$99 Cheap Flights from Toronto (YYZ) to Chicago (ORD)

View $99 flight on Fri, Nov 21, 2025Opens in a new window

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

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Cheap Flights from Toronto to Chicago (YYZ-ORD)

Prices were available within the past 7 days and start at $99 for one-way flights and $148 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

United
Fri, Nov 21 - Mon, Nov 24
YYZ
Toronto
ORD
Chicago
$148 Roundtrip, found 2 hours ago
$148
Roundtrip
found 2 hours ago
Select United flight, departing Fri, Nov 21 from Toronto to Chicago, returning Mon, Nov 24, priced at $148 found 2 hours ago
Air Canada
Fri, Nov 21 - Mon, Nov 24
YYZ
Toronto
ORD
Chicago
$148 Roundtrip, found 2 hours ago
$148
Roundtrip
found 2 hours ago
Select Air Canada flight, departing Fri, Nov 21 from Toronto to Chicago, returning Mon, Nov 24, priced at $148 found 2 hours ago
United
Thu, Oct 30 - Mon, Nov 3
YYZ
Toronto
ORD
Chicago
$152 Roundtrip, found 3 days ago
$152
Roundtrip
found 3 days ago
Select United flight, departing Thu, Oct 30 from Toronto to Chicago, returning Mon, Nov 3, priced at $152 found 3 days ago
Air Canada
Thu, Sep 18 - Mon, Sep 22
YYZ
Toronto
ORD
Chicago
$154 Roundtrip, found 5 days ago
$154
Roundtrip
found 5 days ago
Select Air Canada flight, departing Thu, Sep 18 from Toronto to Chicago, returning Mon, Sep 22, priced at $154 found 5 days ago
United
Thu, Oct 23 - Wed, Oct 29
YYZ
Toronto
ORD
Chicago
$155 Roundtrip, found 3 days ago
$155
Roundtrip
found 3 days ago
Select United flight, departing Thu, Oct 23 from Toronto to Chicago, returning Wed, Oct 29, priced at $155 found 3 days ago
United
Sat, Nov 1 - Sun, Nov 2
YYZ
Toronto
ORD
Chicago
$157 Roundtrip, found 6 days ago
$157
Roundtrip
found 6 days ago
Select United flight, departing Sat, Nov 1 from Toronto to Chicago, returning Sun, Nov 2, priced at $157 found 6 days ago
Air Canada
Fri, Nov 21 - Mon, Nov 24
YYZ
Toronto
ORD
Chicago
$158 Roundtrip, found 2 hours ago
$158
Roundtrip
found 2 hours ago
Select Air Canada flight, departing Fri, Nov 21 from Toronto to Chicago, returning Mon, Nov 24, priced at $158 found 2 hours ago
Air Canada
Sat, Nov 1 - Thu, Nov 6
YYZ
Toronto
ORD
Chicago
$158 Roundtrip, found 3 days ago
$158
Roundtrip
found 3 days ago
Select Air Canada flight, departing Sat, Nov 1 from Toronto to Chicago, returning Thu, Nov 6, priced at $158 found 3 days ago
American Airlines
Thu, Oct 30 - Mon, Nov 3
YYZ
Toronto
ORD
Chicago
$161 Roundtrip, found 3 days ago
$161
Roundtrip
found 3 days ago
Select American Airlines flight, departing Thu, Oct 30 from Toronto to Chicago, returning Mon, Nov 3, priced at $161 found 3 days ago
Delta
Sat, Sep 20 - Thu, Sep 25
YYZ
Toronto
ORD
Chicago
$205 Roundtrip, found 3 days ago
$205
Roundtrip
found 3 days ago
Select Delta flight, departing Sat, Sep 20 from Toronto to Chicago, returning Thu, Sep 25, priced at $205 found 3 days ago

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

September is typically the cheapest month to fly

From $153 - $257 per traveler.

Graph displaying average flight prices per month

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 $288
MDW
Midway Intl.
Closest
Average driving time to city center16 min
Flights from $288
0
Flights from Toronto (YYZ) to Chicago (ORD)
Origin airport
Pearson Intl.
Destination airport
O'Hare Intl.
Airlines serving
Air Canada, American Airlines, Delta, United, WestJet
Roundtrip price
$148
Distance
436 mi

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 November. 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 $99 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.

 

Frequently asked questions

How much does a flight from Pearson Intl. Airport (YYZ) to O'Hare Intl. Airport (ORD) cost?
You can pick up cheap return tickets starting at $155 from Pearson Intl. Airport (YYZ) to O'Hare Intl. Airport (ORD). This information is based on the cheapest price found on Expedia for this return journey departing within the next three months. This airfare is for a United flight leaving YYZ on July 25 2025 and touching down at ORD. The price was last updated on July 7 2025 and has not changed since.
What is the cheapest month to fly from YYZ to ORD?
The cheapest flights from YYZ to ORD are usually during off-peak season, when demand is lower. To save money, avoid flying during public holidays, school breaks and major local events.
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 YYZ to ORD?
At the moment, the cheapest airline operating one-way flights from YYZ to ORD is Air Canada. You can jet off on this route from $103. This fare is based on the lowest price found on Expedia departing within the next three months. The flight takes off from YYZ on October 2 2025. Prices were last updated on July 7 2025 and have not changed since.
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.

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