£105 Cheap Flights from Toronto (YYZ) to Chicago (ORD)

View £105 flight on Wed, 6 May 2026Opens in a new window

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

  • Be in the know

    Get alerts if flight prices drop or rise*

  • Book smarter

    Save up to 25% on select hotels after you book a flight*

  • Earn twice

    Earn your airline miles on top of our rewards
    Sign in

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

Prices were available within the past 7 days and start at £105 for one-way flights and £169 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

United
Tue, 5 May - Sat, 16 May
YYZ
Toronto
ORD
Chicago
£169 Return, found 3 days ago
£169
Return
found 3 days ago
Select United flight, departing Tue, 5 May from Toronto to Chicago, returning Sat, 16 May, priced at £169 found 3 days ago
Air Canada
Sat, 23 May - Fri, 29 May
YYZ
Toronto
ORD
Chicago
£172 Return, found 5 hours ago
£172
Return
found 5 hours ago
Select Air Canada flight, departing Sat, 23 May from Toronto to Chicago, returning Fri, 29 May, priced at £172 found 5 hours ago
Delta
Tue, 12 May - Thu, 14 May
YYZ
Toronto
ORD
Chicago
£172 Return, found 5 days ago
£172
Return
found 5 days ago
Select Delta flight, departing Tue, 12 May from Toronto to Chicago, returning Thu, 14 May, priced at £172 found 5 days ago
Air Canada
Tue, 26 May - Tue, 9 Jun
YYZ
Toronto
ORD
Chicago
£173 Return, found 1 day ago
£173
Return
found 1 day ago
Select Air Canada flight, departing Tue, 26 May from Toronto to Chicago, returning Tue, 9 Jun, priced at £173 found 1 day ago
Air Canada
Tue, 16 Jun - Sun, 21 Jun
YYZ
Toronto
ORD
Chicago
£174 Return, found 5 days ago
£174
Return
found 5 days ago
Select Air Canada flight, departing Tue, 16 Jun from Toronto to Chicago, returning Sun, 21 Jun, priced at £174 found 5 days ago
Air Canada
Fri, 22 May - Sat, 6 Jun
YYZ
Toronto
ORD
Chicago
£175 Return, found 1 day ago
£175
Return
found 1 day ago
Select Air Canada flight, departing Fri, 22 May from Toronto to Chicago, returning Sat, 6 Jun, priced at £175 found 1 day ago
Air Canada
Tue, 16 Jun - Thu, 18 Jun
YYZ
Toronto
ORD
Chicago
£177 Return, found 6 days ago
£177
Return
found 6 days ago
Select Air Canada flight, departing Tue, 16 Jun from Toronto to Chicago, returning Thu, 18 Jun, priced at £177 found 6 days ago
Air Canada
Sat, 23 May - Fri, 29 May
YYZ
Toronto
ORD
Chicago
£177 Return, found 5 hours ago
£177
Return
found 5 hours ago
Select Air Canada flight, departing Sat, 23 May from Toronto to Chicago, returning Fri, 29 May, priced at £177 found 5 hours ago
Air Canada
Sat, 9 May - Wed, 13 May
YYZ
Toronto
ORD
Chicago
£178 Return, found 1 day ago
£178
Return
found 1 day ago
Select Air Canada flight, departing Sat, 9 May from Toronto to Chicago, returning Wed, 13 May, priced at £178 found 1 day ago
American Airlines
Sat, 23 May - Sun, 24 May
YYZ
Toronto
ORD
Chicago
£181 Return, found 4 days ago
£181
Return
found 4 days ago
Select American Airlines flight, departing Sat, 23 May from Toronto to Chicago, returning Sun, 24 May, priced at £181 found 4 days ago

Alternative airports near Chicago

Prices were available within the past 7 days. Prices and availability are subject to change.

Select flight to Midway Intl. MDW. Cheapest and Closest option available. Average driving time to city centre is 16 minutes. Flights from £172
MDW
Midway Intl.
CheapestClosest
Average driving time to city centre16 min
Flights from £172

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 £169. 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.

