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Cheap flights from Toronto Pearson Intl Airport to Chicago O'Hare Intl Airport from £101
This is the cheapest one-way flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 28/11. Fares are subject to change and may not be available on all flights or dates of travel.
YYZ — ORD
29 Nov — 6 Dec1
Cheapflights Tip: The best prices from Toronto Pearson Intl to Chicago O'Hare Intl are usually found in April or May, booked 41 days in advance, depart on a Friday or Thursday and return on a Thursday
Find flight deals from Pearson Intl to O'Hare Intl
Cheapest flights from Pearson Intl to O'Hare IntlExplore the most affordable flight options available from Pearson Intl to O'Hare Intl. Find the lowest fares from popular airlines and budget airlines, with prices last updated on 30 October 2025.
Explore the most affordable flight options available from Pearson Intl to O'Hare Intl. Find the lowest fares from popular airlines and budget airlines, with prices last updated on 30 October 2025.
Wed 26/1117:30YYZ - ORD
Nonstop2h 09mUnited Airlines
Sun 30/1107:10ORD - YYZ
Nonstop1h 48mUnited Airlines
Deal found 28/10£153
Tue 16/1209:00YYZ - ORD
Nonstop2h 02mUnited Airlines
Thu 15/107:10ORD - YYZ
Nonstop1h 48mUnited Airlines
Deal found 28/10£157
Thu 27/1106:05YYZ - ORD
1 stop3h 52mDelta
Tue 2/1210:45ORD - YYZ
1 stop5h 30mDelta
Deal found 28/10£160
Mon 15/1219:40YYZ - ORD
1 stop5h 03mUnited Airlines
Fri 16/111:15ORD - YYZ
Nonstop1h 46mUnited Airlines
Deal found 28/10£160
Mon 15/1214:09YYZ - ORD
1 stop5h 18mDelta
Wed 14/109:35ORD - YYZ
1 stop5h 37mDelta
Deal found 28/10£169
Wed 26/1106:05YYZ - ORD
1 stop4h 56mDelta
Sun 30/1106:45ORD - YYZ
1 stop7h 03mDelta
Deal found 29/10£169
Sat 22/1119:40YYZ - ORD
1 stop5h 03mUnited Airlines
Thu 27/1111:52ORD - YYZ
1 stop4h 57mUnited Airlines
Deal found 27/10£172
Fri 21/1121:00YYZ - ORD
Nonstop2h 05mMultiple Airlines
Fri 28/1114:00ORD - YYZ
Nonstop1h 39mMultiple Airlines
Deal found 28/10£173
Thu 4/1221:00YYZ - ORD
Nonstop2h 05mUnited Airlines
Sun 7/1207:10ORD - YYZ
Nonstop1h 48mUnited Airlines
Deal found 28/10£174
Thu 11/1211:00YYZ - ORD
Nonstop2h 05mUnited Airlines
Sun 14/1206:00ORD - YYZ
1 stop4h 48mUnited Airlines
Deal found 29/10£175
Mon 15/1209:00YYZ - ORD
Nonstop2h 02mUnited Airlines
Thu 1/121:20ORD - YYZ
Nonstop1h 39mUnited Airlines
Deal found 28/10£176
Cheap flight deals from Pearson Intl to O'Hare Intl
Discover tips and strategies to find the most affordable flight options for your journey from Pearson Intl (YYZ) to O'Hare Intl (ORD). Learn about various techniques such as flexible date searches, comparing prices across and setting up price alerts. Use these methods to find the cheapest flights available for your travel needs. Data last updated 30 October 2025.
Cheapflights Fare Finder
Customise your flight search to find flights from Pearson Intl to O'Hare Intl that fit within your specific budget. Explore options based on user searches and filter the results based on your desired price range. Find flights that match your budget for a cost-effective journey. Over the last 7 days, Cheapflights users made 858,174 searches. Data last updated 30 October 2025.
Use the filters below to find and compare flights from Toronto Pearson Intl Airport to Chicago O'Hare Intl Airport that are best for you.
