Direct flights from Toronto to Chicago

  • Usually $425 round trip
  • Several times daily
  • 3 airlines

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The same flight. 12 days apart.

1.6x the price $208 more
The cheap date
Air Canada
Thu, Nov 5
2:35 PM YYZ
3:38 PM ORD
7 nights
Thu, Nov 12
12:50 PM ORD
3:33 PM YYZ
$349 round-trip Book →
12 days later
Air Canada
Tue, Nov 17
2:35 PM YYZ
3:38 PM ORD
7 nights
Tue, Nov 24
12:50 PM ORD
3:33 PM YYZ
$557 round-trip Book →

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checked 3 days ago · track this route free

Nonstop departures observed in recent fares

Across 4 recent dates we priced, Toronto (YYZ) to Chicago (ORD) showed up to 3 nonstop departures a day, with the earliest around 6:45 AM and the latest around 2:35 PM, operated by Air Canada, United, and American.

6:45 AM 7:09 AM 10:53 AM 12:00 PM 1:17 PM 1:22 PM 2:35 PM

Departure times seen while pricing this route over the last few weeks — a sample, not the full timetable. Airlines adjust schedules seasonally.

More nonstops from Toronto

YYZ → MCO Orlando 4 airlines YYZ → NAS Nassau 4 airlines YYZ → YYC Calgary 4 airlines YYZ → MIA Miami 3 airlines YYZ → PVR Puerto Vallarta 5 airlines YYZ → YUL Montreal 5 airlines YYZ → LGA New York 4 airlines YYZ → LIR Liberia 4 airlines ORD → YYZ The return trip YYZ All nonstops from Toronto ORD All nonstops from Chicago

Frequently asked questions

Is there a direct flight from Toronto to Chicago?

Yes. Air Canada, American Airlines and United Airlines fly nonstop from Toronto (YYZ) to Chicago (ORD), several times daily. The flight takes about 1h 24m and covers 435 miles (700 km). Round-trip fares typically run around $425, with recent bookable fares from $327. Fares last checked 15 October 2026.

Which airlines fly direct from Toronto to Chicago?

Air Canada, American Airlines, United Airlines operate nonstop flights from Toronto to Chicago.

How long is the flight from Toronto to Chicago?

The nonstop flight from Toronto to Chicago takes ~1h 24m (approximately 700 km).

How often do direct flights operate from Toronto to Chicago?

Nonstop flights from Toronto to Chicago operate several times daily.

How much is a round-trip flight from Toronto to Chicago?

Round-trip flights from Toronto (YYZ) to Chicago (ORD) start at $327, with a typical fare around $425. Based on 96 recent fare combinations.