When searching for a good deal, it’s best to be prepared for potential fluctuations in price. We recommend booking at least 27 days in advance, which can save you up to 78% on flights from Toronto Kitchener-Waterloo Airport to Chicago O'Hare Intl Airport compared to booking the week you need them. Waiting 27 days out may not be for everyone, so we have options available for flights within the next two weeks, with the lowest price starting at C$ 490. For sooner than that we have options available in the next 3 days from C$ 667.
Our data shows that January tends to be the cheapest month to fly to Chicago O'Hare Intl Airport from Toronto Kitchener-Waterloo Airport. Users have commonly found prices around C$ 398 for the month, but tickets can be as low as C$ 243. Due to multiple factors, prepare for potentially higher prices in July.
When flying from Toronto Kitchener-Waterloo Airport to Chicago O'Hare Intl Airport, 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
C$ 788 - C$ 1,352
Route
Depart
Return
Price
Toronto Kitchener-WaterlooChicago O'Hare Intl
YKF - ORD
YKFORD
Toronto Kitchener-Waterloo
Fri 24/5
3 stops33h 05m
Chicago O'Hare Intl
Mon 27/5
2 stops34h 57m
Toronto Kitchener-WaterlooChicago O'Hare Intl
YKF - ORD
YKFORD
Toronto Kitchener-Waterloo
Fri 24/5
2 stops28h 40m
Chicago O'Hare Intl
Mon 27/5
2 stops34h 57m
Toronto Kitchener-WaterlooChicago O'Hare Intl
YKF - ORD
YKFORD
Toronto Kitchener-Waterloo
Fri 24/5
3 stops33h 05m
Chicago O'Hare Intl
Mon 27/5
3 stops34h 00m
Toronto Kitchener-WaterlooChicago O'Hare Intl
YKF - ORD
YKFORD
Toronto Kitchener-Waterloo
Fri 24/5
2 stops28h 40m
Chicago O'Hare Intl
Mon 27/5
1 stop11h 45m
Toronto Kitchener-WaterlooChicago O'Hare Intl
YKF - ORD
YKFORD
Toronto Kitchener-Waterloo
Thu 9/5
2 stops21h 32m
Chicago O'Hare Intl
Thu 16/5
1 stop11h 45m
Toronto Kitchener-WaterlooChicago O'Hare Intl
YKF - ORD
YKFORD
Toronto Kitchener-Waterloo
Sat 25/5
1 stop11h 50m
Chicago O'Hare Intl
Sat 1/6
1 stop30h 15m
Toronto Kitchener-WaterlooChicago O'Hare Intl
YKF - ORD
YKFORD
Toronto Kitchener-Waterloo
Fri 24/5
1 stop11h 50m
Chicago O'Hare Intl
Fri 31/5
1 stop30h 15m
Toronto Kitchener-WaterlooChicago O'Hare Intl
YKF - ORD
YKFORD
Toronto Kitchener-Waterloo
Mon 10/6
1 stop11h 50m
Chicago O'Hare Intl
Sat 15/6
1 stop29h 57m
Toronto Kitchener-WaterlooChicago O'Hare Intl
YKF - ORD
YKFORD
Toronto Kitchener-Waterloo
Fri 31/5
1 stop11h 50m
Chicago O'Hare Intl
Sun 2/6
1 stop30h 15m
No data available for this route at this time. Please check back soon.
Food
Crew
Overall
Boarding
Comfort
Entertainment
Reviews
Flights good. Our original flight from Halifax to Toronto was delayed 4 days Unacceptable We flew with Air Canada a picked up original flight in Toronto Cost extra $500 Maybe Westjet could give us a voucher or pay for this inconvenience. Thank You. Garry Barkman
Food
Crew
Overall
Boarding
Comfort
Entertainment
Reviews
Flights good. Our original flight from Halifax to Toronto was delayed 4 days Unacceptable We flew with Air Canada a picked up original flight in Toronto Cost extra $500 Maybe Westjet could give us a voucher or pay for this inconvenience. Thank You. Garry Barkman
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