$134+ Cheap flights from Boston (BOS) to Winnipeg (YWG)
This is the cheapest round-trip flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 12/7. Fares are subject to change and may not be available on all flights or dates of travel.
BOS — YWG
Nov 23 — Nov 301
Round-trip
1 adult, Economy
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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.Cheap flight deals from Boston to Winnipeg
Cheapest
Best
Last-minute
One-way
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 October 24, 2026.
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 October 24, 2026.
This Air Canada deal was found by Cheapflights users on 10/22. 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.
Tue 12/85:30 am -
1 stop5h 45m
Sat 12/129:05 am -
1 stop5h 48m
Deal found 10/22![Air Canada logo]()
$304
This Booking.com deal was found by Cheapflights users on 10/23. 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 Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/81:15 pm -
1 stop5h 59m
Tue 12/1512:40 pm -
2 stops8h 59m
Deal found 10/23![Porter Airlines logo]()
$327
This Air Canada deal was found by Cheapflights users on 10/20. 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 12/35:30 am -
1 stop5h 45m
Mon 12/79:05 am -
1 stop5h 48m
Deal found 10/20![Air Canada logo]()
$355
This Kiwi.com deal was found by Cheapflights users on 10/20. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/81:15 pm -
1 stop5h 59m
Sat 12/1211:00 am -
2 stops29h 46m
Deal found 10/20![Multiple Airlines logo]()
$359
This United Airlines deal was found by Cheapflights users on 10/21. 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 12/38:27 am -
2 stops13h 28m
Mon 12/73:15 pm -
1 stop6h 38m
Deal found 10/21![United Airlines logo]()
$369
This Kiwi.com deal was found by Cheapflights users on 10/24. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/37:50 pm -
1 stop14h 25m
Sat 12/1211:00 am -
1 stop8h 10m
Deal found 10/24![Multiple Airlines logo]()
$376
This Porter Airlines deal was found by Cheapflights users on 10/20. 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 Porter Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/38:00 am -
2 stops11h 14m
Mon 12/712:40 pm -
2 stops8h 59m
Deal found 10/20![Porter Airlines logo]()
$388
Best flights from Boston to WinnipegDiscover 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 October 24, 2026.
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 October 24, 2026.
This FlightHub deal was found by Cheapflights users on 10/20. 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 2/41:15 pm -
1 stop5h 55m
Tue 2/911:40 am -
2 stops10h 02m
Deal found 10/20![Porter Airlines logo]()
$305
This Air Canada deal was found by Cheapflights users on 10/21. 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.
Tue 3/210:25 am -
1 stop7h 12m
Fri 3/53:45 pm -
1 stop6h 50m
Deal found 10/21![Air Canada logo]()
$360
This United Airlines deal was found by Cheapflights users on 10/21. 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 12/38:27 am -
2 stops13h 28m
Mon 12/73:15 pm -
1 stop6h 38m
Deal found 10/21![United Airlines logo]()
$369
This Justfly.com deal was found by Cheapflights users on 10/23. 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 Justfly.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 3/18:00 am -
2 stops11h 10m
Tue 3/911:40 am -
2 stops10h 02m
Deal found 10/23![Porter Airlines logo]()
$326
This FlightHub deal was found by Cheapflights users on 10/21. 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.
Tue 3/28:00 am -
2 stops11h 10m
Fri 3/511:40 am -
2 stops10h 02m
Deal found 10/21![Porter Airlines logo]()
$329
This United Airlines deal was found by Cheapflights users on 10/21. 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 12/58:27 am -
2 stops13h 28m
Sat 12/123:15 pm -
1 stop6h 38m
Deal found 10/21![United Airlines logo]()
$369
This Air Canada deal was found by Cheapflights users on 10/19. 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.
Mon 2/2210:25 am -
1 stop7h 13m
Tue 3/23:05 pm -
1 stop6h 20m
Deal found 10/19![Air Canada logo]()
$387
This Porter Airlines deal was found by Cheapflights users on 10/20. 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 Porter Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/38:00 am -
2 stops11h 14m
Mon 12/712:40 pm -
2 stops8h 59m
Deal found 10/20![Porter Airlines logo]()
$388
Last-minute flights from Boston to WinnipegDiscover last-minute flight deals from Boston to Winnipeg. Data last updated October 24, 2026 and is based on user searches.
Discover last-minute flight deals from Boston to Winnipeg. Data last updated October 24, 2026 and is based on user searches.
