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Cheap flights from Boston to Windsor, ON from C$ 578

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 21/9. Fares are subject to change and may not be available on all flights or dates of travel.
BOS — YQG
4 Aug — 11 Aug1
1 adult

Cheap flight deals from Boston to Windsor

Discover tips and strategies to find the most affordable flight options for your journey from Boston (BOS) to Windsor (YQG). 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 30 July 2025.

Round-trip from

C$ 578
Air Canada
  • Air Canada
  • 21/9-23/9
  • 3 total stops
  • 15h 21m total
  • Boston to Windsor
Search Deals

Find flight deals from Boston to Windsor

Cheapest flights from Boston to Windsor
Explore the most affordable flight options available from Boston to Windsor. Find the lowest fares from popular airlines and budget airlines, with prices last updated on 30 July 2025.

Sun 21/96:00 a.m.BOS - YQG
2 stops9h 17mAir Canada
Tue 23/99:55 a.m.YQG - BOS
1 stop6h 04mAir Canada
Deal found 29/7C$ 578
Sun 12/109:20 a.m.BOS - YQG
1 stop11h 20mMultiple Airlines
Tue 14/108:50 a.m.YQG - BOS
1 stop5h 51mMultiple Airlines
Deal found 29/7C$ 668
Mon 4/88:45 a.m.BOS - YQG
1 stop5h 05mPorter Airlines
Wed 6/82:30 p.m.YQG - BOS
1 stop7h 01mPorter Airlines
Deal found 27/7C$ 1,185

Cheapflights Fare Finder

 
Customize your flight search to find flights from Boston to Windsor 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 30 July 2025.
Use the filters below to find and compare flights from Boston to Windsor that are best for you.

Fly from

Boston

Fly to

Windsor

Route

Depart

Return

Price

BostonWindsor

BOS - YQG

BOSYQG

Boston Logan Intl

Sun 21/9

6:00 a.m.-3:17 p.m.

2 stops9h 17m

Windsor

Tue 23/9

9:55 a.m.-3:59 p.m.

1 stop6h 04m

C$ 578

BostonWindsor

BOS - YQG

BOSYQG

Boston Logan Intl

Sun 12/10

9:20 a.m.-8:40 p.m.

1 stop11h 20m

Windsor

Tue 14/10

8:50 a.m.-2:41 p.m.

1 stop5h 51m

C$ 668

Flights are sorted by cheapest round-trip flights first.

Deals found on 29/7

Best time to book a flight from Boston to Windsor

Have a flexible travel schedule? Discover the best time to fly to Windsor from Boston 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.

Reviews of airlines servicing Windsor

Get insights into the airlines that provide service to Windsor. 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 Windsor. Reviews last updated 30 July 2025.
See what other customers who have flown with Porter Airlines and Air Canada from Boston to Windsor have to say. You can also see how each airline compares in terms of entertainment options, comfort, food, crew/service, and boarding process.
Porter Airlines
8.0
Very good
318 reviews
Check prices

Crew

8.7

Entertainment

7.0

Boarding

8.2

Food

7.6

Comfort

8.0

Overall

8.0

Reviews

1 / 20
8.0
Excellent

Anonymous,Jul 2025

LIS - YYZ

Everything was on time and easy. Crew were nice on flights and helpful. International flight, so long and typically uncomfortable but not more than most. Food and drink service were below average but you get what you pay for. Overall, good experience
Porter Airlines
8.0
Very good
318 reviews
Porter Airlines
8.0
Very good
318 reviews
Check prices

Crew

8.7

Entertainment

7.0

Boarding

8.2

Food

7.6

Comfort

8.0

Overall

8.0

Reviews

1 / 20
8.0
Excellent

Anonymous,Jul 2025

LIS - YYZ

Everything was on time and easy. Crew were nice on flights and helpful. International flight, so long and typically uncomfortable but not more than most. Food and drink service were below average but you get what you pay for. Overall, good experience
Air Canada
7.1
Good
9,837 reviews
Porter Airlines
8.0
Very good
318 reviews
Check prices

Crew

8.7

Entertainment

7.0

Boarding

8.2

Food

7.6

Comfort

8.0

Overall

8.0

Reviews

1 / 20
8.0
Excellent

Anonymous,Jul 2025

LIS - YYZ

Everything was on time and easy. Crew were nice on flights and helpful. International flight, so long and typically uncomfortable but not more than most. Food and drink service were below average but you get what you pay for. Overall, good experience

Related info for your journey

Find useful and relevant information for your journey from Boston to Windsor. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.

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

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

  • How can I find direct flights from Boston to Windsor?

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

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

    Yes. Cheapflights offers flight deals from Boston to Windsor 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 Boston to Windsor, Ontario?

    Currently, February is the cheapest month in which you can book a flight from Boston to Windsor, Ontario (average of C$ 352). Flying from Boston to Windsor, Ontario in March is currently the most expensive (average of C$ 530). 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.

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