Users have found that booking a flight from Canada to Chicago at least 27 days early can save you up to 78% on average compared to booking a flight this week. If booking 27 days before your flight isn’t an option for you, users have found flights from Canada to Chicago for as little as C$ 491 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$ 668 for flights departing within the next 3 days.
Flights from Canada to Chicago lean towards being more expensive in July. Prices are generally better when you fly from Canada to Chicago in January, with the cheapest ticket starting at C$ 244.
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$ 279 - C$ 408
Route
Depart
Return
Price
Toronto Pearson IntlChicago O'Hare Intl
YYZ - ORD
YYZORD
Toronto Pearson Intl
Tue 14/5
1 stop12h 10m
Chicago O'Hare Intl
Wed 15/5
3 stops31h 37m
Toronto IslandChicago Midway
YTZ - MDW
YTZMDW
Toronto Island
Thu 23/5
Nonstop1h 47m
Chicago Midway
Thu 30/5
Nonstop1h 42m
Toronto Pearson IntlChicago O'Hare Intl
YYZ - ORD
YYZORD
Toronto Pearson Intl
Thu 20/6
Nonstop1h 54m
Chicago O'Hare Intl
Sun 23/6
Nonstop1h 48m
Toronto Pearson IntlChicago O'Hare Intl
YYZ - ORD
YYZORD
Toronto Pearson Intl
Fri 24/5
Nonstop1h 56m
Chicago O'Hare Intl
Fri 31/5
Nonstop1h 43m
Toronto Pearson IntlChicago O'Hare Intl
YYZ - ORD
YYZORD
Toronto Pearson Intl
Sat 8/6
1 stop5h 18m
Chicago O'Hare Intl
Wed 19/6
1 stop8h 25m
Toronto Pearson IntlChicago O'Hare Intl
YYZ - ORD
YYZORD
Toronto Pearson Intl
Fri 24/5
Nonstop1h 55m
Chicago O'Hare Intl
Fri 31/5
1 stop6h 00m
CalgaryChicago O'Hare Intl
YYC - ORD
YYCORD
Calgary
Thu 11/7
Nonstop3h 27m
Chicago O'Hare Intl
Sun 14/7
Nonstop3h 45m
Toronto Pearson IntlChicago O'Hare Intl
YYZ - ORD
YYZORD
Toronto Pearson Intl
Thu 23/5
1 stop5h 39m
Chicago O'Hare Intl
Sun 26/5
Nonstop1h 40m
Vancouver IntlChicago O'Hare Intl
YVR - ORD
YVRORD
Vancouver Intl
Mon 20/5
Nonstop4h 13m
Chicago O'Hare Intl
Wed 29/5
Nonstop4h 20m
No data available for this route at this time. Please check back soon.
Boarding
Crew
Entertainment
Comfort
Food
Overall
Reviews
Paid a lot for our exit row seats and they weren’t that roomy.
Boarding
Crew
Entertainment
Comfort
Food
Overall
Reviews
Paid a lot for our exit row seats and they weren’t that roomy.
Boarding
Crew
Entertainment
Comfort
Food
Overall
Reviews
Paid a lot for our exit row seats and they weren’t that roomy.
Boarding
Crew
Entertainment
Comfort
Food
Overall
Reviews
Paid a lot for our exit row seats and they weren’t that roomy.
Boarding
Crew
Entertainment
Comfort
Food
Overall
Reviews
Paid a lot for our exit row seats and they weren’t that roomy.
Boarding
Crew
Entertainment
Comfort
Food
Overall
Reviews
Paid a lot for our exit row seats and they weren’t that roomy.
17%of flight departures | Early morningMidnight to 6 am |
---|---|
31%of flight departures | Morning6 am to noon |
48%of flight departures | AfternoonNoon to 6 pm |
4%of flight departures | Evening6 pm to midnight |
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