What are the cheapest airlines flying from Boston to Winnipeg round-trip?

Currently priced at $295, United Airlines will fly you from Boston to Winnipeg and back. In addition to United Airlines, many other airlines offer competitively priced options for your trip. Search Cheapflights for deals from Delta and Air Canada - these airlines can fly you to your destination from $318 and $334, respectively. United Airlines is currently priced 41% below the average price you’ll pay for this route.

What is the cheapest day to fly from Boston to Winnipeg?

Travelers seeking maximum savings on their Boston to Winnipeg flight should consider departing on Sunday at noon when fares are most often at their lowest. Monday mornings flights should be avoided if possible as fares are typically the most expensive at this time.

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

The most popular airlines flying from Boston to Winnipeg are Air Canada, Delta and Porter Airlines. Something to consider prior to booking your flight.

What is the cheapest day to fly round-trip from Boston to Winnipeg?

Leaving on a Saturday is a viable option for saving on travel. Heavily demanded days of the week can typically drive up the prices you see. Booking your travel for a less competitive day can save up to 122% on the overall cost on flights from Boston to Winnipeg.

How far in advance should I book a flight from Boston to Winnipeg?

To save on the cost of your flight from Boston to Winnipeg, book at least 21 days before your planned departure. Booking around this time can save you about 103% on the cost of this flight compared to booking a flight leaving this week. We have found prices from $340 if you need a flight within two weeks. For flights within the next 72 hours, you can find tickets from as low as $744.

What is the cheapest month to fly from Boston to Winnipeg?

Due to multiple factors, expect to potentially pay more when booking in April. For low rates, January can be a great choice for travel to Winnipeg. Flights to Winnipeg from Boston in January are about $500 on average during January, but can be found for as low as $163.

Most accurate provider : When it comes to deals on Boston-Winnipeg flights, users find the pricing of FlightHub to be most consistent on Cheapflights vs. FlightHub Users can find the same prices on Boston-Winnipeg flight deals on Cheapflights vs. FlightHub >95% of the time. Price accuracy is based on data collected from Boston-Winnipeg flight searches over the past month and is updated monthly.

Most trusted provider : When it comes to deals on Boston-Winnipeg flights, Cheapflights users trust eDreams the most. eDreams has received a user feedback score of 3 out of 3 stars (3 being the best), meaning they have been trusted the most by Cheapflights users looking for Boston-Winnipeg flight deals. Provider user feedback score is based on Cheapflights searches over the past month and is updated monthly.

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

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

How can I find direct flights from Boston to Winnipeg?

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

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

Yes. Cheapflights offers flight deals from Boston to Winnipeg by cabin class. In addition to browsing deals, you can also filter by cabin class on the search results page after making a search.

$124+ Flights from Boston to Winnipeg - Compare & Save Big

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Find cheap flights from Boston to Winnipeg 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.

Cheapflights Tip: The best prices from Boston Logan Intl to Winnipeg are usually found in January or October, booked 22 days in advance, depart on a Sunday or Friday and return on a Saturday

Cheap flight deals from Boston to Winnipeg

Most accurate provider	FlightHub 3 stars
Most trusted provider	eDreams 3 stars
Round-trip from	$295 (United Airlines)
One-way from	$124 (United Airlines)
Popular in	April
Cheapest in	January
Average price	$770

Provider with most accurate pricing for Boston Logan Intl-Winnipeg flight deals.

Search Deals

Provider most trusted by Cheapflights users for Boston Logan Intl-Winnipeg flights.

Search Deals

From Boston Logan Intl to Winnipeg

Search Deals

One-way flight from Boston Logan Intl to Winnipeg

Search Deals

Highest demand for flights based on searches. 23% potential increase in price ($151 potential increase over avg. RT price).

Search Deals

Cheapest flight prices on average. 5% potential price decrease ($25 potential savings vs. average RT price).

