A spacious airport terminal with high ceilings, check-in counters, and a Starbucks coffee shop.

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

View AU$213 flight on Wed, 9 Dec 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 35% 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 for one-way flights and round trip tickets for the period specified. Prices and availability are subject to change. Additional terms apply.

American Airlines
Wed, 9 Dec - Tue, 15 Dec
YYZ
Toronto
ORD
Chicago
AU$351 Return, found 5 days ago
AU$351
Return
found 5 days ago
Select American Airlines flight, departing Wed, 9 Dec from Toronto to Chicago, returning Tue, 15 Dec, priced at AU$351 found 5 days ago
United
Wed, 9 Dec - Tue, 15 Dec
YYZ
Toronto
ORD
Chicago
AU$351 Return, found 5 days ago
AU$351
Return
found 5 days ago
Select United flight, departing Wed, 9 Dec from Toronto to Chicago, returning Tue, 15 Dec, priced at AU$351 found 5 days ago
United
Wed, 9 Dec - Tue, 15 Dec
YYZ
Toronto
ORD
Chicago
AU$351 Return, found 5 days ago
AU$351
Return
found 5 days ago
Select United flight, departing Wed, 9 Dec from Toronto to Chicago, returning Tue, 15 Dec, priced at AU$351 found 5 days ago
Air Canada
Thu, 23 July - Mon, 27 July
YYZ
Toronto
ORD
Chicago
AU$352 Return, found 5 days ago
AU$352
Return
found 5 days ago
Select Air Canada flight, departing Thu, 23 July from Toronto to Chicago, returning Mon, 27 July, priced at AU$352 found 5 days ago
Air Canada
Fri, 4 Sept - Sun, 6 Sept
YYZ
Toronto
ORD
Chicago
AU$353 Return, found 4 days ago
AU$353
Return
found 4 days ago
Select Air Canada flight, departing Fri, 4 Sept from Toronto to Chicago, returning Sun, 6 Sept, priced at AU$353 found 4 days ago
Air Canada
Thu, 23 July - Mon, 27 July
YYZ
Toronto
ORD
Chicago
AU$356 Return, found 5 days ago
AU$356
Return
found 5 days ago
Select Air Canada flight, departing Thu, 23 July from Toronto to Chicago, returning Mon, 27 July, priced at AU$356 found 5 days ago
Air Canada
Tue, 4 Aug - Tue, 11 Aug
YYZ
Toronto
ORD
Chicago
AU$357 Return, found 1 day ago
AU$357
Return
found 1 day ago
Select Air Canada flight, departing Tue, 4 Aug from Toronto to Chicago, returning Tue, 11 Aug, priced at AU$357 found 1 day ago
United
Wed, 9 Dec - Tue, 15 Dec
YYZ
Toronto
ORD
Chicago
AU$359 Return, found 5 days ago
AU$359
Return
found 5 days ago
Select United flight, departing Wed, 9 Dec from Toronto to Chicago, returning Tue, 15 Dec, priced at AU$359 found 5 days ago
Delta
Sun, 2 Aug - Sat, 8 Aug
YYZ
Toronto
ORD
Chicago
AU$388 Return, found 3 days ago
AU$388
Return
found 3 days ago
Select Delta flight, departing Sun, 2 Aug from Toronto to Chicago, returning Sat, 8 Aug, priced at AU$388 found 3 days ago
WestJet
Sun, 10 Jan - Sun, 31 Jan
YYZ
Toronto
ORD
Chicago
AU$691 Return, found 17 hours ago
AU$691
Return
found 17 hours ago
Select WestJet flight, departing Sun, 10 Jan from Toronto to Chicago, returning Sun, 31 Jan, priced at AU$691 found 17 hours 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. Closest option available. Average driving time to city centre is 16 minutes. Flights from AU$391
MDW
Midway Intl.
Closest
Average driving time to city centre16 min
Flights from AU$391

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

January is typically the cheapest month to fly

From AU$320 - AU$926 per traveller.

