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 November , December 2025

28 Nov - 12 Dec $ 461.00
YUL
Montreal
Porter Airlines
DIRECT
CHI
Chicago
CHI
Chicago
Porter Airlines
DIRECT
YUL
Montreal
Pick dates
22 Nov - 10 Dec $ 670.00
YUL
Montreal
WestJet
1 STOPS
CHI
Chicago
CHI
Chicago
WestJet
1 STOPS
YUL
Montreal
Pick dates
22 Nov - 08 Dec $ 670.00
YUL
Montreal
WestJet
1 STOPS
CHI
Chicago
CHI
Chicago
WestJet
1 STOPS
YUL
Montreal
Pick dates

Last minute flights from Montreal to Chicago

28 Nov - 30 Nov $ 557.00
YUL
Montreal
United Airlines
DIRECT
CHI
Chicago
CHI
Chicago
United Airlines
DIRECT
YUL
Montreal
Pick dates
22 Nov - 30 Nov $ 642.00
YUL
Montreal
Porter Airlines
1 STOPS
CHI
Chicago
CHI
Chicago
Porter Airlines
1 STOPS
YUL
Montreal
Pick dates
23 Nov - 30 Nov $ 738.00
YUL
Montreal
United Airlines
DIRECT
CHI
Chicago
CHI
Chicago
United Airlines
DIRECT
YUL
Montreal
Pick dates

One-way flights to Chicago from Montreal

4:45 PM - 4:45 PM
United Airlines
0 Stops
3h
YUL - CHI
$ 291
Kiwi
Pick dates
9:15 AM - 12:40 PM
United Airlines
1 Stops
5h 40m
YUL - CHI
$ 459
Kiwi
Pick dates
9:25 AM - 9:25 AM
United Airlines
0 Stops
2h 41m
YUL - CHI
$ 1,097
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.