$59 Cheap Flights from Chicago (CHI) to Toronto (YTO)

View $59 flight on Thu, Nov 27, 2025Opens in a new window

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Cheap Flights from Chicago to Toronto (CHI-YTO)

Prices were available within the past 7 days and start at $59 for one-way flights and $153 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

United
Mon, Nov 24 - Tue, Nov 25
ORD
Chicago
YYZ
Toronto
$153 Roundtrip, found 7 hours ago
$153
Roundtrip
found 7 hours ago
Select United flight, departing Mon, Nov 24 from Chicago to Toronto, returning Tue, Nov 25, priced at $153 found 7 hours ago
Air Canada
Tue, Nov 11 - Fri, Nov 21
ORD
Chicago
YYZ
Toronto
$157 Roundtrip, found 2 hours ago
$157
Roundtrip
found 2 hours ago
Select Air Canada flight, departing Tue, Nov 11 from Chicago to Toronto, returning Fri, Nov 21, priced at $157 found 2 hours ago
Air Canada
Wed, Nov 5 - Sat, Nov 8
ORD
Chicago
YYZ
Toronto
$158 Roundtrip, found 8 hours ago
$158
Roundtrip
found 8 hours ago
Select Air Canada flight, departing Wed, Nov 5 from Chicago to Toronto, returning Sat, Nov 8, priced at $158 found 8 hours ago
Air Canada
Tue, Nov 18 - Fri, Nov 28
ORD
Chicago
YYZ
Toronto
$158 Roundtrip, found 2 hours ago
$158
Roundtrip
found 2 hours ago
Select Air Canada flight, departing Tue, Nov 18 from Chicago to Toronto, returning Fri, Nov 28, priced at $158 found 2 hours ago
Air Canada
Mon, Nov 3 - Mon, Nov 10
ORD
Chicago
YYZ
Toronto
$164 Roundtrip, found 9 hours ago
$164
Roundtrip
found 9 hours ago
Select Air Canada flight, departing Mon, Nov 3 from Chicago to Toronto, returning Mon, Nov 10, priced at $164 found 9 hours ago
Air Canada
Fri, Nov 7 - Mon, Nov 17
ORD
Chicago
YYZ
Toronto
$165 Roundtrip, found 2 hours ago
$165
Roundtrip
found 2 hours ago
Select Air Canada flight, departing Fri, Nov 7 from Chicago to Toronto, returning Mon, Nov 17, priced at $165 found 2 hours ago
American Airlines
Wed, Nov 5 - Sat, Nov 8
ORD
Chicago
YYZ
Toronto
$166 Roundtrip, found 8 hours ago
$166
Roundtrip
found 8 hours ago
Select American Airlines flight, departing Wed, Nov 5 from Chicago to Toronto, returning Sat, Nov 8, priced at $166 found 8 hours ago
Air Canada
Mon, Nov 24 - Fri, Nov 28
ORD
Chicago
YKF
Kitchener
$167 Roundtrip, found 1 day ago
$167
Roundtrip
found 1 day ago
Select Air Canada flight, departing Mon, Nov 24 from Chicago to Kitchener, returning Fri, Nov 28, priced at $167 found 1 day ago
Delta
Sat, Oct 4 - Sun, Oct 5
MDW
Chicago
YYZ
Toronto
$233 Roundtrip, found 1 hour ago
$233
Roundtrip
found 1 hour ago
Select Delta flight, departing Sat, Oct 4 from Chicago to Toronto, returning Sun, Oct 5, priced at $233 found 1 hour ago
Porter Airlines
Thu, Oct 16 - Wed, Nov 12
MDW
Chicago
YTZ
Toronto
$236 Roundtrip, just found
$236
Roundtrip
just found
Select Porter Airlines flight, departing Thu, Oct 16 from Chicago to Toronto, returning Wed, Nov 12, priced at $236 just found

Find the cheapest month to fly from Chicago (CHI) to Toronto (YTO)

November is typically the cheapest month to fly

From $143 - $326 per traveler.

Graph displaying average flight prices per month

Alternative airports near Toronto

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

Select flight to Pearson Intl. YYZ. Average driving time to city center is 22 minutes. Flights from $354
YYZ
Pearson Intl.
Average driving time to city center22 min
Flights from $354
Select flight to Billy Bishop Toronto City YTZ. Cheapest and Closest option available. Average driving time to city center is 4 minutes. Flights from $348
YTZ
Billy Bishop Toronto City
CheapestClosest
Average driving time to city center4 min
Flights from $348
Select flight to John C. Munro Hamilton Intl. YHM. Average driving time to city center is 1 hour 0 minutes. Flights from $464
YHM
John C. Munro Hamilton Intl.
Average driving time to city center1 h 0 min
Flights from $464
Select flight to Region of Waterloo Intl. YKF. Average driving time to city center is 1 hour 13 minutes. Flights from $464
YKF
Region of Waterloo Intl.
Average driving time to city center1 h 13 min
Flights from $464
Flights from Chicago (ORD) to Toronto (YYZ)
Origin airport
O'Hare Intl.
Destination airport
Pearson Intl.
Airlines serving
Air Canada, Air Transat, American Airlines, Delta, Porter Airlines, United, WestJet
Roundtrip price
$141
Distance
436 mi

