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

CA $190 Cheap Flights from Toronto (YTZ) to Chicago (ORD)

View CA $190 flight on Sun, Nov 22, 2026Opens in a new window

Popular airlines from Billy Bishop Toronto City Airport (YTZ) to Chicago O'Hare International Airport (ORD)

  • Be in the know

    Get alerts if flight prices drop or rise*

  • Book smarter

    Save up to 30% 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 (YTZ) to Chicago (ORD)

Prices were available within the past 7 days and start at CA $190 for one-way flights and CA $314 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

Air Canada
Wed, Nov 11 - Thu, Nov 26
YTZ
Toronto
ORD
Chicago
CA $314 Roundtrip, found 3 hours ago
CA $314
Roundtrip
found 3 hours ago
Select Air Canada flight, departing Wed, Nov 11 from Toronto to Chicago, returning Thu, Nov 26, priced at CA $314 found 3 hours ago
Air Canada
Wed, Nov 11 - Thu, Nov 26
YTZ
Toronto
ORD
Chicago
CA $318 Roundtrip, found 3 hours ago
CA $318
Roundtrip
found 3 hours ago
Select Air Canada flight, departing Wed, Nov 11 from Toronto to Chicago, returning Thu, Nov 26, priced at CA $318 found 3 hours ago
Porter Airlines
Sun, Nov 8 - Tue, Nov 10
YTZ
Toronto
ORD
Chicago
CA $335 Roundtrip, just found
CA $335
Roundtrip
just found
Select Porter Airlines flight, departing Sun, Nov 8 from Toronto to Chicago, returning Tue, Nov 10, priced at CA $335 just found
Air Canada
Sun, Nov 22 - Mon, Nov 23
YTZ
Toronto
ORD
Chicago
CA $338 Roundtrip, found 1 hour ago
CA $338
Roundtrip
found 1 hour ago
Select Air Canada flight, departing Sun, Nov 22 from Toronto to Chicago, returning Mon, Nov 23, priced at CA $338 found 1 hour ago
Air Canada
Sat, Oct 24 - Sat, Oct 31
YTZ
Toronto
ORD
Chicago
CA $339 Roundtrip, just found
CA $339
Roundtrip
just found
Select Air Canada flight, departing Sat, Oct 24 from Toronto to Chicago, returning Sat, Oct 31, priced at CA $339 just found
Porter Airlines
Wed, Nov 11 - Thu, Nov 26
YTZ
Toronto
ORD
Chicago
CA $359 Roundtrip, found 3 hours ago
CA $359
Roundtrip
found 3 hours ago
Select Porter Airlines flight, departing Wed, Nov 11 from Toronto to Chicago, returning Thu, Nov 26, priced at CA $359 found 3 hours ago
Air Canada
Sun, Nov 22 - Mon, Nov 23
YTZ
Toronto
ORD
Chicago
CA $360 Roundtrip, found 1 hour ago
CA $360
Roundtrip
found 1 hour ago
Select Air Canada flight, departing Sun, Nov 22 from Toronto to Chicago, returning Mon, Nov 23, priced at CA $360 found 1 hour ago
Porter Airlines
Thu, Oct 29 - Mon, Nov 2
YTZ
Toronto
ORD
Chicago
CA $364 Roundtrip, found 4 hours ago
CA $364
Roundtrip
found 4 hours ago
Select Porter Airlines flight, departing Thu, Oct 29 from Toronto to Chicago, returning Mon, Nov 2, priced at CA $364 found 4 hours ago
Air Transat
Sun, Nov 8 - Tue, Nov 10
YTZ
Toronto
ORD
Chicago
CA $377 Roundtrip, just found
CA $377
Roundtrip
just found
Select Air Transat flight, departing Sun, Nov 8 from Toronto to Chicago, returning Tue, Nov 10, priced at CA $377 just found
United
Tue, Oct 20 - Fri, Nov 6
YTZ
Toronto
ORD
Chicago
CA $417 Roundtrip, found 1 hour ago
CA $417
Roundtrip
found 1 hour ago
Select United flight, departing Tue, Oct 20 from Toronto to Chicago, returning Fri, Nov 6, priced at CA $417 found 1 hour 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 CA $335
MDW
Midway Intl.
Closest
Average driving time to city centre16 min
Flights from CA $335

