$121+ Cheap flights from Boston (BOS) to Winnipeg (YWG)
This is the cheapest round-trip flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 10/6. Fares are subject to change and may not be available on all flights or dates of travel.
BOS — YWG
Oct 23 — Oct 301
Round-trip
1 adult, Economy
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Find cheap flights from Boston to Winnipeg with Cheapflights
1. Tell us where you want to go
Enter your travel information like dates, passengers, trip type (one-way or round trip), and preferred cabin class then click “Find deals”2. Select your favorite providers
We find the providers serving your travel needs. Choose up to four travel providers to compare side-by-side for flights, hotels, or car rentals.3. Compare prices and book
Review each provider’s pricing and select the best option for you! Book through your favorite provider’s website for a seamless experience.Cheap flight deals from Boston to Winnipeg
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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 September 23, 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 September 23, 2026.
This Trip.com deal was found by Cheapflights users on 9/22. 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/710:05 am -
1 stop6h 15m
Wed 10/149:20 am -
1 stop8h 15m
Deal found 9/22![Porter Airlines logo]()
$270
This Kiwi.com deal was found by Cheapflights users on 9/22. 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.
Fri 10/167:00 am -
2 stops11h 58m
Mon 10/199:20 am -
1 stop8h 15m
Deal found 9/22![Porter Airlines logo]()
$280
This Kiwi.com deal was found by Cheapflights users on 9/22. 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 10/610:05 am -
1 stop6h 15m
Thu 10/159:20 am -
1 stop8h 15m
Deal found 9/22![Porter Airlines logo]()
$284
This Trip.com deal was found by Cheapflights users on 9/22. 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/1610:05 am -
1 stop6h 15m
Mon 10/196:00 am -
1 stop10h 40m
Deal found 9/22![Multiple Airlines logo]()
$292
This FlightHub deal was found by Cheapflights users on 9/22. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/610:05 am -
1 stop6h 15m
Wed 10/149:20 am -
1 stop8h 15m
Deal found 9/22![Porter Airlines logo]()
$297
This Booking.com deal was found by Cheapflights users on 9/22. 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 11/68:00 am -
2 stops11h 10m
Fri 11/1311:40 am -
2 stops8h 52m
Deal found 9/22![Porter Airlines logo]()
$299
This Kiwi.com deal was found by Cheapflights users on 9/22. 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 10/610:05 am -
1 stop6h 15m
Sat 10/176:00 am -
1 stop10h 40m
Deal found 9/22![Multiple Airlines logo]()
$300
This United Airlines deal was found by Cheapflights users on 9/22. 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.
Tue 10/66:00 am -
1 stop7h 37m
Fri 10/168:45 am -
1 stop14h 14m
Deal found 9/22![United Airlines logo]()
$303
This Air Canada deal was found by Cheapflights users on 9/22. 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.
Wed 10/710:50 am -
1 stop8h 22m
Tue 10/135:00 am -
1 stop5h 50m
Deal found 9/22![Air Canada logo]()
$305
This Air Canada deal was found by Cheapflights users on 9/21. 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 10/225:50 am -
2 stops11h 37m
Sat 10/243:05 pm -
1 stop5h 22m
Deal found 9/21![Air Canada logo]()
$308
This United deal was found by Cheapflights users on 9/22. 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 is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/78:30 pm -
1 stop17h 07m
Wed 10/145:00 am -
2 stops8h 41m
Deal found 9/22![Multiple Airlines logo]()
$310
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 September 23, 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 September 23, 2026.
This Air Canada deal was found by Cheapflights users on 9/22. 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.
