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Stops
- Nonstopfrom $392
- Up to 1 stop$393
Airlines
- Air Canada$558
- American Airlines$392
Cabin Class
- Business$392
Departure Airports
- Toronto Pearson Airport$392
Arrival Airports
- Chicago O Hare Airport$392
Layover Airports
- Charlotte Douglas International Airport$402
- Philadelphia International Airport$393
- Washington Dulles Airport$638
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05/29/25
YYZ
1h 55m
Direct
05/29/25
ORD
06/05/25
ORD
1h 35m
Direct
06/05/25
YYZ
$392
Free cancellation within 83 hours of booking
05/29/25
YYZ
1h 55m
Direct
05/29/25
ORD
06/05/25
ORD
1h 35m
Direct
06/05/25
YYZ
$392
Free cancellation within 83 hours of booking
05/29/25
YYZ
1h 55m
Direct
05/29/25
ORD
06/05/25
ORD
1h 45m
Direct
06/05/25
YYZ
$392
Free cancellation within 83 hours of booking
05/29/25
YYZ
1h 55m
Direct
05/29/25
ORD
06/05/25
ORD
1h 35m
Direct
06/05/25
YYZ
$392
Free cancellation within 83 hours of booking
05/29/25
YYZ
1h 55m
Direct
05/29/25
ORD
06/05/25
ORD
2h
Direct
06/05/25
YYZ
$392
Free cancellation within 83 hours of booking
05/29/25
YYZ
1h 55m
Direct
05/29/25
ORD
06/05/25
ORD
1h 45m
Direct
06/05/25
YYZ
$392
Free cancellation within 83 hours of booking
05/29/25
YYZ
1h 55m
Direct
05/29/25
ORD
06/05/25
ORD
1h 35m
Direct
06/05/25
YYZ
$392
Free cancellation within 83 hours of booking
05/29/25
YYZ
1h 55m
Direct
05/29/25
ORD
06/05/25
ORD
11h 19m
PHL
06/05/25
YYZ
$393
Free cancellation within 83 hours of booking
05/29/25
YYZ
1h 55m
Direct
05/29/25
ORD
06/05/25
ORD
11h 19m
PHL
06/05/25
YYZ
$393
Free cancellation within 83 hours of booking
05/29/25
YYZ
1h 55m
Direct
05/29/25
ORD
06/05/25
ORD
11h 19m
PHL
06/05/25
YYZ
$393
Free cancellation within 83 hours of booking
05/29/25
YYZ
1h 55m
Direct
05/29/25
ORD
06/05/25
ORD
11h 19m
PHL
06/05/25
YYZ
$393
Free cancellation within 83 hours of booking
05/29/25
YYZ
1h 55m
Direct
05/29/25
ORD
06/05/25
ORD
8h 22m
CLT
06/05/25
YYZ
$402
Free cancellation within 83 hours of booking
05/29/25
YYZ
1h 55m
Direct
05/29/25
ORD
06/05/25
ORD
8h 22m
CLT
06/05/25
YYZ
$402
Free cancellation within 83 hours of booking
05/29/25
YYZ
1h 55m
Direct
05/29/25
ORD
06/05/25
ORD
8h 22m
CLT
06/05/25
YYZ
$402
Free cancellation within 83 hours of booking
05/29/25
YYZ
1h 55m
Direct
05/29/25
ORD
06/05/25
ORD
8h 22m
CLT
06/05/25
YYZ
$402
Free cancellation within 83 hours of booking
05/29/25
YYZ
5h 56m
CLT
05/30/25
ORD
06/05/25
ORD
1h 35m
Direct
06/05/25
YYZ
$418
Free cancellation within 83 hours of booking
05/29/25
YYZ
5h 56m
CLT
05/30/25
ORD
06/05/25
ORD
1h 45m
Direct
06/05/25
YYZ
$418
Free cancellation within 83 hours of booking
05/29/25
YYZ
5h 56m
CLT
05/30/25
ORD
06/05/25
ORD
2h
Direct
06/05/25
YYZ
$418
Free cancellation within 83 hours of booking
05/29/25
YYZ
1h 59m
Direct
05/29/25
ORD
06/05/25
ORD
1h 42m
Direct
06/05/25
YYZ
$558
Free cancellation within 83 hours of booking
05/29/25
YYZ
2h 1m
Direct
05/29/25
ORD
06/05/25
ORD
1h 42m
Direct
06/05/25
YYZ
$558
Free cancellation within 83 hours of booking
05/29/25
YYZ
2h 1m
Direct
05/29/25
ORD
06/05/25
ORD
1h 42m
Direct
06/05/25
YYZ
$558
Free cancellation within 83 hours of booking
05/29/25
YYZ
1h 59m
Direct
05/29/25
ORD
06/05/25
ORD
1h 42m
Direct
06/05/25
YYZ
$558
Free cancellation within 83 hours of booking
05/29/25
YYZ
2h 1m
Direct
05/29/25
ORD
06/05/25
ORD
1h 59m
Direct
06/05/25
YYZ
$584
Free cancellation within 83 hours of booking
05/29/25
YYZ
2h 1m
Direct
05/29/25
ORD
06/05/25
ORD
1h 44m
Direct
06/05/25
YYZ
$584