Frequently asked questions

How much does a flight from Toronto, ON (YTZ-Billy Bishop Toronto City) to Chicago, IL (ORD-O'Hare Intl.) cost?
You can find cheap one-way flights from CA $190 and cheap return flights from CA $314 YTZ to ORD with Expedia. One-way flights typically cost between CA$200 and CA$1479, and return flights often range between CA$478 and CA$4779. 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 YTZ to ORD ticket fares go up or down.
What is the cheapest month to fly from Toronto, ON (YTZ-Billy Bishop Toronto City) to Chicago, IL (ORD-O'Hare Intl.)?
The cheapest months to fly from YTZ to ORD are typically during off-peak season when demand is low. Traveling in off-peak or shoulder months is usually a good way to secure cheap tickets, just remember to avoid flying during holidays if you are able to. Use the calendar view in your search to see which months have low fares on this route.
Which airlines fly direct from Toronto, ON (YTZ-Billy Bishop Toronto City) to Chicago, IL (ORD-O'Hare Intl.)?
There are 2 airlines that offer direct flights from Billy Bishop Toronto City (YTZ) to Chicago O'Hare Intl. (ORD):
  • Air Canada operates 14 direct flights from Billy Bishop Toronto City (YTZ) to Chicago O'Hare Intl. (ORD) every week.
  • United operates 10 direct flights from Billy Bishop Toronto City (YTZ) to Chicago O'Hare Intl. (ORD) every week.
What is the cheapest airline that flies from Toronto, ON (YTZ-Billy Bishop Toronto City) to Chicago, IL (ORD-O'Hare Intl.)?
Air Canada is one of the cheapest airlines offering nonstop return flights from Toronto, ON (YTZ-Billy Bishop Toronto City) to Chicago, IL (ORD-O'Hare Intl.), with tickets starting from around CA$274 for flights that can be booked for departure within the next year. Porter Airlines offers one of the cheapest connecting return flights on this route, with tickets starting from around CA$680. These prices are per adult for economy/coach class. 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.
How do I find cheap flights from Toronto, ON (YTZ-Billy Bishop Toronto City) to Chicago, IL (ORD-O'Hare Intl.)?
To find a cheap flight from Toronto, ON (YTZ-Billy Bishop Toronto City) 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 (YTZ-Billy Bishop Toronto City) to Chicago, IL (ORD-O'Hare Intl.)?
The best airline to fly with from Toronto, ON (YTZ-Billy Bishop Toronto City) 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, Passaredo Transportes Aereos typically offers the lowest fares. Air Canada offers the most daily flights from Toronto, ON (YTZ-Billy Bishop Toronto City) 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 (YTZ-Billy Bishop Toronto City) to Chicago, IL (ORD-O'Hare Intl.)?
The best time to fly is usually mid-week (Tuesday or Wednesday) and during early morning hours as flights tend to be cheaper, less crowded, and generally more on-time. Avoid major holidays and peak vacation seasons for smoother travel. Combining off-peak days and hours often gives the best combination of cost, comfort, and convenience.
How many flights per day from Toronto, ON (YTZ-Billy Bishop Toronto City) to Chicago, IL (ORD-O'Hare Intl.)?
You'll find approximately 2 nonstop flights per day from Billy Bishop Toronto City (YTZ) to O'Hare Intl. (ORD). For even more choices, look at flights that include layovers, as there are around 16 connecting flights per day. Some common connection points include LaGuardia (LGA), Pierre Elliott Trudeau Intl. (YUL), and Macdonald-Cartier Intl. (YOW).
What is the earliest flight from Toronto, ON (YTZ-Billy Bishop Toronto City) to Chicago, IL (ORD-O'Hare Intl.)?
The earliest flight from Billy Bishop Toronto City (YTZ) to O'Hare Intl. (ORD) typically departs around 6:45 AM. This flight is operated by Air Canada. This is a seasonal service, active in December. An early departure like this can help you make the most of 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 (YTZ-Billy Bishop Toronto City) to Chicago, IL (ORD-O'Hare Intl.)?
You'll typically find the most flights from Billy Bishop Toronto City (YTZ) to O'Hare Intl. (ORD) on a Tuesday, with around 33 flights available. This gives you plenty of options for your travel plans. Major airlines on this route include Air Canada, Porter Airlines, and Passaredo Transportes Aereos. Flight options are notably more abundant on Tuesdays compared to other days of the week.
What are the most popular departure times for flights from Toronto, ON (YTZ-Billy Bishop Toronto City) to Chicago, IL (ORD-O'Hare Intl.)?
The most popular departure times for flights from Billy Bishop Toronto City (YTZ) to O'Hare Intl. (ORD) are in the early afternoon, from 12pm to 3pm. Many major carriers, including Air Canada, Porter Airlines and Passaredo Transportes Aereos, offer flights during this window. Many travelers prefer this time because it allows for a relaxed morning before heading to the airport, and you'll arrive at your destination with plenty of time to settle in.
How long does it take to fly from Toronto, ON (YTZ-Billy Bishop Toronto City) to Chicago, IL (ORD-O'Hare Intl.)?
A non-stop flight from Billy Bishop Toronto City (YTZ) to Chicago, IL (ORD-O'Hare Intl.) typically takes about 2 hours. This route covers a distance of approximately 718 kilometres. If you opt for a one-stop flight, your travel time will be longer, usually around 7 hours 30 minutes. Flights with two or more stops generally take even longer, averaging about 12 hours 18 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 (YTZ) to Chicago, IL (ORD)?
Select the "Business class" and "First class" filters when looking for Toronto, ON (YTZ) to Chicago, IL (ORD) flights on Expedia. This is the easiest way to compare prices, routes and flight times for your trip.
How do I earn miles on a Toronto, ON (YTZ-Billy Bishop Toronto City) to Chicago, IL (ORD-O'Hare Intl.) flight with Expedia?
It's easy to earn miles on a Toronto, ON (YTZ-Billy Bishop Toronto City) 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, IL (ORD) from Toronto, ON (YTZ)?
If you're planning to travel to Chicago from Billy Bishop Toronto City (YTZ), you can fly directly into O'Hare Intl. (ORD). Some flights may connect through major hubs like Pierre Elliott Trudeau Intl. (YUL), 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 (YTZ-Billy Bishop Toronto City) to Chicago, IL (ORD-O'Hare Intl.) at the last minute?
Typically, booking a last minute flight from Toronto, ON (YTZ-Billy Bishop Toronto City) 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 (YTZ-Billy Bishop Toronto City) to Chicago, IL (ORD-O'Hare Intl.) flight and hotel package?
Securing a Toronto, ON (YTZ-Billy Bishop Toronto City) 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 (YTZ-Billy Bishop Toronto City) to Chicago, IL (ORD-O'Hare Intl.)?
If you booked your Toronto, ON (YTZ-Billy Bishop Toronto City) 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