Fri 10/166:00 am -
1 stop6h 12m
Mon 10/195:00 am -
1 stop5h 50m
Deal found 9/22![Air Canada logo]()
$305
This United deal was found by Cheapflights users on 9/22. 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 is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/78:30 pm -
1 stop17h 07m
Wed 10/145:00 am -
2 stops8h 41m
Deal found 9/22![Multiple Airlines logo]()
$310
This Justfly.com deal was found by Cheapflights users on 9/19. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Justfly.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 3/11:15 pm -
1 stop5h 55m
Tue 3/911:40 am -
2 stops8h 52m
Deal found 9/19![Porter Airlines logo]()
$327
This United Airlines deal was found by Cheapflights users on 9/19. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 11/116:00 am -
1 stop7h 23m
Wed 11/182:15 pm -
1 stop8h 20m
Deal found 9/19![United Airlines logo]()
$337
This Delta deal was found by Cheapflights users on 9/20. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 11/47:27 am -
1 stop5h 21m
Mon 11/95:32 pm -
1 stop5h 12m
Deal found 9/20![Delta logo]()
$337
This United deal was found by Cheapflights users on 9/19. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/36:00 am -
1 stop7h 37m
Sun 10/118:10 am -
1 stop5h 31m
Deal found 9/19![Multiple Airlines logo]()
$331
This Air Canada deal was found by Cheapflights users on 9/19. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Air Canada is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/2210:50 am -
1 stop6h 37m
Sat 10/243:05 pm -
1 stop5h 22m
Deal found 9/19![Air Canada logo]()
$334
This United Airlines deal was found by Cheapflights users on 9/20. 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.
Tue 11/37:15 am -
1 stop14h 42m
Thu 11/122:15 pm -
1 stop9h 31m
Deal found 9/20![United Airlines logo]()
$337
Last-minute flights from Boston to WinnipegDiscover last-minute flight deals from Boston to Winnipeg. Data last updated September 23, 2026 and is based on user searches.
Discover last-minute flight deals from Boston to Winnipeg. Data last updated September 23, 2026 and is based on user searches.
This Kiwi.com deal was found by Cheapflights users on 9/22. 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 10/610:05 am -
1 stop6h 15m
Thu 10/159:20 am -
1 stop8h 15m
Deal found 9/22![Porter Airlines logo]()
$284
This FlightHub deal was found by Cheapflights users on 9/22. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/610:05 am -
1 stop6h 15m
Wed 10/149:20 am -
1 stop8h 15m
Deal found 9/22![Porter Airlines logo]()
$297
This Kiwi.com deal was found by Cheapflights users on 9/22. 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 10/610:05 am -
1 stop6h 15m
Sat 10/176:00 am -
1 stop10h 40m
Deal found 9/22![Multiple Airlines logo]()
$300
This United Airlines deal was found by Cheapflights users on 9/22. 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.
Tue 10/66:00 am -
1 stop7h 37m
Fri 10/168:45 am -
1 stop14h 14m
Deal found 9/22![United Airlines logo]()
$303
This Trip.com deal was found by Cheapflights users on 9/22. 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/710:05 am -
1 stop6h 15m
Wed 10/149:20 am -
1 stop8h 15m
Deal found 9/22![Porter Airlines logo]()
$270
This Air Canada deal was found by Cheapflights users on 9/22. 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.
Wed 10/710:50 am -
1 stop8h 22m
Tue 10/135:00 am -
1 stop5h 50m
Deal found 9/22![Air Canada logo]()
$305
This United deal was found by Cheapflights users on 9/22. 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 is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/78:30 pm -
1 stop17h 07m
Wed 10/145:00 am -
2 stops8h 41m
Deal found 9/22![Multiple Airlines logo]()
$310
This Air Canada deal was found by Cheapflights users on 9/18. 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 10/156:00 am -
1 stop6h 12m
Thu 10/151:30 pm -
2 stops6h 56m
Deal found 9/18![Air Canada logo]()
$311
This Kiwi.com deal was found by Cheapflights users on 9/22. 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.
Fri 10/167:00 am -
2 stops11h 58m
Mon 10/199:20 am -
1 stop8h 15m
Deal found 9/22![Porter Airlines logo]()
$280
This Trip.com deal was found by Cheapflights users on 9/22. 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/1610:05 am -
1 stop6h 15m
Mon 10/196:00 am -
1 stop10h 40m
Deal found 9/22![Multiple Airlines logo]()
$292
This Air Canada deal was found by Cheapflights users on 9/22. 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 10/225:50 am -
2 stops11h 37m
Sat 10/243:05 pm -
1 stop5h 22m
Deal found 9/22![Air Canada logo]()
$308
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 September 23, 2026.
Search for one-way flight options from Boston to Winnipeg. Find affordable one-way fares based on user searches. Data last updated September 23, 2026.
This FlightHub deal was found by Cheapflights users on 9/22. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/610:05 am -
1 stop6h 15m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/22![Porter Airlines logo]()
$121
This United Airlines deal was found by Cheapflights users on 9/22. 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.
