How long is the flight from Winnipeg to Massachusetts?

There are many flights that can get you from Winnipeg to Massachusetts in 5h 37m. Fly via Air Canada or United Airlines to get the fastest option. The distance from Winnipeg to Massachusetts is about 1350 mi. Both multi-stop and nonstop flights can be found to your destination and back.

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.

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).

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.

What are the most popular airlines that fly from Winnipeg to Massachusetts?

Before booking your flight from Winnipeg to Massachusetts check out the most popular airlines for this route: Air Canada, Delta or United Airlines.

What is the cheapest time of day to fly from YWG to MA?

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.

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.

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.

$132+ Flights from Winnipeg to Massachusetts

Home Search by date Vacation packages Hotels Flight deals Car rental Travel tips & news

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

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 December 16, 2025.

Thu 12/252:20 pmYWG - ALB

1 stop5h 45mUnited Airlines

Thu 1/16:00 amALB - YWG

1 stop6h 57mUnited Airlines

Deal found 12/13

$671

Best flights from Winnipeg to Massachusetts
Discover carefully curated flight deals from Winnipeg to Massachusetts that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated December 16, 2025.

Mon 1/128:00 amYWG - BOS

1 stop14h 57mMultiple Airlines

Mon 1/195:34 amBOS - YWG

1 stop13h 29mMultiple Airlines

Deal found 12/14

$263

Thu 1/158:15 amYWG - BOS

1 stop5h 37mAir Canada

Thu 1/2210:15 amBOS - YWG

1 stop7h 20mAir Canada

Deal found 12/16

$318

Mon 3/22:20 pmYWG - ALB

1 stop5h 56mUnited Airlines

Wed 3/47:30 pmALB - YWG

2 stops17h 27mUnited Airlines

Deal found 12/13

$353

Fri 1/237:30 amYWG - ALB

1 stop28h 54mWestJet

Sun 1/256:00 amALB - YWG

1 stop10h 07mWestJet

Deal found 12/14

$466

Fri 1/3012:55 pmYWG - BOS

2 stops35h 18mMultiple Airlines

Fri 2/66:00 amBOS - YWG

1 stop10h 09mMultiple Airlines

Deal found 12/16

$290

Fri 2/138:15 amYWG - BOS

1 stop5h 37mAir Canada

Sun 2/155:30 amBOS - YWG

1 stop5h 45mAir Canada

Deal found 12/15

$329

Thu 1/155:00 amYWG - BOS

1 stop29h 05mMultiple Airlines

Thu 1/226:00 amBOS - YWG

2 stops19h 41mMultiple Airlines

Deal found 12/16

$308

Fri 1/235:30 amYWG - ALB

2 stops14h 52mUnited Airlines

Sun 1/256:00 amALB - YWG

1 stop6h 57mUnited Airlines

Deal found 12/14

$413

Last-minute flights from Winnipeg to Massachusetts
Discover last-minute flight deals from Winnipeg to Massachusetts. Data last updated December 16, 2025 and is based on user searches.

Thu 12/252:20 pmYWG - ALB

1 stop5h 45mUnited Airlines

Thu 1/16:00 amALB - YWG

1 stop6h 57mUnited Airlines

Deal found 12/13

$671

Mon 1/128:00 amYWG - BOS

1 stop14h 57mMultiple Airlines

Mon 1/195:34 amBOS - YWG

1 stop13h 29mMultiple Airlines

Deal found 12/14

$263

Thu 1/155:00 amYWG - BOS

1 stop29h 05mMultiple Airlines

Thu 1/226:00 amBOS - YWG

2 stops19h 41mMultiple Airlines

Deal found 12/16

$308

Thu 1/158:15 amYWG - BOS

1 stop5h 37mAir Canada

Thu 1/2210:15 amBOS - YWG

1 stop7h 20mAir Canada

Deal found 12/16

$318

Fri 1/235:30 amYWG - ALB

2 stops14h 52mUnited Airlines

Sun 1/257:25 pmALB - YWG

2 stops17h 32mUnited Airlines

Deal found 12/14

$413

Fri 1/237:30 amYWG - ALB

1 stop28h 54mWestJet

Sun 1/256:00 amALB - YWG

1 stop10h 07mWestJet

Deal found 12/14

$466

Fri 1/2312:10 pmYWG - ALB

2 stops26h 10mAmerican Airlines

Sun 1/257:23 amALB - YWG

3 stops17h 12mAmerican Airlines

Deal found 12/14

$691

Fri 1/3012:55 pmYWG - BOS

2 stops35h 18mMultiple Airlines

Fri 2/66:00 amBOS - YWG

1 stop10h 09mMultiple Airlines

Deal found 12/16

$290

Fri 1/305:30 pmYWG - BOS

1 stop15h 32mAir Canada

Fri 2/610:15 amBOS - YWG

1 stop7h 20mAir Canada

Deal found 12/16

$345

One-way flights from Winnipeg to Massachusetts
Search for one-way flight options from Winnipeg to Massachusetts. Find affordable one-way fares based on user searches. Data last updated December 16, 2025.

