$180+ Cheap flights from Winnipeg (YWG) to Boston (BOS)
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 11/21. Fares are subject to change and may not be available on all flights or dates of travel.
YWG — BOS
Nov 11 — Nov 181
Round-trip
1 adult, Economy
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Find cheap flights from Winnipeg to Boston 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 Boston
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Last-minute
One-way
Cheapest flights from Winnipeg to BostonExplore the most affordable flight options available from Winnipeg to Boston. Find the lowest fares from popular airlines and budget airlines, with prices last updated on October 12, 2026.
Explore the most affordable flight options available from Winnipeg to Boston. Find the lowest fares from popular airlines and budget airlines, with prices last updated on October 12, 2026.
This Delta deal was found by Cheapflights users on 10/9. 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.
Fri 11/136:35 am -
1 stop9h 09m
Sun 11/225:45 am -
1 stop8h 10m
Deal found 10/9![Delta logo]()
$304
This Air Canada deal was found by Cheapflights users on 10/7. 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 10/218:15 am -
1 stop6h 50m
Thu 10/226:00 am -
1 stop6h 12m
Deal found 10/7![Air Canada logo]()
$361
This FlightHub deal was found by Cheapflights users on 10/11. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 11/2411:35 am -
2 stops9h 00m
Sun 11/298:00 am -
2 stops11h 06m
Deal found 10/11![Porter Airlines logo]()
$362
This Justfly.com deal was found by Cheapflights users on 10/11. 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 Justfly.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 11/1811:35 am -
2 stops9h 00m
Tue 11/248:00 am -
2 stops11h 06m
Deal found 10/11![Porter Airlines logo]()
$374
This FlightHub deal was found by Cheapflights users on 10/11. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/1111:40 am -
2 stops8h 59m
Tue 12/151:15 pm -
1 stop5h 59m
Deal found 10/11![Porter Airlines logo]()
$379
This FlightHub deal was found by Cheapflights users on 10/11. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 11/2211:35 am -
2 stops9h 00m
Thu 11/268:00 am -
2 stops11h 06m
Deal found 10/11![Porter Airlines logo]()
$383
This lastminute.com deal was found by Cheapflights users on 10/9. 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 lastminute.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/1311:35 am -
2 stops9h 00m
Sun 11/221:15 pm -
1 stop5h 51m
Deal found 10/9![Porter Airlines logo]()
$385
This Justfly.com deal was found by Cheapflights users on 10/11. 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 Justfly.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 11/1011:35 am -
2 stops9h 00m
Wed 11/181:15 pm -
1 stop5h 51m
Deal found 10/11![Porter Airlines logo]()
$392
This Porter Airlines deal was found by Cheapflights users on 10/7. 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.
Wed 10/219:20 am -
1 stop8h 15m
Thu 10/229:00 am -
2 stops9h 58m
Deal found 10/7![Porter Airlines logo]()
$396
This Justfly.com deal was found by Cheapflights users on 10/12. 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 Justfly.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/911:35 am -
2 stops9h 00m
Wed 11/181:15 pm -
1 stop5h 51m
Deal found 10/12![Porter Airlines logo]()
$397
Best flights from Winnipeg to BostonDiscover carefully curated flight deals from Winnipeg to Boston that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated October 12, 2026.
Discover carefully curated flight deals from Winnipeg to Boston that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated October 12, 2026.
This Delta deal was found by Cheapflights users on 10/9. 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.