Search Deals

Average for round-trip flights in April 2025

Search Deals

Find flight deals from Boston to Winnipeg

Cheapest flights from Boston to Winnipeg
Explore the most affordable flight options available from Boston to Winnipeg. Find the lowest fares from popular airlines and budget airlines, with prices last updated on abril 29, 2025.

vie. 6/138:59 pmBOS - YWG

1 stop17h 10mUnited Airlines

vie. 6/205:00 amYWG - BOS

1 stop5h 28mUnited Airlines

Deal found 4/29

$338

vie. 8/225:40 amBOS - YWG

1 stop6h 50mDelta

mar. 8/2612:40 pmYWG - BOS

1 stop8h 45mDelta

Deal found 4/29

$374

mié. 7/95:50 amBOS - YWG

2 stops11h 23mAir Canada

lun. 7/145:00 amYWG - BOS

1 stop5h 28mAir Canada

Deal found 4/29

$377

vie. 6/1312:15 pmBOS - YWG

2 stops11h 31mMultiple Airlines

vie. 6/206:30 amYWG - BOS

2 stops33h 11mMultiple Airlines

Deal found 4/29

$435

sáb. 11/84:15 pmBOS - YWG

1 stop5h 54mPorter Airlines

sáb. 11/1511:35 amYWG - BOS

1 stop5h 40mPorter Airlines

Deal found 4/29

$456

Best flights from Boston to Winnipeg
Discover carefully curated flight deals from Boston to Winnipeg that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated abril 29, 2025.

lun. 6/96:00 amBOS - YWG

1 stop17h 33mUnited Airlines

dom. 6/155:00 amYWG - BOS

1 stop5h 28mUnited Airlines

Deal found 4/28

$295

mié. 6/1111:16 amBOS - YWG

1 stop9h 56mDelta

vie. 6/2012:26 pmYWG - BOS

1 stop8h 54mDelta

Deal found 4/28

$318

lun. 6/910:09 amBOS - YWG

2 stops15h 22mMultiple Airlines

vie. 6/1311:45 amYWG - BOS

1 stop5h 23mMultiple Airlines

Deal found 4/27

$328

mié. 7/95:50 amBOS - YWG

2 stops11h 23mAir Canada

lun. 7/145:00 amYWG - BOS

1 stop5h 28mAir Canada

Deal found 4/28

$334

lun. 6/912:15 pmBOS - YWG

2 stops11h 31mPorter Airlines

dom. 6/1511:45 amYWG - BOS

1 stop5h 23mPorter Airlines

Deal found 4/28

$407

Last-minute flights from Boston to Winnipeg
Discover last-minute flight deals from Boston to Winnipeg. Data last updated abril 29, 2025 and is based on user searches.

vie. 5/910:30 amBOS - YWG

2 stops32h 45mMultiple Airlines

dom. 5/1111:25 amYWG - BOS

1 stop5h 43mMultiple Airlines

Deal found 4/28

$672

vie. 5/98:45 amBOS - YWG

2 stops10h 15mPorter Airlines

dom. 5/1111:25 amYWG - BOS

2 stops9h 06mPorter Airlines

Deal found 4/28

$801

vie. 5/308:59 pmBOS - YWG

1 stop17h 10mUnited Airlines

lun. 6/22:20 pmYWG - BOS

1 stop9h 39mUnited Airlines

Deal found 4/29

$341

vie. 5/305:20 amBOS - YWG

2 stops12h 25mDelta

lun. 6/212:52 pmYWG - BOS

2 stops11h 25mDelta

Deal found 4/29

$376

vie. 5/308:45 amBOS - YWG

2 stops10h 15mPorter Airlines

lun. 6/211:25 amYWG - BOS

1 stop5h 43mPorter Airlines

Deal found 4/29

$475

vie. 5/305:45 amBOS - YWG

1 stop12h 00mMultiple Airlines

lun. 6/211:25 amYWG - BOS

1 stop5h 43mMultiple Airlines

Deal found 4/29

$626

One-way flights from Boston to Winnipeg
Search for one-way flight options from Boston to Winnipeg. Find affordable one-way fares based on user searches. Data last updated abril 29, 2025.