Frequently asked questions

How much does a flight from Toronto, ON (YYZ-Pearson Intl.) to Chicago, IL (ORD-O'Hare Intl.) cost?
One-way flights typically cost between £226 and £789 and return flights often range between £389 and £1,356. Flight prices vary based on the month and day of the week you want to travel, as well as the airline and how far in advance you book your ticket. Filter your search on Expedia by "Price (lowest to highest)" to see the cheapest fares first, and use the Price Tracking tool to receive alerts when Anaa (AAA) to Toronto, ON (YYZ-Pearson Intl.) ticket fares go up or down.
What is the cheapest month to fly from Toronto, ON (YYZ-Pearson Intl.) to Chicago, IL (ORD-O'Hare Intl.)?
April is typically the cheapest month to fly from Toronto Pearson International Airport (YYZ) to Chicago O'Hare International Airport (ORD), with average return fares of approximately £394. This is about 10% lower than the average price throughout the past year. April often sees lower prices as the peak spring break travel subsides and before the busy summer season begins. Other cheap months to fly from Toronto Pearson International Airport (YYZ) to Chicago O'Hare International Airport (ORD) include February and May.
Which airlines fly direct from Toronto, ON (YYZ-Pearson Intl.) to Chicago, IL (ORD-O'Hare Intl.)?
Enter YYZ to ORD and your travel dates, then apply the 'Nonstop' filter to see only direct flights.
How do I find cheap flights from Toronto, ON (YYZ-Pearson Intl.) to Chicago, IL (ORD-O'Hare Intl.)?
To find a cheap flight from Toronto, ON (YYZ-Pearson Intl.) to Chicago, IL (ORD-O'Hare Intl.), be flexible with your dates. Traveling outside of peak vacation months and booking a mid-week flight can help you save. Early morning and late night flights are often more affordable, too. Expedia allows you to compare flight times, airlines and routes all in one place to find low fares. You can also set up Price Tracking and receive alerts when fares go up or down.
What is the best airline to fly with from Toronto, ON (YYZ-Pearson Intl.) to Chicago, IL (ORD-O'Hare Intl.)?
The best airline to fly with from Toronto, ON (YYZ-Pearson Intl.) (YYZ) to Chicago, IL (ORD-O'Hare Intl.) (ORD) will differ from traveller to traveller. If you like to fly early, AA offers early morning flights. If price is the most important factor, YX typically offers the lowest fares. AC offers the most daily flights from Toronto, ON (YYZ-Pearson Intl.) (YYZ) to Chicago, IL (ORD-O'Hare Intl.) (ORD), which is brilliant if flexibility is what you value most. The best carrier for this journey could also be the one you have a loyalty membership with, as flying with that airline or another airline within the same alliance could help you collect points or enjoy lounge access.
What is the best time to fly from Toronto, ON (YYZ-Pearson Intl.) to Chicago, IL (ORD-O'Hare Intl.)?
The best time to fly from Toronto Pearson International Airport (YYZ) to Chicago O'Hare International Airport (ORD) is typically May. This month offers a great balance, as it's one of the cheapest times to fly, with average return flights around £394, and it's also a very popular time to travel, meaning you'll have plenty of flight options. This information is based on booking data from the past year.
How many flights per day from Toronto, ON (YYZ-Pearson Intl.) to Chicago, IL (ORD-O'Hare Intl.)?
There are approximately 22 nonstop flights per day from Toronto, ON (YYZ-Pearson Intl.) to Chicago, IL (ORD-O'Hare Intl.). For even more choice, look at flights that include layovers, as there are around 91 connecting flights per day. Some common connection points include LaGuardia (LGA), Pierre Elliott Trudeau Intl. (YUL), and Detroit Metropolitan Wayne County (DTW).
What is the earliest flight from Toronto, ON (YYZ-Pearson Intl.) to Chicago, IL (ORD-O'Hare Intl.)?
The earliest flight from Toronto, ON (YYZ-Pearson Intl.) to Chicago, IL (ORD-O'Hare Intl.) typically departs at approximately 12:30 AM local time, operated by Air Canada. This service operates year-round. An early departure like this can help you maximise your time at your destination. To compare early flights on Expedia, select the "Early Morning" and "Morning" filters in your search.
What day of the week has the most flights from Toronto, ON (YYZ-Pearson Intl.) to Chicago, IL (ORD-O'Hare Intl.)?
You'll typically find the most flights from Toronto Pearson International Airport (YYZ) to Chicago O'Hare International Airport (ORD) on a Friday, with around 107 flights available. This gives you plenty of options for your travel plans. Major airlines on this route include Air Canada, United Airlines, and Delta Air Lines. Fridays offer notably more flight options compared to other days of the week.
What are the most popular departure times for flights from Toronto, ON (YYZ-Pearson Intl.) to Chicago, IL (ORD-O'Hare Intl.)?
