Find a great deal and save up to 92% by booking at least 40 days prior to your desired departure date, rather than waiting until the week of travel. According to our data, there are a number of flights available from Chicago to Canada within the next two weeks, with the cheapest ticket starting at $359.
January is one of the best times of the year to fly to Canada from Chicago. Prices for January average $324 per person but you can even find prices for as low as $170. The most expensive prices can be found in the month of September. Opting for a January flight can save you 18% on your journey compared to booking in September
When flying from Chicago to Canada, the time of day you decide to fly out makes little to no difference towards the overall price you’ll pay on tickets.
Fly from
Fly to
Budget
$205 - $313
Route
Depart
Return
Price
Chicago O'Hare IntlCalgary
ORD - YYC
ORDYYC
Chicago O'Hare Intl
Sat 6/1
Nonstop3h 27m
Calgary
Sun 6/9
Nonstop3h 35m
Chicago O'Hare IntlToronto Pearson Intl
ORD - YYZ
ORDYYZ
Chicago O'Hare Intl
Tue 6/4
1 stop18h 20m
Toronto Pearson Intl
Tue 6/18
1 stop10h 58m
Chicago MidwayToronto Island
MDW - YTZ
MDWYTZ
Chicago Midway
Tue 6/4
Nonstop1h 42m
Toronto Island
Tue 6/18
Nonstop1h 47m
Chicago O'Hare IntlCalgary
ORD - YYC
ORDYYC
Chicago O'Hare Intl
Sun 10/20
Nonstop3h 51m
Calgary
Wed 10/23
1 stop8h 43m
Chicago MidwayCalgary
MDW - YYC
MDWYYC
Chicago Midway
Wed 10/2
1 stop7h 43m
Calgary
Sun 10/13
1 stop5h 12m
Chicago O'Hare IntlMontreal Pierre Elliott Trudeau Intl
ORD - YUL
ORDYUL
Chicago O'Hare Intl
Tue 5/21
1 stop11h 30m
Montreal Pierre Elliott Trudeau Intl
Wed 5/22
Nonstop2h 45m
Chicago O'Hare IntlToronto Pearson Intl
ORD - YYZ
ORDYYZ
Chicago O'Hare Intl
Sun 6/16
Nonstop1h 43m
Toronto Pearson Intl
Fri 6/21
Nonstop1h 56m
Chicago O'Hare IntlToronto Pearson Intl
ORD - YYZ
ORDYYZ
Chicago O'Hare Intl
Thu 5/30
Nonstop1h 35m
Toronto Pearson Intl
Thu 5/30
1 stop5h 29m
Chicago O'Hare IntlVancouver Intl
ORD - YVR
ORDYVR
Chicago O'Hare Intl
Thu 5/30
Nonstop4h 38m
Vancouver Intl
Wed 6/5
Nonstop4h 12m
No data available for this route at this time. Please check back soon.
Crew
Comfort
Food
Boarding
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.
Crew
Comfort
Food
Boarding
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.
Crew
Comfort
Food
Boarding
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.
Crew
Comfort
Food
Boarding
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.
Crew
Comfort
Food
Boarding
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.
Crew
Comfort
Food
Boarding
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 |
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