Origin airport
Billy Bishop Toronto City
Destination airport
O'Hare Intl.
Airlines serving
Air Canada, Air Transat, Porter Airlines, United
Roundtrip price
CA $313
Distance
713 km
Average flight time
1 hour 6 mins

Book with confidence

Toronto to Chicago Flights

The easy way to book your flights from Toronto to Chicago 

With Expedia, it’s simple to find and book flights to Chicago from Toronto whether you’re traveling for business or pleasure. Enter your travel dates, hit search, and choose your flight from 20 airlines that cover this route. There are nonstop flights to O'Hare Intl., too.  

Choose your preferred carrier and cabin class with the advanced search tool and select your ideal departure time. Then, if you want, you can see just nonstop or refundable flights. And if you’re traveling last minute, just enter the date to check out flights from Toronto to Chicago today, tomorrow, or this week.  

 

Save dollars with cheap flights from Billy Bishop Toronto City, YTZ to O'Hare Intl., ORD 

Sort your search results by price to find great deals on your flight from Toronto to Chicago—you get all your cheapest options first. Grab yourself a bargain now—the lowest price on flights to Chicago from Toronto currently is just CA $314 rising to CA $417.  

Here are more money-saving tips: 

  • Fly in November when flight prices are normally at their lowest 
  • Book about a month to 6 weeks before you travel for the best prices to Chicago  
  • Avoid peak season and weekends when flights can cost more
  • Early morning and late-night flights are sometimes cheaper, so try varying your travel times 
  • One surefire way to save money on your flight is to book your flight and hotel together with Expedia. Sometimes, the savings are so large that the flight is basically free! 

 

Reasons to choose Expedia for your flight to Chicago from Toronto 

Whatever your destination, budget, or reason to travel, in just one quick search, you can choose from loads of flights, airlines, and cabin classes. The filters make it quick and easy to find your ideal flights, and if you choose one of the flexible options, you won’t be charged to change your flight. So book your flight to Chicago with Expedia today.

Toronto to Chicago Flights

Explore a world of travel with Expedia

*Available to Expedia members.