This Kiwi.com deal was found by Cheapflights users on 10/22. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/227:30 pm -
1 stop21h 55m
Fri 2/128:05 pm -
1 stop13h 05m
Deal found 10/22![Multiple Airlines logo]()
$712
This Kiwi.com deal was found by Cheapflights users on 10/24. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 11/35:25 pm -
1 stop16h 50m
Sun 11/87:55 pm -
1 stop13h 15m
Deal found 10/24![Multiple Airlines logo]()
$610
This Kiwi.com deal was found by Cheapflights users on 10/24. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/165:25 pm -
1 stop18h 17m
Fri 11/209:35 pm -
2 stops11h 35m
Deal found 10/24![Multiple Airlines logo]()
$459
This Kiwi.com deal was found by Cheapflights users on 10/24. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/165:25 pm -
1 stop18h 17m
Fri 11/208:00 pm -
1 stop13h 10m
Deal found 10/24![Porter Airlines logo]()
$465
This Kiwi.com deal was found by Cheapflights users on 10/24. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/211:15 pm -
1 stop5h 51m
Sat 11/2811:00 am -
2 stops27h 38m
Deal found 10/24![Multiple Airlines logo]()
$601
This FlightHub deal was found by Cheapflights users on 10/24. 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.
Sat 11/218:00 am -
2 stops11h 06m
Sat 11/287:00 am -
2 stops14h 11m
Deal found 10/24![Porter Airlines logo]()
$630
One-way flights from Boston to WinnipegSearch for one-way flight options from Boston to Winnipeg. Find affordable one-way fares based on user searches. Data last updated October 24, 2026.
Search for one-way flight options from Boston to Winnipeg. Find affordable one-way fares based on user searches. Data last updated October 24, 2026.
This Air Canada deal was found by Cheapflights users on 10/23. 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.
Mon 12/75:30 am -
1 stop5h 45m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/23![Air Canada logo]()
$134
This deal was found by Cheapflights users on 10/20. 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 is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 2/310:25 am -
1 stop7h 13m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/20![Air Canada logo]()
$170
This United Airlines deal was found by Cheapflights users on 10/23. 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.
Mon 12/76:00 am -
2 stops15h 55m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/23![United Airlines logo]()
$171
This Kiwi.com deal was found by Cheapflights users on 10/23. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 12/75:30 pm -
3 stops31h 40m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/23![Multiple Airlines logo]()
$252
This deal was found by Cheapflights users on 10/20. 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 is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/163:10 pm -
1 stop7h 04m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/20![Air Canada logo]()
$382
This oojo deal was found by Cheapflights users on 10/23. 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 oojo is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 11/39:50 am -
1 stop25h 52m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/23![Porter Airlines logo]()
$561
This Kiwi.com deal was found by Cheapflights users on 10/23. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 11/31:15 pm -
2 stops22h 27m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/23![Multiple Airlines logo]()
$658
Find flight deals from Boston to Winnipeg
Discover tips and strategies to find the most affordable flight options for your journey from Boston (BOS) to Winnipeg (YWG). 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 October 24, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $304 (Air Canada) |
One-way from | $134 (Air Canada) |
Popular in | January |
Cheapest in | September |
Average price | $366 |
Cheapflights Fare Finder
Customize your flight search to find flights from Boston to Winnipeg 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 7,457,451 searches. Data last updated October 24, 2026.
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
Cheapest round-trip
Quickest round-trip
BostonWinnipeg
BOS Boston Logan Intl - YWG Winnipeg
BOSYWG
Boston Logan Intl
Mon 12/7
5:30 am-11:15 am
1 stop5h 45m
Winnipeg
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$134
BostonWinnipeg
BOS Boston Logan Intl - YWG Winnipeg
BOSYWG
Boston Logan Intl
Wed 2/3
10:25 am-5:38 pm
1 stop7h 13m
Winnipeg
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$170
BostonWinnipeg
BOS Boston Logan Intl - YWG Winnipeg
BOSYWG
Boston Logan Intl
Mon 12/7
6:00 am-9:55 pm
2 stops15h 55m
Winnipeg
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$171
BostonWinnipeg
BOS Boston Logan Intl - YWG Winnipeg
BOSYWG
Boston Logan Intl
Thu 2/4
1:15 pm-7:10 pm
1 stop5h 55m
Winnipeg
Tue 2/9
11:40 am-9:42 pm
2 stops10h 02m
$305
BostonWinnipeg
BOS Boston Logan Intl - YWG Winnipeg
BOSYWG
Boston Logan Intl
Mon 3/1
8:00 am-7:10 pm
2 stops11h 10m
Winnipeg
Tue 3/9
11:40 am-9:42 pm
2 stops10h 02m
$326
BostonWinnipeg
BOS Boston Logan Intl - YWG Winnipeg
BOSYWG
Boston Logan Intl
Tue 3/2
8:00 am-7:10 pm
2 stops11h 10m
Winnipeg
Fri 3/5
11:40 am-9:42 pm
2 stops10h 02m
$329
BostonWinnipeg
BOS Boston Logan Intl - YWG Winnipeg
BOSYWG
Boston Logan Intl
Tue 3/2
10:25 am-5:37 pm
1 stop7h 12m
Winnipeg
Fri 3/5
3:45 pm-10:35 pm
1 stop6h 50m
$360
BostonWinnipeg
BOS Boston Logan Intl - YWG Winnipeg
BOSYWG
Boston Logan Intl
Thu 12/3
8:27 am-9:55 pm
2 stops13h 28m
Winnipeg
Mon 12/7
3:15 pm-9:53 pm
1 stop6h 38m
$369
BostonWinnipeg
BOS Boston Logan Intl - YWG Winnipeg
BOSYWG
Boston Logan Intl
Sat 12/5
8:27 am-9:55 pm
2 stops13h 28m
Winnipeg
Sat 12/12
3:15 pm-9:53 pm
1 stop6h 38m
$369
BostonWinnipeg
BOS Boston Logan Intl - YWG Winnipeg
BOSYWG
Boston Logan Intl
Mon 11/16
3:10 pm-10:14 pm
1 stop7h 04m
Winnipeg
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$382
Showing 1-10 of 14 resultsSorted by cheapest first
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 October.
