$1,126 Cheap Flights from Chicago (MDW) to Windsor (YQG)

View $1,126 flight on Fri, Sep 26, 2025Opens in a new window

Popular airlines from Chicago Midway Airport (MDW) to Windsor, ON (YQG)

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Cheap Flights from Chicago to Windsor (MDW-YQG)

Prices were available within the past 7 days and start at $1,126 for one-way flights and $654 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

Porter Airlines
Thu, Sep 25 - Sun, Sep 28
MDW
Chicago
YQG
Windsor
$654 Roundtrip, found 4 days ago
$654
Roundtrip
found 4 days ago
Select Porter Airlines flight, departing Thu, Sep 25 from Chicago to Windsor, returning Sun, Sep 28, priced at $654 found 4 days ago
Porter Airlines
Wed, Aug 27 - Fri, Aug 29
MDW
Chicago
YQG
Windsor
$656 Roundtrip, found 6 hours ago
$656
Roundtrip
found 6 hours ago
Select Porter Airlines flight, departing Wed, Aug 27 from Chicago to Windsor, returning Fri, Aug 29, priced at $656 found 6 hours ago
Porter Airlines
Fri, Sep 26 - Sun, Sep 28
MDW
Chicago
YQG
Windsor
$1,904 Roundtrip, found 4 days ago
$1,904
Roundtrip
found 4 days ago
Select Porter Airlines flight, departing Fri, Sep 26 from Chicago to Windsor, returning Sun, Sep 28, priced at $1,904 found 4 days ago
Porter Airlines
Fri, Sep 26 - Sun, Sep 28
MDW
Chicago
YQG
Windsor
$2,456 Roundtrip, found 4 days ago
$2,456
Roundtrip
found 4 days ago
Select Porter Airlines flight, departing Fri, Sep 26 from Chicago to Windsor, returning Sun, Sep 28, priced at $2,456 found 4 days ago

Alternative airports near Windsor

Prices were available within the past 7 days. Prices and availability are subject to change.

Select flight to Detroit Metropolitan Wayne County DTW. Cheapest option available. Average driving time to city center is 29 minutes. Flights from $188
DTW
Detroit Metropolitan Wayne County
Cheapest
Average driving time to city center29 min
Flights from $188
Flights from Chicago (MDW) to Windsor (YQG)
Origin airport
Midway Intl.
Destination airport
Windsor
Roundtrip price
$653
Distance
247 mi

Chicago to Windsor Flights

The cheapest times to fly from Chicago to Windsor

On average, Thursday can be the cheapest time to fly, according to data from the Airlines Reporting Corporation (ARC), one of the world's biggest databases for global airline sales. The data reveals that you could save up to 16% by flying on a Thursday—the cheapest day to travel on average—instead of a Sunday—the most expensive. Some of the most affordable flights from Chicago to Windsor are during the month of September. You can find some of the cheapest flights from Chicago to Windsor with Expedia's search tool and vast selection of airlines.

 

The best time to book a flight from Chicago to Windsor

Sunday is one of the best days to book for cheap flights from Chicago to Windsor: Tickets reserved on a Sunday cost between 6% and 13% less than those reserved on a Friday, according to ARC data. The data also suggests booking early can also lead to cheaper airfares. You could save 24% by buying your tickets for domestic flights at least a month in advance and 10% by booking international flights 2 months in advance.

 

How to find cheap round-trip tickets from Chicago to Windsor

Being flexible with your dates and using Expedia's Price Drop Protection and Price Tracking features are some of the best ways of finding a cheap ticket from Chicago to Windsor in 2025. You can also book with separate airlines for your outbound and return journeys, from $1,126 one-way. Expedia also offers Price Drop Protection, so if the cost of your airfare goes down after booking, you'll receive a credit for the difference*. This is available for a small fee, and is free to One Key Gold and Platinum tier members.