Fly from
Pearson Intl
Fly to
O'Hare Intl
Route
Depart
Return
Price
TorontoChicago
YYZ - ORD
YYZORD
Toronto Pearson Intl
Fri 27/2
15:30-16:39
Nonstop2h 09m
Chicago O'Hare Intl
Sun 1/3
16:47-19:45
Nonstop1h 58m
£139
TorontoChicago
YYZ - ORD
YYZORD
Toronto Pearson Intl
Tue 24/2
08:55-10:02
Nonstop2h 07m
Chicago O'Hare Intl
Sat 28/2
20:15-22:54
Nonstop1h 39m
£139
TorontoChicago
YYZ - ORD
YYZORD
Toronto Pearson Intl
Thu 11/12
15:30-16:52
Nonstop2h 22m
Chicago O'Hare Intl
Sun 14/12
08:00-10:40
Nonstop1h 40m
£153
TorontoChicago
YYZ - ORD
YYZORD
Toronto Pearson Intl
Wed 3/12
15:30-16:52
Nonstop2h 22m
Chicago O'Hare Intl
Sun 7/12
10:00-12:40
Nonstop1h 40m
£153
TorontoChicago
YYZ - ORD
YYZORD
Toronto Pearson Intl
Thu 18/12
21:00-22:05
Nonstop2h 05m
Chicago O'Hare Intl
Tue 13/1
13:13-16:02
Nonstop1h 49m
£157
TorontoChicago
YYZ - ORD
YYZORD
Toronto Pearson Intl
Tue 16/12
09:00-10:02
Nonstop2h 02m
Chicago O'Hare Intl
Wed 14/1
16:50-19:45
Nonstop1h 55m
£157
TorontoChicago
YYZ - ORD
YYZORD
Toronto Pearson Intl
Tue 16/12
09:00-10:02
Nonstop2h 02m
Chicago O'Hare Intl
Tue 13/1
11:15-14:01
Nonstop1h 46m
£157
TorontoChicago
YYZ - ORD
YYZORD
Toronto Pearson Intl
Thu 18/12
21:00-22:05
Nonstop2h 05m
Chicago O'Hare Intl
Wed 14/1
21:15-23:59
Nonstop1h 44m
£157
TorontoChicago
YYZ - ORD
YYZORD
Toronto Pearson Intl
Wed 17/12
09:00-10:02
Nonstop2h 02m
Chicago O'Hare Intl
Sat 17/1
21:15-23:59
Nonstop1h 44m
£157
TorontoChicago
YYZ - ORD
YYZORD
Toronto Pearson Intl
Wed 17/12
21:00-22:05
Nonstop2h 05m
Chicago O'Hare Intl
Fri 16/1
11:15-14:01
Nonstop1h 46m
£157
Showing 1-10 of 20 results
Best time to book a flight from Pearson Intl to O'Hare Intl
Have a flexible travel schedule? Discover the best time to fly to O'Hare Intl from Pearson Intl with our price prediction graph.
Estimated return price
Rates are based on past data. Find the cheapest month and day to book your flight based on your travel requirements, then search for cheap deals.
Cheapflights Insights
Everything you need to know about your flight from Toronto Pearson Intl Airport to Chicago O'Hare Intl Airport
Prices
Delays
How far ahead should I book a flight from Toronto Pearson Intl Airport to Chicago O'Hare Intl Airport?
Use this chart to determine the optimal time to book a return flight from Pearson Intl to O'Hare Intl. Price data was last updated on 24 October 2025.
Booking 41 days in advance of your planned departure date is, on average, the best time to get cheap flights from Toronto Pearson Intl Airport to Chicago O'Hare Intl Airport. The general trend is that the closer you book to the departure date, the more expensive your flight will be.
What is the cheapest month to book a flight from Toronto Pearson Intl Airport to Chicago O'Hare Intl Airport?
Currently, January is the cheapest month in which you can book a flight from Toronto Pearson Intl Airport to Chicago O'Hare Intl Airport (average of £104). Flying from Toronto Pearson Intl Airport to Chicago O'Hare Intl Airport in February is currently the most expensive (average of £178). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.
What is the cheapest time of day to fly from YYZ to ORD?
Find hourly flight availability from Pearson Intl to O'Hare Intl. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated 30 October 2025.
