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 September , October 2026

30 Sep - 27 Oct $ 476.00
YUL
Montreal
Air Canada
DIRECT
CHI
Chicago
CHI
Chicago
Air Canada
DIRECT
YUL
Montreal
Pick dates
30 Sep - 07 Oct $ 576.00
YUL
Montreal
Air Canada
DIRECT
CHI
Chicago
CHI
Chicago
Air Canada
DIRECT
YUL
Montreal
Pick dates
30 Sep - 07 Oct $ 576.00
YUL
Montreal
Air Canada
DIRECT
CHI
Chicago
CHI
Chicago
Air Canada
DIRECT
YUL
Montreal
Pick dates

Last minute flights from Montreal to Chicago

29 Sep - 30 Sep $ 494.00
YUL
Montreal
United Airlines
1 STOPS
CHI
Chicago
CHI
Chicago
United Airlines
DIRECT
YUL
Montreal
Pick dates
29 Sep - 30 Sep $ 509.00
YUL
Montreal
United Airlines
DIRECT
CHI
Chicago
CHI
Chicago
United Airlines
DIRECT
YUL
Montreal
Pick dates
29 Sep - 30 Sep $ 510.00
YUL
Montreal
Air Canada
DIRECT
CHI
Chicago
CHI
Chicago
Air Canada
DIRECT
YUL
Montreal
Pick dates

One-way flights to Chicago from Montreal

9:45 AM - 9:45 AM
United Airlines
0 Stops
2h 36m
YUL - CHI
$ 266
Kiwi
Pick dates
6:10 AM - 6:10 AM
United Airlines
0 Stops
2h 41m
YUL - CHI
$ 266
Kiwi
Pick dates
9:45 AM - 9:45 AM
Air Canada
0 Stops
2h 36m
YUL - CHI
$ 337
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.