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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 October , November 2026

29 Oct - 17 Nov $ 333.00
YTO
Toronto
Porter Airlines
DIRECT
CHI
Chicago
CHI
Chicago
Porter Airlines
DIRECT
YTO
Toronto
Pick dates
27 Oct - 06 Nov $ 398.00
YTO
Toronto
Air Canada
DIRECT
CHI
Chicago
CHI
Chicago
Air Canada
DIRECT
YTO
Toronto
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21 Oct - 04 Nov $ 505.00
YTO
Toronto
Air Canada
DIRECT
CHI
Chicago
CHI
Chicago
Air Canada
DIRECT
YTO
Toronto
Pick dates

Last minute flights from Toronto to Chicago

28 Oct - 31 Oct $ 399.00
YTO
Toronto
Air Canada
DIRECT
CHI
Chicago
CHI
Chicago
Air Canada
DIRECT
YTO
Toronto
Pick dates
28 Oct - 31 Oct $ 399.00
YTO
Toronto
Air Canada
DIRECT
CHI
Chicago
CHI
Chicago
Air Canada
DIRECT
YTO
Toronto
Pick dates
21 Oct - 31 Oct $ 551.00
YTO
Toronto
United Airlines
DIRECT
CHI
Chicago
CHI
Chicago
United Airlines
DIRECT
YTO
Toronto
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One-way flights to Chicago from Toronto

10:35 AM - 10:35 AM
Porter Airlines
0 Stops
2h 5m
YTO - CHI
$ 234
Kiwi
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6:55 PM - 6:55 PM
Air Canada
0 Stops
2h 3m
YTO - CHI
$ 241
Kiwi
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8:05 AM - 8:05 AM
Air Canada
0 Stops
1h 55m
YTO - CHI
$ 356
Kiwi
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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.