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 2025

28 Nov - 12 Dec $ 308.00
YTO
Toronto
Porter Airlines
DIRECT
CHI
Chicago
CHI
Chicago
Porter Airlines
DIRECT
YTO
Toronto
Pick dates
30 Nov - 10 Dec $ 445.00
YTO
Toronto
WestJet
1 STOPS
CHI
Chicago
CHI
Chicago
WestJet
1 STOPS
YTO
Toronto
Pick dates
24 Nov - 01 Dec $ 1,159.00
YTO
Toronto
WestJet
1 STOPS
CHI
Chicago
CHI
Chicago
WestJet
1 STOPS
YTO
Toronto
Pick dates

Last minute flights from Toronto to Chicago

26 Nov - 30 Nov $ 448.00
YTO
Toronto
Porter Airlines
DIRECT
CHI
Chicago
CHI
Chicago
Porter Airlines
DIRECT
YTO
Toronto
Pick dates
27 Nov - 30 Nov $ 501.00
YTO
Toronto
United Airlines
DIRECT
CHI
Chicago
CHI
Chicago
United Airlines
DIRECT
YTO
Toronto
Pick dates
29 Nov - 30 Nov $ 526.00
YTO
Toronto
Porter Airlines
1 STOPS
CHI
Chicago
CHI
Chicago
Porter Airlines
DIRECT
YTO
Toronto
Pick dates

One-way flights to Chicago from Toronto

2:30 PM - 2:30 PM
Porter Airlines
0 Stops
1h 50m
YTO - CHI
$ 226
Kiwi
Pick dates
11:32 AM - 11:32 AM
Porter Airlines
0 Stops
1h 55m
YTO - CHI
$ 246
Kiwi
Pick dates
9:00 PM - 9:00 PM
United Airlines
0 Stops
1h 52m
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.