| Provider | Price Accuracy | Trust Score* |
|---|---|---|
| Price Accuracy1 star | Trust Score*3 stars | |
| Price Accuracy3 stars | Trust Score*3 stars | |
| Price Accuracy3 stars | Trust Score*2 stars |
- 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 FlightHub the most. FlightHub 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.
BOS-YWG
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
What is the cheapest month to book a flight from Boston to Winnipeg?
Currently, September is the cheapest month in which you can book a flight from Boston to Winnipeg (average of $364). Flying from Boston to Winnipeg in January is currently the most expensive (average of $776). 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.
How much does it cost to fly round-trip from Boston to Winnipeg?
Airfare is below average for this route at the moment.
Boston to Winnipeg flights typically cost between $351 and $612 in December.The cheapest round-trip price found within the last 5 days was $304 on Air Canada (Dec 8-Dec 12).
Reviews of airlines servicing Winnipeg
Get insights into the airlines that provide service to Winnipeg. 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 Winnipeg. Reviews last updated October 24, 2026.
Peruse reviews from past customers who have flown with Porter Airlines,Delta, andUnited Airlines from Boston to Winnipeg to help guide your decision. You can also see how each airline stacks up in terms of entertainment options, comfort, food, crew/service, and boarding process.
Entertainment
6.9
Overall
8.0
Crew
8.6
Food
7.6
Comfort
8.0
Boarding
8.2
Reviews
1 / 20
8.0
ExcellentD,Sep 2026
YHM - YVR
Entertainment
6.9
Overall
8.0
Crew
8.6
Food
7.6
Comfort
8.0
Boarding
8.2
Reviews
1 / 20
8.0
ExcellentD,Sep 2026
YHM - YVR
Entertainment
6.9
Overall
8.0
Crew
8.6
Food
7.6
Comfort
8.0
Boarding
8.2
Reviews
1 / 20
8.0
ExcellentD,Sep 2026
YHM - YVR
Entertainment
6.9
Overall
8.0
Crew
8.6
Food
7.6
Comfort
8.0
Boarding
8.2
Reviews
1 / 20
8.0
ExcellentD,Sep 2026
YHM - YVR
Entertainment
6.9
Overall
8.0
Crew
8.6
Food
7.6
Comfort
8.0
Boarding
8.2
Reviews
1 / 20
8.0
ExcellentD,Sep 2026
YHM - YVR
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.
Traveling to a place near Winnipeg?
Book flights to Winnipeg if you plan to visit one of these locationsPortage la Prairie
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Boston and Winnipeg flights
Browse other Boston and Winnipeg flight options. Last updated on October 24, 2026.
Other flights from Boston
Browse through other flights departing from Boston. Flights are based on user searches made on Cheapflights and were last updated on October 24, 2026.
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Other flights to Winnipeg
Explore flights to Winnipeg departing from other origins. Flights are based on user searches made on Cheapflights and were last updated on October 24, 2026.
Top 4 airlines flying from Boston to Winnipeg
Discover the top 4 airlines that operate flights from Boston to Winnipeg. 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 7,457,451 searches. Data last updated October 24, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$111 | Average$681 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$204 | Average$534 | FlexibilityNo cancel fee | On-time67% | |
| Cheapest$256 | Average$573 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$352 | Average$509 | FlexibilityNo cancel fee | On-time52% |