Fri 11/136:35 am -
1 stop9h 09m
Sun 11/225:45 am -
1 stop8h 10m
Deal found 10/9![Delta logo]()
$304
This Porter Airlines deal was found by Cheapflights users on 10/12. 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 Porter Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/1211:35 am -
2 stops9h 00m
Sat 11/141:15 pm -
1 stop5h 51m
Deal found 10/12![Porter Airlines logo]()
$406
This Porter Airlines deal was found by Cheapflights users on 10/11. 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 Porter Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/1211:35 am -
2 stops9h 00m
Thu 11/191:15 pm -
1 stop5h 51m
Deal found 10/11![Porter Airlines logo]()
$406
This Porter Airlines deal was found by Cheapflights users on 10/12. 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 Porter Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/1311:35 am -
2 stops9h 00m
Tue 11/171:15 pm -
2 stops9h 37m
Deal found 10/12![Porter Airlines logo]()
$414
This Delta deal was found by Cheapflights users on 10/10. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 11/221:45 pm -
1 stop8h 59m
Sun 11/297:15 am -
1 stop11h 27m
Deal found 10/10![Delta logo]()
$471
This Delta deal was found by Cheapflights users on 10/10. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 11/241:45 pm -
1 stop8h 59m
Sun 11/297:15 am -
1 stop11h 27m
Deal found 10/10![Delta logo]()
$471
This Delta deal was found by Cheapflights users on 10/11. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 11/186:35 am -
1 stop6h 19m
Tue 11/242:59 pm -
1 stop10h 34m
Deal found 10/11![Delta logo]()
$471
This Kiwi.com deal was found by Cheapflights users on 10/10. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 11/2411:35 am -
2 stops9h 00m
Sun 11/291:15 pm -
1 stop5h 51m
Deal found 10/10![Porter Airlines logo]()
$476
This Mytrip deal was found by Cheapflights users on 10/10. 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.
Fri 11/2011:35 am -
2 stops9h 00m
Sun 12/61:15 pm -
2 stops9h 42m
Deal found 10/10![Porter Airlines logo]()
$483
This Delta deal was found by Cheapflights users on 10/7. 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.
Sat 12/265:22 pm -
1 stop5h 33m
Fri 1/15:30 am -
1 stop7h 55m
Deal found 10/7![Delta logo]()
$539
This Delta deal was found by Cheapflights users on 10/8. 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 2/45:38 pm -
1 stop5h 15m
Tue 2/95:40 am -
1 stop8h 10m
Deal found 10/8![Delta logo]()
$539
Last-minute flights from Winnipeg to BostonDiscover last-minute flight deals from Winnipeg to Boston. Data last updated October 12, 2026 and is based on user searches.
Discover last-minute flight deals from Winnipeg to Boston. Data last updated October 12, 2026 and is based on user searches.
This Air Canada deal was found by Cheapflights users on 10/7. 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 10/218:15 am -
1 stop6h 50m
Thu 10/226:00 am -
1 stop6h 12m
Deal found 10/7![Air Canada logo]()
$361
This Porter Airlines deal was found by Cheapflights users on 10/7. 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.
Wed 10/219:20 am -
1 stop8h 15m
Thu 10/229:00 am -
2 stops9h 58m
Deal found 10/7![Porter Airlines logo]()
$396
This Justfly.com deal was found by Cheapflights users on 10/12. 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 Justfly.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/911:35 am -
2 stops9h 00m
Wed 11/181:15 pm -
1 stop5h 51m
Deal found 10/12![Porter Airlines logo]()
$397
This Justfly.com deal was found by Cheapflights users on 10/12. 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 Justfly.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/911:35 am -
2 stops9h 00m
Sat 11/148:00 am -
2 stops11h 06m
Deal found 10/12![Porter Airlines logo]()
$400
This Justfly.com deal was found by Cheapflights users on 10/11. 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 Justfly.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 11/1011:35 am -
2 stops9h 00m
Wed 11/181:15 pm -
1 stop5h 51m
Deal found 10/11![Porter Airlines logo]()
$392
This Delta deal was found by Cheapflights users on 10/9. 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.
Fri 11/136:35 am -
1 stop9h 09m
Sun 11/225:45 am -
1 stop8h 10m
Deal found 10/9![Delta logo]()
$304
This lastminute.com deal was found by Cheapflights users on 10/9. 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 lastminute.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/1311:35 am -
2 stops9h 00m
Sun 11/221:15 pm -
1 stop5h 51m
Deal found 10/9![Porter Airlines logo]()
$385
This Justfly.com deal was found by Cheapflights users on 10/11. 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 Justfly.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 11/1811:35 am -
2 stops9h 00m
Tue 11/248:00 am -
2 stops11h 06m
Deal found 10/11![Porter Airlines logo]()
$374
This FlightHub deal was found by Cheapflights users on 10/11. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 11/2211:35 am -
2 stops9h 00m
Thu 11/268:00 am -
2 stops11h 06m
Deal found 10/11![Porter Airlines logo]()
$383
This FlightHub deal was found by Cheapflights users on 10/11. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 11/2411:35 am -
2 stops9h 00m
Sun 11/298:00 am -
2 stops11h 06m
Deal found 10/11![Porter Airlines logo]()
$362
One-way flights from Winnipeg to BostonSearch for one-way flight options from Winnipeg to Boston. Find affordable one-way fares based on user searches. Data last updated October 12, 2026.
