Which city has the cheapest flights to Windsor?

Based on fares booked in the past 5 days, the cheapest flights to Windsor are from Chicago, starting at $289 round-trip, and from New York, starting at $526 round-trip.

How do I know if a flight to Windsor is a good deal?

A good deal on a flight to Windsor is around $526 round-trip. This fare is in the lowest 25% of round-trip prices searched on KAYAK, averaged across the cities most often searched as origins by KAYAK users.

What is the cheapest flight to Windsor?

Chicago O'Hare Intl Airport to Windsor is the cheapest route at $289 round-trip, found in the past 5 days on KAYAK. KAYAK data shows this is also the most popular route.

How much is a flight to Windsor?

On average, a round-trip flight from the United States to Windsor costs $616, based on KAYAK data over the past 12 months. Round-trip fares from New York average $500, while Boston runs a bit higher at $575.

What’s the cheapest month to fly to Windsor?

•January is the cheapest month to fly to Windsor with an average price of $378 round-trip. •August ($1,792) and February ($1,056) are the most expensive. Based on KAYAK data over the past 12 months.

What is the cheapest time of day to fly to Windsor?

Afternoon flights to Windsor are the cheapest at $500 round-trip on average. Evening flights are the most expensive at $969.

What is a good deal for flights to Windsor?

Flights under $526 are considered a good deal. 25% of KAYAK users found round-trip flights to Windsor at or below these prices, with the lowest fares from: •New York $466.

What are the most popular airlines flying to Windsor?

Air Canada is the most popular airline flying to Windsor on KAYAK, followed by Porter Airlines.

$184 CHEAP FLIGHTS to Windsor in 2026/27

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Cheapest round-trip

$289

Typical prices: $526-$761

Air Canada

Sat 11/24Sat 12/1

ORD - YQG • 1 stop

Cheapest one-way

$184

Typical prices: $252-$419

Air Canada

Tue 11/27

SAN - YQG • 2 stops

Top airlines

Porter Airlines

Best reviews • 8.0 score

Airline reviews

Top routes

NYC - YQG

Cheapest • 43% average savings

BOS - YQG

Most popular

Insights

When to travel

January

Cheapest • 39% price drop

June

Most popular

Good to know

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We hope you love your trip to Windsor!

Flight Deals

Cheap Flights to Windsor

Discover the best prices for you by selecting your travel dates on KAYAK.

