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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 August , September 2026

31 Aug - 09 Sep $ 251.00
YTO
Toronto
Air Canada
DIRECT
CHI
Chicago
CHI
Chicago
Air Canada
DIRECT
YTO
Toronto
Pick dates
27 Aug - 09 Sep $ 343.00
YTO
Toronto
Air Canada
DIRECT
CHI
Chicago
CHI
Chicago
Air Canada
DIRECT
YTO
Toronto
Pick dates
26 Aug - 10 Sep $ 349.00
YTO
Toronto
Air Canada
DIRECT
CHI
Chicago
CHI
Chicago
Air Canada
DIRECT
YTO
Toronto
Pick dates

Last minute flights from Toronto to Chicago

31 Aug - 31 Aug $ 336.00
YTO
Toronto
Air Transat
DIRECT
CHI
Chicago
CHI
Chicago
Air Transat
DIRECT
YTO
Toronto
Pick dates
27 Aug - 31 Aug $ 363.00
YTO
Toronto
Air Canada
DIRECT
CHI
Chicago
CHI
Chicago
Air Canada
DIRECT
YTO
Toronto
Pick dates
27 Aug - 31 Aug $ 452.00
YTO
Toronto
Porter Airlines
DIRECT
CHI
Chicago
CHI
Chicago
Porter Airlines
DIRECT
YTO
Toronto
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One-way flights to Chicago from Toronto

8:55 AM - 8:55 AM
Porter Airlines
0 Stops
1h 50m
YTO - CHI
$ 200
Kiwi
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7:00 AM - 7:00 AM
United Airlines
0 Stops
2h
YTO - CHI
$ 230
Kiwi
Pick dates
2:00 PM - 2:00 PM
Air Canada
0 Stops
1h 55m
YTO - CHI
$ 242
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.