Search for one-way flight options from Winnipeg to Boston. Find affordable one-way fares based on user searches. Data last updated October 12, 2026.
This Delta deal was found by Cheapflights users on 10/7. 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.
Sat 11/211:45 pm -
1 stop8h 59m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/7![Delta logo]()
$180
This FlightHub deal was found by Cheapflights users on 10/8. 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 2/911:40 am -
2 stops8h 52m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/8![Porter Airlines logo]()
$220
This Expedia deal was found by Cheapflights users on 10/11. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 11/2510:35 am -
2 stops10h 00m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/11![Porter Airlines logo]()
$236
This Trip.com deal was found by Cheapflights users on 10/11. 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 11/2511:00 am -
1 stop21h 10m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/11![Multiple Airlines logo]()
$237
This Kiwi.com deal was found by Cheapflights users on 10/8. 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.
Fri 11/2011:00 am -
1 stop7h 10m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/8![Multiple Airlines logo]()
$240
This Expedia deal was found by Cheapflights users on 10/11. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 11/1010:35 am -
2 stops10h 00m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/11![Porter Airlines logo]()
$246
This Orbitz deal was found by Cheapflights users on 10/7. 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 Orbitz is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/2610:35 am -
2 stops10h 00m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/7![Porter Airlines logo]()
$248
This Kiwi.com deal was found by Cheapflights users on 10/7. 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 11/2611:00 am -
1 stop21h 10m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/7![Multiple Airlines logo]()
$254
This Delta deal was found by Cheapflights users on 10/11. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 11/101:45 pm -
1 stop8h 59m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/11![Delta logo]()
$263
This Trip.com deal was found by Cheapflights users on 10/7. 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/219:35 pm -
2 stops10h 35m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/7![Multiple Airlines logo]()
$281
This Kiwi.com deal was found by Cheapflights users on 10/11. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 11/109:35 pm -
3 stops37h 09m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/11![Multiple Airlines logo]()
$289
This Delta deal was found by Cheapflights users on 10/8. 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.
Tue 2/95:38 pm -
1 stop5h 15m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/8![Delta logo]()
$297
Find flight deals from Winnipeg to Boston
Discover tips and strategies to find the most affordable flight options for your journey from Winnipeg (YWG) to Boston (BOS). 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 12, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $304 (Delta) |
One-way from | $178 (Delta) |
Popular in | April |
Cheapest in | August |
Average price | $486 |
Cheapflights Fare Finder
Customize your flight search to find flights from Winnipeg to Boston 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 12, 2026.
Use the filters below to find and compare flights from Winnipeg to Boston that are best for you.
Fly from
Fly to
Route
Depart
Return
Cheapest round-trip
WinnipegBoston
YWG Winnipeg - BOS Boston Logan Intl
YWGBOS
Winnipeg
Sat 11/21
1:45 pm-10:44 pm
1 stop8h 59m
Boston Logan Intl
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$180
WinnipegBoston
YWG Winnipeg - BOS Boston Logan Intl
YWGBOS
Winnipeg
Wed 11/25
11:00 am-8:10 am
1 stop21h 10m
Boston Logan Intl
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$237
WinnipegBoston
YWG Winnipeg - BOS Boston Logan Intl
YWGBOS
Winnipeg
Thu 11/26
11:00 am-8:10 am
1 stop21h 10m
Boston Logan Intl
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$254
WinnipegBoston
YWG Winnipeg - BOS Boston Logan Intl
YWGBOS
Winnipeg
Tue 11/10
1:45 pm-10:44 pm
1 stop8h 59m
Boston Logan Intl
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$263
WinnipegBoston
YWG Winnipeg - BOS Boston Logan Intl
YWGBOS
Winnipeg
Sat 11/21
9:35 pm-8:10 am
2 stops10h 35m
Boston Logan Intl
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$281
Quickest round-trip
WinnipegBoston
YWG Winnipeg - BOS Boston Logan Intl
YWGBOS
Winnipeg
Tue 2/9
5:38 pm-10:53 pm
1 stop5h 15m
Boston Logan Intl
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$297
WinnipegBoston
YWG Winnipeg - BOS Boston Logan Intl
YWGBOS
Winnipeg
Fri 11/13
6:35 am-3:44 pm
1 stop9h 09m
Boston Logan Intl
Sun 11/22
5:45 am-1:55 pm
1 stop8h 10m
$304
WinnipegBoston
YWG Winnipeg - BOS Boston Logan Intl
YWGBOS
Winnipeg
Fri 10/23
5:10 pm-9:05 am
1 stop14h 55m
Boston Logan Intl
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$380
WinnipegBoston
YWG Winnipeg - BOS Boston Logan Intl
YWGBOS
Winnipeg
Sat 10/17
6:40 am-4:41 pm
1 stop9h 01m
Boston Logan Intl
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$401
WinnipegBoston
YWG Winnipeg - BOS Boston Logan Intl
YWGBOS
Winnipeg
Thu 11/12
11:35 am-8:35 pm
2 stops9h 00m
Boston Logan Intl
Sat 11/14
1:15 pm-7:06 pm
1 stop5h 51m
$406
Showing 1-10 of 20 resultsSorted by cheapest first
Compare providers for flights from Winnipeg to Boston
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 Winnipeg to Boston in October.