Round-trip

One-way

Last minute

All Flight Deals

Recent round-trip flight deals to Windsor

Tue, Nov 24 - Tue, Dec 1

8:45 am - 6:40 pmORD Chicago O'Hare Intl-YQG Windsor

8h 55m1 stop Toronto Pearson Intl

7:20 pm - 3:38 pmYQG Windsor-ORD Chicago O'Hare Intl

21h 18m1 stop Toronto Pearson Intl

$289Air Canada

Wed, Nov 25 - Wed, Dec 2

12:55 pm - 9:55 amSAN San Diego-YQG Windsor

18h 00m1 stop Toronto Pearson Intl

7:20 pm - 4:10 pmYQG Windsor-SAN San Diego

23h 50m2 stops Toronto Pearson Intl Vancouver Intl

$506Air Canada

Thu, Nov 26 - Thu, Dec 3

12:50 pm - 6:51 pmEWR Newark-YQG Windsor

6h 01m1 stop Ottawa

7:00 am - 12:06 pmYQG Windsor-EWR Newark

5h 06m1 stop Ottawa

$526Porter Airlines

Fri, Nov 27 - Fri, Dec 4

12:50 pm - 6:51 pmEWR Newark-YQG Windsor

6h 01m1 stop Ottawa

7:00 am - 4:55 pmYQG Windsor-EWR Newark

9h 55m1 stop Ottawa

$548Porter Airlines

Wed, Nov 25 - Wed, Dec 2

12:50 pm - 6:51 pmEWR Newark-YQG Windsor

6h 01m1 stop Ottawa

7:00 am - 12:06 pmYQG Windsor-EWR Newark

5h 06m1 stop Ottawa

$549Porter Airlines

Wed, Nov 25 - Wed, Dec 2

8:00 am - 6:51 pmEWR Newark-YQG Windsor

10h 51m2 stops Toronto Island Ottawa

7:00 am - 4:55 pmYQG Windsor-EWR Newark

9h 55m1 stop Ottawa

$567Porter Airlines

Wed, Nov 25 - Mon, Nov 30

12:50 pm - 6:51 pmEWR Newark-YQG Windsor

6h 01m1 stop Ottawa

7:00 am - 8:36 pmYQG Windsor-EWR Newark

13h 36m2 stops Ottawa Toronto Island

$571Porter Airlines

Mon, Nov 23 - Mon, Nov 30

4:45 pm - 9:55 amSAN San Diego-YQG Windsor

14h 10m2 stops Vancouver Intl Toronto Pearson Intl

7:20 pm - 1:42 pmYQG Windsor-SAN San Diego

21h 22m2 stops Toronto Pearson Intl San Francisco

$571Air Canada

Tue, Nov 17 - Thu, Nov 19

5:15 pm - 9:55 amSAN San Diego-YQG Windsor

13h 40m2 stops Vancouver Intl Toronto Pearson Intl

10:35 am - 6:37 pmYQG Windsor-SAN San Diego

11h 02m2 stops Toronto Pearson Intl San Francisco

$573Air Canada

Wed, Nov 25 - Mon, Nov 30

12:50 pm - 6:51 pmEWR Newark-YQG Windsor

6h 01m1 stop Ottawa

7:00 am - 12:06 pmYQG Windsor-EWR Newark

5h 06m1 stop Ottawa

$581Porter Airlines

Recent last minute flight deals to Windsor

Mon, Oct 19 - Tue, Oct 20

8:28 pm - 9:22 amEWR Newark-YQG Windsor

12h 54m1 stop Toronto Pearson Intl

7:25 pm - 9:10 amYQG Windsor-EWR Newark

13h 45m1 stop Toronto Pearson Intl

$989Air Canada

Mon, Oct 19 - Tue, Oct 20

2:35 pm - 6:42 pmEWR Newark-YQG Windsor

4h 07m1 stop Toronto Pearson Intl

10:05 am - 5:59 pmYQG Windsor-EWR Newark

7h 54m2 stops Toronto Pearson Intl Montreal Pierre Elliott Trudeau Intl

$1,018Air Canada

Thu, Oct 15 - Sun, Oct 18

8:00 am - 3:46 pmEWR Newark-YQG Windsor

7h 46m2 stops Toronto Island Ottawa

4:30 pm - 8:15 amYQG Windsor-EWR Newark

15h 45m2 stops Ottawa Toronto Island

$1,087Porter Airlines

Thu, Oct 15 - Sun, Oct 18

8:55 am - 3:46 pmEWR Newark-YQG Windsor

6h 51m2 stops Toronto Island Ottawa

4:30 pm - 3:45 pmYQG Windsor-EWR Newark

23h 15m1 stop Ottawa

$1,128Porter Airlines

Thu, Oct 15 - Sun, Oct 18

9:55 am - 3:46 pmLGA New York LaGuardia-YQG Windsor

29h 51m2 stops Toronto Pearson Intl Ottawa

4:30 pm - 8:55 amYQG Windsor-LGA New York LaGuardia

16h 25m2 stops Ottawa Toronto Pearson Intl

$1,162Multiple Airlines

Sat, Oct 17 - Sun, Oct 18

2:30 pm - 6:42 pmLGA New York LaGuardia-YQG Windsor

