Question 1

What are the cheapest airlines flying from Boston to Winnipeg round-trip?

Accepted Answer

Our cheapest airline available from Boston to Winnipeg is WestJet. Our recent data shows that you can find tickets from as low as C$ 354 on this airline. Additional options worth looking into are Air Canada and Delta, starting at C$ 466 and C$ 490 round-trip. Users have found that WestJet is 44% cheaper than the other options available to this destination.

Question 2

What are the cheapest airlines to fly from Boston to Winnipeg one-way?

Accepted Answer

To fly one-way, consider booking your trip with WestJet, which is currently one of the cheapest options available, starting at C$ 165. Air Canada flights start at C$ 206 while deals on United Airlines start at C$ 288 one-way.

Question 3

How far ahead should I book a flight from Boston to Winnipeg?

Accepted Answer

The price you pay for your flight from Boston to Winnipeg may vary depending on when you book. For the best chance of a lower fare, look to book 20 days in advance of your trip. Fares are likely to increase a fortnight or so before your departure date.

Question 4

What is the cheapest month to book a flight from Boston to Winnipeg?

Accepted Answer

Currently, January is the cheapest month in which you can book a flight from Boston to Winnipeg (average of C$ 123). Flying from Boston to Winnipeg in July is currently the most expensive (average of C$ 232). 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.

Question 5

What is the cheapest day to fly from Boston to Winnipeg?

Accepted Answer

Travelers seeking maximum savings on their Boston to Winnipeg flight should consider departing on Wednesday mornings when fares are most often at their lowest. Thursday mornings flights should be avoided if possible as fares are typically the most expensive at this time.

Question 6

E

Accepted Answer

In terms of precipitation, rainfall in Winnipeg ranges from 20.0 - 80.0 mm per month. June is typically the wettest month, when rainfall can reach 80.0 mm. January is typically the driest time to visit Winnipeg when rainfall is around 20.0 mm.

Question 7

E

Accepted Answer

If weather is an important factor for your trip to Winnipeg, use this chart to help with planning. For those seeking warmer temperatures, July is the ideal time of year to visit, when temperatures reach an average of 20.0 C. Travellers hoping to avoid the cold should look outside of January, when temperatures are typically at their lowest (around -16.0 C).

Question 8

What is the cheapest day to fly round-trip from Boston to Winnipeg?

Accepted Answer

Tuesday is generally a great day to depart. Flying on this day could help you save up to 34%.

Question 9

How far in advance should I book a flight from Boston to Winnipeg?

Accepted Answer

Travellers have found it’s best to book a flight 21 days in advance to save up to 70% compared to booking the same week of travel. As your travel date approaches, the cost of this flight route may potentially increase. While opting to book 21 days out may not be an option for all, there are still additional ways to secure a deal in the near future. You might find a flight from Boston to Winnipeg 1-2 weeks in advance for as low as C$ 391, or C$ 1,021 for flights within the next 24 hours.

Question 10

What is the cheapest month to fly from Boston to Winnipeg?

Accepted Answer

Due to multiple factors, expect to potentially pay more when booking in March. For low rates, January can be a great choice for travel to Winnipeg. Flights to Winnipeg from Boston in January are about C$ 635 on average during January, but can be found for as low as C$ 224.

Question 11

What is the cheapest time of day to fly from BOS to YWG?

Accepted Answer

When flying from Boston to Winnipeg, the time of day you decide to fly out makes little to no difference towards the overall price you’ll pay on tickets.

Question 12

Can I find deals for flights from Boston to Winnipeg that include hotel bookings?

Accepted Answer

Yes. In addition to deals on Boston to Winnipeg flights, Cheapflights offers vacation packages that include both flights and hotel.

Question 13

How can I find direct flights from Boston to Winnipeg?

Accepted Answer

After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Boston to Winnipeg.

Question 14

Can I find deals for business class flights from Boston to Winnipeg?

Accepted Answer

Yes. Cheapflights offers flight deals from Boston to Winnipeg by cabin class. In addition to browsing deals, you can also filter by cabin class on the search results page after making a search.

Question 15

How does Cheapflights help users find flights from Boston to Winnipeg?

Accepted Answer

900+ travel sites are searched through when a user searches for a flight using Cheapflights. From the search interface, users can use filters to choose airlines, airports, flight times, cabin classes and more to their preference. Book your flight to Winnipeg from Boston today with Cheapflights!

Question 16

Why should you use Cheapflights to find cheap flight tickets from Boston to Winnipeg?

Accepted Answer

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 Winnipeg from Boston.

Question 17

Can Cheapflights find flights from Boston to Winnipeg with no change fees?

Accepted Answer

Users can book flights with no change fees policies with our dedicated filters. Book flights from Boston to Winnipeg flexibly with Cheapflights today.

Question 18

Can Cheapflights notify me if prices for flights from Boston to Winnipeg become cheaper?

Accepted Answer

Yes! Start tracking prices for Boston to Winnipeg flights today and get alerted whenever prices for these flights change. To access this feature, click the bell icon next to the flight deals above, which will prompt you for a valid email address to receive your alerts.

Round-trip from	C$ 354
One-way from	C$ 165
Popular in	March
Cheapest in	January
Average price	C$ 505

Cheap flights from Boston to Winnipeg from C$ 165

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 27/8. Fares are subject to change and may not be available on all flights or dates of travel.

Cheapflights Tip: The best prices from Boston Logan Intl to Winnipeg are usually found in January or October, booked 22 days in advance, depart on a Tuesday or Monday and return on a Tuesday

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Find flight deals from Boston to Winnipeg

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 29 July 2025.

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 29 July 2025.

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Best time to book a flight from Boston to Winnipeg

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Everything you need to know about your flight from Boston to Winnipeg

How far ahead should I book a flight from Boston to Winnipeg?

Use this chart to determine the optimal time to book a round-trip flight from Boston to Winnipeg. Price data was last updated on 25 July 2025.

What is the cheapest month to book a flight from Boston to Winnipeg?

Reviews of airlines servicing Winnipeg

Get a feel of what it's like to fly with Delta,United Airlines, andWestJet from Boston to Winnipeg by reading reviews from past customers. Users have also rated airlines in terms of entertainment options, comfort, food, crew/service, and boarding process.

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.

What are the cheapest airlines flying from Boston to Winnipeg round-trip?

What are the cheapest airlines to fly from Boston to Winnipeg one-way?

Can I find deals for flights from Boston to Winnipeg that include hotel bookings?

How can I find direct flights from Boston to Winnipeg?

Can I find deals for business class flights from Boston to Winnipeg?

What is the cheapest month to book a flight from Boston to Winnipeg?

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Alternative routes for Boston to Winnipeg

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How does Cheapflights help users find flights from Boston to Winnipeg?

Why should you use Cheapflights to find cheap flight tickets from Boston to Winnipeg?

Can Cheapflights find flights from Boston to Winnipeg with no change fees?

Can Cheapflights notify me if prices for flights from Boston to Winnipeg become cheaper?

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Cheapest flights from Boston to Winnipeg
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 29 July 2025.