Earn point on your loyalty program!arrow arc left

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

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 Chicago (CHI) to Toronto (YTO)

How to find the cheapest flight from Chicago (CHI) to Toronto (YTO)
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 Chicago (CHI) to Toronto (YTO)
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 Chicago (CHI) to Toronto (YTO)
Some placeholder content for the first accordion panel. This panel is shown by default, thanks to the .show class.

Cheap flights from Chicago to Toronto in December 2025 , January 2026

31 Dec - 01 Jan $ 254.00
CHI
Chicago
United Airlines
DIRECT
YTO
Toronto
YTO
Toronto
United Airlines
DIRECT
CHI
Chicago
Pick dates
27 Dec - 08 Jan $ 421.00
CHI
Chicago
WestJet
1 STOPS
YTO
Toronto
YTO
Toronto
WestJet
1 STOPS
CHI
Chicago
Pick dates
18 Dec - 15 Jan $ 724.00
CHI
Chicago
United Airlines
DIRECT
YTO
Toronto
YTO
Toronto
United Airlines
DIRECT
CHI
Chicago
Pick dates

Last minute flights from Chicago to Toronto

25 Dec - 31 Dec $ 433.00
CHI
Chicago
Porter Airlines
DIRECT
YTO
Toronto
YTO
Toronto
Porter Airlines
DIRECT
CHI
Chicago
Pick dates
27 Dec - 31 Dec $ 486.00
CHI
Chicago
Porter Airlines
1 STOPS
YTO
Toronto
YTO
Toronto
Porter Airlines
DIRECT
CHI
Chicago
Pick dates
24 Dec - 31 Dec $ 756.00
CHI
Chicago
United Airlines
DIRECT
YTO
Toronto
YTO
Toronto
United Airlines
DIRECT
CHI
Chicago
Pick dates

One-way flights to Toronto from Chicago

9:20 PM - 9:20 PM
United Airlines
0 Stops
1h 39m
CHI - YTO
$ 102
Kiwi
Pick dates
9:20 PM - 9:20 PM
United Airlines
0 Stops
1h 39m
CHI - YTO
$ 330
Kiwi
Pick dates
3:55 PM - 3:55 PM
United Airlines
0 Stops
1h 39m
CHI - YTO
$ 339
Kiwi
Pick dates

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

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 Chicago (CHI) to Toronto (YTO)
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 Chicago (CHI) to Toronto (YTO)
Some placeholder content for the first accordion panel. This panel is shown by default, thanks to the .show class.