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AED 580 Cheap Flights from Toronto (YTO) to Chicago (CHI)

Cheap Flights from Toronto to Chicago (YTO-CHI)

Prices were available within the past 7 days and start at AED 580 for one-way flights and AED 1,150 for roundtrip, for the period specified. Prices and availability are subject to change.
United
Monday, 21 September, 2026 - Saturday, 3 October, 2026
YYZ
Toronto
ORD
Chicago
AED 1,150
Roundtrip
Found 1 day ago
Select United flight, departing Monday, 21 September, 2026 from Toronto to Chicago, returning Saturday, 3 October, 2026, priced at AED 1,150 Found 1 day ago
Air Canada
Monday, 21 September, 2026 - Saturday, 3 October, 2026
YYZ
Toronto
ORD
Chicago
AED 1,150
Roundtrip
Found 1 day ago
Select Air Canada flight, departing Monday, 21 September, 2026 from Toronto to Chicago, returning Saturday, 3 October, 2026, priced at AED 1,150 Found 1 day ago
Air Canada
Monday, 21 September, 2026 - Saturday, 3 October, 2026
YYZ
Toronto
ORD
Chicago
AED 1,170
Roundtrip
Found 1 day ago
Select Air Canada flight, departing Monday, 21 September, 2026 from Toronto to Chicago, returning Saturday, 3 October, 2026, priced at AED 1,170 Found 1 day ago
Delta
Monday, 28 September, 2026 - Saturday, 10 October, 2026
YYZ
Toronto
MDW
Chicago
AED 1,180
Roundtrip
Found 1 day ago
Select Delta flight, departing Monday, 28 September, 2026 from Toronto to Chicago, returning Saturday, 10 October, 2026, priced at AED 1,180 Found 1 day ago
Delta
Monday, 21 September, 2026 - Saturday, 3 October, 2026
YYZ
Toronto
ORD
Chicago
AED 1,180
Roundtrip
Found 1 day ago
Select Delta flight, departing Monday, 21 September, 2026 from Toronto to Chicago, returning Saturday, 3 October, 2026, priced at AED 1,180 Found 1 day ago
United
Monday, 21 September, 2026 - Friday, 2 October, 2026
YYZ
Toronto
ORD
Chicago
AED 1,190
Roundtrip
Found 1 day ago
Select United flight, departing Monday, 21 September, 2026 from Toronto to Chicago, returning Friday, 2 October, 2026, priced at AED 1,190 Found 1 day ago
United
Monday, 21 September, 2026 - Saturday, 3 October, 2026
YYZ
Toronto
ORD
Chicago
AED 1,200
Roundtrip
Found 1 day ago
Select United flight, departing Monday, 21 September, 2026 from Toronto to Chicago, returning Saturday, 3 October, 2026, priced at AED 1,200 Found 1 day ago
Delta
Monday, 28 September, 2026 - Sunday, 11 October, 2026
YYZ
Toronto
MDW
Chicago
AED 1,220
Roundtrip
Found 1 day ago
Select Delta flight, departing Monday, 28 September, 2026 from Toronto to Chicago, returning Sunday, 11 October, 2026, priced at AED 1,220 Found 1 day ago
Porter Airlines
Sunday, 4 October, 2026 - Saturday, 10 October, 2026
YTZ
Toronto
MDW
Chicago
AED 1,420
Roundtrip
Found 1 day ago
Select Porter Airlines flight, departing Sunday, 4 October, 2026 from Toronto to Chicago, returning Saturday, 10 October, 2026, priced at AED 1,420 Found 1 day ago
American Airlines
Tuesday, 24 November, 2026 - Friday, 27 November, 2026
YYZ
Toronto
ORD
Chicago
AED 1,620
Roundtrip
Found 1 day ago
Select American Airlines flight, departing Tuesday, 24 November, 2026 from Toronto to Chicago, returning Friday, 27 November, 2026, priced at AED 1,620 Found 1 day ago

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 center is 23 minutes. Flights from AED 1,340
ORD
O'Hare Intl.
Cheapest
Average driving time to city center23 min
Flights from AED 1,340

Travel information

Origin airport
Billy Bishop Toronto City Airport
Destination airport
Chicago O'Hare Intl. Airport
Distance
717 km away
Airlines serving
Air Canada, PD, Air Transat, United
Popular airline
Air Canada
Roundtrip price
AED 1,150
Average flight time
2 hours 6 mins
*Available to One Key members.