dom. 5/259:30 amBOS - YWG

2 stops14h 03mUnited Airlines

Deal found 4/28

$124

jue. 6/128:15 amBOS - YWG

1 stop9h 37mDelta

Deal found 4/28

$164

Cheapflights Fare Finder

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

Fly from

Fly to

Route

Depart

Return

Price

BostonWinnipeg

BOS - YWG

BOSYWG

Boston Logan Intl

vie. 6/13

8:59 pm-1:09 pm

1 stop17h 10m

Winnipeg

vie. 6/20

5:00 am-11:28 am

1 stop5h 28m

$338

BostonWinnipeg

BOS - YWG

BOSYWG

Boston Logan Intl

vie. 8/22

5:40 am-11:30 am

1 stop6h 50m

Winnipeg

mar. 8/26

12:40 pm-10:25 pm

1 stop8h 45m

$374

BostonWinnipeg

BOS - YWG

BOSYWG

Boston Logan Intl

mié. 7/9

5:50 am-4:13 pm

2 stops11h 23m

Winnipeg

lun. 7/14

5:00 am-11:28 am

1 stop5h 28m

$377

BostonWinnipeg

BOS - YWG

BOSYWG

Boston Logan Intl

vie. 6/13

12:15 pm-10:46 pm

2 stops11h 31m

Winnipeg

vie. 6/20

6:30 am-4:41 pm

2 stops33h 11m

$435

BostonWinnipeg

BOS - YWG

BOSYWG

Boston Logan Intl

vie. 5/30

8:45 am-6:00 pm

2 stops10h 15m

Winnipeg

lun. 6/2

11:25 am-6:08 pm

1 stop5h 43m

$475

BostonWinnipeg

BOS - YWG

BOSYWG

Boston Logan Intl

dom. 5/25

9:30 am-10:33 pm

2 stops14h 03m

$144

BostonWinnipeg

BOS - YWG

BOSYWG

Boston Logan Intl

vie. 8/1

3:50 pm-10:46 pm

1 stop7h 56m

$251

BostonWinnipeg

BOS - YWG

BOSYWG

Boston Logan Intl

mié. 5/7

3:50 pm-11:43 pm

2 stops32h 53m

$361

BostonWinnipeg

BOS - YWG

BOSYWG

Boston Logan Intl

mié. 5/7

10:20 am-3:00 pm

1 stop5h 40m

$386

Flights are sorted by cheapest round-trip flights first.

Deals found on 4/29

Compare providers for flights from Boston to Winnipeg

Use the table below to compare price accuracy, trust ratings, and cancellation policies for each provider offering flight deals from Boston to Winnipeg in April.

Provider	Price Accuracy	Trust Score*
FlightHub	Price Accuracy3 stars	Trust Score*2 stars
eDreams	Price Accuracy3 stars	Trust Score*3 stars
Expedia	Price Accuracy1 star	Trust Score*3 stars

*The Trust Score is based on feedback from users after their booking experience. It measures overall satisfaction, helping us identify issues like hidden fees, problems during the ticketing process, and the quality of customer service. This score is our best indicator of the provider's quality and reliability.

Most accurate provider: When it comes to deals on Boston-Winnipeg flights, users find the pricing of FlightHub to be most consistent on Cheapflights vs. FlightHub Users can find the same prices on Boston-Winnipeg flight deals on Cheapflights vs. FlightHub >95% of the time. Price accuracy is based on data collected from Boston-Winnipeg flight searches over the past month and is updated monthly.
Most trusted provider: When it comes to deals on Boston-Winnipeg flights, Cheapflights users trust eDreams the most. eDreams has received a user feedback score of 3 out of 3 stars (3 being the best), meaning they have been trusted the most by Cheapflights users looking for Boston-Winnipeg flight deals. Provider user feedback score is based on Cheapflights searches over the past month and is updated monthly.

Best time to book a flight from Boston to Winnipeg

Have a flexible travel schedule? Discover the best time to fly to Winnipeg from Boston 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 Boston to Winnipeg

How far ahead should I book a flight from Boston to Winnipeg?

Booking 20 days in advance of your planned departure date is, on average, the best time to get cheap flights from Boston to Winnipeg. The general trend is that the closer you book to the departure date, the more expensive your flight will be.

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

Currently, August is the cheapest month in which you can book a flight from Boston to Winnipeg (average of $358). Flying from Boston to Winnipeg in December is currently the most expensive (average of $501). 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 BOS to YWG?

It’s typically best to fly out from Boston to Winnipeg at noon. Doing so could potentially save you 27% on the flight price compared to flying in the afternoon, which is usually more expensive.

Rainfall in Winnipeg by month

In terms of precipitation, rainfall in Winnipeg ranges from 0.8 - 3.1 inches per month. June is typically the wettest month, when rainfall can reach 3.1 in. January is typically the driest time to visit Winnipeg when rainfall is around 0.8 in.

Temperature in Winnipeg by month

If weather is an important factor for your trip to Winnipeg, 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 68.0 F. Travelers looking to avoid the cold should look outside of January, when temperatures are typically at their lowest (around 3.2 F).

