Popular airlines from Toronto to Chicago
Air CanadaAir Canada
WestJetWestJet
Porter AirlinesPorter Airlines
Air TransatAir Transat
DeltaDelta
UnitedUnited
American AirlinesAmerican Airlines
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Cheap Flights from Toronto (YTO) to Chicago (CHI)
Prices were available within the past 7 days and start at £78 for one-way flights and £123 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.
Find the cheapest month to fly from Toronto (YTO) to Chicago (CHI)
September is typically the cheapest month to fly
Graph displaying average flight prices per month
Origin airport | Billy Bishop Toronto City |
Destination airport | O'Hare Intl. |
Airlines serving | Air Canada, Air Transat, American Airlines, Delta, Porter Airlines, United, WestJet |
Return price | £122 |
Distance | 713 km |
Compare flights from Toronto to Chicago easily and book with confidence
For travelling on business or for pleasure, Expedia makes it easy to book your flights from Toronto to Chicago. Operating between them flights per day, 20 airlines cover the route. And fly direct, getting you to CHI-All Airports in just hours. If you have a preferred carrier, use our advanced search tool to find the right flight from YTO-All Airports to CHI-All Airports.
To make things even better, in the advanced search, you can also choose to fly economy, premium economy, business or first class, select your maximum number of stops, and pick your preferred departure and arrival time. You can also opt for refundable and direct flights.
Grab a great deal on your flight from YTO-All Airports (YTO) to CHI-All Airports (CHI)
The easiest way to view the best deals on flights from Toronto to Chicago today is to enter your travel dates and hit search. From here, you can sort your results by price to see the cheapest flights first. Right now, return flights from YTO-All Airports to CHI-All Airports start at just £123 and range up to £150.
To find an even better deal, try
- being flexible on your dates – midweek flights can be cheaper
- looking for other airports near Toronto and Chicago
- booking your flight during October, the cheapest month on this route
- varying your flight times – early morning and late at night are sometimes cheaper
Why you should book your Toronto to Chicago flight with Expedia!
We cater for all flight types, cabin classes and airlines. So whether you’re booking flights from YTO-All Airports to CHI-All Airports for a budget break or a business trip with a bit of pleasure thrown in, we make it easy to secure the seat that’s right for you.
Thanks to our supersized inventory that offers great choice all in one place, you know you’ll get a great deal with Expedia. Especially if you bundle your flight together with your hotel, you will unlock amazing savings. For added peace of mind, you can choose flexible bookings or filter to find refundable options, so you won’t pay a fee to change your flight.
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