4h 12m1 stop Toronto Pearson Intl

7:25 pm - 6:10 pmYQG Windsor-LGA New York LaGuardia

22h 45m1 stop Toronto Pearson Intl

$1,195Multiple Airlines

Thu, Oct 15 - Sun, Oct 18

2:30 pm - 6:42 pmLGA New York LaGuardia-YQG Windsor

4h 12m1 stop Toronto Pearson Intl

10:05 am - 3:46 pmYQG Windsor-LGA New York LaGuardia

5h 41m1 stop Toronto Pearson Intl

$1,229Air Canada

Thu, Oct 15 - Sun, Oct 18

7:25 pm - 3:46 pmEWR Newark-YQG Windsor

20h 21m3 stops Toronto Island Fredericton Ottawa

4:30 pm - 8:15 amYQG Windsor-EWR Newark

15h 45m2 stops Ottawa Toronto Island

$1,267Multiple Airlines

Thu, Oct 15 - Sun, Oct 18

2:35 pm - 3:46 pmEWR Newark-YQG Windsor

25h 11m1 stop Ottawa

4:30 pm - 3:45 pmYQG Windsor-EWR Newark

23h 15m1 stop Ottawa

$1,291Porter Airlines

Mon, Oct 19 - Tue, Oct 20

8:00 am - 6:42 pmEWR Newark-YQG Windsor

10h 42m2 stops Chicago O'Hare Intl Toronto Pearson Intl

10:05 am - 5:59 pmYQG Windsor-EWR Newark

7h 54m2 stops Toronto Pearson Intl Montreal Pierre Elliott Trudeau Intl

$1,360Air Canada

All round-trip flight deals to Windsor

Tue, Nov 24 - Tue, Dec 1

8:45 am - 6:40 pmORD Chicago O'Hare Intl-YQG Windsor

8h 55m1 stop Toronto Pearson Intl

7:20 pm - 3:38 pmYQG Windsor-ORD Chicago O'Hare Intl

21h 18m1 stop Toronto Pearson Intl

$289Air Canada

Wed, Nov 25 - Wed, Dec 2

12:55 pm - 9:55 amSAN San Diego-YQG Windsor

18h 00m1 stop Toronto Pearson Intl

7:20 pm - 4:10 pmYQG Windsor-SAN San Diego

23h 50m2 stops Toronto Pearson Intl Vancouver Intl

$506Air Canada

Thu, Nov 26 - Thu, Dec 3

12:50 pm - 6:51 pmEWR Newark-YQG Windsor

6h 01m1 stop Ottawa

7:00 am - 12:06 pmYQG Windsor-EWR Newark

5h 06m1 stop Ottawa

$526Porter Airlines

Fri, Nov 27 - Fri, Dec 4

12:50 pm - 6:51 pmEWR Newark-YQG Windsor

6h 01m1 stop Ottawa

7:00 am - 4:55 pmYQG Windsor-EWR Newark

9h 55m1 stop Ottawa

$548Porter Airlines

Wed, Nov 25 - Wed, Dec 2

12:50 pm - 6:51 pmEWR Newark-YQG Windsor

6h 01m1 stop Ottawa

7:00 am - 12:06 pmYQG Windsor-EWR Newark

5h 06m1 stop Ottawa

$549Porter Airlines

Wed, Nov 25 - Wed, Dec 2

8:00 am - 6:51 pmEWR Newark-YQG Windsor

10h 51m2 stops Toronto Island Ottawa

7:00 am - 4:55 pmYQG Windsor-EWR Newark

9h 55m1 stop Ottawa

$567Porter Airlines

Wed, Nov 25 - Mon, Nov 30

12:50 pm - 6:51 pmEWR Newark-YQG Windsor

6h 01m1 stop Ottawa

7:00 am - 8:36 pmYQG Windsor-EWR Newark

13h 36m2 stops Ottawa Toronto Island

$571Porter Airlines

Mon, Nov 23 - Mon, Nov 30

4:45 pm - 9:55 amSAN San Diego-YQG Windsor

14h 10m2 stops Vancouver Intl Toronto Pearson Intl

7:20 pm - 1:42 pmYQG Windsor-SAN San Diego

21h 22m2 stops Toronto Pearson Intl San Francisco

$571Air Canada

Tue, Nov 17 - Thu, Nov 19

5:15 pm - 9:55 amSAN San Diego-YQG Windsor

13h 40m2 stops Vancouver Intl Toronto Pearson Intl

10:35 am - 6:37 pmYQG Windsor-SAN San Diego

11h 02m2 stops Toronto Pearson Intl San Francisco

$573Air Canada

Wed, Nov 25 - Mon, Nov 30

12:50 pm - 6:51 pmEWR Newark-YQG Windsor

6h 01m1 stop Ottawa

7:00 am - 12:06 pmYQG Windsor-EWR Newark

5h 06m1 stop Ottawa

$581Porter Airlines

Booking Insights

Price, demand and travel trends for flights to Windsor

Use KAYAK data on prices, travel dates, airlines and seasonal trends to compare options and book flights with more confidence.

