S$167 Cheap Flights from Toronto to Chicago

View S$167 flight on Sat, 28 Feb, 2026Opens 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 S$167 for one-way flights and S$265 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

United
Wed, 11 Feb - Mon, 23 Feb
YYZ
Toronto
ORD
Chicago
S$265 Return, found 4 days ago
S$265
Return
found 4 days ago
Select United flight, departing Wed, 11 Feb from Toronto to Chicago, returning Mon, 23 Feb, priced at S$265 found 4 days ago
Air Canada
Sat, 24 Jan - Sat, 7 Feb
YYZ
Toronto
ORD
Chicago
S$294 Return, found 4 days ago
S$294
Return
found 4 days ago
Select Air Canada flight, departing Sat, 24 Jan from Toronto to Chicago, returning Sat, 7 Feb, priced at S$294 found 4 days ago
Air Canada
Thu, 22 Jan - Sat, 31 Jan
YYZ
Toronto
ORD
Chicago
S$323 Return, found 4 days ago
S$323
Return
found 4 days ago
Select Air Canada flight, departing Thu, 22 Jan from Toronto to Chicago, returning Sat, 31 Jan, priced at S$323 found 4 days ago
Delta
Fri, 16 Jan - Fri, 23 Jan
YYZ
Toronto
ORD
Chicago
S$331 Return, found 5 days ago
S$331
Return
found 5 days ago
Select Delta flight, departing Fri, 16 Jan from Toronto to Chicago, returning Fri, 23 Jan, priced at S$331 found 5 days ago
Air Canada
Fri, 16 Jan - Fri, 23 Jan
YYZ
Toronto
ORD
Chicago
S$349 Return, found 5 days ago
S$349
Return
found 5 days ago
Select Air Canada flight, departing Fri, 16 Jan from Toronto to Chicago, returning Fri, 23 Jan, priced at S$349 found 5 days ago
United
Sat, 21 Feb - Sun, 8 Mar
YYZ
Toronto
ORD
Chicago
S$352 Return, found 4 days ago
S$352
Return
found 4 days ago
Select United flight, departing Sat, 21 Feb from Toronto to Chicago, returning Sun, 8 Mar, priced at S$352 found 4 days ago
Air Canada
Fri, 16 Jan - Fri, 23 Jan
YYZ
Toronto
ORD
Chicago
S$354 Return, found 5 days ago
S$354
Return
found 5 days ago
Select Air Canada flight, departing Fri, 16 Jan from Toronto to Chicago, returning Fri, 23 Jan, priced at S$354 found 5 days ago
Air Canada
Fri, 29 May - Fri, 5 Jun
YYZ
Toronto
ORD
Chicago
S$373 Return, found 2 days ago
S$373
Return
found 2 days ago
Select Air Canada flight, departing Fri, 29 May from Toronto to Chicago, returning Fri, 5 Jun, priced at S$373 found 2 days ago
Air Canada
Tue, 21 Apr - Thu, 23 Apr
YYZ
Toronto
ORD
Chicago
S$377 Return, found 2 days ago
S$377
Return
found 2 days ago
Select Air Canada flight, departing Tue, 21 Apr from Toronto to Chicago, returning Thu, 23 Apr, priced at S$377 found 2 days ago
American Airlines
Fri, 16 Jan - Fri, 23 Jan
YYZ
Toronto
ORD
Chicago
S$391 Return, found 5 days ago
S$391
Return
found 5 days ago
Select American Airlines flight, departing Fri, 16 Jan from Toronto to Chicago, returning Fri, 23 Jan, priced at S$391 found 5 days ago

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

February is typically the cheapest month to fly

From S$198 - S$335 per traveller.

Alternative airports near Chicago

Prices were available within the past 7 days. Prices and availability are subject to change.

Select flight to O'Hare Intl. ORD. Cheapest option available. Average driving time to city centre is 23 minutes. Flights from S$294
ORD
O'Hare Intl.
Cheapest
Average driving time to city centre23 min
Flights from S$294
0
Toronto to Chicago route information
Origin airport
Pearson Intl.
Destination airport
O'Hare Intl.
Return price
S$264
Distance
697 km

Flights from Toronto to Chicago

There are several airlines that operate frequent flights from Toronto (YYZ) to Chicago (ORD) including

The earliest flight leaves Pearson Intl. Airport at 06:30 and arrives at O'Hare Intl. Airport at 07:13. The last flight of the day departs Toronto at 20:55 and arrives at Chicago at 21:42.

The flight distance from Toronto to Chicago is about 703 km, the shortest flight is 01 hours 42 minutes with WestJet.

Expedia lets you search across the largest number of airlines and Chicago flights, which means that you’ll be able to find a great flight deal at the perfect travel date and time. Our simple-to-use booking engine makes looking for terrific bargains easy and hassle-free; just enter your travel dates and departure city, and let Expedia do the rest! Adjust your travel dates and explore connecting flights to find an even better deal on your Toronto Chicago flight!

Browse through dozens of options and rest assured that you’re seeing the best price guaranteed! Our friendly customer service representatives are here to serve you 24 hours day to provide assistance and answer any questions that you may have about booking your Toronto to Chicago trip. There’s simply no substitute for great prices suited to your travel needs and backed by excellent customer support.

Combine your Chicago flight with a hotel and/or car rental for a package deal designed to save you even more money! Discover additional savings by booking in advance or find a last minute deal. There are tons of ways to save on your flights from Toronto to Chicago with Expedia. Use us as your stop travel destination and have the confidence that you’re getting a bargain!

Frequently asked questions

How much is a flight from Toronto Pearson Airport to O'Hare Airport?
The lowest price advertised for a round-trip flight between Toronton Pearson and O'Hare Airport is S$265. But you better get a move on. This price is based on fares available within the last 7 days on Expedia for flights departing within the next year. Prices and availability are subject to change. Additional terms apply.
Do I need to pay a cancellation fee if I cancel my flight from Pearson Intl. Airport (YYZ) to ORD?
Most flights can be cancelled online, but every airline has its own terms and conditions. If you do decide to cancel your flight, go to our Customer Service Portal and follow the instructions.
How do I find cheap flights from Pearson Intl. Airport (YYZ) to ORD that have flexible change policies?
Many airlines offer the option to reschedule your flight without a change fee. All you pay is the difference between the original flight and the new flight. When you're searching for Pearson Intl. Airport (YYZ) to O'Hare Airport flights, you'll see a "no change fees" filter for you to select.
How far is the flight from Pearson Intl. Airport (YYZ) to O'Hare Intl. Airport (ORD)?
It's just 700 kilometres between Toronto Pearson Airport and O'Hare Intl. Airport (ORD). Chances are you'll spend more time travelling to and from the airport than you will actually flying!
Which airlines fly direct from YYZ to ORD?
American Airlines (AA) is one of the top choices for travellers jetting between YYZ and O'Hare Intl. Airport (ORD). Select from the 152 flights it offers on this route each month. You could also have a look at the deals on offer with United Airlines (UA). This carrier operates 152 flights a month between Mississauga and Chicago.
Are Pearson Intl. Airport (YYZ) to O'Hare Intl. Airport (ORD) flight tickets cheaper when they're purchased at the last minute?
Booking your trip from Pearson Intl. Airport (YYZ) to O'Hare Airport at the last minute could save you some serious cash. However, it could end up costing a good deal more! If you'd rather avoid the risk, book well ahead of your departure date. In fact, Expedia has some of the best bargains as far ahead as 12 months in advance. If your preferred carrier hasn't released tickets yet, check back frequently as deals are updated on Expedia all the time.

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