$175+ Cheap flights from Boston (BOS) to Winnipeg (YWG)
This is the cheapest one-way flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 7/15. Fares are subject to change and may not be available on all flights or dates of travel.
BOS — YWG
Jun 24 — Jul 11
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
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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 May 25, 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 May 25, 2026.
This Trip.com deal was found by Cheapflights users on 5/21. 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/210:05 am
BOS
- YWG
1 stop6h 14m
Multiple Airlines
Wed 10/77:00 am
YWG
- BOS
1 stop9h 40m
Multiple Airlines
Deal found 5/21![Multiple Airlines logo]()
$348
This FlightHub deal was found by Cheapflights users on 5/20. 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 10/1510:05 am
BOS
- YWG
1 stop6h 14m
Porter Airlines
Wed 10/219:20 am
YWG
- BOS
1 stop8h 55m
Porter Airlines
Deal found 5/20![Porter Airlines logo]()
$353
This Air Canada deal was found by Cheapflights users on 5/21. 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.
Sun 9/66:00 am
BOS
- YWG
1 stop6h 15m
Air Canada
Sat 9/128:10 am
YWG
- BOS
1 stop5h 31m
Air Canada
Deal found 5/21![Air Canada logo]()
$361
This Delta deal was found by Cheapflights users on 5/21. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/28:15 am
BOS
- YWG
1 stop9h 39m
Delta
Wed 10/712:30 pm
YWG
- BOS
1 stop10h 23m
Delta
Deal found 5/21![Delta logo]()
$364
This Air Canada deal was found by Cheapflights users on 5/20. 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.
Fri 9/46:00 am
BOS
- YWG
1 stop6h 15m
Air Canada
Tue 9/83:20 pm
YWG
- BOS
1 stop6h 20m
Air Canada
Deal found 5/20![Air Canada logo]()
$366
This Gotogate deal was found by Cheapflights users on 5/21. 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 Gotogate is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 7/2610:05 am
BOS
- YWG
1 stop6h 14m
Porter Airlines
Sat 8/112:15 pm
YWG
- BOS
1 stop6h 00m
Porter Airlines
Deal found 5/21![Porter Airlines logo]()
$368
This Gotogate deal was found by Cheapflights users on 5/21. 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 Gotogate is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 7/1210:05 am
BOS
- YWG
1 stop6h 14m
Porter Airlines
Sat 7/1812:15 pm
YWG
- BOS
1 stop6h 00m
Porter Airlines
Deal found 5/21![Porter Airlines logo]()
$369
This Air Canada deal was found by Cheapflights users on 5/20. 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 10/1510:40 am
BOS
- YWG
1 stop5h 29m
Air Canada
Thu 10/225:10 am
YWG
- BOS
2 stops8h 31m
Air Canada
Deal found 5/20![Air Canada logo]()
$370
This FlightHub deal was found by Cheapflights users on 5/21. 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.
Fri 7/1010:05 am
BOS
- YWG
1 stop6h 14m
Porter Airlines
Wed 7/1512:15 pm
YWG
- BOS
1 stop6h 00m
Porter Airlines
Deal found 5/21![Porter Airlines logo]()
$373
This Air Canada deal was found by Cheapflights users on 5/21. 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.
Thu 9/245:50 am
BOS
- YWG
2 stops9h 32m
Air Canada
Mon 9/283:20 pm
YWG
- BOS
1 stop6h 20m
Air Canada
Deal found 5/21![Air Canada logo]()
$374
This United Airlines deal was found by Cheapflights users on 5/21. 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.
Tue 9/16:00 am
BOS
- YWG
1 stop6h 52m
United Airlines
Fri 9/47:00 am
YWG
- BOS
1 stop8h 27m
United Airlines
Deal found 5/21![United Airlines logo]()
$385
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 May 25, 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 May 25, 2026.
This FlightHub deal was found by Cheapflights users on 5/20. 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 10/1510:05 am
BOS
- YWG
1 stop6h 14m
Porter Airlines
Wed 10/219:20 am
YWG
- BOS
1 stop8h 55m
Porter Airlines
Deal found 5/20![Porter Airlines logo]()
$353
This United Airlines deal was found by Cheapflights users on 5/20. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/163:13 pm
BOS
- YWG
1 stop8h 11m
United Airlines
Wed 10/218:30 am
YWG
- BOS
1 stop12h 12m
United Airlines
Deal found 5/20![United Airlines logo]()
$364
This Kiwi.com deal was found by Cheapflights users on 5/20. 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.
