$167+ Cheap flights from Winnipeg (YWG) to Boston (BOS)
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 10/7. Fares are subject to change and may not be available on all flights or dates of travel.
YWG — BOS
Sep 9 — Sep 161
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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Best
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 August 10, 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 August 10, 2026.
This Air Canada deal was found by Cheapflights users on 8/7. 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.
Sat 9/195:00 am -
1 stop5h 51m
Sat 9/263:35 pm -
1 stop6h 39m
Deal found 8/7![Air Canada logo]()
$286
This Air Canada deal was found by Cheapflights users on 8/6. 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 9/35:00 am -
1 stop5h 47m
Thu 9/1010:50 am -
1 stop8h 22m
Deal found 8/6![Air Canada logo]()
$291
This Air Canada deal was found by Cheapflights users on 8/7. 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.
Fri 10/162:05 pm -
1 stop7h 35m
Fri 10/235:50 am -
1 stop7h 39m
Deal found 8/7![Air Canada logo]()
$300
This FlightHub deal was found by Cheapflights users on 8/7. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/29:20 am -
1 stop8h 15m
Mon 10/510:05 am -
1 stop6h 14m
Deal found 8/7![Porter Airlines logo]()
$302
This Air Canada deal was found by Cheapflights users on 8/7. 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 9/305:00 am -
1 stop5h 51m
Mon 10/56:00 am -
1 stop6h 12m
Deal found 8/7![Air Canada logo]()
$305
This Justfly.com deal was found by Cheapflights users on 8/7. 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 Justfly.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/169:20 am -
1 stop8h 15m
Fri 10/237:00 am -
2 stops11h 58m
Deal found 8/7![Porter Airlines logo]()
$308
This Air Canada deal was found by Cheapflights users on 8/6. 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.
Fri 11/65:15 am -
1 stop11h 43m
Mon 11/95:30 am -
1 stop5h 35m
Deal found 8/6![Air Canada logo]()
$310
This Air Canada deal was found by Cheapflights users on 8/7. 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.
Fri 8/287:45 pm -
1 stop15h 07m
Wed 9/2310:50 am -
1 stop6h 37m
Deal found 8/7![Air Canada logo]()
$315
This Kiwi.com deal was found by Cheapflights users on 8/7. 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.
Fri 9/1111:15 am -
2 stops22h 15m
Mon 9/147:30 pm -
1 stop6h 25m
Deal found 8/7![Multiple Airlines logo]()
$320
This Booking.com deal was found by Cheapflights users on 8/6. 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.
Fri 11/611:35 am -
2 stops9h 42m
Mon 11/98:00 am -
2 stops11h 10m
Deal found 8/6![Porter Airlines logo]()
$323
This Kiwi.com deal was found by Cheapflights users on 8/7. 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.
Sat 9/1911:15 am -
2 stops22h 15m
Sat 9/2610:05 am -
1 stop15h 50m
Deal found 8/7![Multiple Airlines logo]()
$325
This Kiwi.com deal was found by Cheapflights users on 8/5. 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 9/194:15 pm -
2 stops15h 50m
Sat 9/2610:05 am -
1 stop6h 14m
Deal found 8/5![Porter Airlines logo]()
$334
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 August 10, 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 August 10, 2026.
This FlightHub deal was found by Cheapflights users on 8/7. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/29:20 am -
1 stop8h 15m
Mon 10/510:05 am -
1 stop6h 14m
Deal found 8/7![Porter Airlines logo]()
$302
This Kiwi.com deal was found by Cheapflights users on 8/7. 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.
Sat 9/1911:15 am -
2 stops22h 15m
Sat 9/2610:05 am -
1 stop15h 50m
Deal found 8/7![Multiple Airlines logo]()
$325
This United Airlines deal was found by Cheapflights users on 8/6. 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 9/32:00 pm -
1 stop10h 11m
Thu 9/109:30 am -
2 stops14h 03m
Deal found 8/6![United Airlines logo]()
$337
This Justfly.com deal was found by Cheapflights users on 8/10. 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 Justfly.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/169:05 pm -
1 stop19h 35m
Fri 10/236:30 pm -
1 stop20h 35m
Deal found 8/10![WestJet logo]()
$345
This Kiwi.com deal was found by Cheapflights users on 8/6. 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 11/611:35 am -
2 stops9h 42m
Mon 11/91:15 pm -
1 stop5h 55m
Deal found 8/6![Porter Airlines logo]()
$305
This United Airlines deal was found by Cheapflights users on 8/5. 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 9/192:00 pm -
2 stops8h 59m
Sat 9/268:00 am -
2 stops13h 57m
Deal found 8/5![United Airlines logo]()
$337
This Kiwi.com deal was found by Cheapflights users on 8/8. 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.
Thu 9/1011:15 am -
2 stops22h 15m
Thu 9/1710:05 am -
1 stop24h 40m
Deal found 8/8![Multiple Airlines logo]()
$340
This United Airlines deal was found by Cheapflights users on 8/5. 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.
