$126+ 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
May 28 — Jun 41
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
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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 Boston to Winnipeg
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Best
Last-minute
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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 April 28, 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 April 28, 2026.
This Air Canada deal was found by Cheapflights users on 4/27. 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 10/310:40 am
BOS
- YWG
1 stop5h 29m
Air Canada
Tue 10/68:10 am
YWG
- BOS
1 stop5h 31m
Air Canada
Deal found 4/27![Air Canada logo]()
$307
This Vliegwinkel deal was found by Cheapflights users on 4/24. 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 Vliegwinkel is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/910:45 am
BOS
- YWG
1 stop6h 33m
Air Canada
Mon 5/188:00 am
YWG
- BOS
1 stop5h 47m
Air Canada
Deal found 4/24![Air Canada logo]()
$309
This Air Canada deal was found by Cheapflights users on 4/26. 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.
Tue 9/155:00 pm
BOS
- YWG
1 stop7h 07m
Air Canada
Sat 9/198:10 am
YWG
- BOS
1 stop5h 31m
Air Canada
Deal found 4/26![Air Canada logo]()
$312
This Delta deal was found by Cheapflights users on 4/23. 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.
Thu 9/177:10 am
BOS
- YWG
1 stop10h 44m
Delta
Tue 9/2912:40 pm
YWG
- BOS
1 stop10h 12m
Delta
Deal found 4/23![Delta logo]()
$315
This Delta deal was found by Cheapflights users on 4/24. 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.
Fri 8/217:10 am
BOS
- YWG
1 stop10h 44m
Delta
Tue 8/2512:40 pm
YWG
- BOS
1 stop8h 40m
Delta
Deal found 4/24![Delta logo]()
$323
This United Airlines deal was found by Cheapflights users on 4/26. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/156:00 am
BOS
- YWG
1 stop6h 52m
United Airlines
Sat 9/198:30 am
YWG
- BOS
2 stops15h 35m
United Airlines
Deal found 4/26![United Airlines logo]()
$324
This Air Canada deal was found by Cheapflights users on 4/23. 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 Air Canada is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 7/410:50 am
BOS
- YWG
1 stop6h 30m
Air Canada
Sat 7/118:15 am
YWG
- BOS
1 stop6h 53m
Air Canada
Deal found 4/23![Air Canada logo]()
$325
This Air Canada deal was found by Cheapflights users on 4/25. 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 Air Canada is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 7/410:40 am
BOS
- YWG
2 stops8h 55m
Air Canada
Fri 7/107:55 am
YWG
- BOS
1 stop5h 46m
Air Canada
Deal found 4/25![Air Canada logo]()
$329
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 April 28, 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 April 28, 2026.
This Air Canada deal was found by Cheapflights users on 4/27. 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 10/310:40 am
BOS
- YWG
1 stop5h 29m
Air Canada
Tue 10/68:10 am
YWG
- BOS
1 stop5h 31m
Air Canada
Deal found 4/27![Air Canada logo]()
$307
This Delta deal was found by Cheapflights users on 4/23. 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.
Wed 10/1411:15 am
BOS
- YWG
1 stop10h 01m
Delta
Wed 10/2112:30 pm
YWG
- BOS
1 stop10h 23m
Delta
Deal found 4/23![Delta logo]()
$315
This United Airlines deal was found by Cheapflights users on 4/24. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/33:13 pm
BOS
- YWG
1 stop8h 11m
United Airlines
Tue 10/67:00 am
YWG
- BOS
1 stop6h 02m
United Airlines
Deal found 4/24![United Airlines logo]()
$315
This Vliegwinkel deal was found by Cheapflights users on 4/24. 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 Vliegwinkel is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/910:45 am
BOS
- YWG
1 stop6h 33m
Air Canada
Mon 5/188:00 am
YWG
- BOS
1 stop5h 47m
Air Canada
Deal found 4/24![Air Canada logo]()
$309
This Delta deal was found by Cheapflights users on 4/23. 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.
Thu 9/177:10 am
BOS
- YWG
1 stop10h 44m
Delta
Tue 9/2912:40 pm
YWG
- BOS
1 stop10h 12m
Delta
Deal found 4/23![Delta logo]()
$315
This United Airlines deal was found by Cheapflights users on 4/25. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 7/25:00 pm
BOS
- YWG
1 stop6h 33m
United Airlines
Wed 7/87:00 am
YWG
- BOS
1 stop15h 18m
United Airlines
Deal found 4/25![United Airlines logo]()
$323
This Delta deal was found by Cheapflights users on 4/27. 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 8/217:10 am
BOS
- YWG
1 stop10h 44m
Delta
Tue 8/256:40 am
YWG
- BOS
1 stop9h 39m
Delta
Deal found 4/27![Delta logo]()
$323
Last-minute flights from Boston to WinnipegDiscover last-minute flight deals from Boston to Winnipeg. Data last updated April 28, 2026 and is based on user searches.