Sat 6/610:05 am
BOS
- YWG
1 stop6h 14m
Multiple Airlines
Sun 6/76:15 am
YWG
- BOS
1 stop9h 31m
Multiple Airlines
Deal found 5/20![Multiple Airlines logo]()
$436
This oojo deal was found by Cheapflights users on 5/23. 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.
Sun 8/307:25 am
BOS
- YWG
1 stop9h 00m
WestJet
Mon 8/317:00 am
YWG
- BOS
1 stop9h 40m
WestJet
Deal found 5/23![WestJet logo]()
$467
This United Airlines deal was found by Cheapflights users on 5/21. 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.
Sun 9/66:00 am
BOS
- YWG
1 stop6h 52m
United Airlines
Sat 9/127:00 am
YWG
- BOS
2 stops15h 59m
United Airlines
Deal found 5/21![United Airlines logo]()
$374
This FlightHub deal was found by Cheapflights users on 5/20. 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.
Fri 7/2410:05 am
BOS
- YWG
1 stop6h 14m
Porter Airlines
Wed 7/2912:15 pm
YWG
- BOS
1 stop6h 00m
Porter Airlines
Deal found 5/20![Porter Airlines logo]()
$392
This United Airlines deal was found by Cheapflights users on 5/21. 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.
Tue 9/16:00 am
BOS
- YWG
1 stop6h 52m
United Airlines
Fri 9/47:00 am
YWG
- BOS
1 stop8h 27m
United Airlines
Deal found 5/21![United Airlines logo]()
$385
This Porter Airlines deal was found by Cheapflights users on 5/21. 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 Porter Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 7/1010:05 am
BOS
- YWG
1 stop6h 14m
Porter Airlines
Thu 7/169:20 am
YWG
- BOS
2 stops10h 35m
Porter Airlines
Deal found 5/21![Porter Airlines logo]()
$417
This Mytrip deal was found by Cheapflights users on 5/20. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 6/277:10 am
BOS
- YWG
2 stops11h 53m
Multiple Airlines
Sun 6/284:15 pm
YWG
- BOS
2 stops15h 50m
Multiple Airlines
Deal found 5/20![Multiple Airlines logo]()
$482
This Porter Airlines deal was found by Cheapflights users on 5/21. 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 Porter Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 7/97:10 am
BOS
- YWG
2 stops11h 48m
Porter Airlines
Thu 7/169:20 am
YWG
- BOS
2 stops10h 35m
Porter Airlines
Deal found 5/21![Porter Airlines logo]()
$425
Last-minute flights from Boston to WinnipegDiscover last-minute flight deals from Boston to Winnipeg. Data last updated May 25, 2026 and is based on user searches.
Discover last-minute flight deals from Boston to Winnipeg. Data last updated May 25, 2026 and is based on user searches.
This Kiwi.com deal was found by Cheapflights users on 5/21. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 6/610:05 am
BOS
- YWG
1 stop6h 14m
Multiple Airlines
Sun 6/75:10 pm
YWG
- BOS
1 stop16h 21m
Multiple Airlines
Deal found 5/21![Multiple Airlines logo]()
$435
This oojo deal was found by Cheapflights users on 5/20. 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 oojo is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 6/67:10 am
BOS
- YWG
2 stops11h 53m
Porter Airlines
Sun 6/79:20 am
YWG
- BOS
2 stops10h 35m
Porter Airlines
Deal found 5/20![Porter Airlines logo]()
$467
This Gotogate deal was found by Cheapflights users on 5/22. 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 Gotogate is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 6/1610:05 am
BOS
- YWG
1 stop6h 14m
Porter Airlines
Tue 6/2311:40 am
YWG
- BOS
1 stop6h 25m
Porter Airlines
Deal found 5/22![Porter Airlines logo]()
$397
This Kiwi.com deal was found by Cheapflights users on 5/22. 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.