Wed 9/27:00 am -
1 stop8h 27m
Sat 9/56:01 am -
1 stop6h 51m
Deal found 8/5![United Airlines logo]()
$337
This Porter Airlines deal was found by Cheapflights users on 8/5. 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 9/212:15 pm -
1 stop5h 20m
Sat 9/57:00 am -
2 stops11h 58m
Deal found 8/5![Porter Airlines logo]()
$347
Last-minute flights from Winnipeg to BostonDiscover last-minute flight deals from Winnipeg to Boston. Data last updated August 10, 2026 and is based on user searches.
Discover last-minute flight deals from Winnipeg to Boston. Data last updated August 10, 2026 and is based on user searches.
This Air Canada deal was found by Cheapflights users on 8/7. 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.
Fri 8/287:45 pm -
1 stop15h 07m
Wed 9/2310:50 am -
1 stop6h 37m
Deal found 8/7![Air Canada logo]()
$315
This United Airlines deal was found by Cheapflights users on 8/7. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 8/282:00 pm -
1 stop10h 11m
Wed 9/239:30 am -
2 stops14h 03m
Deal found 8/7![United Airlines logo]()
$338
This United Airlines deal was found by Cheapflights users on 8/5. 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.
Wed 9/27:00 am -
1 stop8h 27m
Sat 9/56:01 am -
1 stop6h 51m
Deal found 8/5![United Airlines logo]()
$337
This Air Canada deal was found by Cheapflights users on 8/6. 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 9/35:00 am -
1 stop5h 47m
Thu 9/1010:50 am -
1 stop8h 22m
Deal found 8/6![Air Canada logo]()
$291
This Kiwi.com deal was found by Cheapflights users on 8/8. 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.
Thu 9/1011:15 am -
2 stops22h 15m
Thu 9/1710:05 am -
1 stop24h 40m
Deal found 8/8![Multiple Airlines logo]()
$340
This Kiwi.com deal was found by Cheapflights users on 8/7. 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.
Fri 9/1111:15 am -
2 stops22h 15m
Mon 9/147:30 pm -
1 stop6h 25m
Deal found 8/7![Multiple Airlines logo]()
$320
This Air Canada deal was found by Cheapflights users on 8/7. 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.
Sat 9/195:00 am -
1 stop5h 51m
Sat 9/263:35 pm -
1 stop6h 39m
Deal found 8/7![Air Canada logo]()
$286
This Kiwi.com deal was found by Cheapflights users on 8/7. 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.
Sat 9/1911:15 am -
2 stops22h 15m
Sat 9/2610:05 am -
1 stop15h 50m
Deal found 8/7![Multiple Airlines logo]()
$325
This Kiwi.com deal was found by Cheapflights users on 8/5. 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 9/194:15 pm -
2 stops15h 50m
Sat 9/2610:05 am -
1 stop6h 14m
Deal found 8/5![Porter Airlines logo]()
$334
This Kiwi.com deal was found by Cheapflights users on 8/5. 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 9/257:55 pm -
1 stop12h 10m
Wed 9/307:30 pm -
1 stop6h 25m
Deal found 8/5![Multiple Airlines logo]()
$335
This Air Canada deal was found by Cheapflights users on 8/7. 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 9/305:00 am -
1 stop5h 51m
Mon 10/56:00 am -
1 stop6h 12m
Deal found 8/7![Air Canada logo]()
$305
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 August 10, 2026.
Search for one-way flight options from Winnipeg to Boston. Find affordable one-way fares based on user searches. Data last updated August 10, 2026.
This Trip.com deal was found by Cheapflights users on 8/7. 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.
Wed 10/76:15 am -
1 stop9h 31m
Deal found 8/7![Multiple Airlines logo]()
$167
This Air Canada deal was found by Cheapflights users on 8/7. 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.
Sat 9/53:20 pm -
1 stop6h 18m
Deal found 8/7![Air Canada logo]()
$170
This Kiwi.com deal was found by Cheapflights users on 8/6. 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.
Wed 9/911:15 am -
2 stops22h 15m
Deal found 8/6![Porter Airlines logo]()
$174
This Air Canada deal was found by Cheapflights users on 8/6. 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 9/92:05 pm -
1 stop7h 35m
Deal found 8/6![Air Canada logo]()
$177
This Kiwi.com deal was found by Cheapflights users on 8/9. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/2511:15 am -
2 stops22h 15m
Deal found 8/9![Porter Airlines logo]()
$181
This Kiwi.com deal was found by Cheapflights users on 8/7. 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.
