$175+ Cheap flights from Winnipeg (YWG) to Boston (BOS)
This is the cheapest one-way flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 5/17. Fares are subject to change and may not be available on all flights or dates of travel.
YWG — BOS
May 4 — May 111
Round-trip
1 adult, Economy
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Find cheap flights from Winnipeg to Boston with Cheapflights
1. Tell us where you want to go
Enter your travel information like dates, passengers, trip type (one-way or round trip), and preferred cabin class then click “Find deals”2. Select your favorite providers
We find the providers serving your travel needs. Choose up to four travel providers to compare side-by-side for flights, hotels, or car rentals.3. Compare prices and book
Review each provider’s pricing and select the best option for you! Book through your favorite provider’s website for a seamless experience.Cheap flight deals from Winnipeg to Boston
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Best
Last-minute
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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 April 4, 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 April 4, 2026.
This Kiwi.com deal was found by Cheapflights users on 3/31. 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 6/19:20 am
YWG
- BOS
1 stop7h 15m
Porter Airlines
Wed 6/1010:05 am
BOS
- YWG
1 stop6h 14m
Porter Airlines
Deal found 3/31![Porter Airlines logo]()
$289
This FlightHub deal was found by Cheapflights users on 4/1. 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 6/29:20 am
YWG
- BOS
2 stops10h 35m
Porter Airlines
Tue 6/910:05 am
BOS
- YWG
1 stop6h 14m
Porter Airlines
Deal found 4/1![Porter Airlines logo]()
$296
This Delta deal was found by Cheapflights users on 3/30. 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.
Tue 6/25:41 pm
YWG
- BOS
1 stop5h 13m
Delta
Tue 6/97:15 am
BOS
- YWG
1 stop8h 49m
Delta
Deal found 3/30![Delta logo]()
$306
This Air Canada deal was found by Cheapflights users on 4/2. 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 6/13:15 pm
YWG
- BOS
1 stop6h 24m
Air Canada
Wed 6/35:50 am
BOS
- YWG
1 stop7h 14m
Air Canada
Deal found 4/2![Air Canada logo]()
$312
This Air Canada deal was found by Cheapflights users on 4/1. 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 6/22:00 pm
YWG
- BOS
1 stop7h 39m
Air Canada
Tue 6/95:00 pm
BOS
- YWG
1 stop7h 18m
Air Canada
Deal found 4/1![Air Canada logo]()
$316
This Air Canada deal was found by Cheapflights users on 4/1. 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 6/153:15 pm
YWG
- BOS
1 stop6h 24m
Air Canada
Fri 6/195:10 am
BOS
- YWG
1 stop7h 05m
Air Canada
Deal found 4/1![Air Canada logo]()
$317
This Air Canada deal was found by Cheapflights users on 3/31. 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 6/15:10 am
YWG
- BOS
2 stops8h 37m
Air Canada
Wed 6/105:10 am
BOS
- YWG
1 stop6h 58m
Air Canada
Deal found 3/31![Air Canada logo]()
$320
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 April 4, 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 April 4, 2026.
This Kiwi.com deal was found by Cheapflights users on 3/31. 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 6/19:20 am
YWG
- BOS
1 stop7h 15m
Porter Airlines
Wed 6/1010:05 am
BOS
- YWG
1 stop6h 14m
Porter Airlines
Deal found 3/31![Porter Airlines logo]()
$289
This Delta deal was found by Cheapflights users on 4/3. 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.
Tue 6/25:41 pm
YWG
- BOS
1 stop5h 13m
Delta
Tue 6/95:55 am
BOS
- YWG
1 stop10h 09m
Delta
Deal found 4/3![Delta logo]()
$306
This United Airlines deal was found by Cheapflights users on 4/3. 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 6/17:00 am
YWG
- BOS
1 stop16h 59m
United Airlines
Wed 6/36:00 am
BOS
- YWG
1 stop6h 52m
United Airlines
Deal found 4/3![United Airlines logo]()
$306
This Air Canada deal was found by Cheapflights users on 4/1. 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 6/22:00 pm
YWG
- BOS
1 stop7h 39m
Air Canada
Tue 6/95:00 pm
BOS
- YWG
1 stop7h 18m
Air Canada
Deal found 4/1![Air Canada logo]()
$316
This Delta deal was found by Cheapflights users on 3/30. 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 5/296:40 am
YWG
- BOS
1 stop9h 30m
Delta
Tue 6/25:51 am
BOS
- YWG
1 stop10h 04m
Delta
Deal found 3/30![Delta logo]()
$306
This Air Canada deal was found by Cheapflights users on 3/31. 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 6/15:10 am
YWG
- BOS
2 stops8h 37m
Air Canada
Wed 6/105:10 am
BOS
- YWG
1 stop6h 58m
Air Canada
Deal found 3/31![Air Canada logo]()
$320
Last-minute flights from Winnipeg to BostonDiscover last-minute flight deals from Winnipeg to Boston. Data last updated April 4, 2026 and is based on user searches.