Frequently asked questions

How much does a flight from Toronto, ON (YYZ-Pearson Intl.) to Chicago, IL (ORD-O'Hare Intl.) cost?
You can find cheap one-way flights from AU$213 and cheap return flights from AU$351 YYZ to ORD with Expedia. One-way flights typically cost between AU$200 and AU$714 and return flights often range between AU$431 and AU$1,366. 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 YYZ to ORD 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 around AU$423. April often sees lower prices as it's before the peak summer travel season, when demand tends to increase. Other budget-friendly months to fly this route include February and May.
Which airlines fly direct from Toronto, ON (YYZ-Pearson Intl.) to Chicago, IL (ORD-O'Hare Intl.)?
There are 6 airlines offering direct flights from Toronto Pearson International Airport (YYZ) to Chicago O'Hare International Airport (ORD). Here are some of the top carriers:
  • United operates 76 direct flights from Toronto Pearson International Airport (YYZ) to Chicago O'Hare International Airport (ORD) every week.
  • American Airlines operates 40 direct flights from Toronto Pearson International Airport (YYZ) to Chicago O'Hare International Airport (ORD) every week.
  • Air Canada operates 37 direct flights from Toronto Pearson International Airport (YYZ) to Chicago O'Hare International Airport (ORD) every week.
  • British Airways operates 21 direct flights from Toronto Pearson International Airport (YYZ) to Chicago O'Hare International Airport (ORD) every week.
  • Japan Airlines operates 7 direct flights from Toronto Pearson International Airport (YYZ) to Chicago O'Hare International Airport (ORD) every week.
How do I find cheap flights from Toronto, ON (YYZ) to Chicago, IL (ORD)?
To find a cheap flight from Toronto, ON (YYZ) to Chicago, IL (ORD), 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.) to Chicago, IL (ORD-O'Hare Intl.) will differ from traveler to traveler. If you like to fly early, Air Canada offers early morning flights. If price is the most important factor, Republic Airlines typically offers the lowest fares. Air Canada offers the most daily flights from Toronto, ON (YYZ-Pearson Intl.) to Chicago, IL (ORD-O'Hare Intl.), which is great 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 cheapest months to fly from Toronto, ON (YYZ-Pearson Intl.) to Chicago, IL (ORD-O'Hare Intl.) are typically April and May, with average return flights costing around AU$423. However, the most popular months for this route are July and June, meaning you'll find plenty of flight options during those times. If you're looking for the best balance of good prices and a wide selection of flights, you might consider travelling in late spring or early summer.
How many flights per day from Toronto, ON (YYZ-Pearson Intl.) to Chicago, IL (ORD-O'Hare Intl.)?
You'll find approximately 22 nonstop flights per day from Toronto Pearson International Airport (YYZ) to Chicago O'Hare International Airport (ORD). For even more choices, look at flights that include layovers, as there are around 93 connecting flights per day. Some common connection points include LaGuardia (LGA), Detroit Metropolitan Wayne County (DTW), and Pierre Elliott Trudeau Intl. (YUL).
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 around 12:30 AM local time. This flight is operated by Air Canada and runs year-round. An early departure like this can be great for maximizing your time in Chicago, allowing you to arrive early and start your day. 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 find the most flights from Toronto Pearson International Airport (YYZ) to Chicago O'Hare International Airport (ORD) on Mondays, with around 105 flights available. This gives you plenty of options for your travel plans. Major airlines on this route include Air Canada, Delta, and United. Flight schedules are quite consistent throughout the week, so you'll have a good selection of flights on most days.
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, ON (YYZ-Pearson Intl.) to Chicago, IL (ORD-O'Hare Intl.) are between 12pm and 3pm. Many major carriers, including Air Canada, Delta and United, offer flights during this window. Many travellers prefer this time as it allows for a productive morning before heading to the airport, and you'll arrive in Chicago with plenty of time to settle in for the evening.
How long does it take to fly from Toronto, ON (YYZ-Pearson Intl.) to Chicago, IL (ORD-O'Hare Intl.)?
A direct flight from Toronto Pearson International Airport (YYZ) to Chicago O'Hare International Airport (ORD) typically takes about 2 hours, covering a distance of approximately 702 kilometers. If you opt for a flight with one stop, your travel time will be longer, usually around 6 hours. Flights with two or more stops generally take about 7 hours 48 minutes. Keep in mind that actual flight times can vary due to factors like wind patterns and air traffic, so it's always a good idea to allow for some extra time when planning your trip.
Can you fly business or first class from Toronto, ON (YYZ-Pearson Intl.) to Chicago, IL (ORD-O'Hare Intl.)?
Yes, you can fly business class or first class between YYZ and ORD.Airlines that offer business class service on this route include:
  • Air Canada
  • Delta
  • United
  • American Airlines
First class cabins are available on Republic Airlines, Alaska Airlines, Skywest Air, Air Canada, Delta, and United.
How do I earn miles on a Toronto, ON (YYZ) to Chicago, IL (ORD) flight with Expedia?
It's easy to earn miles on a Toronto, ON (YYZ) to Chicago, IL (ORD) 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, IL (ORD) from Toronto, ON (YYZ)?
If you're planning to travel to Chicago from Pearson Intl. (YYZ), you can fly directly into O'Hare Intl. (ORD). Some flights may connect through major hubs like Winnipeg James Armstrong Richardson Intl. (YWG), Macdonald-Cartier Intl. (YOW), or LaGuardia (LGA) 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) to Chicago, IL (ORD) at the last minute?
Typically, booking a last minute flight from Toronto, ON (YYZ) to Chicago, IL (ORD) 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) to Chicago, IL (ORD) flight and hotel package?
Securing a Toronto, ON (YYZ) to Chicago, IL (ORD) 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) to Chicago, IL (ORD)?
If you booked your Toronto, ON (YYZ) to Chicago, IL (ORD) 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
AU$351
Distance
697 km

Book with confidence

Your quick guide to flights from Toronto to Chicago

Pick up great flights from Toronto to Chicago

With Expedia, you have your pick of flights a day with 20 airlines covering flights from Toronto to Chicago. Whether you’re on a business trip, a family holiday or a luxury break, just enter your travel dates, hit search then check out your choice of flights. Select from return, one way or multi-city flights, and use the advance search tool if you want a direct or refundable flight. You can narrow your search to show you just your preferred cabin class and airline, too. It’s all easy. You can book direct flights from Toronto to Chicago that take around hours.

Find cheap flights from Toronto to Chicago

From the great flight deals with prices currently ranging from AU$351 to AU$691, you can choose to see the cheapest flights first. Generally, you can book the cheapest flights from Toronto to Chicago around 4 to 6 weeks in advance. If your travel dates are flexible, try to avoid weekends and peak seasons – when you are more likely to grab the lowest prices. Even last minute, there are some impressive deals. The cheapest time to fly to Chicago is normally in December.

Reasons to book your flight from Toronto to Chicago with Expedia

Expedia makes it easy to find, book, and travel, with everything you need all in one place. When you enter your travel details, find fantastic deals just for you on flight tickets from Toronto to Chicago across all the main airline carriers, so you can save time, dollars, and hassle finding the perfect flight. If you think your plans could change, choose refundable flights so any changes won’t cost you more. Book your flight to Chicago right now and, if you join Expedia Rewards, you earn points this time and every time you travel with Expedia.

Your quick guide to flights from Toronto to Chicago

Explore a world of travel with Expedia

*Available to Expedia members.