$257 Cheap Flights from Ottawa (YOW) to Chicago (MDW)

View $257 flight on Thu, Jan 15, 2026Opens in a new window

Popular airlines from Ottawa International Airport (YOW) to Chicago Midway Airport (MDW)

    notification illustration

    Be in the know

    Get alerts if flight prices drop or rise*
    deals illustration

    Book smarter

    Save up to 30% on select hotels after you book a flight*
    trophy illustration

    Earn twice

    Earn your airline miles on top of our OneKeyCash
    Learn about One Key

Cheap Flights from Ottawa to Chicago (YOW-MDW)

Prices were available within the past 7 days and start at $257 for one-way flights and $495 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

Porter Airlines
Tue, Nov 18 - Sat, Nov 22
YOW
Ottawa
MDW
Chicago
$495 Roundtrip, found 4 days ago
$495
Roundtrip
found 4 days ago
Select Porter Airlines flight, departing Tue, Nov 18 from Ottawa to Chicago, returning Sat, Nov 22, priced at $495 found 4 days ago
Porter Airlines
Fri, Nov 28 - Tue, Dec 2
YOW
Ottawa
MDW
Chicago
$506 Roundtrip, found 2 days ago
$506
Roundtrip
found 2 days ago
Select Porter Airlines flight, departing Fri, Nov 28 from Ottawa to Chicago, returning Tue, Dec 2, priced at $506 found 2 days ago
Porter Airlines
Thu, Dec 4 - Mon, Dec 8
YOW
Ottawa
MDW
Chicago
$507 Roundtrip, found 5 hours ago
$507
Roundtrip
found 5 hours ago
Select Porter Airlines flight, departing Thu, Dec 4 from Ottawa to Chicago, returning Mon, Dec 8, priced at $507 found 5 hours ago
Porter Airlines
Tue, Nov 18 - Mon, Dec 1
YOW
Ottawa
MDW
Chicago
$522 Roundtrip, found 6 hours ago
$522
Roundtrip
found 6 hours ago
Select Porter Airlines flight, departing Tue, Nov 18 from Ottawa to Chicago, returning Mon, Dec 1, priced at $522 found 6 hours ago
Porter Airlines
Thu, Dec 18 - Fri, Jan 9
YOW
Ottawa
MDW
Chicago
$529 Roundtrip, found 8 hours ago
$529
Roundtrip
found 8 hours ago
Select Porter Airlines flight, departing Thu, Dec 18 from Ottawa to Chicago, returning Fri, Jan 9, priced at $529 found 8 hours ago
Porter Airlines
Fri, Nov 28 - Tue, Dec 2
YOW
Ottawa
MDW
Chicago
$529 Roundtrip, found 2 days ago
$529
Roundtrip
found 2 days ago
Select Porter Airlines flight, departing Fri, Nov 28 from Ottawa to Chicago, returning Tue, Dec 2, priced at $529 found 2 days ago
Porter Airlines
Thu, Dec 4 - Mon, Dec 8
YOW
Ottawa
MDW
Chicago
$531 Roundtrip, found 5 hours ago
$531
Roundtrip
found 5 hours ago
Select Porter Airlines flight, departing Thu, Dec 4 from Ottawa to Chicago, returning Mon, Dec 8, priced at $531 found 5 hours ago
Porter Airlines
Thu, Nov 13 - Thu, Dec 4
YOW
Ottawa
MDW
Chicago
$539 Roundtrip, found 6 hours ago
$539
Roundtrip
found 6 hours ago
Select Porter Airlines flight, departing Thu, Nov 13 from Ottawa to Chicago, returning Thu, Dec 4, priced at $539 found 6 hours ago
Porter Airlines
Sat, Nov 15 - Wed, Dec 3
YOW
Ottawa
MDW
Chicago
$540 Roundtrip, found 6 hours ago
$540
Roundtrip
found 6 hours ago
Select Porter Airlines flight, departing Sat, Nov 15 from Ottawa to Chicago, returning Wed, Dec 3, priced at $540 found 6 hours ago
WestJet
Wed, May 6 - Wed, May 13
YOW
Ottawa
MDW
Chicago
$974 Roundtrip, found 5 days ago
$974
Roundtrip
found 5 days ago
Select WestJet flight, departing Wed, May 6 from Ottawa to Chicago, returning Wed, May 13, priced at $974 found 5 days ago

Find the cheapest month to fly from Ottawa (YOW) to Chicago (MDW)

July is typically the cheapest month to fly

From $241 - $849 per traveler.