Free cancellation within 83 hours of booking
05/29/25
YYZ
1h 59m
Direct
05/29/25
ORD
06/05/25
ORD
1h 44m
Direct
06/05/25
YYZ
$584
Free cancellation within 83 hours of booking
05/29/25
YYZ
1h 59m
Direct
05/29/25
ORD
06/05/25
ORD
15h 11m
IAD
06/06/25
YYZ
$638
Free cancellation within 83 hours of booking
05/29/25
YYZ
2h 1m
Direct
05/29/25
ORD
06/05/25
ORD
11h 33m
IAD
06/06/25
YYZ
$638
Free cancellation within 83 hours of booking
05/29/25
YYZ
2h 1m
Direct
05/29/25
ORD
06/05/25
ORD
15h 11m
IAD
06/06/25
YYZ
$638
Free cancellation within 83 hours of booking
05/29/25
YYZ
1h 59m
Direct
05/29/25
ORD
06/05/25
ORD
11h 33m
IAD
06/06/25
YYZ
$638
Free cancellation within 83 hours of booking
05/29/25
YYZ
2h 1m
Direct
05/29/25
ORD
06/05/25
ORD
15h 11m
IAD
06/06/25
YYZ
$638
Free cancellation within 83 hours of booking
Top Deals on flights Business Class from Toronto to Chicago
Toronto, CA (YTO) - Chicago, US (CHI)
May 29
YYZ
1h 55m
Direct
May 29
ORD
as low as
$210
Toronto, CA (YTO) - Chicago, US (CHI)
May 29
YYZ
1h 55m
Direct
May 29
ORD
as low as
$210
Toronto, CA (YTO) - Chicago, US (CHI)
May 29
YYZ
1h 55m
Direct
May 29
ORD
as low as
$210
Toronto, CA (YTO) - Chicago, US (CHI)
May 29
YYZ
11h 33m
PHL
May 29
ORD
as low as
$238
Toronto, CA (YTO) - Chicago, US (CHI)
May 29
YYZ
18h 16m
CLT
May 30
ORD
as low as
$238
Toronto, CA (YTO) - Chicago, US (CHI)
May 29
YYZ
19h 11m
CLT
May 30
ORD
as low as
$238
Toronto, CA (YTO) - Chicago, US (CHI)
May 29
YYZ
16h 26m
CLT
May 30
ORD
as low as
$238
Toronto, CA (YTO) - Chicago, US (CHI)
May 29
YYZ
1h 59m
Direct
May 29
ORD
as low as
$317
Toronto, CA (YTO) - Chicago, US (CHI)
May 29
YYZ
1h 59m
Direct
May 29
ORD
as low as
$317
Toronto, CA (YTO) - Chicago, US (CHI)
May 29
YYZ
2h 1m
Direct
May 29
ORD
as low as
$317
Toronto, CA (YTO) - Chicago, US (CHI)
May 29
YYZ
5h 54m
PHL
May 29
ORD
as low as
$380
Toronto, CA (YTO) - Chicago, US (CHI)
May 29
YYZ
6h 9m
YUL
May 29
ORD
as low as
$717
Frequently Asked Questions
Are there convenient layover flights from Toronto to Chicago?
Yes, there are convenient layover flights from Toronto to Chicago. Airlines include Air Canada at $160, United Airlines at $171, Delta Air Lines at $258, American Airlines at $260, and Virgin Atlantic at $290.
What are the most convenient layover airports for the flight?
Convenient layover airports for your flight include Montreal Trudeau with Air Canada, Nashville International with United Airlines, Detroit Metropolitan with Delta Air Lines and Virgin Atlantic, and Charlotte Douglas International with American Airlines.
What is the cheapest and fastest flight from Toronto to Chicago?
The cheapest and fastest flight is with Porter Airlines, priced at $155, with a flight time of 0 hours 49 minutes, from Toronto Island Airport to Chicago Midway Airport.
What are all possible destination arrival airports?
The possible destination arrival airports from Toronto are Chicago Midway Airport and Chicago O'Hare Airport.
What is the time difference between Toronto and Chicago?
Toronto and Chicago have a time difference of one hour, with Toronto being one hour ahead of Chicago.
Is there a direct flight from Toronto to Chicago?
Yes, there are direct flights from Toronto to Chicago. The non-stop options include Porter Airlines for $155, Air Canada for $161, and Air Transat for $187. All offer no layovers, with flight times ranging from 49 to 50 minutes.
Flights to Chicago
Return flights
Business Class Flights From Chicago To TorontoBrowse origins
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