Discover last-minute flight deals from Winnipeg to Boston. Data last updated April 4, 2026 and is based on user searches.
This Kiwi.com deal was found by Cheapflights users on 4/3. 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 4/227:30 am
YWG
- BOS
1 stop17h 01m
Multiple Airlines
Sun 4/266:30 pm
BOS
- YWG
1 stop18h 45m
Multiple Airlines
Deal found 4/3![Multiple Airlines logo]()
$419
This Kiwi.com deal was found by Cheapflights users on 4/1. 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 4/304:25 pm
YWG
- BOS
1 stop21h 16m
Multiple Airlines
Thu 5/77:10 am
BOS
- YWG
1 stop11h 05m
Multiple Airlines
Deal found 4/1![Multiple Airlines logo]()
$397
This Air Canada deal was found by Cheapflights users on 4/2. 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 5/15:10 am
YWG
- BOS
1 stop11h 49m
Air Canada
Sat 5/95:10 am
BOS
- YWG
1 stop5h 53m
Air Canada
Deal found 4/2![Air Canada logo]()
$329
This Delta deal was found by Cheapflights users on 3/30. 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 5/113:50 pm
YWG
- BOS
1 stop7h 04m
Delta
Tue 5/195:51 am
BOS
- YWG
1 stop6h 03m
Delta
Deal found 3/30![Delta logo]()
$346
This Justfly.com deal was found by Cheapflights users on 3/30. 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 5/116:00 am
YWG
- BOS
1 stop10h 40m
Multiple Airlines
Tue 5/1910:05 am
BOS
- YWG
2 stops8h 53m
Multiple Airlines
Deal found 3/30![Multiple Airlines logo]()
$413
This Flightnetwork deal was found by Cheapflights users on 3/31. 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.
Fri 5/159:20 am
YWG
- BOS
1 stop7h 15m
Porter Airlines
Fri 5/2210:05 am
BOS
- YWG
1 stop6h 14m
Porter Airlines
Deal found 3/31![Porter Airlines logo]()
$388
This Delta deal was found by Cheapflights users on 3/30. 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 5/296:40 am
YWG
- BOS
1 stop9h 30m
Delta
Tue 6/25:51 am
BOS
- YWG
1 stop10h 04m
Delta
Deal found 3/30![Delta logo]()
$306
This Air Canada deal was found by Cheapflights users on 4/1. 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 5/297:20 pm
YWG
- BOS
2 stops18h 27m
Air Canada
Tue 6/25:10 am
BOS
- YWG
1 stop6h 58m
Air Canada
Deal found 4/1![Air Canada logo]()
$357
This Porter Airlines deal was found by Cheapflights users on 3/30. 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 5/299:20 am
YWG
- BOS
2 stops10h 35m
Porter Airlines
Tue 6/210:05 am
BOS
- YWG
1 stop6h 14m
Porter Airlines
Deal found 3/30![Porter Airlines logo]()
$366
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 April 4, 2026.
Search for one-way flight options from Winnipeg to Boston. Find affordable one-way fares based on user searches. Data last updated April 4, 2026.
This Kiwi.com deal was found by Cheapflights users on 4/1. 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.