The most popular departure times for flights from Toronto Pearson International Airport (YYZ) to Chicago O'Hare International Airport (ORD) are in the morning, from 6am to 9am. About 25% of passengers prefer this time. Many major carriers, including Delta Air Lines, United Airlines and Air Canada, offer flights during this window. This timing works well because it allows you to get an early start on your travel day, arriving in Chicago with plenty of time for business or leisure activities.
How long does it take to fly from Toronto, ON (YYZ-Pearson Intl.) to Chicago, IL (ORD-O'Hare Intl.)?
A nonstop flight from YYZ to ORD typically takes around 2 hours, covering approximately 436 miles. Connecting flights on this route usually add 4 hours to your travel time. Keep in mind that actual flight times can vary due to wind patterns, weather, and air traffic.
Can you fly business or first class from Toronto, ON (YYZ-Pearson Intl.) to Chicago, IL (ORD-O'Hare Intl.)?
Select the "Business class" and "First class" filters when looking for YYZ to ORD flights on Expedia. This is the easiest way to compare prices, routes and flight times for your trip.
How much is a business class flight from Toronto, ON (YYZ-Pearson Intl.) to Chicago, IL (ORD-O'Hare Intl.)?
A direct, return business class ticket from Toronto, ON (YYZ-Pearson Intl.) to Chicago, IL (ORD-O'Hare Intl.) typically costs between £970 - £1,327. A non-stop, one-way business class flight is usually around £521 - £888. You may also be able to find a cheaper business class journey between Toronto, ON (YYZ-Pearson Intl.) to Chicago, IL (ORD-O'Hare Intl. Prices often fluctuate based on seasonality and how early you book. You may also be able to find a cheaper business class journey between Anaa (AAA) (AAA) to Toronto, ON (YYZ-Pearson Intl.) (YYZ) if you opt for a connecting flight.
How do I earn miles on a Toronto, ON (YYZ-Pearson Intl.) to Chicago, IL (ORD-O'Hare Intl.) flight with Expedia?
It's easy to earn miles on a Toronto, ON (YYZ-Pearson Intl.) to Chicago, IL (ORD-O'Hare Intl.) flight when you book with Expedia. Before you confirm your booking, simply select your frequent flyer program and enter your program number. As a member of One Key™, you can also earn OneKeyCash™* on top of your airline miles when you book with Expedia. *Excludes taxes and fees. OneKeyCash is not redeemable for cash and can only be used on Expedia and other participating brands.
What airports do you fly into for Chicago from Pearson Intl. (YYZ)?
From Pearson Intl. (YYZ), you can fly into Midway Intl. (MDW) and O'Hare Intl. (ORD) in Chicago. Some flights may connect through major hubs like Liberty Intl. (EWR), Washington Dulles Intl. (IAD), Nashville Intl. (BNA) before reaching Chicago. Compare routes and airports on Expedia to find the best flight options for your travel plans.
Is it cheaper to buy a plane ticket from Toronto, ON (YYZ-Pearson Intl.) to Chicago, IL (ORD-O'Hare Intl.) at the last minute?
Typically, booking a last minute flight from Toronto, ON (YYZ-Pearson Intl.) to Chicago, IL (ORD-O'Hare Intl.) will be more expensive than booking in advance. As the departure date approaches, there are usually fewer seats available which can drive up the cost. However, if there's some wiggle room with your travel dates and times, you could bag a cheap last-minute fare.
Is it cheaper to book a Toronto, ON (YYZ-Pearson Intl.) to Chicago, IL (ORD-O'Hare Intl.) flight and hotel package?
Securing a Toronto, ON (YYZ-Pearson Intl.) to Chicago, IL (ORD-O'Hare Intl.) flight and hotel package is usually cheaper than booking separately. With Expedia, you can enjoy the ease of organizing your travels all in one place. Select from our extensive range of stays and then add flights, activities and car rentals to your booking. Bundle everything together, and you could save hundreds of dollars.
Can I cancel or change the date of my flight from Toronto, ON (YYZ-Pearson Intl.) to Chicago, IL (ORD-O'Hare Intl.)?
If you booked your Toronto, ON (YYZ-Pearson Intl.) to Chicago, IL (ORD-O'Hare Intl.) flight within the last 24 hours, you may be able to modify or cancel it without any fees. Depending on the airline and the type of ticket you have, additional charges may apply for changes beyond this timeframe. Airline policies and contact information can be found in your itinerary or confirmation email. Or, head to our Customer Service portal if you'd like more information.

Travel information

0
Origin airport
Pearson Intl.
Destination airport
O'Hare Intl.
Airlines serving
Air Canada, American Airlines, Delta, United, WestJet
Return price
£169
Distance
697 km

Book with confidence

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 £169 and range up to £181.  

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 May, 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.  

Compare flights from Toronto to Chicago easily and book with confidence

Explore a world of travel with Expedia

*Available to Expedia members.