Earn point on your loyalty program!arrow arc left

Cheap flights from Montreal (YUL) 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 Montreal (YUL) to Chicago (CHI)

How to find the cheapest flight from Montreal (YUL) 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 Montreal (YUL) 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 Montreal (YUL) 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 Montreal to Chicago in October , November 2026

31 Oct - 29 Nov $ 345.00
YUL
Montreal
Air Canada
DIRECT
CHI
Chicago
CHI
Chicago
Air Canada
DIRECT
YUL
Montreal
Pick dates
31 Oct - 10 Nov $ 455.00
YUL
Montreal
Porter Airlines
DIRECT
CHI
Chicago
CHI
Chicago
Porter Airlines
1 STOPS
YUL
Montreal
Pick dates
23 Oct - 07 Nov $ 510.00
YUL
Montreal
Air Canada
DIRECT
CHI
Chicago
CHI
Chicago
Air Canada
DIRECT
YUL
Montreal
Pick dates

Last minute flights from Montreal to Chicago

28 Oct - 31 Oct $ 471.00
YUL
Montreal
Air Canada
DIRECT
CHI
Chicago
CHI
Chicago
Air Canada
1 STOPS
YUL
Montreal
Pick dates
28 Oct - 31 Oct $ 484.00
YUL
Montreal
Air Canada
DIRECT
CHI
Chicago
CHI
Chicago
Air Canada
DIRECT
YUL
Montreal
Pick dates
23 Oct - 31 Oct $ 590.00
YUL
Montreal
Air Canada
DIRECT
CHI
Chicago
CHI
Chicago
Air Canada
DIRECT
YUL
Montreal
Pick dates

One-way flights to Chicago from Montreal

1:10 PM - 1:10 PM
Air Canada
0 Stops
2h 42m
YUL - CHI
$ 267
Kiwi
Pick dates
6:10 PM - 6:10 PM
Air Canada
0 Stops
2h 42m
YUL - CHI
$ 267
Kiwi
Pick dates
9:45 AM - 9:45 AM
United Airlines
0 Stops
2h 36m
YUL - CHI
$ 336
Kiwi
Pick dates

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