Reviews of airlines servicing Winnipeg

Porter Airlines

8.0

Very good

285 reviews

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

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

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

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

9,244 reviews

Porter Airlines

8.0

Very good

285 reviews

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

What are the cheapest airlines flying from Boston to Winnipeg round-trip?
Currently priced at $295, United Airlines will fly you from Boston to Winnipeg and back. In addition to United Airlines, many other airlines offer competitively priced options for your trip. Search Cheapflights for deals from Delta and Air Canada - these airlines can fly you to your destination from $318 and $334, respectively. United Airlines is currently priced 41% below the average price you’ll pay for this route.
Can I find deals for flights from Boston to Winnipeg that include hotel bookings?
Yes. In addition to deals on Boston to Winnipeg flights, Cheapflights offers vacation packages that include both flights and hotel.
How can I find direct flights from Boston to Winnipeg?
After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Boston to Winnipeg.
Can I find deals for business class flights from Boston to Winnipeg?
Yes. Cheapflights offers flight deals from Boston to Winnipeg 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 Boston to Winnipeg?
Currently, August is the cheapest month in which you can book a flight from Boston to Winnipeg (average of $358). Flying from Boston to Winnipeg in December is currently the most expensive (average of $501). 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

Complete your trip

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Other flights to Winnipeg

Top 4 airlines flying from Boston to Winnipeg

Airline	Cheapest	Average	Flexibility	On-time
Air Canada	Cheapest$134	Average$462	FlexibilityNo cancel fee	On-time67%
United Airlines	Cheapest$172	Average$586	FlexibilityNo cancel fee	On-time69%
Porter Airlines	Cheapest$283	Average$417	FlexibilityNo cancel fee	On-time52%
Delta	Cheapest$328	Average$630	FlexibilityNo cancel fee	On-timeN/A

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$124+ Cheap flights from Boston (BOS) to Winnipeg (YWG)

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 5/25. Fares are subject to change and may not be available on all flights or dates of travel.

Find cheap flights from Boston to Winnipeg with Cheapflights

1. Tell us where you want to go

2. Select your favorite providers

3. Compare prices and book

Cheapflights Tip: The best prices from Boston Logan Intl to Winnipeg are usually found in January or October, booked 22 days in advance, depart on a Sunday or Friday and return on a Saturday

Cheap flight deals from Boston to Winnipeg

Most accurate provider

Most trusted provider

Round-trip from

One-way from

Popular in

Cheapest in

Average price

Find flight deals from Boston to Winnipeg

Cheapest flights from Boston to WinnipegExplore the most affordable flight options available from Boston to Winnipeg. Find the lowest fares from popular airlines and budget airlines, with prices last updated on abril 29, 2025.

Explore the most affordable flight options available from Boston to Winnipeg. Find the lowest fares from popular airlines and budget airlines, with prices last updated on abril 29, 2025.

Cheapflights Fare Finder

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

Compare providers for flights from Boston to Winnipeg

Provider information is updated monthly. Please note that these providers often have deals for this flight, but the availability may vary on a day-by-day basis on Cheapflights.

Use the table below to compare price accuracy, trust ratings, and cancellation policies for each provider offering flight deals from Boston to Winnipeg in April.

Best time to book a flight from Boston to Winnipeg

Have a flexible travel schedule? Discover the best time to fly to Winnipeg from Boston with our price prediction graph.

Cheapflights Insights

Everything you need to know about your flight from Boston to Winnipeg

How far ahead should I book a flight from Boston to Winnipeg?

Use this chart to determine the optimal time to book a round-trip flight from Boston to Winnipeg. Price data was last updated on April 25, 2025.

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

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

Find hourly flight availability from Boston to Winnipeg. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated abril 29, 2025.

Rainfall in Winnipeg by month

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

Temperature in Winnipeg by month

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

Reviews of airlines servicing Winnipeg

Related info for your journey

Find useful and relevant information for your journey from Boston to Winnipeg. 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 Boston to Winnipeg round-trip?

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

How can I find direct flights from Boston to Winnipeg?

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

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

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.

Complete your trip

Complete your trip to Winnipeg by adding a car rental and/or hotel reservation to your travel itinerary.

Top 4 airlines flying from Boston to Winnipeg

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Cheapest flights from Boston to Winnipeg
Explore the most affordable flight options available from Boston to Winnipeg. Find the lowest fares from popular airlines and budget airlines, with prices last updated on abril 29, 2025.