Fri 1/306:55 pmYWG - BOS

3 stops29h 18mMultiple Airlines

Deal found 12/16

$132

Wed 6/311:45 amYWG - BOS

1 stop5h 43mPorter Airlines

Deal found 12/14

$233

Thu 6/47:00 amYWG - BOS

2 stops15h 59mMultiple Airlines

Deal found 12/14

$241

Wed 6/312:15 pmYWG - BOS

2 stops8h 12mAir Canada

Deal found 12/14

$261

Wed 6/36:10 amYWG - BOS

3 stops15h 05mAmerican Airlines

Deal found 12/14

$513

Find flight deals from Winnipeg to Massachusetts

Most accurate provider	eDreams 3 stars
Most trusted provider	eDreams 3 stars
Round-trip from	$263 (Kiwi.com)
One-way from	$132 (Kiwi.com)
Popular in	December
Cheapest in	June
Average price	$583

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. 21% potential increase in price ($112 potential increase over avg. RT price).

Search Deals

Cheapest flight prices on average. 3% potential price decrease ($16 potential savings vs. average RT price).

Search Deals

Average for round-trip flights in December 2025

Search Deals

Cheapflights Fare Finder

Use the filters below to find and compare flights from Winnipeg to Massachusetts that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

WinnipegBoston

YWG - BOS

YWGBOS

Winnipeg

Mon 1/12

8:00 am-11:57 pm

1 stop14h 57m

Boston Logan Intl

Mon 1/19

5:34 am-6:03 pm

1 stop13h 29m

$263

WinnipegBoston

YWG - BOS

YWGBOS

Winnipeg

Fri 1/30

12:55 pm-1:13 am

2 stops35h 18m

Boston Logan Intl

Fri 2/6

6:00 am-3:09 pm

1 stop10h 09m

$290

WinnipegBoston

YWG - BOS

YWGBOS

Winnipeg

Thu 1/15

5:00 am-11:05 am

1 stop29h 05m

Boston Logan Intl

Thu 1/22

6:00 am-12:41 am

2 stops19h 41m

$308

WinnipegBoston

YWG - BOS

YWGBOS

Winnipeg

Thu 1/15

8:15 am-2:52 pm

1 stop5h 37m

Boston Logan Intl

Thu 1/22

10:15 am-4:35 pm

1 stop7h 20m

$318

WinnipegBoston

YWG - BOS

YWGBOS

Winnipeg

Fri 2/13

8:15 am-2:52 pm

1 stop5h 37m

Boston Logan Intl

Sun 2/15

5:30 am-10:15 am

1 stop5h 45m

$329

WinnipegAlbany

YWG - ALB

YWGALB

Winnipeg

Mon 3/2

2:20 pm-9:16 pm

1 stop5h 56m

Albany Intl

Wed 3/4

7:30 pm-11:57 am

2 stops17h 27m

$353

WinnipegAlbany

YWG - ALB

YWGALB

Winnipeg

Fri 1/23

5:30 am-9:22 pm

2 stops14h 52m

Albany Intl

Sun 1/25

6:00 am-11:57 am

1 stop6h 57m

$413

WinnipegAlbany

YWG - ALB

YWGALB

Winnipeg

Fri 1/23

7:30 am-1:24 pm

1 stop28h 54m

Albany Intl

Sun 1/25

6:00 am-3:07 pm

1 stop10h 07m

$466

WinnipegBoston

YWG - BOS

YWGBOS

Winnipeg

Fri 1/30

6:55 pm-1:13 am

3 stops29h 18m

$132

WinnipegBoston

YWG - BOS

YWGBOS

Winnipeg

Thu 6/4

11:45 am-6:28 pm

1 stop5h 43m

$233

Flights are sorted by cheapest round-trip flights first.

Deals found on 12/16

Showing 1-10 of 14 results

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, May is the cheapest month in which you can book a flight from Winnipeg to Massachusetts (average of $161). Flying from Winnipeg to Massachusetts in March is currently the most expensive (average of $328). 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.

Reviews of airlines servicing Massachusetts

Read reviews from past customers who have flown Delta, United Airlines, and Air Canada from Winnipeg to Massachusetts. Reviews also offer insight into each airline's entertainment options, comfort, food, crew/service, and boarding process.

Delta

7.9

Good

8,009 reviews

Reviews

1 / 20

6.0

Good

Jim,Nov 2025

AVL - ATL

The exit row seats without a seat in front are great for leg room but don’t have a fold out entertainment console so you’re forced to use the screen several feet in front of you (there is, at least, a remote). Best to bring a tablet loaded with entertainment or a book.

