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 25/1. Fares are subject to change and may not be available on all flights or dates of travel.
YWG — BOS
11 Jan — 18 Jan1
Round-trip
1 adult
Economy
Round-trip
1 adult, Economy, 0 bags
Cheapflights Tip: The best prices from Winnipeg to Boston Logan Intl are usually found in June or August, booked 24 days in advance, depart on a Tuesday or Thursday and return on a Tuesday
Cheap flight deals from Winnipeg to Boston
Enter your travel dates to find the best prices.
Cheapest flights from Winnipeg to Boston
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 12 December 2025.
Mon 22/121:30 p.m.YWG - BOS
1 stop8h 07mUnited Airlines
Wed 31/126:15 a.m.BOS - YWG
1 stop7h 24mUnited Airlines
Deal found 11/12C$ 818
Wed 17/127:30 a.m.YWG - BOS
1 stop25h 38mMultiple Airlines
Wed 24/123:40 p.m.BOS - YWG
2 stops28h 55mMultiple Airlines
Deal found 10/12C$ 1,009
Wed 17/122:20 p.m.YWG - BOS
2 stops8h 21mUnited Airlines
Wed 24/122:15 p.m.BOS - YWG
2 stops22h 42mUnited Airlines
Deal found 10/12C$ 1,043
Mon 22/126:00 a.m.YWG - BOS
2 stops13h 26mAmerican Airlines
Wed 31/122:14 p.m.BOS - YWG
2 stops34h 21mAmerican Airlines
Deal found 11/12C$ 1,120
Mon 22/125:45 p.m.YWG - BOS
1 stop5h 09mDelta
Wed 31/123:15 p.m.BOS - YWG
1 stop9h 29mDelta
Deal found 11/12C$ 1,281
Wed 17/1212:10 p.m.YWG - BOS
3 stops21h 56mAmerican Airlines
Wed 24/126:15 a.m.BOS - YWG
2 stops42h 20mAmerican Airlines
Deal found 10/12C$ 1,525
Best flights from Winnipeg to Boston
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 12 December 2025.
Wed 21/17:30 a.m.YWG - BOS
1 stop16h 33mMultiple Airlines
Wed 28/16:00 a.m.BOS - YWG
2 stops19h 41mMultiple Airlines
Deal found 10/12C$ 325
Thu 15/18:15 a.m.YWG - BOS
1 stop5h 37mAir Canada
Wed 21/110:15 a.m.BOS - YWG
1 stop7h 20mAir Canada
Deal found 10/12C$ 407
Thu 15/18:20 p.m.YWG - BOS
1 stop23h 10mMultiple Airlines
Wed 21/16:00 a.m.BOS - YWG
1 stop10h 07mMultiple Airlines
Deal found 11/12C$ 415
Thu 5/28:15 a.m.YWG - BOS
1 stop5h 37mAir Canada
Mon 9/25:30 a.m.BOS - YWG
1 stop5h 45mAir Canada
Deal found 11/12C$ 451
Fri 27/27:30 a.m.YWG - BOS
1 stop16h 34mMultiple Airlines
Sat 14/310:52 a.m.BOS - YWG
1 stop29h 17mMultiple Airlines
Deal found 9/12C$ 423
Sun 22/37:30 a.m.YWG - BOS
1 stop25h 27mMultiple Airlines
Wed 1/46:00 a.m.BOS - YWG
1 stop10h 09mMultiple Airlines
Deal found 9/12C$ 448
Wed 4/37:30 a.m.YWG - BOS
1 stop15h 35mMultiple Airlines
Sat 14/33:30 p.m.BOS - YWG
2 stops21h 02mMultiple Airlines
Deal found 9/12C$ 466
Tue 24/38:05 p.m.YWG - BOS
1 stop14h 00mMultiple Airlines
Wed 1/46:00 a.m.BOS - YWG
1 stop10h 09mMultiple Airlines
Deal found 9/12C$ 473
Thu 5/35:00 a.m.YWG - BOS
2 stops12h 10mMultiple Airlines
Sat 14/310:52 a.m.BOS - YWG
1 stop29h 17mMultiple Airlines
Deal found 9/12C$ 480
Last-minute flights from Winnipeg to Boston
Discover last-minute flight deals from Winnipeg to Boston. Data last updated 12 December 2025 and is based on user searches.