Wed 10/711:15 am -
2 stops20h 50m
Deal found 8/7![Porter Airlines logo]()
$184
This Trip.com deal was found by Cheapflights users on 8/9. 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/97:45 am -
1 stop9h 50m
Deal found 8/9![Multiple Airlines logo]()
$187
This Air Canada deal was found by Cheapflights users on 8/7. 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 10/75:10 am -
1 stop5h 45m
Deal found 8/7![Air Canada logo]()
$194
This Kiwi.com deal was found by Cheapflights users on 8/10. 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.
Thu 9/248:45 pm -
2 stops18h 05m
Deal found 8/10![Porter Airlines logo]()
$206
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 August 10, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $286 (Air Canada) |
One-way from | $167 (Trip.com) |
Popular in | April |
Cheapest in | August |
Average price | $348 |
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 2,558,603 searches. Data last updated August 10, 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
Quickest round-trip
WinnipegBoston
YWG Winnipeg - BOS Boston Logan Intl
YWGBOS
Winnipeg
Fri 10/2
9:20 am-6:35 pm
1 stop8h 15m
Boston Logan Intl
Mon 10/5
10:05 am-3:19 pm
1 stop6h 14m
$302
WinnipegBoston
YWG Winnipeg - BOS Boston Logan Intl
YWGBOS
Winnipeg
Fri 11/6
11:35 am-10:17 pm
2 stops9h 42m
Boston Logan Intl
Mon 11/9
1:15 pm-6:10 pm
1 stop5h 55m
$305
WinnipegBoston
YWG Winnipeg - BOS Boston Logan Intl
YWGBOS
Winnipeg
Sat 9/19
11:15 am-10:30 am
2 stops22h 15m
Boston Logan Intl
Sat 9/26
10:05 am-12:55 am
1 stop15h 50m
$325
WinnipegBoston
YWG Winnipeg - BOS Boston Logan Intl
YWGBOS
Winnipeg
Thu 9/3
2:00 pm-1:11 am
1 stop10h 11m
Boston Logan Intl
Thu 9/10
9:30 am-10:33 pm
2 stops14h 03m
$337
WinnipegBoston
YWG Winnipeg - BOS Boston Logan Intl
YWGBOS
Winnipeg
Sat 9/19
2:00 pm-11:59 pm
2 stops8h 59m
Boston Logan Intl
Sat 9/26
8:00 am-8:57 pm
2 stops13h 57m
$337
WinnipegBoston
YWG Winnipeg - BOS Boston Logan Intl
YWGBOS
Winnipeg
Wed 9/2
7:00 am-4:27 pm
1 stop8h 27m
Boston Logan Intl
Sat 9/5
6:01 am-11:52 am
1 stop6h 51m
$337
WinnipegBoston
YWG Winnipeg - BOS Boston Logan Intl
YWGBOS
Winnipeg
Thu 9/10
11:15 am-10:30 am
2 stops22h 15m
Boston Logan Intl
Thu 9/17
10:05 am-9:45 am
1 stop24h 40m
$340
WinnipegBoston
YWG Winnipeg - BOS Boston Logan Intl
YWGBOS
Winnipeg
Fri 10/16
9:05 pm-5:40 pm
1 stop19h 35m
Boston Logan Intl
Fri 10/23
6:30 pm-2:05 pm
1 stop20h 35m
$345
WinnipegBoston
YWG Winnipeg - BOS Boston Logan Intl
YWGBOS
Winnipeg
Wed 9/2
12:15 pm-6:35 pm
1 stop5h 20m
Boston Logan Intl
Sat 9/5
7:00 am-5:58 pm
2 stops11h 58m
$347
Cheapest one-way
WinnipegBoston
YWG Winnipeg - BOS Boston Logan Intl
YWGBOS
Winnipeg
Wed 10/7
6:15 am-4:46 pm
1 stop9h 31m
$167
Showing 1-10 of 16 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 August.
| 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 $322 and $448 in September.The cheapest round-trip price found within the last 5 days was $286 on Air Canada (Sep 19-Sep 26).
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 August 10, 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
Crew
8.6
Food
7.5
Overall
8.0
Boarding
8.2
Entertainment
6.9
Reviews
1 / 20
10.0
ExcellentRegan,Aug 2026
YYZ - YVR
Comfort
8.0
Crew
8.6
Food
7.5
Overall
8.0
Boarding
8.2
Entertainment
6.9
Reviews
1 / 20
10.0
ExcellentRegan,Aug 2026
YYZ - YVR
Comfort
8.0
Crew
8.6
Food
7.5
Overall
8.0
Boarding
8.2
Entertainment
6.9
Reviews
1 / 20
10.0
ExcellentRegan,Aug 2026
YYZ - 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
Cambridge
Concord
Brockton
Seekonk
Cranston
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Explore flights to Boston departing from other origins. Flights are based on user searches made on Cheapflights and were last updated on August 10, 2026.
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Winnipeg and Boston flights
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Browse through other flights departing from Winnipeg. Flights are based on user searches made on Cheapflights and were last updated on August 10, 2026.
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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 2,558,603 searches. Data last updated August 10, 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% |