To save up to 92% on this flight, we recommend booking at least 40 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$ 492 1-2 weeks out and tickets from C$ 764 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$ 444 on average during January, but can be found for as low as C$ 233.
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$ 281 - C$ 429
Route
Depart
Return
Price
Chicago O'Hare IntlCalgary
ORD - YYC
ORDYYC
Chicago O'Hare Intl
Sat 1/6
Nonstop3h 27m
Calgary
Sun 9/6
Nonstop3h 35m
Chicago O'Hare IntlToronto Pearson Intl
ORD - YYZ
ORDYYZ
Chicago O'Hare Intl
Tue 4/6
1 stop18h 20m
Toronto Pearson Intl
Tue 18/6
1 stop10h 58m
Chicago MidwayToronto Island
MDW - YTZ
MDWYTZ
Chicago Midway
Tue 4/6
Nonstop1h 42m
Toronto Island
Tue 18/6
Nonstop1h 47m
Chicago O'Hare IntlCalgary
ORD - YYC
ORDYYC
Chicago O'Hare Intl
Sun 20/10
Nonstop3h 51m
Calgary
Wed 23/10
1 stop8h 43m
Chicago MidwayCalgary
MDW - YYC
MDWYYC
Chicago Midway
Wed 2/10
1 stop7h 43m
Calgary
Sun 13/10
1 stop5h 12m
Chicago O'Hare IntlMontreal Pierre Elliott Trudeau Intl
ORD - YUL
ORDYUL
Chicago O'Hare Intl
Tue 21/5
1 stop11h 30m
Montreal Pierre Elliott Trudeau Intl
Wed 22/5
Nonstop2h 45m
Chicago O'Hare IntlToronto Pearson Intl
ORD - YYZ
ORDYYZ
Chicago O'Hare Intl
Sun 16/6
Nonstop1h 43m
Toronto Pearson Intl
Fri 21/6
Nonstop1h 56m
Chicago O'Hare IntlToronto Pearson Intl
ORD - YYZ
ORDYYZ
Chicago O'Hare Intl
Thu 30/5
Nonstop1h 35m
Toronto Pearson Intl
Thu 30/5
1 stop5h 29m
Chicago O'Hare IntlVancouver Intl
ORD - YVR
ORDYVR
Chicago O'Hare Intl
Thu 30/5
Nonstop4h 38m
Vancouver Intl
Wed 5/6
Nonstop4h 12m
No data available for this route at this time. Please check back soon.
Boarding
Comfort
Crew
Food
Overall
Entertainment
Reviews
Bad experience with the staff boarding the gate. I couldn’t board with my carry on, personal item and a funny bag. I had to put my passport inside my pockets and put the funny bag inside the personal item. Then after passing the staff pull out everything again.
Boarding
Comfort
Crew
Food
Overall
Entertainment
Reviews
Bad experience with the staff boarding the gate. I couldn’t board with my carry on, personal item and a funny bag. I had to put my passport inside my pockets and put the funny bag inside the personal item. Then after passing the staff pull out everything again.
Boarding
Comfort
Crew
Food
Overall
Entertainment
Reviews
Bad experience with the staff boarding the gate. I couldn’t board with my carry on, personal item and a funny bag. I had to put my passport inside my pockets and put the funny bag inside the personal item. Then after passing the staff pull out everything again.
Boarding
Comfort
Crew
Food
Overall
Entertainment
Reviews
Bad experience with the staff boarding the gate. I couldn’t board with my carry on, personal item and a funny bag. I had to put my passport inside my pockets and put the funny bag inside the personal item. Then after passing the staff pull out everything again.
Boarding
Comfort
Crew
Food
Overall
Entertainment
Reviews
Bad experience with the staff boarding the gate. I couldn’t board with my carry on, personal item and a funny bag. I had to put my passport inside my pockets and put the funny bag inside the personal item. Then after passing the staff pull out everything again.
Boarding
Comfort
Crew
Food
Overall
Entertainment
Reviews
Bad experience with the staff boarding the gate. I couldn’t board with my carry on, personal item and a funny bag. I had to put my passport inside my pockets and put the funny bag inside the personal item. Then after passing the staff pull out everything again.
1%of flight departures | Early morningMidnight to 6 am |
---|---|
38%of flight departures | Morning6 am to noon |
45%of flight departures | AfternoonNoon to 6 pm |
16%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.
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