Users have found that booking a flight from Canada to Chicago at least 38 days early can save you up to 90% on average compared to booking a flight this week. If booking 38 days before your flight isn’t an option for you, users have found flights from Canada to Chicago for as little as C$ 468 when booking for a departure date within the next two weeks. You can also check prices now. Some users have found airline tickets as low as C$ 666 for flights departing within the next 3 days.
Flights from Canada to Chicago lean towards being more expensive in September. Prices are generally better when you fly from Canada to Chicago in April, with the cheapest ticket starting at C$ 263.
Regardless of the time of day you decide to fly, the ticket price will remain around the same. Book flights from Canada to Chicago as you normally would.
Fly from
Fly to
Budget
C$ 263 - C$ 459
Route
Depart
Return
Price
CalgaryChicago O'Hare Intl
YYC - ORD
YYCORD
Calgary
Sat 21/9
Nonstop3h 39m
Chicago O'Hare Intl
Fri 27/9
Nonstop3h 50m
Toronto IslandChicago Midway
YTZ - MDW
YTZMDW
Toronto Island
Wed 11/9
Nonstop1h 47m
Chicago Midway
Sun 15/9
Nonstop1h 42m
Toronto IslandChicago Midway
YTZ - MDW
YTZMDW
Toronto Island
Thu 24/10
Nonstop1h 47m
Chicago Midway
Thu 24/10
Nonstop1h 42m
Toronto Pearson IntlChicago O'Hare Intl
YYZ - ORD
YYZORD
Toronto Pearson Intl
Wed 31/7
Nonstop2h 02m
Chicago O'Hare Intl
Sat 3/8
Nonstop1h 48m
CalgaryChicago O'Hare Intl
YYC - ORD
YYCORD
Calgary
Wed 23/10
Nonstop3h 29m
Chicago O'Hare Intl
Mon 28/10
Nonstop3h 44m
Toronto Pearson IntlChicago O'Hare Intl
YYZ - ORD
YYZORD
Toronto Pearson Intl
Tue 18/6
1 stop10h 58m
Chicago O'Hare Intl
Tue 25/6
1 stop18h 20m
Toronto Pearson IntlChicago O'Hare Intl
YYZ - ORD
YYZORD
Toronto Pearson Intl
Fri 14/6
Nonstop1h 55m
Chicago O'Hare Intl
Tue 18/6
1 stop5h 29m
CalgaryChicago O'Hare Intl
YYC - ORD
YYCORD
Calgary
Tue 16/7
1 stop6h 26m
Chicago O'Hare Intl
Mon 29/7
Nonstop3h 45m
Vancouver IntlChicago O'Hare Intl
YVR - ORD
YVRORD
Vancouver Intl
Mon 3/6
2 stops10h 01m
Chicago O'Hare Intl
Wed 12/6
1 stop14h 23m
No data available for this route at this time. Please check back soon.
Comfort
Crew
Boarding
Food
Overall
Entertainment
Reviews
Paid a lot for our exit row seats and they weren’t that roomy.
Comfort
Crew
Boarding
Food
Overall
Entertainment
Reviews
Paid a lot for our exit row seats and they weren’t that roomy.
Comfort
Crew
Boarding
Food
Overall
Entertainment
Reviews
Paid a lot for our exit row seats and they weren’t that roomy.
Comfort
Crew
Boarding
Food
Overall
Entertainment
Reviews
Paid a lot for our exit row seats and they weren’t that roomy.
Comfort
Crew
Boarding
Food
Overall
Entertainment
Reviews
Paid a lot for our exit row seats and they weren’t that roomy.
Comfort
Crew
Boarding
Food
Overall
Entertainment
Reviews
Paid a lot for our exit row seats and they weren’t that roomy.
14%of flight departures | Early morningMidnight to 6 am |
---|---|
37%of flight departures | Morning6 am to noon |
40%of flight departures | AfternoonNoon to 6 pm |
9%of flight departures | Evening6 pm to midnight |
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