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Free cancellation for many rates
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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
Best Price. GUARANTEED.
Exclusively for Priceline Members
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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 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
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
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 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
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
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
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
11h 33m
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
15h 11m
IAD
06/06/25
YYZ
$638
Free cancellation within 83 hours of booking
Top Deals on flights Business Class from Toronto Pearson Airport to Chicago O Hare Airport
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
19h 11m
CLT
May 30
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
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
2h 1m
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
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
Flights to Chicago
Browse origins
- Flights
- North America
- Canada
- Ontario
- Toronto
- Toronto Pearson Airport
Browse destinations
- Flights
- North America
- United States
- Illinois
- Chicago
- Chicago O Hare Airport
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