Delta

7.9

Good

8,009 reviews

Delta

7.9

Good

8,009 reviews

Reviews

1 / 20

6.0

Good

Jim,Nov 2025

AVL - ATL

United Airlines

7.4

Good

9,094 reviews

Delta

7.9

Good

8,009 reviews

Reviews

1 / 20

6.0

Good

Jim,Nov 2025

AVL - ATL

Air Canada

7.1

Good

10,530 reviews

Delta

7.9

Good

8,009 reviews

Reviews

1 / 20

6.0

Good

Jim,Nov 2025

AVL - ATL

Related info for your journey

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.
How long is the flight from Winnipeg to Massachusetts?
There are many flights that can get you from Winnipeg to Massachusetts in 5h 37m. Fly via Air Canada or United Airlines to get the fastest option. The distance from Winnipeg to Massachusetts is about 1350 mi. Both multi-stop and nonstop flights can be found to your destination and back.
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, May is the cheapest month in which you can book a flight from Winnipeg to Massachusetts (average of $161). Flying from Winnipeg to Massachusetts in March is currently the most expensive (average of $328). 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

Alternative routes for Winnipeg to Massachusetts

Winnipeg to Orlando flights

Winnipeg to Las Vegas flights

Winnipeg to Sky Harbor Intl flights

Winnipeg to John F Kennedy Intl flights

Winnipeg to Newark flights

Winnipeg to Fort Lauderdale flights

Winnipeg to Minneapolis flights

Winnipeg to LaGuardia flights

Winnipeg to Los Angeles flights

Winnipeg to Miami flights

Winnipeg to O'Hare Intl flights

Winnipeg to Atlanta flights

Winnipeg to Dallas/Fort Worth flights

Winnipeg to Ontario flights

Winnipeg to Sacramento flights

Winnipeg to Nashville flights

Winnipeg to Reagan-National flights

Winnipeg to Fort Myers flights

Winnipeg to San Francisco flights

Winnipeg to George Bush Intcntl flights

Winnipeg to Palm Springs flights

Winnipeg to Honolulu flights

Winnipeg to Baltimore flights

Winnipeg to Hobby flights

Winnipeg to San Diego flights

Winnipeg to New Orleans flights

Winnipeg to Midway flights

Winnipeg to Tampa flights

Winnipeg to Denver flights

Winnipeg to Pittsburgh flights

Winnipeg to Boston flights

Winnipeg to Dulles Intl flights

Winnipeg to Seattle flights

Winnipeg to Kahului flights

Winnipeg to Portland flights

Winnipeg to Detroit flights

Winnipeg to Philadelphia flights

Winnipeg to Love Field flights

Winnipeg to Reno flights

Winnipeg to Columbus flights

Winnipeg to Santa Ana flights

Winnipeg to Albany flights

Winnipeg to Harrisburg flights

Winnipeg to Savannah flights

Winnipeg to Lihue flights

Winnipeg to Louisville flights

Winnipeg to Charlotte flights

Winnipeg to Sarasota flights

Winnipeg to San Jose flights

Winnipeg to Anchorage flights

Complete your trip

Massachusetts car rentals

Boston Logan Intl Airport car rentals

Worcester Airport car rentals

Nantucket Memorial Airport car rentals

Provincetown Airport car rentals

Hyannis Barnstable Airport car rentals

New Bedford Regional Airport car rentals

Bedford Hanscom Field Airport car rentals

Boston car rentals

Worcester car rentals

Springfield car rentals

Hyannis car rentals

Top 3 airlines flying from Winnipeg to Massachusetts

Airline	Cheapest	Average	Flexibility	On-time
United Airlines	Cheapest$100	Average$310	FlexibilityNo cancel fee	On-time69%
Air Canada	Cheapest$212	Average$419	FlexibilityNo cancel fee	On-time67%
Delta	Cheapest$241	Average$605	FlexibilityNo cancel fee	On-timeN/A

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.

$132+ 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 1/30. Fares are subject to change and may not be available on all flights or dates of travel.

Find cheap flights from Winnipeg to Massachusetts with Cheapflights

1. Tell us where you want to go

2. Select your favorite providers

3. Compare prices and book

Cheap flight deals from Winnipeg to Massachusetts

Cheapest flights from Winnipeg to MassachusettsExplore 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 December 16, 2025.

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 December 16, 2025.

Find flight deals from Winnipeg to Massachusetts

Keep the following information in mind while searching for Winnipeg to Massachusetts flight deals. Data was last updated December 16, 2025.

Most accurate provider

Most trusted provider

Round-trip from

One-way from

Popular in

Cheapest in

Average price

Cheapflights Fare Finder

Use the filters below to find and compare flights from Winnipeg to Massachusetts that are best for you.

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.

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?

Reviews of airlines servicing Massachusetts

Read reviews from past customers who have flown Delta, United Airlines, and Air Canada from Winnipeg to Massachusetts. Reviews also offer insight into each airline's entertainment options, comfort, food, crew/service, and boarding process.

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?

How long is the flight from Winnipeg to Massachusetts?

What are the most popular routes from Winnipeg to Massachusetts?

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

How can I find direct flights from Winnipeg to Massachusetts?

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

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

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.

Top 3 airlines flying from Winnipeg to Massachusetts

100% Free

Book with Flexibility

Travel Smart

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 December 16, 2025.