$167+ 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 12/7. Fares are subject to change and may not be available on all flights or dates of travel.
YWG — BOS
Nov 26 — Dec 31
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
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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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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 27, 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 27, 2026.
This Booking.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 Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/137:00 am -
1 stop26h 10m
Sat 11/141:15 pm -
1 stop5h 51m
Deal found 10/22![Porter Airlines logo]()
$260
This FlightHub 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/412:40 pm -
2 stops8h 59m
Sun 12/61:15 pm -
1 stop5h 59m
Deal found 10/23![Porter Airlines logo]()
$283
This Air Canada deal was found by Cheapflights users on 10/26. 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 11/257:00 am -
2 stops7h 53m
Wed 12/25:30 am -
1 stop5h 45m
Deal found 10/26![Air Canada logo]()
$295
This Air Canada deal was found by Cheapflights users on 10/26. 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 11/276:15 am -
1 stop8h 03m
Sat 11/2810:25 am -
2 stops9h 00m
Deal found 10/26![Air Canada logo]()
$300
This United Airlines 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 12/63:15 pm -
1 stop6h 38m
Sun 12/139:15 am -
2 stops12h 40m
Deal found 10/22![United Airlines logo]()
$301
This Air Canada deal was found by Cheapflights users on 10/26. 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 11/266:15 am -
2 stops8h 38m
Fri 11/2710:25 am -
1 stop7h 13m
Deal found 10/26![Air Canada logo]()
$303
This Justfly.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 Justfly.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/2712:35 pm -
2 stops9h 00m
Mon 11/308:00 am -
2 stops11h 06m
Deal found 10/22![Porter Airlines logo]()
$304
This Booking.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 Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/812:40 pm -
2 stops8h 59m
Tue 12/158:00 am -
2 stops11h 14m
Deal found 10/24![Porter Airlines logo]()
$306
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.
Sat 11/217:55 pm -
1 stop14h 27m
Sat 11/285:45 am -
1 stop16h 29m
Deal found 10/22![Air Canada logo]()
$308
This Air Canada deal was found by Cheapflights users on 10/26. 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 11/257:00 am -
2 stops7h 53m
Fri 11/275:30 am -
2 stops9h 19m
Deal found 10/26![Air Canada logo]()
$309
This Justfly.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 Justfly.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/2612:35 pm -
2 stops9h 00m
Mon 11/308:00 am -
2 stops11h 06m
Deal found 10/22![Porter Airlines logo]()
$311
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 27, 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 27, 2026.
This FlightHub 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/412:40 pm -
2 stops8h 59m
Sun 12/61:15 pm -
1 stop5h 59m
Deal found 10/23![Porter Airlines logo]()
$283
This United Airlines 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 3/68:00 am -
1 stop5h 50m
Wed 3/1010:30 am -
2 stops9h 11m
Deal found 10/22![United Airlines logo]()
$301
This Delta 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 12/65:24 pm -
1 stop6h 23m
Sun 12/135:35 am -
1 stop7h 29m
Deal found 10/22![Delta logo]()
$301
This United Airlines 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 12/63:15 pm -
1 stop6h 38m
Sun 12/139:15 am -
2 stops12h 40m
Deal found 10/22![United Airlines logo]()
$301
This Justfly.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 Justfly.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/2312:35 pm -
2 stops9h 00m
Sat 11/281:15 pm -
1 stop5h 51m
Deal found 10/24![Porter Airlines logo]()
$312
This Porter Airlines deal was found by Cheapflights users on 10/25. 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 1/2711:40 am -
2 stops10h 02m
Thu 1/281:15 pm -
1 stop5h 55m
Deal found 10/25![Porter Airlines logo]()
$322
This FlightHub deal was found by Cheapflights users on 10/26. 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.
Wed 11/1812:35 pm -
2 stops9h 00m
Tue 11/248:00 am -
2 stops11h 06m
Deal found 10/26![Porter Airlines logo]()
$342
Last-minute flights from Winnipeg to BostonDiscover last-minute flight deals from Winnipeg to Boston. Data last updated October 27, 2026 and is based on user searches.
