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Cheap flights from Toronto (YTO) to Chicago (CHI)

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1 Adults (11+)
0 Children (2~11)
0 Infants (0~2)
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How to find the cheapest flight from Toronto (YTO) to Chicago (CHI)

How to find the cheapest flight from Toronto (YTO) to Chicago (CHI)
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How to find the cheapest flight from Toronto (YTO) to Chicago (CHI)
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How to find the cheapest flight from Toronto (YTO) to Chicago (CHI)
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Cheap flights from Toronto to Chicago in July , August 2026

28 Jul - 26 Aug $ 326.00
YTO
Toronto
Porter Airlines
DIRECT
CHI
Chicago
CHI
Chicago
Porter Airlines
DIRECT
YTO
Toronto
Pick dates
27 Jul - 17 Aug $ 409.00
YTO
Toronto
Air Canada
DIRECT
CHI
Chicago
CHI
Chicago
Air Canada
DIRECT
YTO
Toronto
Pick dates
27 Jul - 01 Aug $ 752.00
YTO
Toronto
Air Canada
DIRECT
CHI
Chicago
CHI
Chicago
Air Canada
DIRECT
YTO
Toronto
Pick dates

Last minute flights from Toronto to Chicago

28 Jul - 31 Jul $ 477.00
YTO
Toronto
Porter Airlines
DIRECT
CHI
Chicago
CHI
Chicago
Porter Airlines
DIRECT
YTO
Toronto
Pick dates
29 Jul - 31 Jul $ 482.00
YTO
Toronto
United Airlines
DIRECT
CHI
Chicago
CHI
Chicago
United Airlines
DIRECT
YTO
Toronto
Pick dates
28 Jul - 31 Jul $ 557.00
YTO
Toronto
United Airlines
DIRECT
CHI
Chicago
CHI
Chicago
United Airlines
DIRECT
YTO
Toronto
Pick dates

One-way flights to Chicago from Toronto

1:45 PM - 1:45 PM
Porter Airlines
0 Stops
1h 50m
YTO - CHI
$ 216
Kiwi
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11:39 AM - 11:39 AM
Porter Airlines
0 Stops
2h 5m
YTO - CHI
$ 240
Kiwi
Pick dates
2:00 PM - 2:00 PM
Air Canada
0 Stops
1h 55m
YTO - CHI
$ 472
Kiwi
Pick dates

How to find the cheapest flight from Toronto (YTO) to Chicago (CHI)

Related info for your journey
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How to find the cheapest flight from Toronto (YTO) to Chicago (CHI)
Some placeholder content for the first accordion panel. This panel is shown by default, thanks to the .show class.
How to find the cheapest flight from Toronto (YTO) to Chicago (CHI)
Some placeholder content for the first accordion panel. This panel is shown by default, thanks to the .show class.