Chicago to Toronto Flights

The cheapest times to fly from Chicago to Toronto

On average, Thursday can be the cheapest time to fly, according to data from the Airlines Reporting Corporation (ARC), one of the world's biggest databases for global airline sales. The data reveals that you could save up to 16% by flying on a Thursday—the cheapest day to travel on average—instead of a Sunday—the most expensive. Some of the most affordable flights from Chicago to Toronto are during the month of November. You can find some of the cheapest flights from Chicago to Toronto with Expedia's search tool and vast selection of airlines.

 

The best time to book a flight from Chicago to Toronto

Sunday is one of the best days to book for cheap flights from Chicago to Toronto: Tickets reserved on a Sunday cost between 6% and 13% less than those reserved on a Friday, according to ARC data. The data also suggests booking early can also lead to cheaper airfares. You could save 24% by buying your tickets for domestic flights at least a month in advance and 10% by booking international flights 2 months in advance.

 

How to find cheap round-trip tickets from Chicago to Toronto

Being flexible with your dates and using Expedia's Price Drop Protection and Price Tracking features are some of the best ways of finding a cheap ticket from Chicago to Toronto in 2025. You can also book with separate airlines for your outbound and return journeys, from $59 one-way. Expedia also offers Price Drop Protection, so if the cost of your airfare goes down after booking, you'll receive a credit for the difference*. This is available for a small fee, and is free to One Key Gold and Platinum tier members.

 

Expedia's Price Tracking feature means you can stay on top of airfares without manually checking every day. It sends you automated price alerts for cheap Chicago to Toronto flights and uses historical data to indicate when the best time to book is. Download Expedia's free app to activate this handy tool in a few easy taps.

 

You could also save big by booking one of Expedia's vacation packages. Bundling together your Chicago to Toronto airfare with your accommodations and car rental is often cheaper than booking everything separately. There’s also One Key, Expedia's generous rewards program. Join for free and you could earn One Key cash on most bookings to save on future adventures.

 

*Terms apply.

 

Disclaimer: ARC The statistics are based on average round-trip ticket prices between January and August 2023. The percentages you see are averages.

 

Frequently asked questions

How much is a flight from Chicago, IL (CHI-All Airports) to Toronto (YTO-All Airports)?
The lowest price advertised for a round-trip flight from Chicago, IL (CHI-All Airports) to Toronto (YTO-All Airports) is $153. But you better act soon. This price is taken from fares offered 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 Chicago, IL (CHI-All Airports) to Toronto (YTO-All Airports)?
The majority of flights can be conveniently canceled online, but whether or not you incur a fee all comes down to your airline. If you do need to cancel your escape, follow the instructions in the Customer Service Portal.
How do I find cheap flights from Chicago, IL (CHI-All Airports) to Toronto (YTO-All Airports) 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 Chicago, IL (CHI-All Airports) to Toronto (YTO-All Airports) flights, you'll see a "no change fees" filter for you to select.
How far is the flight from Chicago, IL (CHI-All Airports) to Toronto (YTO-All Airports)?
That new movie you've been wanting to see will just have to wait — the flight distance between Chicago, IL (CHI-All Airports) (CHI) and Toronto (YTO-All Airports) (YTO) is only 460 mi. The captain will be instructing you to put your seat upright for landing before you know it.
Which airlines fly direct from Chicago, IL (CHI-All Airports) to Toronto (YTO-All Airports)?
It's easy to fly directly from Chicago, IL (CHI-All Airports) to Toronto (YTO-All Airports). Here are the most sought-after carriers that operate nonstop services on this route:

  • American Airlines - (AA) with 152 monthly flights
  • United Airlines - (UA) with 147 monthly flights
  • Air Canada - (AC) with 147 monthly flights
  • Porter Airlines - (PD) with 82 monthly flights

Are Chicago, IL (CHI-All Airports) to Toronto (YTO-All Airports) flight tickets cheaper when they're purchased at the last minute?
Last-minute bookings from Chicago, IL (CHI-All Airports) to Toronto (YTO-All Airports) can be hit-or-miss. You might be lucky and score a bargain, but then again, you could miss out entirely! If you'd prefer to start your trip planning early, Expedia compares flight deals up to a year in advance. Just bear in mind that not all airlines advertise their prices so far in advance. Our suggestion? Check back often as prices are updated frequently.

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*Available to One Key members.