$102 Cheap Flights from Toronto (YYZ) to Chicago (ORD)

View $102 flight on Thu, Feb 26, 2026Opens in a new window

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

Cheap Flights from Toronto to Chicago (YYZ-ORD)

Prices were available within the past 7 days and start at $102 for one-way flights and $153 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

Air Canada
Wed, Jan 21 - Sat, Jan 31
YYZ
Toronto
ORD
Chicago
$153 Roundtrip, found 1 day ago
$153
Roundtrip
found 1 day ago
Select Air Canada flight, departing Wed, Jan 21 from Toronto to Chicago, returning Sat, Jan 31, priced at $153 found 1 day ago
United
Fri, Feb 20 - Fri, Feb 27
YYZ
Toronto
ORD
Chicago
$153 Roundtrip, found 1 day ago
$153
Roundtrip
found 1 day ago
Select United flight, departing Fri, Feb 20 from Toronto to Chicago, returning Fri, Feb 27, priced at $153 found 1 day ago
Air Canada
Thu, Feb 26 - Mon, Mar 2
YYZ
Toronto
ORD
Chicago
$153 Roundtrip, just found
$153
Roundtrip
just found
Select Air Canada flight, departing Thu, Feb 26 from Toronto to Chicago, returning Mon, Mar 2, priced at $153 just found
American Airlines
Tue, Nov 18 - Wed, Dec 10
YYZ
Toronto
ORD
Chicago
$157 Roundtrip, found 1 day ago
$157
Roundtrip
found 1 day ago
Select American Airlines flight, departing Tue, Nov 18 from Toronto to Chicago, returning Wed, Dec 10, priced at $157 found 1 day ago
Air Canada
Thu, Feb 26 - Mon, Mar 2
YYZ
Toronto
ORD
Chicago
$166 Roundtrip, just found
$166
Roundtrip
just found
Select Air Canada flight, departing Thu, Feb 26 from Toronto to Chicago, returning Mon, Mar 2, priced at $166 just found
Air Canada
Fri, Jan 9 - Thu, Jan 15
YYZ
Toronto
ORD
Chicago
$167 Roundtrip, found 16 hours ago
$167
Roundtrip
found 16 hours ago
Select Air Canada flight, departing Fri, Jan 9 from Toronto to Chicago, returning Thu, Jan 15, priced at $167 found 16 hours ago
American Airlines
Fri, Jan 9 - Thu, Jan 15
YYZ
Toronto
ORD
Chicago
$169 Roundtrip, found 16 hours ago
$169
Roundtrip
found 16 hours ago
Select American Airlines flight, departing Fri, Jan 9 from Toronto to Chicago, returning Thu, Jan 15, priced at $169 found 16 hours ago
American Airlines
Fri, Feb 6 - Wed, Feb 11
YYZ
Toronto
ORD
Chicago
$170 Roundtrip, just found
$170
Roundtrip
just found
Select American Airlines flight, departing Fri, Feb 6 from Toronto to Chicago, returning Wed, Feb 11, priced at $170 just found
Delta
Fri, Feb 20 - Fri, Feb 27
YYZ
Toronto
ORD
Chicago
$192 Roundtrip, found 1 day ago
$192
Roundtrip
found 1 day ago
Select Delta flight, departing Fri, Feb 20 from Toronto to Chicago, returning Fri, Feb 27, priced at $192 found 1 day ago
Porter Airlines
Thu, Nov 13 - Sun, Nov 16
YYZ
Toronto
ORD
Chicago
$335 Roundtrip, just found
$335
Roundtrip
just found
Select Porter Airlines flight, departing Thu, Nov 13 from Toronto to Chicago, returning Sun, Nov 16, priced at $335 just found

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

September is typically the cheapest month to fly

From $164 - $184 per traveler.

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. Closest option available. Average driving time to city center is 16 minutes. Flights from $309
MDW
Midway Intl.
Closest
Average driving time to city center16 min
Flights from $309

Frequently asked questions

How much does a flight from Pearson Intl. Airport (YYZ) to O'Hare Intl. Airport (ORD) cost?
Lock in a cheap one-way flight from $102 or cheap return flight from $153 from Pearson Intl. Airport (YYZ) to O'Hare Intl. Airport (ORD) with Expedia. Enter your travel dates and sort by "Price (lowest to highest)" to find our cheapest flight offers on this route.
What is the cheapest month to fly from Pearson Intl. Airport (YYZ) to O'Hare Intl. Airport (ORD)?
January is the least expensive month to fly from YYZ to ORD. Timing your trip outside of the busy season is often the key to finding better fares.
Which airlines fly direct from Pearson Intl. Airport (YYZ) to O'Hare Intl. Airport (ORD)?
Enjoy an uninterrupted journey to O'Hare Intl. Airport (ORD). 3 carriers operate nonstop flights from Pearson Intl. Airport (YYZ), including:

