NZ$188 Cheap Flights Toronto to Chicago (YYZ-ORD)

View NZ$188 flight on Fri, 12 Sep. 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 for one-way flights and round trip tickets for the period specified. Prices and availability are subject to change. Additional terms apply.

Air Canada
Fri, 12 Sep. - Sun, 14 Sep.
YYZ
Toronto
ORD
Chicago
NZ$290 Return, found 1 day ago
NZ$290
Return
found 1 day ago
Select Air Canada flight, departing Fri, 12 Sep. from Toronto to Chicago, returning Sun, 14 Sep., priced at NZ$290 found 1 day ago
United
Thu, 6 Nov. - Wed, 12 Nov.
YYZ
Toronto
ORD
Chicago
NZ$302 Return, found 4 days ago
NZ$302
Return
found 4 days ago
Select United flight, departing Thu, 6 Nov. from Toronto to Chicago, returning Wed, 12 Nov., priced at NZ$302 found 4 days ago
Air Canada
Thu, 6 Nov. - Wed, 12 Nov.
YYZ
Toronto
ORD
Chicago
NZ$318 Return, found 4 days ago
NZ$318
Return
found 4 days ago
Select Air Canada flight, departing Thu, 6 Nov. from Toronto to Chicago, returning Wed, 12 Nov., priced at NZ$318 found 4 days ago
Air Canada
Thu, 30 Oct. - Sun, 2 Nov.
YYZ
Toronto
ORD
Chicago
NZ$319 Return, found 1 day ago
NZ$319
Return
found 1 day ago
Select Air Canada flight, departing Thu, 30 Oct. from Toronto to Chicago, returning Sun, 2 Nov., priced at NZ$319 found 1 day ago
American Airlines
Thu, 6 Nov. - Wed, 12 Nov.
YYZ
Toronto
ORD
Chicago
NZ$322 Return, found 4 days ago
NZ$322
Return
found 4 days ago
Select American Airlines flight, departing Thu, 6 Nov. from Toronto to Chicago, returning Wed, 12 Nov., priced at NZ$322 found 4 days ago
American Airlines
Thu, 30 Oct. - Sun, 2 Nov.
YYZ
Toronto
ORD
Chicago
NZ$329 Return, found 1 day ago
NZ$329
Return
found 1 day ago
Select American Airlines flight, departing Thu, 30 Oct. from Toronto to Chicago, returning Sun, 2 Nov., priced at NZ$329 found 1 day ago
American Airlines
Thu, 30 Oct. - Sun, 2 Nov.
YYZ
Toronto
ORD
Chicago
NZ$335 Return, found 1 day ago
NZ$335
Return
found 1 day ago
Select American Airlines flight, departing Thu, 30 Oct. from Toronto to Chicago, returning Sun, 2 Nov., priced at NZ$335 found 1 day ago
American Airlines
Thu, 30 Oct. - Sun, 2 Nov.
YYZ
Toronto
ORD
Chicago
NZ$338 Return, found 1 day ago
NZ$338
Return
found 1 day ago
Select American Airlines flight, departing Thu, 30 Oct. from Toronto to Chicago, returning Sun, 2 Nov., priced at NZ$338 found 1 day ago
United
Thu, 6 Nov. - Wed, 12 Nov.
YYZ
Toronto
ORD
Chicago
NZ$341 Return, found 4 days ago
NZ$341
Return
found 4 days ago
Select United flight, departing Thu, 6 Nov. from Toronto to Chicago, returning Wed, 12 Nov., priced at NZ$341 found 4 days ago
Delta
Thu, 6 Nov. - Wed, 12 Nov.
YYZ
Toronto
ORD
Chicago
NZ$380 Return, found 4 days ago
NZ$380
Return
found 4 days ago
Select Delta flight, departing Thu, 6 Nov. from Toronto to Chicago, returning Wed, 12 Nov., priced at NZ$380 found 4 days ago
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Flight from Toronto to Chicago route information
Origin airport
Pearson Intl.
Destination airport
O'Hare Intl.
Return price
NZ$290
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 NZ$188 and roundtrip prices from NZ$290. 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 NZ$290. 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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