Prices

Airlines

What is the cheapest flight to Windsor?: Chicago O'Hare Intl Airport to Windsor is the cheapest route at $289 round-trip, found in the past 5 days on KAYAK. KAYAK data shows this is also the most popular route.
How much is a flight to Windsor? Average and cheapest price for all round-trip flights to Windsor from each origin found by users searching on KAYAK in the last 12 months.: On average, a round-trip flight from the United States to Windsor costs $616, based on KAYAK data over the past 12 months. Round-trip fares from New York average $500, while Boston runs a bit higher at $575.
What’s the cheapest month to fly to Windsor? To calculate monthly average prices, KAYAK takes all prices for each month over the last 12 months for flights to Windsor, removes the top 0.1% to account for outliers, then takes the median of all values for each month.: •January is the cheapest month to fly to Windsor with an average price of $378 round-trip.
•August ($1,792) and February ($1,056) are the most expensive.

Based on KAYAK data over the past 12 months.
What is the cheapest time of day to fly to Windsor? Average price for all round-trip flights depending on time of departure, seen by users on KAYAK in the last 12 months.: Afternoon flights to Windsor are the cheapest at $500 round-trip on average. Evening flights are the most expensive at $969.
What is a good deal for flights to Windsor?: Flights under $526 are considered a good deal. 25% of KAYAK users found round-trip flights to Windsor at or below these prices, with the lowest fares from:
•New York $466.

Find deals

Expert advice

Our travel experts

Stefanie Waldek

Expert on Air Canada

Stefanie Waldek is a freelance space, travel, and design writer based in Saratoga Springs, NY. Her words have appeared in Space.com, Travel + Leisure, Condé Nast Traveler, Architectural Digest, and House Beautiful, among other publications. An expert in aviation and expedition cruising, Stefanie is frequently up in the air or on the sea, likely en route to Antarctica or the Arctic.

John Walton

Expert on Porter Airlines

Independent aviation journalist John Walton took his first flight at eight weeks old and hasn’t stopped travelling since. A world-renowned expert in airlines and the passenger experience, he writes in depth on aviation, is a resident expert on travel in Japan and France, and offers a uniquely queer perspective on travelling the world.

Low season	March
High season	June
Cheapest flight	$184

Beat the crowds with an average 60% drop in travelers.

The most popular month to fly with an average 50% increase in travelers.

One-way flight from San Diego to Windsor

When to book flights to Windsor

Are your dates flexible? Find out the best times to travel to Windsor based on our flight data from the last year. Discover the cheapest month and even day to fly.

Estimated round-trip price

KAYAK looks at all historical flight data for each date to provide a predicted price for one-way trips or round-trips with a duration up to 40 days. The information is for flights to Windsor based on your location. While we try to provide actual minimum prices for each date, some prices are predictions and actual prices may differ.

How do I know if a flight to Windsor is a good deal?
A good deal on a flight to Windsor is around $526 round-trip. This fare is in the lowest 25% of round-trip prices searched on KAYAK, averaged across the cities most often searched as origins by KAYAK users.
Which city has the cheapest flights to Windsor?
Based on fares booked in the past 5 days, the cheapest flights to Windsor are from Chicago, starting at $289 round-trip, and from New York, starting at $526 round-trip.

For flights to Windsor, a good round-trip fare is around $526. If you find a fare below that, you're getting a strong deal.
If your travel dates are flexible, consider flying to Windsor in January. Round-trip fares historically average $378, making January the cheapest month to travel based on KAYAK data from the last 12 months.
Before you book:

• Check the route's typical price range so you can spot a deal.
• Confirm baggage fees and seat-selection costs on budget carriers.
• Verify whether you need any travel documents beyond ID.
• Pick a departure airport, since your nearest may not be the cheapest origin.
Shift your departure to noon to save up to $469 per round-trip. Noon flights to Windsor average $500 compared to $969 for afternoon flights.
Once you arrive in Windsor, a few great places to start are Caesars Windsor and Detroit Windsor Tunnel. These are popular with first-time visitors and can give you a good feel for the area.