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$ 461 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$ 669 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$ 264.
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$ 261 - C$ 521
Route
Depart
Return
Price
CalgaryChicago O'Hare Intl
YYC - ORD
YYCORD
Calgary
Thu 27/6
Nonstop3h 27m
Chicago O'Hare Intl
Thu 4/7
Nonstop3h 45m
Toronto IslandChicago Midway
YTZ - MDW
YTZMDW
Toronto Island
Sat 29/6
Nonstop1h 47m
Chicago Midway
Sat 6/7
Nonstop1h 42m
CalgaryChicago O'Hare Intl
YYC - ORD
YYCORD
Calgary
Sat 26/10
1 stop7h 06m
Chicago O'Hare Intl
Tue 29/10
1 stop5h 53m
Toronto Pearson IntlChicago O'Hare Intl
YYZ - ORD
YYZORD
Toronto Pearson Intl
Wed 19/6
Nonstop1h 57m
Chicago O'Hare Intl
Wed 26/6
Nonstop1h 48m
CalgaryChicago O'Hare Intl
YYC - ORD
YYCORD
Calgary
Tue 18/6
1 stop6h 30m
Chicago O'Hare Intl
Wed 19/6
Nonstop3h 45m
Toronto Pearson IntlChicago O'Hare Intl
YYZ - ORD
YYZORD
Toronto Pearson Intl
Mon 30/9
Nonstop1h 56m
Chicago O'Hare Intl
Sat 12/10
Nonstop1h 43m
Toronto Pearson IntlChicago O'Hare Intl
YYZ - ORD
YYZORD
Toronto Pearson Intl
Tue 18/6
Nonstop1h 55m
Chicago O'Hare Intl
Fri 21/6
1 stop5h 29m
Vancouver IntlChicago O'Hare Intl
YVR - ORD
YVRORD
Vancouver Intl
Thu 18/7
Nonstop4h 01m
Chicago O'Hare Intl
Tue 23/7
Nonstop4h 38m
Vancouver IntlChicago O'Hare Intl
YVR - ORD
YVRORD
Vancouver Intl
Sat 29/6
1 stop28h 46m
Chicago O'Hare Intl
Tue 2/7
1 stop16h 47m
No data available for this route at this time. Please check back soon.
Entertainment
Boarding
Food
Comfort
Crew
Overall
Reviews
Crew and airport staff were excellent. They accommodated my needs and were super professional and kind.
Entertainment
Boarding
Food
Comfort
Crew
Overall
Reviews
Crew and airport staff were excellent. They accommodated my needs and were super professional and kind.
Entertainment
Boarding
Food
Comfort
Crew
Overall
Reviews
Crew and airport staff were excellent. They accommodated my needs and were super professional and kind.
Entertainment
Boarding
Food
Comfort
Crew
Overall
Reviews
Crew and airport staff were excellent. They accommodated my needs and were super professional and kind.
Entertainment
Boarding
Food
Comfort
Crew
Overall
Reviews
Crew and airport staff were excellent. They accommodated my needs and were super professional and kind.
Entertainment
Boarding
Food
Comfort
Crew
Overall
Reviews
Crew and airport staff were excellent. They accommodated my needs and were super professional and kind.
16%of flight departures | Early morningMidnight to 6 am |
---|---|
36%of flight departures | Morning6 am to noon |
38%of flight departures | AfternoonNoon to 6 pm |
10%of flight departures | Evening6 pm to midnight |
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