Thu 8/17:05 p.m.YWG - BOS
1 stop13h 57mAir Canada
Sun 11/15:30 a.m.BOS - YWG
1 stop5h 46mAir Canada
Deal found 10/12C$ 505
Fri 9/15:30 a.m.YWG - BOS
1 stop9h 27mAir Canada
Sun 11/15:30 a.m.BOS - YWG
1 stop5h 46mAir Canada
Deal found 11/12C$ 472
Thu 15/18:15 a.m.YWG - BOS
1 stop5h 37mAir Canada
Wed 21/110:15 a.m.BOS - YWG
1 stop7h 20mAir Canada
Deal found 10/12C$ 407
Thu 15/18:20 p.m.YWG - BOS
2 stops25h 59mMultiple Airlines
Wed 21/16:00 a.m.BOS - YWG
1 stop10h 07mMultiple Airlines
Deal found 11/12C$ 412
Wed 21/17:30 a.m.YWG - BOS
1 stop16h 33mMultiple Airlines
Wed 28/16:00 a.m.BOS - YWG
1 stop10h 07mMultiple Airlines
Deal found 10/12C$ 310
Fri 30/18:20 p.m.YWG - BOS
1 stop12h 42mMultiple Airlines
Thu 5/25:27 p.m.BOS - YWG
2 stops23h 03mMultiple Airlines
Deal found 11/12C$ 473
One-way flights from Winnipeg to Boston
Search for one-way flight options from Winnipeg to Boston. Find affordable one-way fares based on user searches. Data last updated 12 December 2025.
Sun 25/14:55 p.m.YWG - BOS
1 stop11h 05mMultiple Airlines
Deal found 11/12C$ 226
Fri 13/27:05 p.m.YWG - BOS
1 stop13h 57mAir Canada
Deal found 11/12C$ 298
Wed 17/127:30 a.m.YWG - BOS
2 stops26h 57mMultiple Airlines
Deal found 9/12C$ 423
Sun 21/128:40 a.m.YWG - BOS
2 stops15h 05mUnited Airlines
Deal found 11/12C$ 510
Thu 18/128:20 p.m.YWG - BOS
1 stop12h 15mMultiple Airlines
Deal found 9/12C$ 538
Sun 21/128:05 p.m.YWG - BOS
2 stops28h 14mMultiple Airlines
Deal found 11/12C$ 553
Sun 21/125:30 p.m.YWG - BOS
1 stop15h 27mAir Canada
Deal found 11/12C$ 554
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 12 December 2025.
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 629,999 searches. Data last updated 12 December 2025.
Use the filters below to find and compare flights from Winnipeg to Boston that are best for you.
Fly from
Winnipeg
Fly to
Boston
Route
Depart
Return
Price
WinnipegBoston
YWG - BOS
YWGBOS
Winnipeg
Wed 21/1
7:30 a.m.-1:03 a.m.
1 stop16h 33m
Boston Logan Intl
Wed 28/1
6:00 a.m.-12:41 a.m.
2 stops19h 41m
C$ 325
WinnipegBoston
YWG - BOS
YWGBOS
Winnipeg
Thu 15/1
8:15 a.m.-2:52 p.m.
1 stop5h 37m
Boston Logan Intl
Wed 21/1
10:15 a.m.-4:35 p.m.
1 stop7h 20m
C$ 407
WinnipegBoston
YWG - BOS
YWGBOS
Winnipeg
Thu 15/1
8:20 p.m.-8:30 p.m.
1 stop23h 10m
Boston Logan Intl
Wed 21/1
6:00 a.m.-3:07 p.m.
1 stop10h 07m
C$ 415
WinnipegBoston
YWG - BOS
YWGBOS
Winnipeg
Fri 27/2
7:30 a.m.-1:04 a.m.
1 stop16h 34m
Boston Logan Intl
Sat 14/3
10:52 a.m.-3:09 p.m.
1 stop29h 17m
C$ 423
WinnipegBoston
YWG - BOS
YWGBOS
Winnipeg
Sun 22/3
7:30 a.m.-9:57 a.m.
1 stop25h 27m
Boston Logan Intl
Wed 1/4
6:00 a.m.-3:09 p.m.
1 stop10h 09m
C$ 448
WinnipegBoston
YWG - BOS
YWGBOS
Winnipeg
Thu 5/2
8:15 a.m.-2:52 p.m.
1 stop5h 37m
Boston Logan Intl
Mon 9/2
5:30 a.m.-10:15 a.m.
1 stop5h 45m
C$ 451
WinnipegBoston
YWG - BOS
YWGBOS
Winnipeg
Wed 4/3
7:30 a.m.-12:05 a.m.
1 stop15h 35m
Boston Logan Intl
Sat 14/3
3:30 p.m.-11:32 a.m.
2 stops21h 02m
C$ 466
WinnipegBoston
YWG - BOS
YWGBOS
Winnipeg
Tue 24/3
8:05 p.m.-11:05 a.m.
1 stop14h 00m
Boston Logan Intl
Wed 1/4
6:00 a.m.-3:09 p.m.
1 stop10h 09m
C$ 473
WinnipegBoston
YWG - BOS
YWGBOS
Winnipeg
Thu 5/3
5:00 a.m.-6:10 p.m.
2 stops12h 10m
Boston Logan Intl
Sat 14/3
10:52 a.m.-3:09 p.m.
1 stop29h 17m
C$ 480
WinnipegBoston
YWG - BOS
YWGBOS
Winnipeg
Sun 25/1
4:55 p.m.-5:00 a.m.
