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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 April , May 2026

29 Apr - 29 May $ 188.00
YTO
Toronto
Porter Airlines
DIRECT
CHI
Chicago
CHI
Chicago
Porter Airlines
DIRECT
YTO
Toronto
Pick dates
17 Apr - 07 May $ 497.00
YTO
Toronto
WestJet
1 STOPS
CHI
Chicago
CHI
Chicago
WestJet
1 STOPS
YTO
Toronto
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15 Apr - 07 May $ 497.00
YTO
Toronto
WestJet
1 STOPS
CHI
Chicago
CHI
Chicago
WestJet
1 STOPS
YTO
Toronto
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Last minute flights from Toronto to Chicago

29 Apr - 30 Apr $ 243.00
YTO
Toronto
Porter Airlines
DIRECT
CHI
Chicago
CHI
Chicago
Porter Airlines
DIRECT
YTO
Toronto
Pick dates
16 Apr - 30 Apr $ 317.00
YTO
Toronto
United Airlines
DIRECT
CHI
Chicago
CHI
Chicago
United Airlines
DIRECT
YTO
Toronto
Pick dates
08 Apr - 30 Apr $ 708.00
YTO
Toronto
United Airlines
DIRECT
CHI
Chicago
CHI
Chicago
United Airlines
DIRECT
YTO
Toronto
Pick dates

One-way flights to Chicago from Toronto

9:25 AM - 9:25 AM
Porter Airlines
0 Stops
1h 50m
YTO - CHI
$ 107
Kiwi
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8:50 AM - 8:50 AM
United Airlines
0 Stops
2h
YTO - CHI
$ 197
Kiwi
Pick dates
6:30 PM - 6:30 PM
United Airlines
0 Stops
1h 55m
YTO - CHI
$ 225
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.