Discover last-minute flight deals from Boston to Winnipeg. Data last updated April 28, 2026 and is based on user searches.
This Vliegwinkel deal was found by Cheapflights users on 4/24. 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 Vliegwinkel is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/910:45 am
BOS
- YWG
1 stop6h 33m
Air Canada
Mon 5/188:00 am
YWG
- BOS
1 stop5h 47m
Air Canada
Deal found 4/24![Air Canada logo]()
$309
This Mytrip deal was found by Cheapflights users on 4/24. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/910:35 am
BOS
- YWG
3 stops25h 35m
Multiple Airlines
Mon 5/185:10 am
YWG
- BOS
2 stops8h 37m
Multiple Airlines
Deal found 4/24![Multiple Airlines logo]()
$412
This Mytrip deal was found by Cheapflights users on 4/26. 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 5/1710:05 am
BOS
- YWG
1 stop6h 14m
Porter Airlines
Wed 5/209:20 am
YWG
- BOS
1 stop7h 15m
Porter Airlines
Deal found 4/26![Porter Airlines logo]()
$351
This Mytrip deal was found by Cheapflights users on 4/26. 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 5/177:10 am
BOS
- YWG
2 stops11h 53m
Multiple Airlines
Wed 5/209:05 pm
YWG
- BOS
3 stops25h 49m
Multiple Airlines
Deal found 4/26![Multiple Airlines logo]()
$423
This Air Canada deal was found by Cheapflights users on 4/25. 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 Air Canada is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/235:10 am
BOS
- YWG
1 stop5h 53m
Air Canada
Sat 5/302:00 pm
YWG
- BOS
1 stop7h 39m
Air Canada
Deal found 4/25![Air Canada logo]()
$375
This Kiwi.com deal was found by Cheapflights users on 4/25. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/2310:05 am
BOS
- YWG
1 stop6h 14m
Porter Airlines
Sat 5/309:20 am
YWG
- BOS
2 stops10h 35m
Porter Airlines
Deal found 4/25![Porter Airlines logo]()
$406
This Trip.com deal was found by Cheapflights users on 4/26. 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.
Tue 5/2610:05 am
BOS
- YWG
1 stop6h 14m
Porter Airlines
Tue 6/29:20 am
YWG
- BOS
1 stop7h 15m
Porter Airlines
Deal found 4/26![Porter Airlines logo]()
$358
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 April 28, 2026.
Search for one-way flight options from Boston to Winnipeg. Find affordable one-way fares based on user searches. Data last updated April 28, 2026.
This oojo deal was found by Cheapflights users on 4/27. 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.
Wed 7/1510:05 am
BOS
- YWG
1 stop6h 14m
Porter Airlines
Deal found 4/27![Porter Airlines logo]()
$126
This United Airlines deal was found by Cheapflights users on 4/24. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/47:10 am
BOS
- YWG
1 stop16h 23m
United Airlines
Deal found 4/24![United Airlines logo]()
$130
This Air Canada deal was found by Cheapflights users on 4/26. 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.
Sat 8/2210:40 am
BOS
- YWG
1 stop5h 34m
Air Canada
Deal found 4/26![Air Canada logo]()
$133
This Delta deal was found by Cheapflights users on 4/27. 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 7/125:55 am
BOS
- YWG
1 stop10h 12m
Delta
Deal found 4/27![Delta logo]()
$134
This Porter Airlines deal was found by Cheapflights users on 4/27. 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 7/1610:05 am
BOS
- YWG
1 stop6h 14m
Porter Airlines
Deal found 4/27![Porter Airlines logo]()
$138
This United Airlines deal was found by Cheapflights users on 4/27. 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 7/145:45 am
BOS
- YWG
2 stops17h 48m
United Airlines
Deal found 4/27![United Airlines logo]()
$140
This Air Canada deal was found by Cheapflights users on 4/27. 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.
Mon 7/136:00 am
BOS
- YWG
1 stop6h 15m
Air Canada
Deal found 4/27![Air Canada logo]()
$143
This Air Canada deal was found by Cheapflights users on 4/27. 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 7/155:45 am
BOS
- YWG
2 stops11h 35m
Air Canada
Deal found 4/27![Air Canada logo]()
$147
This United Airlines deal was found by Cheapflights users on 4/26. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/166:00 am
BOS
- YWG
1 stop6h 52m
United Airlines
Deal found 4/26![United Airlines logo]()
$159
This Air Canada deal was found by Cheapflights users on 4/26. 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.
