฿3,855 Cheap Flights from Toronto (YYZ) to Chicago (ORD)

View ฿3,855 flight on Tue, 26 Aug 2025Opens in a new window

Popular airlines from Toronto Pearson Intl. Airport (YYZ) to Chicago O'Hare International Airport (ORD)

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Cheap Flights from Toronto (YYZ) to Chicago (ORD)

Prices were available within the past 7 days and start at ฿3,855 for one-way flights and ฿8,180 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

United
Fri, 22 Aug - Sun, 24 Aug
YYZ
Toronto
ORD
Chicago
฿8,180 Return, found 2 days ago
฿8,180
Return
found 2 days ago
Select United flight, departing Fri, 22 Aug from Toronto to Chicago, returning Sun, 24 Aug, priced at ฿8,180 found 2 days ago
American Airlines
Fri, 22 Aug - Sun, 24 Aug
YYZ
Toronto
ORD
Chicago
฿8,365 Return, found 2 days ago
฿8,365
Return
found 2 days ago
Select American Airlines flight, departing Fri, 22 Aug from Toronto to Chicago, returning Sun, 24 Aug, priced at ฿8,365 found 2 days ago
American Airlines
Fri, 22 Aug - Sun, 24 Aug
YYZ
Toronto
ORD
Chicago
฿9,285 Return, found 2 days ago
฿9,285
Return
found 2 days ago
Select American Airlines flight, departing Fri, 22 Aug from Toronto to Chicago, returning Sun, 24 Aug, priced at ฿9,285 found 2 days ago
United
Fri, 22 Aug - Sun, 24 Aug
YYZ
Toronto
ORD
Chicago
฿9,310 Return, found 2 days ago
฿9,310
Return
found 2 days ago
Select United flight, departing Fri, 22 Aug from Toronto to Chicago, returning Sun, 24 Aug, priced at ฿9,310 found 2 days ago
United
Fri, 22 Aug - Sun, 24 Aug
YYZ
Toronto
ORD
Chicago
฿9,320 Return, found 2 days ago
฿9,320
Return
found 2 days ago
Select United flight, departing Fri, 22 Aug from Toronto to Chicago, returning Sun, 24 Aug, priced at ฿9,320 found 2 days ago
United
Fri, 22 Aug - Sun, 24 Aug
YYZ
Toronto
ORD
Chicago
฿9,495 Return, found 2 days ago
฿9,495
Return
found 2 days ago
Select United flight, departing Fri, 22 Aug from Toronto to Chicago, returning Sun, 24 Aug, priced at ฿9,495 found 2 days ago
American Airlines
Fri, 22 Aug - Sun, 24 Aug
YYZ
Toronto
ORD
Chicago
฿9,505 Return, found 2 days ago
฿9,505
Return
found 2 days ago
Select American Airlines flight, departing Fri, 22 Aug from Toronto to Chicago, returning Sun, 24 Aug, priced at ฿9,505 found 2 days ago
American Airlines
Fri, 22 Aug - Sun, 24 Aug
YYZ
Toronto
ORD
Chicago
฿9,620 Return, found 2 days ago
฿9,620
Return
found 2 days ago
Select American Airlines flight, departing Fri, 22 Aug from Toronto to Chicago, returning Sun, 24 Aug, priced at ฿9,620 found 2 days ago
Air Canada
Fri, 22 Aug - Sun, 24 Aug
YYZ
Toronto
ORD
Chicago
฿9,875 Return, found 2 days ago
฿9,875
Return
found 2 days ago
Select Air Canada flight, departing Fri, 22 Aug from Toronto to Chicago, returning Sun, 24 Aug, priced at ฿9,875 found 2 days ago
United
Fri, 22 Aug - Sun, 24 Aug
YYZ
Toronto
ORD
Chicago
฿9,925 Return, found 2 days ago
฿9,925
Return
found 2 days ago
Select United flight, departing Fri, 22 Aug from Toronto to Chicago, returning Sun, 24 Aug, priced at ฿9,925 found 2 days ago

Find the cheapest month to fly from Toronto (YYZ) to Chicago (ORD)

November is typically the cheapest month to fly

From ฿4,970 - ฿11,486 per traveller.