Alternative airports near Chicago

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

Select flight to O'Hare Intl. ORD. Average driving time to city center is 23 minutes. Flights from $644
ORD
O'Hare Intl.
Average driving time to city center23 min
Flights from $644

Frequently asked questions

How much does a flight from Macdonald-Cartier Intl. Airport (YOW) to Midway Intl. Airport (MDW) cost?
Secure a cheap one-way flight from $257 or cheap return flight from $495 from Macdonald-Cartier Intl. Airport (YOW) to Midway Intl. Airport (MDW) with Expedia. Enter your travel dates and sort by "Price (lowest to highest)" to see our cheapest flight deals on this route.
What is the cheapest month to fly from Macdonald-Cartier Intl. Airport (YOW) to Midway Intl. Airport (MDW)?
Planning your getaway for November is a great way to save, as it's the cheapest month for flights between YOW and MDW. You'll usually find the lowest fares during the off-season.
What is the cheapest airline that flies from Macdonald-Cartier Intl. Airport (YOW) to Midway Intl. Airport (MDW)?
Expedia's filter tool lets you easily compare airlines, flight times and baggage options all in one place. Tailor the search to your trip, then sort by "Price (lowest to highest)" to see which carrier offers the cheapest YOW to MDW flight.
How many flights per day from Macdonald-Cartier Intl. Airport (YOW) to Midway Intl. Airport (MDW)?
You'll have to book a flight with a layover when traveling from Macdonald-Cartier Intl. Airport (YOW) to Midway Intl. Airport (MDW). There are no daily direct flights on this route. However, simply filter your search to include one or more stops to discover an option that works for you.
What day of the week has the most flights from YOW to MDW?
Friday is usually the busiest day for flights, while Tuesday tends to be the quietest.* Remember that flight schedules can change depending on a range of factors, including the carrier and season.*Busiest/quietest day to travel is based on Expedia flight demand through January to December 2024.
What is the best time to fly from Macdonald-Cartier Intl. Airport (YOW) to Midway Intl. Airport (MDW)?
To avoid possible delays on the Macdonald-Cartier Intl. Airport (YOW) to Midway Intl. Airport (MDW) route, travel 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 Chicago from Macdonald-Cartier Intl. Airport (YOW)?
If you're flying on a direct flight from Macdonald-Cartier Intl. Airport (YOW) to Chicago, O'Hare Intl. Airport (ORD) is the only airport you can land at.
Is it cheaper to buy a plane ticket from Macdonald-Cartier Intl. Airport (YOW) to Midway Intl. Airport (MDW) last-minute?
Holding off until just before your departure to book a flight from YOW to MDW generally means paying more. While you might find some last-minute deals, they're not always guaranteed. Allow some flexibility in your schedule to boost your chances of scoring a bargain.
Is it cheaper to book a YOW to MDW flight and hotel package?
Booking a YOW to MDW flight and hotel package tends to be cheaper than booking separately. With Expedia, you can enjoy the convenience of organizing your travels in one place. Choose from our impressive range of accommodations and then add activities, flights and car rentals to your booking. Bundle everything together, and you could save hundreds of dollars.
Can I cancel or change the date of my flight from Macdonald-Cartier Intl. Airport (YOW) to Midway Intl. Airport (MDW)?
If you reserved your YOW to MDW flight within the last 24 hours, you may be able to cancel or modify it at no cost. Depending on the airline and the type of ticket you have, additional charges may apply for changes beyond this timeframe. Airline policies and contact information can be found in your itinerary or confirmation email. Or, go to our Customer Service portal if you'd like more information.

Travel information

Origin airport
Macdonald-Cartier Intl.
Destination airport
Midway Intl.
Airlines serving
Porter Airlines, WestJet
Roundtrip price
$495
Distance
651 mi

Book with confidence

Ottawa to Chicago Flights

The cheapest times to fly from Ottawa to Chicago

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 Ottawa to Chicago are during the month of November. You can find some of the cheapest flights from Ottawa to Chicago with Expedia's search tool and vast selection of airlines.

 

The best time to book a flight from Ottawa to Chicago

Sunday is one of the best days to book for cheap flights from Ottawa to Chicago: 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 Ottawa to Chicago

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 Ottawa to Chicago in 2025. You can also book with separate airlines for your outbound and return journeys, from $257 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 Ottawa to Chicago 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 Ottawa to Chicago 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.

 

Ottawa to Chicago Flights

Explore a world of travel with Expedia

*Available to One Key members.