 

Expedia's Price Tracking feature means you can stay on top of airfares without manually checking every day. It sends you automated price alerts for cheap Chicago to Windsor flights and uses historical data to indicate when the best time to book is. Download Expedia's free app to activate this handy tool in a few easy taps.

 

You could also save big by booking one of Expedia's vacation packages. Bundling together your Chicago to Windsor airfare with your accommodations and car rental is often cheaper than booking everything separately. There’s also One Key, Expedia's generous rewards program. Join for free and you could earn One Key cash on most bookings to save on future adventures.

 

*Terms apply.

 

Disclaimer: ARC The statistics are based on average round-trip ticket prices between January and August 2023. The percentages you see are averages.

 

Frequently asked questions

How much does a flight from Midway Intl. Airport (MDW) to Windsor Airport (YQG) cost?
Lock in a cheap one-way flight from $1,126 or cheap return flight from $654 from Midway Intl. Airport (MDW) to Windsor Airport (YQG) with Expedia. Enter your travel dates and sort by "Price (lowest to highest)" to find our cheapest flight offers on this route.
What is the cheapest month to fly from Midway Intl. Airport (MDW) to Windsor Airport (YQG)?
Planning your trip for September can help you save, as it's the cheapest month for flights between MDW and YQG. You'll typically find the lowest prices during the off-season.
What is the cheapest airline that flies from Midway Intl. Airport (MDW) to Windsor Airport (YQG)?
Use the filters on Expedia to compare different airlines and find the cheapest carrier that'll take you from MDW to YQG. Then, sort your results by "Price (lowest to highest)" to snap up the best deal available.
How many flights per day from Midway Intl. Airport (MDW) to Windsor Airport (YQG)?
Direct flights from Midway Intl. Airport (MDW) to Windsor Airport (YQG) aren't available daily, so you'll need to take a flight with a layover. Explore your options with our filter tool. Enter your dates and select either "1 Stop" or "2+ Stops."
What day of the week has the most flights from MDW to YQG?
You'll generally find Tuesday the quietest day for flights, while Fridays tend to be the busiest.* However this can vary from season to season and during peak travel times or public holidays.*Busiest/quietest day to travel is based on Expedia flight demand through January to December 2024.
What is the best time to fly from Midway Intl. Airport (MDW) to Windsor Airport (YQG)?
To avoid possible delays on the Midway Intl. Airport (MDW) to Windsor Airport (YQG) route, aim to fly before 3 PM. Departures after this hour are 22% more likely to be canceled.**Most reliable time of the day and month to travel recommendation is based on January through August 2024 flight status data sourced from OAG's global flight data platform.
What airports do you fly into for Windsor from Midway Intl. Airport (MDW)?
Compare your flight options from Midway Intl. Airport (MDW) to Detroit Metropolitan Wayne County Airport (DTW). This is the only Windsor airport you can jet into if you're taking a direct flight.
Is it cheaper to buy a plane ticket from Midway Intl. Airport (MDW) to Windsor Airport (YQG) last-minute?
Waiting until just before your trip to book your flight from MDW to YQG generally means paying more. While you may find some last-minute discounts, they aren't always guaranteed. Allow some flexibility in your schedule to boost your chances of landing a bargain.
Is it cheaper to book a MDW to YQG flight and hotel package?
Compared with arranging flights and hotels separately, booking a MDW to YQG flight and hotel package with Expedia could lead to significant savings. What's more, managing everything in one place will take the stress out of planning your trip. Just pick your flights and choose from our extensive range of stays, then tailor your trip with other add-ons like car rentals and activities.
Can I cancel or change the date of my flight from Midway Intl. Airport (MDW) to Windsor Airport (YQG)?
You can usually cancel or reschedule your MDW to YQG flight. However, if the booking was made more than 24 hours ago, additional charges may apply. Check your airline's policies in your itinerary to see what changes are allowed and whether any costs are involved. You'll also find more details on our Customer Service portal.

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