Tue 6/166:35 pm
BOS
- YWG
1 stop16h 10m
Multiple Airlines
Tue 6/236:15 am
YWG
- BOS
2 stops11h 50m
Multiple Airlines
Deal found 5/22![Multiple Airlines logo]()
$405
This Kiwi.com deal was found by Cheapflights users on 5/20. 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 6/2310:05 am
BOS
- YWG
1 stop10h 44m
Multiple Airlines
Sun 6/284:15 pm
YWG
- BOS
2 stops15h 50m
Multiple Airlines
Deal found 5/20![Multiple Airlines logo]()
$464
This Kiwi.com deal was found by Cheapflights users on 5/21. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 6/247:10 am
BOS
- YWG
2 stops11h 48m
Multiple Airlines
Sun 6/285:10 pm
YWG
- BOS
1 stop14h 55m
Multiple Airlines
Deal found 5/21![Multiple Airlines logo]()
$422
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 May 25, 2026.
Search for one-way flight options from Boston to Winnipeg. Find affordable one-way fares based on user searches. Data last updated May 25, 2026.
This Air Canada deal was found by Cheapflights users on 5/21. 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.
Wed 7/1510:40 am
BOS
- YWG
1 stop5h 34m
Air Canada
Deal found 5/21![Air Canada logo]()
$175
This Delta deal was found by Cheapflights users on 5/24. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 6/177:15 am
BOS
- YWG
1 stop10h 36m
Delta
Deal found 5/24![Delta logo]()
$198
This Kiwi.com deal was found by Cheapflights users on 5/24. 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.
Wed 6/173:25 pm
BOS
- YWG
2 stops19h 20m
Multiple Airlines
Deal found 5/24![Multiple Airlines logo]()
$202
This Kiwi.com deal was found by Cheapflights users on 5/22. 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.
Tue 7/711:10 am
BOS
- YWG
2 stops31h 48m
Porter Airlines
Deal found 5/22![Porter Airlines logo]()
$207
This Kiwi.com deal was found by Cheapflights users on 5/24. 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.
Wed 7/87:10 am
BOS
- YWG
2 stops11h 48m
Porter Airlines
Deal found 5/24![Porter Airlines logo]()
$216
This oojo deal was found by Cheapflights users on 5/22. 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 oojo is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 7/77:25 am
BOS
- YWG
1 stop11h 00m
WestJet
Deal found 5/22![WestJet logo]()
$217
This Trip.com deal was found by Cheapflights users on 5/24. 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 7/810:05 am
BOS
- YWG
1 stop7h 20m
Multiple Airlines
Deal found 5/24![Multiple Airlines logo]()
$219
This FlightHub deal was found by Cheapflights users on 5/23. 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.
Tue 7/287:25 am
BOS
- YWG
1 stop11h 00m
WestJet
Deal found 5/23![WestJet logo]()
$220
This oojo deal was found by Cheapflights users on 5/24. 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 oojo is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/156:30 pm
BOS
- YWG
1 stop31h 25m
WestJet
Deal found 5/24![WestJet logo]()
$221
This Kiwi.com deal was found by Cheapflights users on 5/23. 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 7/283:55 pm
BOS
- YWG
2 stops17h 45m
Multiple Airlines
Deal found 5/23![Multiple Airlines logo]()
$238
This Kiwi.com deal was found by Cheapflights users on 5/23. 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.
