CA $168 Cheap Flights from Toronto (YYZ) to Chicago (ORD)

View CA $168 flight on Fri, May 23, 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 CA $168 for one-way flights and CA $266 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

United
Sat., Jun. 28 - Mon., Jun. 30
YYZ
Toronto
ORD
Chicago
CA $266 Roundtrip, just found
CA $266
Roundtrip
just found
Select United flight, departing Sat., Jun. 28 from Toronto to Chicago, returning Mon., Jun. 30, priced at CA $266 just found
American Airlines
Thu., Jun. 12 - Sat., Jun. 21
YYZ
Toronto
ORD
Chicago
CA $266 Roundtrip, just found
CA $266
Roundtrip
just found
Select American Airlines flight, departing Thu., Jun. 12 from Toronto to Chicago, returning Sat., Jun. 21, priced at CA $266 just found
Air Canada
Wed., Jun. 11 - Tue., Jul. 8
YYZ
Toronto
ORD
Chicago
CA $266 Roundtrip, just found
CA $266
Roundtrip
just found
Select Air Canada flight, departing Wed., Jun. 11 from Toronto to Chicago, returning Tue., Jul. 8, priced at CA $266 just found
United
Sat., Jun. 28 - Mon., Jun. 30
YYZ
Toronto
ORD
Chicago
CA $274 Roundtrip, just found
CA $274
Roundtrip
just found
Select United flight, departing Sat., Jun. 28 from Toronto to Chicago, returning Mon., Jun. 30, priced at CA $274 just found
United
Sat., Jun. 28 - Mon., Jun. 30
YYZ
Toronto
ORD
Chicago
CA $284 Roundtrip, just found
CA $284
Roundtrip
just found
Select United flight, departing Sat., Jun. 28 from Toronto to Chicago, returning Mon., Jun. 30, priced at CA $284 just found
United
Sun., May 25 - Wed., Jun. 4
YYZ
Toronto
ORD
Chicago
CA $291 Roundtrip, just found
CA $291
Roundtrip
just found
Select United flight, departing Sun., May 25 from Toronto to Chicago, returning Wed., Jun. 4, priced at CA $291 just found
United
Thu., May 8 - Wed., May 14
YYZ
Toronto
ORD
Chicago
CA $292 Roundtrip, just found
CA $292
Roundtrip
just found
Select United flight, departing Thu., May 8 from Toronto to Chicago, returning Wed., May 14, priced at CA $292 just found
American Airlines
Fri., May 23 - Mon., May 26
YYZ
Toronto
ORD
Chicago
CA $297 Roundtrip, just found
CA $297
Roundtrip
just found
Select American Airlines flight, departing Fri., May 23 from Toronto to Chicago, returning Mon., May 26, priced at CA $297 just found
United
Sun., May 11 - Sun., May 25
YYZ
Toronto
ORD
Chicago
CA $300 Roundtrip, just found
CA $300
Roundtrip
just found
Select United flight, departing Sun., May 11 from Toronto to Chicago, returning Sun., May 25, priced at CA $300 just found
Delta
Fri., May 23 - Mon., May 26
YYZ
Toronto
ORD
Chicago
CA $309 Roundtrip, just found
CA $309
Roundtrip
just found
Select Delta flight, departing Fri., May 23 from Toronto to Chicago, returning Mon., May 26, priced at CA $309 just found
Flight from Toronto to Chicago (YYZ - ORD) route information
Origin airport
Pearson Intl.
Destination airport
O'Hare Intl.
Airlines serving
Air Canada, American Airlines, Delta, United, WestJet
Roundtrip price
CA $265
Distance
697 km

Toronto to Chicago Flights

Ready for an adventure? Thought so! Prepare to see the sights when you book your trip from Toronto to Chicago with Expedia.ca. Whether you’re visiting for business or pleasure, we know how important it is to bring home travel stories. Maybe your tales will include the best dinner of your life, or the weirdest street art you saw in the city, or the concert that turned you into a fan of a new band. Whatever it is, your new favourite anecdote is right around the corner. Book your trip from YYZ to ORD and begin your journey!

Getting a cheap deal on your trip sets the tone for the perfect holiday. And with Expedia.ca, you know you can travel from Toronto to Chicago on the cheap, with enough money left over for a stellar time in the city. That could mean more tours with the kids, more concerts with the spouse, more dessert amongst co-workers, or even front row seats to a sports game if you’re travelling solo. It’s your holiday! Make it great.

Travelling shouldn’t cost an arm and a leg before you even get to relax on the plane’s armrests. Count on Expedia.ca to get you the best discounts on flights from YYZ to ORD. And remember this: You can also save big when you bundle. Add a hotel or car rental deal to your flight and witness those savings add up. Hey, more money for more souvenirs, right? Right! Pack your bags and we’ll see you on the route.

Combine your Chicago flight with a hotel and/or car rental for a package deal designed to save you even more money! Discover additional savings by booking in advance or find a last minute deal. There are tons of ways to save on your flights from with Expedia Canada. Use us as your top travel destination and have the confidence that you’re getting a bargain!

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 CA $266. 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 canceled 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 kilometers between Toronto Pearson Airport and O’Hare Intl. Airport (ORD). Chances are you’ll spend more time traveling 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 travelers 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.

Explore a world of travel with Expedia

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