1 stop11h 05m
C$ 226
Flights are sorted by cheapest round-trip flights first.
Deals found on 11/12
Showing 1-10 of 16 results
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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.
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
Prices
More
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 5 December 2025.
To ensure you get the cheapest price possible for a flight from Winnipeg to Boston, you should look to book at least 24 days in advance of your intended travel date. The price of your flight may increase if you delay and leave booking until a week or so before departure.
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 C$ 222). Flying from Winnipeg to Boston in March is currently the most expensive (average of C$ 452). 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.
What is the cheapest time of day to fly from YWG to BOS?
Find hourly flight availability from Winnipeg to Boston. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated 12 December 2025.
One of the essential ways to save on airfare from Winnipeg to Boston is to remain as flexible as possible. Flights that are in the evening tend to be the most expensive. A flight in the morning could potentially save you up to 24% on airfare.
What’s the top layover airport for flights from Winnipeg to Boston?
Share of one-stop round-trip flights from Winnipeg to Boston chosen by Cheapflights users in the past 12 months, using the same layover each way.
Toronto (YYZ) – chosen by Cheapflights users on 35% of one-stop itineraries from Winnipeg to Boston on Cheapflights.
What’s the cheapest layover airport for flights from Winnipeg to Boston?
Average round-trip fare for 1-stop flights from Winnipeg to Boston, chosen by Cheapflights users in the past 12 months, with the same layover each way.
Chicago (ORD) is the most affordable 1-stop option, with an average round-trip price of C$ 474.
What’s the fastest layover option from Winnipeg to Boston?
Shortest average travel time for 1-stop one-way flights from Winnipeg to Boston, based on itineraries clicked by Cheapflights users over the past 12 months, grouped by layover airport.
Flights via Ottawa (YOW) have the shortest average one-way travel time for 1-stop routes: 5h 26m.
Which airport typically offers the quickest layover for flights from Winnipeg to Boston?
Average layover duration for 1-stop one-way flights from Winnipeg to Boston, chosen by Cheapflights users in the last 12 months, grouped by stopover airport.
Flights via Montreal (YUL) offer the fastest connection on this route, with an average layover time of 1h 58m.
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 12 December 2025.
Read through reviews of airlines operating flights from Winnipeg to Boston, such as Porter Airlines,United Airlines, andWestJet. Reviews also offer insight into each airline's entertainment options, comfort, food, crew/service, and boarding process.
It's good. Planes are new and fresh. WiFi is best and stands out
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.
How long is the flight from Winnipeg to Boston?
A quick flight from Winnipeg to Boston can take about 5h 37m. Air Canada provides one of the quickest options available for as low as C$ 407. The distance from Winnipeg to Boston is about 2173 km.
What are the cheapest airlines flying from Winnipeg to Boston round-trip?
Cheapflights users have booked flights from Winnipeg to Boston round-trip from C$ 215. Other airlines that can offer you cheap pricing are Air Canada, from C$ 343, and Porter Airlines, from C$ 406. Users have found that United Airlines is 62% cheaper than the other options available to this destination.
Can I find deals for business class flights from Winnipeg to Boston?
Yes. Cheapflights offers flight deals from Winnipeg to Boston by cabin class. In addition to browsing deals, you can also filter by cabin class on the search results page after making a search.
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 C$ 222). Flying from Winnipeg to Boston in March is currently the most expensive (average of C$ 452). 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.
Explore flights to Boston departing from other origins. Flights are based on user searches made on Cheapflights and were last updated on 12 December 2025.
Browse through other flights departing from Winnipeg. Flights are based on user searches made on Cheapflights and were last updated on 12 December 2025.
Discover the top 4 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 629,999 searches. Data last updated 12 December 2025.
Find the best flight deals on Cheapflights, where travelers can enjoy low prices and a wide availability of flights to their desired destinations.
How does Cheapflights help users find flights from Winnipeg to Boston?
Cheapflights goes through 900+ travel sites to look for the best flight deals for flights from Winnipeg to Boston. Too many options? Cheapflights also provides filters for things like airlines, price ranges, and number of stops to help you make a decision easily.
Why should you use Cheapflights to find cheap flight tickets from Winnipeg to Boston?
By finding flights from multiple airlines and providers at completely no cost, Cheapflights helps millions of users like you annually find the best flights to Boston from Winnipeg.
Can Cheapflights find flights from Winnipeg to Boston with no change fees?
Certainly. Search results for flights to Boston from Winnipeg shown to you on Cheapflights can be narrowed down with different useful search filters, which includes flexible booking options.
Can Cheapflights notify me if prices for flights from Winnipeg to Boston become cheaper?
Yes, Cheapflights has a feature called Price Alert, which notifies users when flight prices change. Track prices for your flight to Boston from Winnipeg today and book when prices fit your budget.
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