Question 1

How much does a flight from Toronto, ON (YYZ-Pearson Intl.) to Chicago, IL (ORD-O'Hare Intl.) cost?

Accepted Answer

You can find cheap one-way flights from $144 and cheap return flights from $233 Toronto, ON (YYZ-Pearson Intl.) to Chicago, IL (ORD-O'Hare Intl.) with Expedia. One-way flights generally range between $134 and $1349, and roundtrip flights usually range from $259 to $1278. 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 Toronto, ON (YYZ-Pearson Intl.) to Chicago, IL (ORD-O'Hare Intl.) ticket fares go up or down.

*Typical price ranges based on flights available on Expedia in the last year. Prices include multi-airline options.

Question 2

What is the cheapest month to fly from Toronto, ON (YYZ-Pearson Intl.) to Chicago, IL (ORD-O'Hare Intl.)?

Accepted Answer

April is the cheapest month to fly from Toronto (YYZ) to Chicago (ORD), with average return fares around $284. This is about 10% lower than the average price throughout the year, as demand tends to decrease after the busy winter months. Other cheap months to fly from Toronto to Chicago include February and May.

*Averages based on flights available on Expedia in the last year.

Question 3

Which airlines fly direct from Toronto, ON (YYZ-Pearson Intl.) to Chicago, IL (ORD-O'Hare Intl.)?

Accepted Answer

Choose from 6 airlines operating direct flights from YYZ to ORD:

United operates around 84 direct flights from YYZ to ORD every week
Air Canada operates around 39 direct flights from YYZ to ORD every week
American Airlines operates around 37 direct flights from YYZ to ORD every week
British Airways operates around 21 direct flights from YYZ to ORD every week
Qantas Airways operates around 21 direct flights from YYZ to ORD every week

Question 4

What is the cheapest airline that flies from Toronto, ON (YYZ-Pearson Intl.) to Chicago, IL (ORD-O'Hare Intl.)?

Accepted Answer

Alaska Airlines is one of the cheapest airlines offering connecting flights from Toronto, ON (YYZ) to Chicago, IL (ORD), starting from around $284 for a round-trip ticket. Use Expedia's search tool to compare the prices and schedules of airlines that fly this route to find the best option for your plans and budget.

*Prices based on flights available on Expedia in the last year.

Question 5

How do I find cheap flights from Toronto, ON (YYZ-Pearson Intl.) to Chicago, IL (ORD-O'Hare Intl.)?

Accepted Answer

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.

Question 6

What is the best airline to fly with from Toronto, ON (YYZ-Pearson Intl.) to Chicago, IL (ORD-O'Hare Intl.)?

Accepted Answer

The best airline to fly with from Toronto (YYZ) to Chicago (ORD) will differ from traveler to traveler. If you like to fly early, American Airlines offers early morning flights. If price is the most important factor, OO typically offers the lowest fares. Air Canada offers the most daily flights from Toronto to Chicago, 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.

Question 7

What is the best time to fly from Toronto, ON (YYZ-Pearson Intl.) to Chicago, IL (ORD-O'Hare Intl.)?

Accepted Answer

For flights from Toronto (YYZ) to Chicago (ORD), April and May are the best months to fly, with average return flight prices around $284. These months offer a nice combination of good weather and lower fares, making it a great time to explore the Windy City.

*Prices based on flights available on Expedia in the last year.

Question 8

How many flights per day from Toronto, ON (YYZ-Pearson Intl.) to Chicago, IL (ORD-O'Hare Intl.)?

Accepted Answer

You can find approximately 23 nonstop flights per day from Pearson Intl. (YYZ) to O'Hare Intl. (ORD). For more options, look at flights that include layovers.

Question 9

What is the earliest flight from Toronto, ON (YYZ-Pearson Intl.) to Chicago, IL (ORD-O'Hare Intl.)?

Accepted Answer

Sort flights by "Departure (earliest)" on Expedia to find the earliest flight from YYZ to ORD. To compare more early flights, use the "Early Morning" and "Morning" filters in your search.

Question 10

How long does it take to fly from Toronto, ON (YYZ-Pearson Intl.) to Chicago, IL (ORD-O'Hare Intl.)?

Accepted Answer

A nonstop flight from YYZ to ORD typically takes around 2 hours, covering approximately 436 miles. Connecting flights on this route usually add 3 hours 50 minutes to your travel time. Keep in mind that actual flight times can vary due to wind patterns, weather, and air traffic.

Question 11

Can you fly business or first class from Toronto, ON (YYZ-Pearson Intl.) to Chicago, IL (ORD-O'Hare Intl.)?

Accepted Answer

You can fly business class between YYZ and ORD. Airlines that offer business class service on this route include:

Air Canada
American Airlines
United Airlines

First class cabins are available on:

United Airlines
Delta Air Lines
Air Canada

Question 12

How much is a business class flight from Toronto, ON (YYZ-Pearson Intl.) to Chicago, IL (ORD-O'Hare Intl.)?

Accepted Answer

A direct, return business class ticket from Toronto, ON (YYZ) to Chicago, IL (ORD) typically costs between $769 - $1,102. A non-stop, one-way business class flight is usually around $381 - $632 per adult. Prices often fluctuate based on seasonality and how early you book. 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.) if you opt for a connecting flight.

*Prices based on flights available on Expedia in the last year.

Question 13

How do I earn miles on a Toronto, ON (YYZ-Pearson Intl.) to Chicago, IL (ORD-O'Hare Intl.) flight with Expedia?

Accepted Answer

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.

Question 14

What airports do you fly into for Chicago from Pearson Intl. (YYZ)?

Accepted Answer

When traveling from Pearson Intl. (YYZ) to Chicago, you can fly into O'Hare Intl. (ORD) and Midway Intl. (MDW). Some flights may connect through major hubs like Winnipeg James Armstrong Richardson Intl. (YWG), Macdonald-Cartier Intl. (YOW), LaGuardia (LGA) before reaching Chicago. Compare routes and airports on Expedia to find the best flight options for your travel plans.

Question 15

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?

Accepted Answer

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.

Question 16

Is it cheaper to book a Toronto, ON (YYZ-Pearson Intl.) to Chicago, IL (ORD-O'Hare Intl.) flight and hotel package?

Accepted Answer

Securing a Toronto, ON (YYZ-Pearson Intl.) to Chicago, IL (ORD-O'Hare Intl.) Chicago Vacation Packages 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.

Question 17

Can I cancel or change the date of my flight from Toronto, ON (YYZ-Pearson Intl.) to Chicago, IL (ORD-O'Hare Intl.)?

Accepted Answer

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.

Origin airport	Pearson Intl.
Destination airport	O'Hare Intl.
Airlines serving	Air Canada, American Airlines, Delta, Porter Airlines, United, WestJet
Roundtrip price	$233
Distance	436 mi

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

Be in the know

Book smarter

Earn twice

Cheap Flights from Toronto to Chicago (YYZ-ORD)

Alternative airports near Chicago

Frequently asked questions

Travel information

Book with confidence

Toronto to Chicago Flights

Explore a world of travel with Expedia

$144 Cheap Flights from Toronto (YYZ) to Chicago (ORD)