Find a great deal and save up to 90% by booking at least 38 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 Canada to Chicago within the next two weeks, with the cheapest ticket starting at $337.
Our data shows that April tends to be the cheapest month to fly to Chicago from Canada. Users have commonly found prices around $291 for the month, but tickets can be as low as $193. Due to multiple factors, prepare for potentially higher prices in September.
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
$191 - $381
Route
Depart
Return
Price
CalgaryChicago O'Hare Intl
YYC - ORD
YYCORD
Calgary
Thu 6/27
Nonstop3h 27m
Chicago O'Hare Intl
Thu 7/4
Nonstop3h 45m
Toronto IslandChicago Midway
YTZ - MDW
YTZMDW
Toronto Island
Mon 7/29
Nonstop1h 47m
Chicago Midway
Sat 8/3
Nonstop1h 42m
CalgaryChicago O'Hare Intl
YYC - ORD
YYCORD
Calgary
Sat 10/26
1 stop7h 06m
Chicago O'Hare Intl
Tue 10/29
1 stop5h 53m
Toronto Pearson IntlChicago O'Hare Intl
YYZ - ORD
YYZORD
Toronto Pearson Intl
Wed 6/19
Nonstop1h 57m
Chicago O'Hare Intl
Wed 6/26
Nonstop1h 48m
CalgaryChicago O'Hare Intl
YYC - ORD
YYCORD
Calgary
Tue 6/18
1 stop6h 30m
Chicago O'Hare Intl
Wed 6/19
Nonstop3h 45m
Toronto Pearson IntlChicago O'Hare Intl
YYZ - ORD
YYZORD
Toronto Pearson Intl
Mon 9/30
Nonstop1h 56m
Chicago O'Hare Intl
Sat 10/12
Nonstop1h 43m
Toronto Pearson IntlChicago O'Hare Intl
YYZ - ORD
YYZORD
Toronto Pearson Intl
Tue 6/18
Nonstop1h 55m
Chicago O'Hare Intl
Fri 6/21
1 stop5h 29m
Vancouver IntlChicago O'Hare Intl
YVR - ORD
YVRORD
Vancouver Intl
Thu 7/18
Nonstop4h 01m
Chicago O'Hare Intl
Tue 7/23
Nonstop4h 38m
Vancouver IntlChicago O'Hare Intl
YVR - ORD
YVRORD
Vancouver Intl
Sat 6/29
1 stop28h 46m
Chicago O'Hare Intl
Tue 7/2
1 stop16h 47m
No data available for this route at this time. Please check back soon.
Boarding
Comfort
Entertainment
Crew
Food
Overall
Reviews
Crew and airport staff were excellent. They accommodated my needs and were super professional and kind.
Boarding
Comfort
Entertainment
Crew
Food
Overall
Reviews
Crew and airport staff were excellent. They accommodated my needs and were super professional and kind.
Boarding
Comfort
Entertainment
Crew
Food
Overall
Reviews
Crew and airport staff were excellent. They accommodated my needs and were super professional and kind.
Boarding
Comfort
Entertainment
Crew
Food
Overall
Reviews
Crew and airport staff were excellent. They accommodated my needs and were super professional and kind.
Boarding
Comfort
Entertainment
Crew
Food
Overall
Reviews
Crew and airport staff were excellent. They accommodated my needs and were super professional and kind.
Boarding
Comfort
Entertainment
Crew
Food
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 |
Cheapflights goes through 900+ travel sites to look for the best flight deals for flights from Canada to Chicago. Too many options? Cheapflights also provides filters for things like airlines, price ranges, and number of stops to help you make a decision easily.
Cheapflights taps into our reliable network of hundreds of airlines and travel agencies to find the best deals for flights from Canada to Chicago for you. Better yet — we are completely free to use.
Cheapflights does show flights with no change fees to all users. To see these options for flights from Canada to Chicago, users can toggle the no change fees filter when performing a flight search.
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