Montreal (YUL) to Chicago (ORD) cheap flight deal from $444 USD in business class

AAAmerican Airlines

Round Trip•Business Class

YUL

Montréal-Pierre Elliott Trudeau International Airport

Montreal, Canada

ORD

O'Hare International Airport

Chicago, United States

$589 USD

-25%$444 USD

Verified Sep 22, 2025 at 3:11 AM

October 2025

Today

Mon

Tue

Wed

Thu

Fri

Sat

Sun

29$663 30$600 1$594 2$600 3$594 4$594 5$729 6$522 7$491 8$588 9$594 10$898 11$558 12$600 13$693 14$546 15$522 16$480 17$594 18$522 19$898 20$594 21$450 22$522 23$480 24$480 25$450 26$693 27$522 28$450 29$485 30$516 31$516 1 2

Limited Availability

18% of dates checked are available within 10% of the lowest price

Wednesday, October 1st, 2025

10 round-trip options

Returning

Mon, Oct 6, 2025•5 Day Trip

$655 USD

Google Flights

Returning

Tue, Oct 7, 2025•6 Day Trip

$600 USD

Google Flights

Returning

Wed, Oct 8, 2025•7 Day Trip

$714 USD

Google Flights

Returning

Thu, Oct 9, 2025•8 Day Trip

$807 USD

Google Flights

Returning

Fri, Oct 10, 2025•9 Day Trip

$708 USD

Google Flights

Returning

Sat, Oct 11, 2025•10 Day Trip

$600 USD

Google Flights

Returning

Sun, Oct 12, 2025•11 Day Trip

$594 USD

Google Flights

Returning

Mon, Oct 13, 2025•12 Day Trip

$807 USD

Google Flights

Returning

Tue, Oct 14, 2025•13 Day Trip

$807 USD

Google Flights

Returning

Wed, Oct 15, 2025•14 Day Trip

$1,012 USD

Google Flights