One of the essential ways to save on airfare from Toronto Pearson Intl Airport to Chicago O'Hare Intl Airport is to remain as flexible as possible. Flights that are at midday tend to be the most expensive. A flight in the morning could potentially save you up to 44% on airfare.
What is the cheapest day to fly from Toronto Pearson Intl Airport to Chicago O'Hare Intl Airport?
Use this chart to determine the cheapest time to fly return from Pearson Intl to O'Hare Intl. Price data was last updated on 26 October 2025.
Travellers seeking maximum savings on their Toronto Pearson Intl Airport to Chicago O'Hare Intl Airport flight should consider departing on Thursday evenings when fares are most often at their lowest. Saturday at midday flights should be avoided if possible as fares are typically the most expensive at this time.
How often are flights from Toronto to Chicago delayed?
About 9% of weekly flights between Toronto and Chicago have experienced delays in the past year, with the average delay time being 143 minutes.
What is the most punctual flight time for Toronto to Chicago flights?
Historically, flights departing at night are less likely to be delayed, whereas flights leaving in the evening tend to experience delays more often.
What day of the week experiences the fewest flight delays on this route?
Tuesday tends to have the lowest number of delays on this route, whereas Friday has historically faced a higher average of delays compared to other days of the week.
Which airline has the best punctuality record on Toronto to Chicago flights?
Over the past year, Air Antilles have had the lowest number of delays on this route, with no flights being classified as delayed.
Reviews of airlines servicing O'Hare Intl
Get insights into the airlines that provide service to O'Hare Intl. Read reviews, discover amenities, and learn about the overall travel experience offered by airlines. Use this information to make informed decisions when choosing an airline for your flight to O'Hare Intl. Reviews last updated 30 October 2025.
Get a feel of what it's like to fly with Air Canada from Toronto Pearson Intl Airport to Chicago O'Hare Intl Airport by reading reviews from past customers. Users have also rated airlines in terms of entertainment options, comfort, food, crew/service, and boarding process.
Entertainment
6.8
Comfort
7.1
Boarding
7.3
Overall
7.1
Crew
7.8
Food
6.3
Reviews
1 / 20
8.0
ExcellentJadi-Ann,Jun 2025
YYZ - KIN
Entertainment
6.8
Comfort
7.1
Boarding
7.3
Overall
7.1
Crew
7.8
Food
6.3
Reviews
1 / 20
8.0
ExcellentJadi-Ann,Jun 2025
YYZ - KIN
Related info for your journey
Find useful and relevant information for your journey from Pearson Intl to O'Hare Intl. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.
Travelling to a place near Chicago O'Hare Intl Airport?
Book flights to Chicago O'Hare Intl Airport if you plan to visit one of these locationsDowners Grove
Elk Grove Village
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Top airline flying from Pearson Intl to O'Hare Intl
Discover the top airline that operate flights from Pearson Intl to O'Hare Intl. Compare their services, reliability, and customer satisfaction ratings to choose the airline that best suits your travel preferences and needs. Over the last 7 days, Cheapflights users made 858,174 searches. Data last updated 30 October 2025.
Fly with Cheapflights
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How does Cheapflights help users find flights from Pearson Intl to O'Hare Intl?
Deals for Pearson Intl to O'Hare Intl flights are sourced from 900+ travel sites when you use Cheapflights. When all flight results come back, Cheapflights lets you sort and filter flights using different criteria to choose better, like price, airport, cabin class, and plenty of other options.
Why should you use Cheapflights to find cheap flight tickets from Pearson Intl to O'Hare Intl?
By finding flights from multiple airlines and providers at completely no cost, Cheapflights helps millions of users like you annually find the best flights to O'Hare Intl from Pearson Intl.
Can Cheapflights find flights from Pearson Intl to O'Hare Intl with no change fees?
Cheapflights does show flights with no change fees to all users. To see these options for flights from Pearson Intl to O'Hare Intl, users can toggle the no change fees filter when performing a flight search.
Can Cheapflights notify me if prices for flights from Pearson Intl to O'Hare Intl become cheaper?
Yes, Cheapflights offers price alerts on Pearson Intl to O'Hare Intl flights so you can book your travel at the perfect time. Price Alerts can be enabled by clicking the bell icon next to the flight deals above and providing your email address where you want to receive the alerts.