To save up to 92% on this flight, we recommend booking at least 50 days prior to travel. The price may fluctuate and will likely increase closer to your departure date. Users on Cheapflights have found tickets from Chicago to Canada from C$ 501 1-2 weeks out and tickets from C$ 656 for flights departing within the next 72 hours.
Due to multiple factors, expect to potentially pay more when booking in September. For low rates, January can be a great choice for travel to Canada. Flights to Canada from Chicago in January are about C$ 424 on average during January, but can be found for as low as C$ 172.
Regardless of the time of day you decide to fly, the ticket price will remain around the same. Book flights from Chicago to Canada as you normally would.
Fly from
Fly to
Budget
C$ 250 - C$ 489
Route
Depart
Return
Price
Chicago O'Hare IntlMontreal Pierre Elliott Trudeau Intl
ORD - YUL
ORDYUL
Chicago O'Hare Intl
Tue 14/5
1 stop18h 20m
Montreal Pierre Elliott Trudeau Intl
Tue 21/5
1 stop9h 44m
Chicago O'Hare IntlMontreal Pierre Elliott Trudeau Intl
ORD - YUL
ORDYUL
Chicago O'Hare Intl
Wed 15/5
1 stop8h 00m
Montreal Pierre Elliott Trudeau Intl
Tue 21/5
1 stop9h 44m
Chicago O'Hare IntlCalgary
ORD - YYC
ORDYYC
Chicago O'Hare Intl
Thu 20/6
Nonstop3h 45m
Calgary
Sat 22/6
Nonstop3h 27m
Chicago MidwayToronto Island
MDW - YTZ
MDWYTZ
Chicago Midway
Sat 25/5
Nonstop1h 42m
Toronto Island
Tue 4/6
Nonstop1h 47m
Chicago O'Hare IntlCalgary
ORD - YYC
ORDYYC
Chicago O'Hare Intl
Thu 16/5
Nonstop3h 44m
Calgary
Mon 20/5
Nonstop3h 30m
Chicago O'Hare IntlCalgary
ORD - YYC
ORDYYC
Chicago O'Hare Intl
Wed 11/9
1 stop9h 49m
Calgary
Sat 14/9
1 stop7h 53m
Chicago O'Hare IntlToronto Pearson Intl
ORD - YYZ
ORDYYZ
Chicago O'Hare Intl
Thu 16/5
1 stop8h 14m
Toronto Pearson Intl
Sun 19/5
1 stop5h 03m
Chicago O'Hare IntlToronto Pearson Intl
ORD - YYZ
ORDYYZ
Chicago O'Hare Intl
Tue 14/5
1 stop6h 29m
Toronto Pearson Intl
Tue 14/5
Nonstop1h 55m
Chicago O'Hare IntlMontreal Pierre Elliott Trudeau Intl
ORD - YUL
ORDYUL
Chicago O'Hare Intl
Thu 18/7
1 stop26h 45m
Montreal Pierre Elliott Trudeau Intl
Mon 22/7
1 stop7h 34m
No data available for this route at this time. Please check back soon.
Comfort
Boarding
Overall
Crew
Entertainment
Food
Reviews
Terrible flight crew that skipped our row for service multiple times.
Comfort
Boarding
Overall
Crew
Entertainment
Food
Reviews
Terrible flight crew that skipped our row for service multiple times.
Comfort
Boarding
Overall
Crew
Entertainment
Food
Reviews
Terrible flight crew that skipped our row for service multiple times.
Comfort
Boarding
Overall
Crew
Entertainment
Food
Reviews
Terrible flight crew that skipped our row for service multiple times.
Comfort
Boarding
Overall
Crew
Entertainment
Food
Reviews
Terrible flight crew that skipped our row for service multiple times.
1%of flight departures | Early morningMidnight to 6 am |
---|---|
43%of flight departures | Morning6 am to noon |
47%of flight departures | AfternoonNoon to 6 pm |
9%of flight departures | Evening6 pm to midnight |
Cheapflights goes through 900+ travel sites to look for the best flight deals for flights from Chicago to Canada. Too many options? Cheapflights also provides filters for things like airlines, price ranges, and number of stops to help you make a decision easily.
It’s simple! Cheapflights, which is free to use for everyone, saves millions of users time and money every year by helping them find the cheapest and most suitable flights from Chicago to Canada.
Cheapflights does show flights with no change fees to all users. To see these options for flights from Chicago to Canada, users can toggle the no change fees filter when performing a flight search.
Not ready to book yet? You can track prices for flights from Chicago to Canada on Cheapflights with our Price Alert feature and get notified when better prices are available.