Wed 10/78:30 pm -
1 stop17h 07m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/22![United Airlines logo]()
$125
This Air Canada deal was found by Cheapflights users on 9/22. 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.
Wed 10/710:50 am -
1 stop8h 22m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/22![Air Canada logo]()
$128
This Flightnetwork deal was found by Cheapflights users on 9/18. 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 Flightnetwork is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/65:50 am -
2 stops11h 37m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/18![Air Canada logo]()
$132
This Kissandfly.com deal was found by Cheapflights users on 9/18. 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 Kissandfly.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/67:01 am -
1 stop6h 36m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/18![Lufthansa logo]()
$134
This Delta deal was found by Cheapflights users on 9/20. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/103:15 pm -
1 stop9h 04m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/20![Delta logo]()
$142
This Air Canada deal was found by Cheapflights users on 9/20. 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 11/510:25 am -
1 stop7h 13m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/20![Air Canada logo]()
$145
This United Airlines deal was found by Cheapflights users on 9/19. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 10/57:00 pm -
2 stops18h 37m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/19![United Airlines logo]()
$147
This United Airlines deal was found by Cheapflights users on 9/20. 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.
Sat 10/108:25 pm -
2 stops25h 32m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/20![United Airlines logo]()
$153
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 September 23, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $270 (Trip.com) |
One-way from | $121 (FlightHub) |
Popular in | February |
Cheapest in | September |
Average price | $364 |
Cheapflights Fare Finder
Customize your flight search to find flights from Boston to Winnipeg that fit within your specific budget. Explore options based on user searches and filter the results based on your desired price range. Find flights that match your budget for a cost-effective journey. Over the last 7 days, Cheapflights users made 7,457,451 searches. Data last updated September 23, 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 Boston Logan Intl - YWG Winnipeg
BOSYWG
Boston Logan Intl
Tue 10/6
5:50 am-4:27 pm
2 stops11h 37m
Winnipeg
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$132
BostonWinnipeg
BOS Boston Logan Intl - YWG Winnipeg
BOSYWG
Boston Logan Intl
Tue 10/6
7:01 am-12:37 pm
1 stop6h 36m
Winnipeg
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$134
Quickest round-trip
BostonWinnipeg
BOS Boston Logan Intl - YWG Winnipeg
BOSYWG
Boston Logan Intl
Wed 10/7
6:00 am-11:12 am
1 stop6h 12m
Winnipeg
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$135
BostonWinnipeg
BOS Boston Logan Intl - YWG Winnipeg
BOSYWG
Boston Logan Intl
Sat 10/10
3:15 pm-11:19 pm
1 stop9h 04m
Winnipeg
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$142
BostonWinnipeg
BOS Boston Logan Intl - YWG Winnipeg
BOSYWG
Boston Logan Intl
Mon 10/5
7:00 pm-12:37 pm
2 stops18h 37m
Winnipeg
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$147
BostonWinnipeg
BOS Boston Logan Intl - YWG Winnipeg
BOSYWG
Boston Logan Intl
Sat 10/10
8:25 pm-8:57 pm
2 stops25h 32m
Winnipeg
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$153
BostonWinnipeg
BOS Boston Logan Intl - YWG Winnipeg
BOSYWG
Boston Logan Intl
Mon 10/19
8:25 pm-12:37 pm
2 stops17h 12m
Winnipeg
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$153
BostonWinnipeg
BOS Boston Logan Intl - YWG Winnipeg
BOSYWG
Boston Logan Intl
Mon 10/5
7:05 pm-9:57 am
1 stop15h 52m
Winnipeg
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$170
BostonWinnipeg
BOS Boston Logan Intl - YWG Winnipeg
BOSYWG
Boston Logan Intl
Mon 10/19
7:30 pm-5:15 pm
1 stop22h 45m
Winnipeg
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$171
BostonWinnipeg
BOS Boston Logan Intl - YWG Winnipeg
BOSYWG
Boston Logan Intl
Thu 11/5
1:15 pm-12:44 am
2 stops12h 29m
Winnipeg
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$175
Showing 1-10 of 19 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 September.
| Provider | Price Accuracy | Trust Score* |
|---|---|---|
| Price Accuracy1 star | Trust Score*3 stars | |
| Price Accuracy3 stars | Trust Score*3 stars | |
| Price Accuracy3 stars | Trust Score*2 stars |
- Most accurate provider: When it comes to deals on Boston-Winnipeg flights, users find the pricing of FlightHub to be most consistent on Cheapflights vs. FlightHub Users can find the same prices on Boston-Winnipeg flight deals on Cheapflights vs. FlightHub >95% of the time. Price accuracy is based on data collected from Boston-Winnipeg flight searches over the past month and is updated monthly.