Sun 5/179:05 pm
YWG
- BOS
2 stops34h 39m
Multiple Airlines
Deal found 4/1![Multiple Airlines logo]()
$175
This Air Canada deal was found by Cheapflights users on 4/1. 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 5/178:00 am
YWG
- BOS
1 stop5h 47m
Air Canada
Deal found 4/1![Air Canada logo]()
$179
This Delta deal was found by Cheapflights users on 4/3. 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 5/183:50 pm
YWG
- BOS
1 stop7h 04m
Delta
Deal found 4/3![Delta logo]()
$181
This Kiwi.com deal was found by Cheapflights users on 4/3. 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 5/189:05 pm
YWG
- BOS
2 stops27h 19m
Multiple Airlines
Deal found 4/3![Multiple Airlines logo]()
$192
This Air Canada deal was found by Cheapflights users on 3/30. 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 8/97:55 am
YWG
- BOS
1 stop5h 46m
Air Canada
Deal found 3/30![Air Canada logo]()
$206
This Mytrip deal was found by Cheapflights users on 3/31. 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.
Fri 5/16:55 pm
YWG
- BOS
1 stop14h 46m
Porter Airlines
Deal found 3/31![Porter Airlines logo]()
$210
This United Airlines deal was found by Cheapflights users on 3/31. 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 5/16:30 am
YWG
- BOS
2 stops17h 29m
United Airlines
Deal found 3/31![United Airlines logo]()
$223
This Kiwi.com deal was found by Cheapflights users on 3/30. 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 5/148:45 pm
YWG
- BOS
2 stops23h 10m
Porter Airlines
Deal found 3/30![Porter Airlines logo]()
$261
This Kiwi.com deal was found by Cheapflights users on 3/30. 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.
Sun 8/99:05 pm
YWG
- BOS
2 stops27h 22m
Multiple Airlines
Deal found 3/30![Multiple Airlines logo]()
$277
This Kiwi.com deal was found by Cheapflights users on 3/31. 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 5/17:10 pm
YWG
- BOS
3 stops35h 48m
Multiple Airlines
Deal found 3/31![Multiple Airlines logo]()
$280
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 April 4, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $289 (Kiwi.com) |
One-way from | $175 (Kiwi.com) |
Popular in | January |
Cheapest in | June |
Average price | $337 |
Cheapflights Fare Finder
Customize your flight search to find flights from Winnipeg to Boston that fit within your specific budget. Explore options based on user searches and filter the results based on your desired price range. Find flights that match your budget for a cost-effective journey. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated April 4, 2026.
Use the filters below to find and compare flights from Winnipeg to Boston that are best for you.
Fly from
Fly to
Route
Depart
Return
Cheapest round-trip
Quickest round-trip
WinnipegBoston
YWG - BOS
YWGBOS
Winnipeg
Mon 6/1
9:20 am-5:35 pm
1 stop7h 15m
Boston Logan Intl
Wed 6/10
10:05 am-3:19 pm
1 stop6h 14m
$289
WinnipegBoston
YWG - BOS
YWGBOS
Winnipeg
Tue 6/2
5:41 pm-11:54 pm
1 stop5h 13m
Boston Logan Intl
Tue 6/9
5:55 am-3:04 pm
1 stop10h 09m
$306
WinnipegBoston
YWG - BOS
YWGBOS
Winnipeg
Mon 6/1
7:00 am-12:59 am
1 stop16h 59m
Boston Logan Intl
Wed 6/3
6:00 am-11:52 am
1 stop6h 52m
$306
WinnipegBoston
YWG - BOS
YWGBOS
Winnipeg
Fri 5/29
6:40 am-5:10 pm
1 stop9h 30m
Boston Logan Intl
Tue 6/2
5:51 am-2:55 pm
1 stop10h 04m
$306
WinnipegBoston
YWG - BOS
YWGBOS
Winnipeg
Tue 6/2
2:00 pm-10:39 pm
1 stop7h 39m
Boston Logan Intl
Tue 6/9
5:00 pm-11:18 pm
1 stop7h 18m
$316
WinnipegBoston
YWG - BOS
YWGBOS
Winnipeg
Mon 6/1
5:10 am-2:47 pm
2 stops8h 37m
Boston Logan Intl
Wed 6/10
5:10 am-11:08 am
1 stop6h 58m
$320
Cheapest one-way
WinnipegBoston
YWG - BOS
YWGBOS
Winnipeg
Mon 5/18
3:50 pm-11:54 pm
1 stop7h 04m
$181
WinnipegBoston
YWG - BOS
YWGBOS
Winnipeg
Mon 5/18
9:05 pm-1:24 am
2 stops27h 19m
$192
Quickest one-way
WinnipegBoston
YWG - BOS
YWGBOS
Winnipeg
Sun 8/9
7:55 am-2:41 pm
1 stop5h 46m
$206
WinnipegBoston
YWG - BOS
YWGBOS
Winnipeg
Fri 5/1
6:30 am-12:59 am
2 stops17h 29m
$223
Showing 1-10 of 14 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 April.
