flights
Winnipeg to LaGuardia flights
Winnipeg to Midway flights
Winnipeg to Orlando flights
Winnipeg to John F Kennedy Intl flights
Winnipeg to Ontario flights
Winnipeg to Honolulu flights
Winnipeg to Nashville flights
Winnipeg to Atlanta flights
Winnipeg to Denver flights
Winnipeg to Fort Lauderdale flights
Winnipeg to Hobby flights
Winnipeg to Dallas/Fort Worth flights
Winnipeg to San Francisco flights
Winnipeg to Miami flights
Winnipeg to George Bush Intcntl flights
Winnipeg to Portland flights
Winnipeg to Dulles Intl flights
Winnipeg to Baltimore flights
Winnipeg to Love Field flights
Winnipeg to Sky Harbor Intl flights
Winnipeg to Tampa flights
Winnipeg to Philadelphia flights
Winnipeg to Detroit flights
Winnipeg to Santa Ana flights
Winnipeg to Reagan-National flights
Winnipeg to Charlotte flights
Winnipeg to Boston flights
Winnipeg to Pittsburgh flights
Winnipeg to St. Louis flights
Winnipeg to Palm Springs flights
Winnipeg to Louisville flights
Winnipeg to Tulsa flights
Winnipeg to Reno flights
Winnipeg to Fort Myers flights
Winnipeg to New Orleans flights
Winnipeg to Myrtle Beach flights
Winnipeg to Kahului flights
Winnipeg to Sacramento flights
Winnipeg to Seattle flights
Winnipeg to Pensacola flights
Winnipeg to Burbank flights
Winnipeg to Oakland flights
Winnipeg to San Diego flights
Winnipeg to Traverse City flights
Winnipeg to Anchorage flights

Top 4 airlines flying from Winnipeg to Massachusetts

Discover the top 4 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 June 12, 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%

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.