Mon 8/246:50 pm
BOS
- YWG
1 stop16h 15m
Air Canada
Deal found 4/26![Air Canada logo]()
$163
This Mytrip deal was found by Cheapflights users on 4/24. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 6/910:05 am
BOS
- YWG
1 stop6h 14m
Porter Airlines
Deal found 4/24![Porter Airlines logo]()
$172
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 April 28, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $307 (Air Canada) |
One-way from | $126 (oojo) |
Popular in | January |
Cheapest in | May |
Average price | $598 |
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 April 28, 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
Quickest round-trip
BostonWinnipeg
BOS - YWG
BOSYWG
Boston Logan Intl
Sat 10/3
10:40 am-3:09 pm
1 stop5h 29m
Winnipeg
Tue 10/6
8:10 am-2:41 pm
1 stop5h 31m
$307
BostonWinnipeg
BOS - YWG
BOSYWG
Boston Logan Intl
Sat 5/9
10:45 am-4:18 pm
1 stop6h 33m
Winnipeg
Mon 5/18
8:00 am-2:47 pm
1 stop5h 47m
$309
BostonWinnipeg
BOS - YWG
BOSYWG
Boston Logan Intl
Wed 10/14
11:15 am-8:16 pm
1 stop10h 01m
Winnipeg
Wed 10/21
12:30 pm-11:53 pm
1 stop10h 23m
$315
BostonWinnipeg
BOS - YWG
BOSYWG
Boston Logan Intl
Sat 10/3
3:13 pm-10:24 pm
1 stop8h 11m
Winnipeg
Tue 10/6
7:00 am-2:02 pm
1 stop6h 02m
$315
BostonWinnipeg
BOS - YWG
BOSYWG
Boston Logan Intl
Thu 9/17
7:10 am-4:54 pm
1 stop10h 44m
Winnipeg
Tue 9/29
12:40 pm-11:52 pm
1 stop10h 12m
$315
BostonWinnipeg
BOS - YWG
BOSYWG
Boston Logan Intl
Thu 7/2
5:00 pm-10:33 pm
1 stop6h 33m
Winnipeg
Wed 7/8
7:00 am-11:18 pm
1 stop15h 18m
$323
BostonWinnipeg
BOS - YWG
BOSYWG
Boston Logan Intl
Fri 8/21
7:10 am-4:54 pm
1 stop10h 44m
Winnipeg
Tue 8/25
6:40 am-5:19 pm
1 stop9h 39m
$323
Cheapest one-way
BostonWinnipeg
BOS - YWG
BOSYWG
Boston Logan Intl
Fri 9/4
7:10 am-10:33 pm
1 stop16h 23m
$130
BostonWinnipeg
BOS - YWG
BOSYWG
Boston Logan Intl
Fri 8/21
7:10 am-4:54 pm
1 stop10h 44m
$134
BostonWinnipeg
BOS - YWG
BOSYWG
Boston Logan Intl
Tue 7/14
8:16 am-4:51 pm
1 stop9h 35m
$134
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 April.
| 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
What is the cheapest month to book a flight from Boston to Winnipeg?
Currently, May is the cheapest month in which you can book a flight from Boston to Winnipeg (average of $409). 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 April 28, 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.
Overall
8.0
Boarding
8.2
Comfort
8.0
Crew
8.6
Entertainment
7.0
Food
7.6
Reviews
1 / 20
10.0
ExcellentJohn,Mar 2026
YYZ - PVR
Overall
8.0
Boarding
8.2
Comfort
8.0
Crew
8.6
Entertainment
7.0
Food
7.6
Reviews
1 / 20
10.0
ExcellentJohn,Mar 2026
YYZ - PVR
Overall
8.0
Boarding
8.2
Comfort
8.0
Crew
8.6
Entertainment
7.0
Food
7.6
Reviews
1 / 20
10.0
ExcellentJohn,Mar 2026
YYZ - PVR
Overall
8.0
Boarding
8.2
Comfort
8.0
Crew
8.6
Entertainment
7.0
Food
7.6
Reviews
1 / 20
10.0
ExcellentJohn,Mar 2026
YYZ - PVR
Overall
8.0
Boarding
8.2
Comfort
8.0
Crew
8.6
Entertainment
7.0
Food
7.6
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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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 April 28, 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 April 28, 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 April 28, 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 2,558,603 searches. Data last updated April 28, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$143 | Average$420 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$149 | Average$644 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$194 | Average$515 | FlexibilityNo cancel fee | On-time67% | |
| Cheapest$420 | Average$493 | FlexibilityNo cancel fee | On-time52% |