£98 Cheap Flights from Toronto (YYZ) to Chicago (ORD)

View £98 flight on Wed, 4 Feb 2026Opens 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 £98 for one-way flights and £165 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

Air Canada
Sun, 26 Oct - Thu, 30 Oct
YYZ
Toronto
ORD
Chicago
£165 Return, found 3 days ago
£165
Return
found 3 days ago
Select Air Canada flight, departing Sun, 26 Oct from Toronto to Chicago, returning Thu, 30 Oct, priced at £165 found 3 days ago
Air Canada
Wed, 10 Dec - Fri, 12 Dec
YYZ
Toronto
ORD
Chicago
£170 Return, found 5 days ago
£170
Return
found 5 days ago
Select Air Canada flight, departing Wed, 10 Dec from Toronto to Chicago, returning Fri, 12 Dec, priced at £170 found 5 days ago
Air Canada
Wed, 10 Dec - Fri, 12 Dec
YYZ
Toronto
ORD
Chicago
£171 Return, found 5 days ago
£171
Return
found 5 days ago
Select Air Canada flight, departing Wed, 10 Dec from Toronto to Chicago, returning Fri, 12 Dec, priced at £171 found 5 days ago
WestJet
Thu, 20 Nov - Thu, 27 Nov
YYZ
Toronto
ORD
Chicago
£198 Return, found 3 days ago
£198
Return
found 3 days ago
Select WestJet flight, departing Thu, 20 Nov from Toronto to Chicago, returning Thu, 27 Nov, priced at £198 found 3 days ago
Air Canada
Mon, 4 May - Fri, 8 May
YYZ
Toronto
ORD
Chicago
£202 Return, found 2 days ago
£202
Return
found 2 days ago
Select Air Canada flight, departing Mon, 4 May from Toronto to Chicago, returning Fri, 8 May, priced at £202 found 2 days ago
WestJet
Mon, 20 Oct - Thu, 23 Oct
YYZ
Toronto
ORD
Chicago
£207 Return, found 1 hour ago
£207
Return
found 1 hour ago
Select WestJet flight, departing Mon, 20 Oct from Toronto to Chicago, returning Thu, 23 Oct, priced at £207 found 1 hour ago
WestJet
Mon, 3 Nov - Mon, 17 Nov
YYZ
Toronto
ORD
Chicago
£207 Return, found 2 days ago
£207
Return
found 2 days ago
Select WestJet flight, departing Mon, 3 Nov from Toronto to Chicago, returning Mon, 17 Nov, priced at £207 found 2 days ago
American Airlines
Sat, 11 Oct - Wed, 15 Oct
YYZ
Toronto
ORD
Chicago
£220 Return, found 2 hours ago
£220
Return
found 2 hours ago
Select American Airlines flight, departing Sat, 11 Oct from Toronto to Chicago, returning Wed, 15 Oct, priced at £220 found 2 hours ago
United
Sat, 11 Oct - Wed, 15 Oct
YYZ
Toronto
ORD
Chicago
£220 Return, found 2 hours ago
£220
Return
found 2 hours ago
Select United flight, departing Sat, 11 Oct from Toronto to Chicago, returning Wed, 15 Oct, priced at £220 found 2 hours ago
Delta
Sun, 12 Oct - Tue, 14 Oct
YYZ
Toronto
ORD
Chicago
£224 Return, found 2 hours ago
£224
Return
found 2 hours ago
Select Delta flight, departing Sun, 12 Oct from Toronto to Chicago, returning Tue, 14 Oct, priced at £224 found 2 hours ago

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

November is typically the cheapest month to fly

From £120 - £213 per traveller.
0
Flight from Toronto to Chicago route information
Origin airport
Pearson Intl.
Destination airport
O'Hare Intl.
Airlines serving
Air Canada, American Airlines, Delta, United, WestJet
Return price
£165
Distance
697 km

Compare flights from Toronto to Chicago easily and book with confidence

For travelling on business or for pleasure, Expedia makes it easy to book your flights from Toronto to Chicago. Operating between them flights per day, 20 airlines cover the route. And fly direct, getting you to O'Hare Intl. in just hours. If you have a preferred carrier, use our advanced search tool to find the right flight from Pearson Intl. to O'Hare Intl..  

To make things even better, in the advanced search, you can also choose to fly economy, premium economy, business or first class, select your maximum number of stops, and pick your preferred departure and arrival time. You can also opt for refundable and direct flights. 

Grab a great deal on your flight from Pearson Intl. (YYZ) to O'Hare Intl. (ORD)

The easiest way to view the best deals on flights from Toronto to Chicago today is to enter your travel dates and hit search. From here, you can sort your results by price to see the cheapest flights first. Right now, return flights from Pearson Intl. to O'Hare Intl. start at just £165 and range up to £224.  

To find an even better deal, try  

  • being flexible on your dates – midweek flights can be cheaper
  • looking for other airports near Toronto and Chicago
  • booking your flight during October, the cheapest month on this route
  • varying your flight times – early morning and late at night are sometimes cheaper 

Why you should book your Toronto to Chicago flight with Expedia!

We cater for all flight types, cabin classes and airlines. So whether you’re booking flights from Pearson Intl. to O'Hare Intl. for a budget break or a business trip with a bit of pleasure thrown in, we make it easy to secure the seat that’s right for you.  

Thanks to our supersized inventory that offers great choice all in one place, you know you’ll get a great deal with Expedia. Especially if you bundle your flight together with your hotel, you will unlock amazing savings. For added peace of mind, you can choose flexible bookings or filter to find refundable options, so you won’t pay a fee to change your flight.  

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 £165. 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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