$149 Cheap Flights from Ottawa (YOW) to Chicago (ORD)

View $149 flight on Mon, Jul 14, 2025Opens in a new window

Popular airlines from Ottawa International Airport (YOW) to Chicago O'Hare Intl. Airport (ORD)

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Find available prices by choosing your travel dates.

Cheap Flights from Ottawa to Chicago (YOW-ORD)

Prices were available within the past 7 days and start at $149 for one-way flights and $259 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

United
Wed, May 14 - Thu, May 15
YOW
Ottawa
ORD
Chicago
$259 Roundtrip, found 3 hours ago
$259
Roundtrip
found 3 hours ago
Select United flight, departing Wed, May 14 from Ottawa to Chicago, returning Thu, May 15, priced at $259 found 3 hours ago
United
Fri, May 9 - Wed, May 14
YOW
Ottawa
ORD
Chicago
$282 Roundtrip, found 3 hours ago
$282
Roundtrip
found 3 hours ago
Select United flight, departing Fri, May 9 from Ottawa to Chicago, returning Wed, May 14, priced at $282 found 3 hours ago
Air Canada
Fri, May 9 - Mon, May 26
YOW
Ottawa
ORD
Chicago
$287 Roundtrip, found 1 hour ago
$287
Roundtrip
found 1 hour ago
Select Air Canada flight, departing Fri, May 9 from Ottawa to Chicago, returning Mon, May 26, priced at $287 found 1 hour ago
United
Fri, May 9 - Thu, May 15
YOW
Ottawa
ORD
Chicago
$292 Roundtrip, found 3 hours ago
$292
Roundtrip
found 3 hours ago
Select United flight, departing Fri, May 9 from Ottawa to Chicago, returning Thu, May 15, priced at $292 found 3 hours ago
Air Canada
Fri, May 9 - Mon, May 26
YOW
Ottawa
ORD
Chicago
$293 Roundtrip, found 1 hour ago
$293
Roundtrip
found 1 hour ago
Select Air Canada flight, departing Fri, May 9 from Ottawa to Chicago, returning Mon, May 26, priced at $293 found 1 hour ago
United
Fri, May 9 - Mon, May 26
YOW
Ottawa
ORD
Chicago
$294 Roundtrip, found 1 hour ago
$294
Roundtrip
found 1 hour ago
Select United flight, departing Fri, May 9 from Ottawa to Chicago, returning Mon, May 26, priced at $294 found 1 hour ago
Air Canada
Fri, May 9 - Mon, May 26
YOW
Ottawa
ORD
Chicago
$299 Roundtrip, found 1 hour ago
$299
Roundtrip
found 1 hour ago
Select Air Canada flight, departing Fri, May 9 from Ottawa to Chicago, returning Mon, May 26, priced at $299 found 1 hour ago
United
Fri, May 9 - Mon, May 26
YOW
Ottawa
ORD
Chicago
$303 Roundtrip, found 1 hour ago
$303
Roundtrip
found 1 hour ago
Select United flight, departing Fri, May 9 from Ottawa to Chicago, returning Mon, May 26, priced at $303 found 1 hour ago
United
Fri, May 9 - Mon, May 26
YOW
Ottawa
ORD
Chicago
$306 Roundtrip, found 1 hour ago
$306
Roundtrip
found 1 hour ago
Select United flight, departing Fri, May 9 from Ottawa to Chicago, returning Mon, May 26, priced at $306 found 1 hour ago
WestJet
Fri, May 9 - Sat, May 10
YOW
Ottawa
ORD
Chicago
$561 Roundtrip, found 16 hours ago
$561
Roundtrip
found 16 hours ago
Select WestJet flight, departing Fri, May 9 from Ottawa to Chicago, returning Sat, May 10, priced at $561 found 16 hours ago
Flights from Ottawa (YOW) to Chicago (ORD)
Origin airport
Macdonald-Cartier Intl.
Destination airport
O'Hare Intl.
Airlines serving
Air Canada, United, WestJet
Roundtrip price
$249
Distance
653 mi

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 May. 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 $149 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.