- Most trusted provider: When it comes to deals on Boston-Winnipeg flights, Cheapflights users trust FlightHub the most. FlightHub has received a user feedback score of 3 out of 3 stars (3 being the best), meaning they have been trusted the most by Cheapflights users looking for Boston-Winnipeg flight deals. Provider user feedback score is based on Cheapflights searches over the past month and is updated monthly.
Best time to book a flight from Boston to Winnipeg
Have a flexible travel schedule? Discover the best time to fly to Winnipeg from Boston with our price prediction graph.
BOS-YWG
Estimated round-trip price
Rates are based on past data. Find the cheapest month and day to book your flight based on your travel requirements, then search for cheap deals.
Cheapflights Insights
Everything you need to know about your flight from Boston to Winnipeg
What is the cheapest month to book a flight from Boston to Winnipeg?
Currently, September is the cheapest month in which you can book a flight from Boston to Winnipeg (average of $364). Flying from Boston to Winnipeg in February is currently the most expensive (average of $918). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.
How much does it cost to fly round-trip from Boston to Winnipeg?
Airfare is below average for this route at the moment.
Boston to Winnipeg flights typically cost between $319 and $573 in October.The cheapest round-trip price found within the last 5 days was $270 on Porter Airlines (Oct 7-Oct 14).
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 September 23, 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.
Boarding
8.2
Food
7.6
Entertainment
6.9
Crew
8.6
Overall
8.0
Comfort
8.0
Reviews
1 / 20
8.0
ExcellentD,Sep 2026
YHM - YVR
Boarding
8.2
Food
7.6
Entertainment
6.9
Crew
8.6
Overall
8.0
Comfort
8.0
Reviews
1 / 20
8.0
ExcellentD,Sep 2026
YHM - YVR
Boarding
8.2
Food
7.6
Entertainment
6.9
Crew
8.6
Overall
8.0
Comfort
8.0
Reviews
1 / 20
8.0
ExcellentD,Sep 2026
YHM - YVR
Boarding
8.2
Food
7.6
Entertainment
6.9
Crew
8.6
Overall
8.0
Comfort
8.0
Reviews
1 / 20
8.0
ExcellentD,Sep 2026
YHM - YVR
Boarding
8.2
Food
7.6
Entertainment
6.9
Crew
8.6
Overall
8.0
Comfort
8.0
Reviews
1 / 20
8.0
ExcellentD,Sep 2026
YHM - YVR
Related info for your journey
Find useful and relevant information for your journey from Boston to Winnipeg. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.
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Book flights to Winnipeg if you plan to visit one of these locationsPortage la Prairie
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Complete your trip to Winnipeg by adding a car rental and/or hotel reservation to your travel itinerary.
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Find flights from Boston to Winnipeg, based on your preferred cabin class, be it economy, premium economy, business, or first class.
Boston and Winnipeg flights
Browse other Boston and Winnipeg flight options. Last updated on September 23, 2026.
Other flights from Boston
Browse through other flights departing from Boston. Flights are based on user searches made on Cheapflights and were last updated on September 23, 2026.
Popular flight searches
Check out other popular destinations found by fellow travelers in 2026
Other flights to Winnipeg
Explore flights to Winnipeg departing from other origins. Flights are based on user searches made on Cheapflights and were last updated on September 23, 2026.
Top 4 airlines flying from Boston to Winnipeg
Discover the top 4 airlines that operate flights from Boston to Winnipeg. Compare their services, reliability, and customer satisfaction ratings to choose the airline that best suits your travel preferences and needs. Over the last 7 days, Cheapflights users made 7,457,451 searches. Data last updated September 23, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$111 | Average$679 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$204 | Average$534 | FlexibilityNo cancel fee | On-time67% | |
| Cheapest$256 | Average$573 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$352 | Average$517 | FlexibilityNo cancel fee | On-time52% |