Earn point on your loyalty program!arrow arc left

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

Know your dates, get live prices in seconds
airplane logo

pin logo

calendar
Departure
calendar backward
Return
airplane logo
1 Adults (11+)
0 Children (2~11)
0 Infants (0~2)
Save up to 31%
Book Flight + Hotel at the same time

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

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.
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.

Cheap flights from Toronto to Chicago in November , December 2026

27 Nov - 30 Dec $ 285.00
YTO
Toronto
Porter Airlines
DIRECT
CHI
Chicago
CHI
Chicago
Porter Airlines
DIRECT
YTO
Toronto
Pick dates
14 Nov - 01 Dec $ 416.00
YTO
Toronto
Air Canada
DIRECT
CHI
Chicago
CHI
Chicago
Air Canada
DIRECT
YTO
Toronto
Pick dates
19 Nov - 01 Dec $ 439.00
YTO
Toronto
Air Canada
DIRECT
CHI
Chicago
CHI
Chicago
Air Canada
DIRECT
YTO
Toronto
Pick dates

Last minute flights from Toronto to Chicago

26 Nov - 30 Nov $ 271.00
YTO
Toronto
Porter Airlines
DIRECT
CHI
Chicago
CHI
Chicago
Porter Airlines
DIRECT
YTO
Toronto
Pick dates
20 Nov - 30 Nov $ 411.00
YTO
Toronto
Porter Airlines
DIRECT
CHI
Chicago
CHI
Chicago
Porter Airlines
DIRECT
YTO
Toronto
Pick dates
20 Nov - 30 Nov $ 439.00
YTO
Toronto
Air Canada
DIRECT
CHI
Chicago
CHI
Chicago
Air Canada
DIRECT
YTO
Toronto
Pick dates

One-way flights to Chicago from Toronto

4:35 PM - 4:35 PM
Porter Airlines
0 Stops
2h 5m
YTO - CHI
$ 160
Kiwi
Pick dates
6:55 PM - 6:55 PM
Air Canada
0 Stops
2h 3m
YTO - CHI
$ 265
Kiwi
Pick dates
2:35 PM - 2:35 PM
Air Canada
0 Stops
2h 3m
YTO - CHI
$ 278
Kiwi
Pick dates

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

Related info for your journey
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.
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.