Frequently asked questions

How much does a flight from Macdonald-Cartier Intl. Airport (YOW) to O'Hare Intl. Airport (ORD) cost?
Book cheap return fares starting at $445 from Macdonald-Cartier Intl. Airport (YOW) to O’Hare Intl. Airport (ORD). This information is based on the cheapest price found on Expedia for this return journey departing within the next three months. This airfare is for a United flight leaving YOW on May 4 2025 and touching down at ORD. The price was last updated on April 22 2025 and has not changed since.
What is the cheapest month to fly from YOW to ORD?
The cheapest flights from YOW to ORD are usually during off-peak season, when demand is lower. To save money, avoid flying during public holidays, school breaks and major local events.
Which airlines fly direct from Macdonald-Cartier Intl. Airport (YOW) to O'Hare Intl. Airport (ORD)?
Take a nonstop flight with United Airlines and head straight from Macdonald-Cartier Intl. Airport (YOW) to O’Hare Intl. Airport (ORD).
What is the cheapest airline that flies from YOW to ORD?
With prices as low as $247 for a one-way flight from YOW to ORD, Air Canada is currently the cheapest carrier flying this route. This fare is based on the lowest price found on Expedia departing within the next three months. The flight takes off from YOW on May 25 2025. Prices were last updated on April 22 2025 and have not changed since.
How many flights per day from Macdonald-Cartier Intl. Airport (YOW) to O'Hare Intl. Airport (ORD)?
When departing from Macdonald-Cartier Intl. Airport (YOW), you’ll have a choice from an average of 2 daily direct flights to O’Hare Intl. Airport (ORD).
What are the most popular departure times for flights from Macdonald-Cartier Intl. Airport (YOW) to O'Hare Intl. Airport (ORD)?
More passengers fly between YOW and ORD at 5 PM than at any other time of day. Rather skip the crowds? Consider flying outside peak hours and you could save on your fare as well.
What day of the week has the most flights from YOW to ORD?
If you depart on a Friday, you’ll get the greatest range of choices for flights from Macdonald-Cartier Intl. Airport (YOW) to O’Hare Intl. Airport (ORD).
What is the earliest flight from Macdonald-Cartier Intl. Airport (YOW) to O'Hare Intl. Airport (ORD)?
Take the earliest flight at around 6:20AM UTC-5, heading out of Macdonald-Cartier Intl. Airport (YOW). You’ll be in the air for around 2h 40m, arriving at O’Hare Intl. Airport (ORD) at approximately 8:00AM UTC-6.
How long does it take to fly from Macdonald-Cartier Intl. Airport (YOW) to O'Hare Intl. Airport (ORD)?
Flights from YOW to ORD have an average travel time of 2 hours and 38 minutes. The total distance between the two is 650 mi.
What is the best time to fly from Macdonald-Cartier Intl. Airport (YOW) to O'Hare Intl. Airport (ORD)?
To land at O’Hare Intl. Airport (ORD) on schedule, select a flight that leaves from Macdonald-Cartier Intl. Airport (YOW) before 3 PM. The chance of cancellations is 22% higher, on average, for departures after this time.**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)?
O’Hare Intl. Airport (ORD) is the only airport in Chicago with direct flights from Macdonald-Cartier Intl. Airport (YOW). Browse your options and find cheap fares on Expedia.
Is it cheaper to buy a plane ticket from Macdonald-Cartier Intl. Airport (YOW) to O'Hare Intl. Airport (ORD) last-minute?
Waiting until just before your departure to book a ticket from YOW to ORD often results in higher prices. Although you may find some last-minute offers, they’re not always guaranteed. Be flexible with your travel plans for the best chance of scoring a bargain.
Is it cheaper to book a YOW to ORD flight and hotel package?
Booking a YOW to ORD flight and hotel package is typically cheaper than booking separately. With Expedia, you can enjoy the ease of organizing your travels in one place. Pick from our wide range of accommodations and then add flights, car rentals and activities to your booking. Bundle it all 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 O'Hare Intl. Airport (ORD)?
In most instances, you can cancel or modify your YOW to ORD flight. However, there may be additional fees, especially if your booking was made more than 24 hours ago. Check your itinerary for the airline’s rules and fees on flight changes, or if you need more details, visit our Customer Service portal.

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