Discover last-minute flight deals from Winnipeg to Boston. Data last updated October 27, 2026 and is based on user searches.
This Booking.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 Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/137:00 am -
1 stop26h 10m
Sat 11/141:15 pm -
1 stop5h 51m
Deal found 10/22![Porter Airlines logo]()
$260
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.
Sat 11/217:55 pm -
1 stop14h 27m
Sat 11/285:45 am -
1 stop16h 29m
Deal found 10/22![Air Canada logo]()
$308
This Justfly.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 Justfly.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/2312:35 pm -
2 stops9h 00m
Sat 11/281:15 pm -
1 stop5h 51m
Deal found 10/24![Porter Airlines logo]()
$312
This Air Canada deal was found by Cheapflights users on 10/26. 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 11/257:00 am -
2 stops7h 53m
Wed 12/25:30 am -
1 stop5h 45m
Deal found 10/26![Air Canada logo]()
$295
This Air Canada deal was found by Cheapflights users on 10/26. 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 11/257:00 am -
2 stops7h 53m
Sat 11/2810:25 am -
2 stops9h 00m
Deal found 10/26![Air Canada logo]()
$301
This Air Canada deal was found by Cheapflights users on 10/26. 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 11/257:00 am -
2 stops7h 53m
Fri 11/275:30 am -
2 stops9h 19m
Deal found 10/26![Air Canada logo]()
$309
This Air Canada deal was found by Cheapflights users on 10/26. 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 11/266:15 am -
2 stops8h 38m
Fri 11/2710:25 am -
1 stop7h 13m
Deal found 10/26![Air Canada logo]()
$303
This Justfly.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 Justfly.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/2612:35 pm -
2 stops9h 00m
Mon 11/308:00 am -
2 stops11h 06m
Deal found 10/22![Porter Airlines logo]()
$311
This Air Canada deal was found by Cheapflights users on 10/26. 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 11/276:15 am -
1 stop8h 03m
Sat 11/2810:25 am -
2 stops9h 00m
Deal found 10/26![Air Canada logo]()
$300
This Justfly.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 Justfly.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/2712:35 pm -
2 stops9h 00m
Mon 11/308:00 am -
2 stops11h 06m
Deal found 10/22![Porter Airlines logo]()
$304
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 27, 2026.
Search for one-way flight options from Winnipeg to Boston. Find affordable one-way fares based on user searches. Data last updated October 27, 2026.
This Delta 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 12/76:25 am -
1 stop10h 36m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/23![Delta logo]()
$167
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.
Thu 2/47:55 pm -
1 stop14h 17m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/22![Air Canada logo]()
$179
This United Airlines 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 2/49:40 am -
2 stops12h 13m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/22![United Airlines logo]()
$186
This Porter 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 Porter Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 12/712:40 pm -
2 stops8h 59m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/23![Porter Airlines logo]()
$195
This Delta deal was found by Cheapflights users on 10/26. 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 11/225:45 pm -
1 stop5h 59m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/26![Delta logo]()
$218
This Mytrip deal was found by Cheapflights users on 10/26. 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.
Sun 11/2212:35 pm -
2 stops9h 00m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/26![Porter Airlines logo]()
$219
This Kiwi.com deal was found by Cheapflights users on 10/26. 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 12/1011:00 am -
1 stop8h 10m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/26![Multiple Airlines logo]()
$232
This Trip.com deal was found by Cheapflights users on 10/26. 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.