| Provider | Price Accuracy | Trust Score* |
|---|---|---|
| Price Accuracy1 star | Trust Score*3 stars | |
| Price Accuracy3 stars | Trust Score*3 stars |
- Most accurate provider: When it comes to deals on Winnipeg-Boston flights, users find the pricing of FlightHub to be most consistent on Cheapflights vs. FlightHub Users can find the same prices on Winnipeg-Boston flight deals on Cheapflights vs. FlightHub >95% of the time. Price accuracy is based on data collected from Winnipeg-Boston flight searches over the past month and is updated monthly.
- Most trusted provider: When it comes to deals on Winnipeg-Boston flights, Cheapflights users trust FlightHub the most. FlightHub has received a user feedback score of 3 out of 3 stars (3 being the best), meaning they have been trusted the most by Cheapflights users looking for Winnipeg-Boston flight deals. Provider user feedback score is based on Cheapflights searches over the past month and is updated monthly.
Best time to book a flight from Winnipeg to Boston
Have a flexible travel schedule? Discover the best time to fly to Boston from Winnipeg with our price prediction graph.
YWG-BOS
Estimated round-trip price
Rates are based on past data. Find the cheapest month and day to book your flight based on your travel requirements, then search for cheap deals.
Cheapflights Insights
Everything you need to know about your flight from Winnipeg to Boston
How far ahead should I book a flight from Winnipeg to Boston?
Use this chart to determine the optimal time to book a round-trip flight from Winnipeg to Boston. Price data was last updated on April 2, 2026.
The best time to book flights from Winnipeg to Boston is 16 days before your desired departure date. The cost of your flight will likely increase significantly if you book two weeks in advance of your flight.
What is the cheapest month to book a flight from Winnipeg to Boston?
Currently, May is the cheapest month in which you can book a flight from Winnipeg to Boston (average of $155). Flying from Winnipeg to Boston in January is currently the most expensive (average of $782). 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?
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 April 4, 2026.
Read reviews from past customers who have flown Delta,United Airlines, andAir 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
8.1
Food
7.2
Overall
7.9
Entertainment
7.8
Comfort
7.9
Crew
8.5
Reviews
1 / 20
6.0
GoodJim,Nov 2025
AVL - ATL
Boarding
8.1
Food
7.2
Overall
7.9
Entertainment
7.8
Comfort
7.9
Crew
8.5
Reviews
1 / 20
6.0
GoodJim,Nov 2025
AVL - ATL
Boarding
8.1
Food
7.2
Overall
7.9
Entertainment
7.8
Comfort
7.9
Crew
8.5
Reviews
1 / 20
6.0
GoodJim,Nov 2025
AVL - ATL
Boarding
8.1
Food
7.2
Overall
7.9
Entertainment
7.8
Comfort
7.9
Crew
8.5
Reviews
1 / 20
6.0
GoodJim,Nov 2025
AVL - ATL
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 locationsMedford
Cambridge
Concord
Hampton Beach
Watertown
Brockton
Seekonk
Seabrook
Cranston
Chelsea
Warwick
Peabody
Waltham
York Beach
Londonderry
Swansea
Old Orchard Beach
Lincoln
Quincy
Lowell
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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Other flights to Boston
Explore flights to Boston departing from other origins. Flights are based on user searches made on Cheapflights and were last updated on April 4, 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 April 4, 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 April 4, 2026.
Popular flight searches
Check out other popular destinations found by fellow travelers in 2026
Top 3 airlines flying from Winnipeg to Boston
Discover the top 3 airlines that operate flights from Winnipeg to Boston. Compare their services, reliability, and customer satisfaction ratings to choose the airline that best suits your travel preferences and needs. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated April 4, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$100 | Average$423 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$182 | Average$605 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$212 | Average$435 | FlexibilityNo cancel fee | On-time67% |