  • United Airlines
  • Air Canada
  • American Airlines

What is the cheapest airline that flies from Pearson Intl. Airport (YYZ) to O'Hare Intl. Airport (ORD)?
The cheapest airline to offer flights between Pearson Intl. Airport (YYZ) and O'Hare Intl. Airport (ORD) will vary based on your travel plans. American Airlines and Air Canada are just some good options offering reasonable prices. Use Expedia's filters to compare airlines in one place and find the right YYZ to ORD flight for your budget.
How many flights per day from Pearson Intl. Airport (YYZ) to O'Hare Intl. Airport (ORD)?
When jetting out of Pearson Intl. Airport (YYZ), you'll have a choice from an average of 13 daily nonstop flights to O'Hare Intl. Airport (ORD).
What are the most popular departure times for flights from Pearson Intl. Airport (YYZ) to O'Hare Intl. Airport (ORD)?
The 6 AM departures from YYZ to ORD are the most sought after. These flights can come with a higher price due to their popularity. If you want to save money, pick a less crowded time to fly.
What day of the week has the most flights from YYZ to ORD?
If you depart on a Wednesday, you'll get the widest range of choices for flights from Pearson Intl. Airport (YYZ) to O'Hare Intl. Airport (ORD).
What is the earliest flight from Pearson Intl. Airport (YYZ) to O'Hare Intl. Airport (ORD)?
Pearson Intl. Airport (YYZ)'s earliest flight to O'Hare Intl. Airport (ORD) is at approximately 6:15AM UTC-5. With a total flight time of 2h 15m, you'll land at around 7:30AM UTC-6.
How long does it take to fly from Pearson Intl. Airport (YYZ) to O'Hare Intl. Airport (ORD)?
Flights from YYZ to ORD have an average travel time of 2 hours and 5 minutes. The distance between the two is 440 mi.
What airline has the least delays from YYZ to ORD?
British Airways has the strongest track record for on-time direct flights from Pearson Intl. Airport (YYZ) to O'Hare Intl. Airport (ORD), with an on-time score of 88%. Use the Expedia App to look up your journey status before you leave and get real-time alerts about any changes.
What is the best time to fly from Pearson Intl. Airport (YYZ) to O'Hare Intl. Airport (ORD)?
To avoid possible delays on the Pearson Intl. Airport (YYZ) to O'Hare Intl. Airport (ORD) route, aim to travel before 3 PM. Flights after this time are 22% more likely to be canceled.**Most reliable time of the day and month to travel recommendation is based on January through August 2024 flight status data sourced from OAG's global flight data platform.
What airports do you fly into for Chicago from Pearson Intl. Airport (YYZ)?
If you're traveling on a direct flight from Pearson Intl. Airport (YYZ) to Chicago, O'Hare Intl. Airport (ORD) is the only airport you can touch down at.
Is it cheaper to buy a plane ticket from Pearson Intl. Airport (YYZ) to O'Hare Intl. Airport (ORD) last-minute?
Waiting until right before your break to book a ticket from YYZ to ORD generally means paying more. While you may find some last-minute discounts, they're not always guaranteed. Be flexible with your itinerary for a better chance of getting a bargain.
Is it cheaper to book a YYZ to ORD flight and hotel package?
Compared with arranging flights and hotels separately, booking a YYZ to ORD flight and hotel package with Expedia could lead to significant savings. Better still, having it all in one place will take the hassle out of planning your trip. Just pick your flights and select from our wide range of hotels, then customize your trip with other add-ons like tours, car rentals and activities.
Can I cancel or change the date of my flight from Pearson Intl. Airport (YYZ) to O'Hare Intl. Airport (ORD)?
Typically, you can reschedule or cancel your YYZ to ORD flight. However, additional fees may apply, especially if you booked more than 24 hours ago. Double-check your itinerary for the airline's fees and rules on flight changes, or if you'd like more information, visit our Customer Service portal.

Travel information

0
Origin airport
Pearson Intl.
Destination airport
O'Hare Intl.
Airlines serving
Air Canada, American Airlines, Delta, Porter Airlines, United, WestJet
Roundtrip price
$152
Distance
436 mi

Book with confidence

Toronto to Chicago Flights

The cheapest times to fly from Toronto to Chicago

On average, Thursday can be the cheapest time to fly, according to data from the Airlines Reporting Corporation (ARC), one of the world's biggest databases for global airline sales. The data reveals that you could save up to 16% by flying on a Thursday—the cheapest day to travel on average—instead of a Sunday—the most expensive. Some of the most affordable flights from Toronto to Chicago are during the month of January. You can find some of the cheapest flights from Toronto to Chicago with Expedia's search tool and vast selection of airlines.

 

The best time to book a flight from Toronto to Chicago

Sunday is one of the best days to book for cheap flights from Toronto to Chicago: Tickets reserved on a Sunday cost between 6% and 13% less than those reserved on a Friday, according to ARC data. The data also suggests booking early can also lead to cheaper airfares. You could save 24% by buying your tickets for domestic flights at least a month in advance and 10% by booking international flights 2 months in advance.

 

How to find cheap round-trip tickets from Toronto to Chicago

Being flexible with your dates and using Expedia's Price Drop Protection and Price Tracking features are some of the best ways of finding a cheap ticket from Toronto to Chicago in 2025. You can also book with separate airlines for your outbound and return journeys, from $102 one-way. Expedia also offers Price Drop Protection, so if the cost of your airfare goes down after booking, you'll receive a credit for the difference*. This is available for a small fee, and is free to One Key Gold and Platinum tier members.

 

Expedia's Price Tracking feature means you can stay on top of airfares without manually checking every day. It sends you automated price alerts for cheap Toronto to Chicago flights and uses historical data to indicate when the best time to book is. Download Expedia's free app to activate this handy tool in a few easy taps.

 

You could also save big by booking one of Expedia's vacation packages. Bundling together your Toronto to Chicago airfare with your accommodations and car rental is often cheaper than booking everything separately. There’s also One Key, Expedia's generous rewards program. Join for free and you could earn One Key cash on most bookings to save on future adventures.

 

*Terms apply.

 

Disclaimer: ARC The statistics are based on average round-trip ticket prices between January and August 2023. The percentages you see are averages.

 

Toronto to Chicago Flights

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*Available to One Key members.