Thu 7/3010:05 am
BOS
- YWG
1 stop23h 35m
Multiple Airlines
Deal found 5/23![Multiple Airlines logo]()
$239
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 May 25, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $348 (Trip.com) |
One-way from | $175 (Air Canada) |
Popular in | January |
Cheapest in | August |
Average price | $517 |
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 2,558,603 searches. Data last updated May 25, 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
BostonWinnipeg
BOS - YWG
BOSYWG
Boston Logan Intl
Thu 10/15
10:05 am-3:19 pm
1 stop6h 14m
Winnipeg
Wed 10/21
9:20 am-7:15 pm
1 stop8h 55m
$353
BostonWinnipeg
BOS - YWG
BOSYWG
Boston Logan Intl
Fri 10/16
3:13 pm-10:24 pm
1 stop8h 11m
Winnipeg
Wed 10/21
8:30 am-9:42 pm
1 stop12h 12m
$364
BostonWinnipeg
BOS - YWG
BOSYWG
Boston Logan Intl
Sun 9/6
6:00 am-11:52 am
1 stop6h 52m
Winnipeg
Sat 9/12
7:00 am-11:59 pm
2 stops15h 59m
$374
BostonWinnipeg
BOS - YWG
BOSYWG
Boston Logan Intl
Tue 9/1
6:00 am-11:52 am
1 stop6h 52m
Winnipeg
Fri 9/4
7:00 am-4:27 pm
1 stop8h 27m
$385
Quickest round-trip
BostonWinnipeg
BOS - YWG
BOSYWG
Boston Logan Intl
Fri 7/24
10:05 am-3:19 pm
1 stop6h 14m
Winnipeg
Wed 7/29
12:15 pm-7:15 pm
1 stop6h 00m
$392
BostonWinnipeg
BOS - YWG
BOSYWG
Boston Logan Intl
Fri 7/10
10:05 am-3:19 pm
1 stop6h 14m
Winnipeg
Thu 7/16
9:20 am-8:55 pm
2 stops10h 35m
$417
BostonWinnipeg
BOS - YWG
BOSYWG
Boston Logan Intl
Thu 7/9
7:10 am-5:58 pm
2 stops11h 48m
Winnipeg
Thu 7/16
9:20 am-8:55 pm
2 stops10h 35m
$425
BostonWinnipeg
BOS - YWG
BOSYWG
Boston Logan Intl
Sat 6/6
10:05 am-3:19 pm
1 stop6h 14m
Winnipeg
Sun 6/7
6:15 am-4:46 pm
1 stop9h 31m
$436
BostonWinnipeg
BOS - YWG
BOSYWG
Boston Logan Intl
Sun 8/30
7:25 am-3:25 pm
1 stop9h 00m
Winnipeg
Mon 8/31
7:00 am-5:40 pm
1 stop9h 40m
$467
BostonWinnipeg
BOS - YWG
BOSYWG
Boston Logan Intl
Sat 6/27
7:10 am-6:03 pm
2 stops11h 53m
Winnipeg
Sun 6/28
4:15 pm-9:05 am
2 stops15h 50m
$482
Showing 1-10 of 20 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 May.
| Provider | Price Accuracy | Trust Score* |
|---|---|---|
| Price Accuracy1 star | Trust Score*3 stars | |
| Price Accuracy3 stars | Trust Score*3 stars | |
| Price Accuracy3 stars | Trust Score*3 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
How far ahead should I book a flight from Boston to Winnipeg?
Booking 42 days in advance of your planned departure date is, on average, the best time to get cheap flights from Boston to Winnipeg. The general trend is that the closer you book to the departure date, the more expensive your flight will be.
What is the cheapest month to book a flight from Boston to Winnipeg?
Currently, August is the cheapest month in which you can book a flight from Boston to Winnipeg (average of $420). Flying from Boston to Winnipeg in January is currently the most expensive (average of $774). 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?
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 May 25, 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
7.0
Comfort
8.0
Crew
8.6
Overall
8.0
Food
7.6
Boarding
8.2
Reviews
1 / 20
10.0
ExcellentJohn,Mar 2026
YYZ - PVR
Entertainment
7.0
Comfort
8.0
Crew
8.6
Overall
8.0
Food
7.6
Boarding
8.2
Reviews
1 / 20
10.0
ExcellentJohn,Mar 2026
YYZ - PVR
Entertainment
7.0
Comfort
8.0
Crew
8.6
Overall
8.0
Food
7.6
Boarding
8.2
Reviews
1 / 20
10.0
ExcellentJohn,Mar 2026
YYZ - PVR
Entertainment
7.0
Comfort
8.0
Crew
8.6
Overall
8.0
Food
7.6
Boarding
8.2
Reviews
1 / 20
10.0
ExcellentJohn,Mar 2026
YYZ - PVR
Entertainment
7.0
Comfort
8.0
Crew
8.6
Overall
8.0
Food
7.6
Boarding
8.2
Reviews
1 / 20
10.0
ExcellentJohn,Mar 2026
YYZ - PVR
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
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Other flights from Boston
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Other flights to Winnipeg
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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 2,558,603 searches. Data last updated May 25, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$149 | Average$679 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$194 | Average$516 | FlexibilityNo cancel fee | On-time67% | |
| Cheapest$228 | Average$491 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$293 | Average$438 | FlexibilityNo cancel fee | On-time52% |