| Provider | Price Accuracy | Trust Score* |
|---|---|---|
| Price Accuracy1 star | Trust Score*3 stars | |
| Price Accuracy3 stars | Trust Score*3 stars |
- Most accurate provider: When it comes to deals on Winnipeg-Boston flights, users find the pricing of FlightHub to be most consistent on Cheapflights vs. FlightHub Users can find the same prices on Winnipeg-Boston flight deals on Cheapflights vs. FlightHub >95% of the time. Price accuracy is based on data collected from Winnipeg-Boston flight searches over the past month and is updated monthly.
- Most trusted provider: When it comes to deals on Winnipeg-Boston 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 Winnipeg-Boston 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 Winnipeg to Boston
Have a flexible travel schedule? Discover the best time to fly to Boston from Winnipeg with our price prediction graph.
YWG-BOS
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 Boston
What is the cheapest month to book a flight from Winnipeg to Boston?
Currently, August is the cheapest month in which you can book a flight from Winnipeg to Boston (average of $348). Flying from Winnipeg to Boston in April is currently the most expensive (average of $915). 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 Winnipeg to Boston?
Airfare is below average for this route at the moment.
Winnipeg to Boston flights typically cost between $414 and $727 in November.The cheapest round-trip price found within the last 5 days was $304 on Delta (Nov 13-Nov 22).
Reviews of airlines servicing Boston
Get insights into the airlines that provide service to Boston. 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 Boston. Reviews last updated October 12, 2026.
Read reviews from past customers who have flown Porter Airlines and Air Canada from Winnipeg to Boston. Users can see the overall rating for each airline as well as how each is rated in terms of entertainment options, comfort, food, crew/service, and boarding process.
Comfort
8.0
Boarding
8.2
Entertainment
7.0
Food
7.6
Overall
8.0
Crew
8.6
Reviews
1 / 20
8.0
ExcellentD,Sep 2026
YHM - YVR
Comfort
8.0
Boarding
8.2
Entertainment
7.0
Food
7.6
Overall
8.0
Crew
8.6
Reviews
1 / 20
8.0
ExcellentD,Sep 2026
YHM - YVR
Comfort
8.0
Boarding
8.2
Entertainment
7.0
Food
7.6
Overall
8.0
Crew
8.6
Reviews
1 / 20
8.0
ExcellentD,Sep 2026
YHM - YVR
Related info for your journey
Find useful and relevant information for your journey from Winnipeg to Boston. 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 Boston?
Book flights to Boston if you plan to visit one of these locationsWaltham
Randolph
Concord
Cambridge
Brockton
Dedham
Cranston
Warwick
Pawtucket
Peabody
Londonderry
York Beach
Revere
Fitchburg
North Falmouth
Chelsea
Swansea
Braintree
Auburn
Sandwich
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Top 2 airlines flying from Winnipeg to Boston
Discover the top 2 airlines that operate flights from Winnipeg to Boston. 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 12, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$215 | Average$618 | FlexibilityNo cancel fee | On-time67% | |
| Cheapest$282 | Average$380 | FlexibilityNo cancel fee | On-time52% |