Graph displaying average flight prices per month

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Flight from Toronto to Chicago route information
Origin airport
Pearson Intl.
Destination airport
O'Hare Intl.
Return price
฿8,180
Distance
697 km

Perfect flights from Toronto to Chicago

Embark on an unforgettable journey without breaking the bank with Expedia's incredible deals on cheap flights from Toronto to Chicago. Whether you're aching for a romantic escape with your partner, craving an adventurous solo expedition, or yearning to immerse yourself in the local history and culture, we've got you covered.
 
Picture yourself strolling through the streets of Chicago, surrounded by breathtaking architecture and absorbing the vibrant atmosphere of this captivating city. Indulge in the mouth-watering local specialties, from tantalizing street food to exquisite fine dining. With Expedia, you can experience all of this and more, without sacrificing your budget.
 
Our flexible Pearson Intl. to O'Hare Intl. ticket options cater to your travel preferences, with incredible one-way fares from ฿3,855 and roundtrip prices from ฿8,180. Whether you're planning a short city break or a longer adventure, our dynamic pricing ensures that you find the best deals for your journey.
 
But the magic doesn't stop there. Expedia offers a range of partner services to enhance your trip. Rent a car at O'Hare Intl. and explore Chicago and its surrounding areas at your own pace. Discover hidden gems off the beaten path, and create unforgettable memories. We also provide a handpicked selection of accommodations, from charming bed and breakfasts to luxury hotels, ensuring that you have a comfortable and memorable stay.
 
Planning your next great adventure is a breeze with Expedia. Our user-friendly platform, unbeatable prices, and round-the-clock customer support are designed to make your travel experience seamless and stress-free. So, why wait? Book your YYZ to ORD travel arrangements today and embark on the journey of a lifetime in Chicago.

Frequently asked questions

How much is a flight from Toronto Pearson Airport to O'Hare Airport?
The lowest price advertised for a round-trip flight between Toronton Pearson and O'Hare Airport is ฿8,180. But you better get a move on. This price is based on fares available within the last 7 days on Expedia for flights departing within the next year. Prices and availability are subject to change. Additional terms apply.
Do I need to pay a cancellation fee if I cancel my flight from Pearson Intl. Airport (YYZ) to ORD?
Most flights can be cancelled online, but every airline has its own terms and conditions. If you do decide to cancel your flight, go to our Customer Service Portal and follow the instructions.
How do I find cheap flights from Pearson Intl. Airport (YYZ) to ORD that have flexible change policies?
Many airlines offer the option to reschedule your flight without a change fee. All you pay is the difference between the original flight and the new flight. When you're searching for Pearson Intl. Airport (YYZ) to O'Hare Airport flights, you'll see a "no change fees" filter for you to select.
How far is the flight from Pearson Intl. Airport (YYZ) to O'Hare Intl. Airport (ORD)?
It's just 700 kilometres between Toronto Pearson Airport and O'Hare Intl. Airport (ORD). Chances are you'll spend more time travelling to and from the airport than you will actually flying!
Which airlines fly direct from YYZ to ORD?
American Airlines (AA) is one of the top choices for travellers jetting between YYZ and O'Hare Intl. Airport (ORD). Select from the 152 flights it offers on this route each month. You could also have a look at the deals on offer with United Airlines (UA). This carrier operates 152 flights a month between Mississauga and Chicago.
Are Pearson Intl. Airport (YYZ) to O'Hare Intl. Airport (ORD) flight tickets cheaper when they're purchased at the last minute?
Booking your trip from Pearson Intl. Airport (YYZ) to O'Hare Airport at the last minute could save you some serious cash. However, it could end up costing a good deal more! If you'd rather avoid the risk, book well ahead of your departure date. In fact, Expedia has some of the best bargains as far ahead as 12 months in advance. If your preferred carrier hasn't released tickets yet, check back frequently as deals are updated on Expedia all the time.

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