Sun 11/227:55 pm -
1 stop23h 15m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/26![Multiple Airlines logo]()
$242
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 2/47:00 am -
3 stops26h 10m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/22![Multiple Airlines logo]()
$277
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 12/77:35 pm -
3 stops23h 35m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/23![Multiple Airlines logo]()
$285
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 27, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $250 (Air Canada) |
One-way from | $167 (Delta) |
Popular in | April |
Cheapest in | August |
Average price | $482 |
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 27, 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
Mon 12/7
6:25 am-5:01 pm
1 stop10h 36m
Boston Logan Intl
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$167
WinnipegBoston
YWG Winnipeg - BOS Boston Logan Intl
YWGBOS
Winnipeg
Thu 2/4
7:55 pm-10:12 am
1 stop14h 17m
Boston Logan Intl
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$179
WinnipegBoston
YWG Winnipeg - BOS Boston Logan Intl
YWGBOS
Winnipeg
Thu 2/4
9:40 am-9:53 pm
2 stops12h 13m
Boston Logan Intl
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$186
WinnipegBoston
YWG Winnipeg - BOS Boston Logan Intl
YWGBOS
Winnipeg
Mon 12/7
12:40 pm-9:39 pm
2 stops8h 59m
Boston Logan Intl
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$195
Quickest round-trip
WinnipegBoston
YWG Winnipeg - BOS Boston Logan Intl
YWGBOS
Winnipeg
Sun 11/22
5:45 pm-11:44 pm
1 stop5h 59m
Boston Logan Intl
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$218
WinnipegBoston
YWG Winnipeg - BOS Boston Logan Intl
YWGBOS
Winnipeg
Sun 11/22
12:35 pm-9:35 pm
2 stops9h 00m
Boston Logan Intl
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$219
WinnipegBoston
YWG Winnipeg - BOS Boston Logan Intl
YWGBOS
Winnipeg
Thu 12/10
11:00 am-7:10 pm
1 stop8h 10m
Boston Logan Intl
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$232
WinnipegBoston
YWG Winnipeg - BOS Boston Logan Intl
YWGBOS
Winnipeg
Sun 11/22
7:55 pm-7:10 pm
1 stop23h 15m
Boston Logan Intl
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$242
WinnipegBoston
YWG Winnipeg - BOS Boston Logan Intl
YWGBOS
Winnipeg
Thu 2/4
7:00 am-9:10 am
3 stops26h 10m
Boston Logan Intl
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$277
WinnipegBoston
YWG Winnipeg - BOS Boston Logan Intl
YWGBOS
Winnipeg
Fri 12/4
12:40 pm-9:39 pm
2 stops8h 59m
Boston Logan Intl
Sun 12/6
1:15 pm-7:14 pm
1 stop5h 59m
$283
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 October.
| Provider | Price Accuracy | Trust Score* |
|---|---|---|
| Price Accuracy1 star | Trust Score*3 stars | |
| Price Accuracy3 stars | Trust Score*3 stars | |
| Price Accuracy2 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 $550 and $869 in November.The cheapest round-trip price found within the last 5 days was $260 on Porter Airlines (Nov 13-Nov 14).
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 27, 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.
Boarding
8.2
Food
7.6
Overall
8.0
Comfort
8.0
Entertainment
6.9
Crew
8.6
Reviews
1 / 20
8.0
ExcellentD,Sep 2026
YHM - YVR
Boarding
8.2
Food
7.6
Overall
8.0
Comfort
8.0
Entertainment
6.9
Crew
8.6
Reviews
1 / 20
8.0
ExcellentD,Sep 2026
YHM - YVR
Boarding
8.2
Food
7.6
Overall
8.0
Comfort
8.0
Entertainment
6.9
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
Fitchburg
Londonderry
York Beach
Revere
North Falmouth
Chelsea
Swansea
Braintree
Auburn
Sandwich
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.
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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 October 27, 2026.
Complete your trip
Complete your trip to Boston by adding a car rental and/or hotel reservation to your travel itinerary.
Search flights from Winnipeg to Boston by cabin class
Find flights from Winnipeg to Boston, based on your preferred cabin class, be it economy, premium economy, business, or first class.
Winnipeg and Boston flights
Browse other Winnipeg and Boston flight options. Last updated on October 27, 2026.
Other flights from Winnipeg
Browse through other flights departing from Winnipeg. Flights are based on user searches made on Cheapflights and were last updated on October 27, 2026.
Popular flight searches
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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 27, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$215 | Average$611 | FlexibilityNo cancel fee | On-time67% | |
| Cheapest$282 | Average$380 | FlexibilityNo cancel fee | On-time52% |