Cheap flights from Toronto Pearson Intl Airport to Chicago O'Hare Intl Airport from £107
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 29/8. Fares are subject to change and may not be available on all flights or dates of travel.
YYZ — ORD
9 Sep — 16 Sep1
Return
1 adult
Economy
Return
1 adult, Economy, 0 bags
Cheapflights Tip: The best prices from Toronto Pearson Intl to Chicago O'Hare Intl are usually found in January or February, booked 84 days in advance, depart on a Friday or Wednesday and return on a Tuesday
Cheap flight deals from Pearson Intl to O'Hare Intl
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Cheapest flights from Pearson Intl to O'Hare Intl
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 10 August 2026.
Thu 17/908:05 -
Nonstop1h 55m
Thu 24/909:55 -
Nonstop1h 45m
Deal found 5/8£150
Wed 16/914:00 -
Nonstop1h 55m
Mon 21/915:45 -
Nonstop1h 46m
Deal found 9/8£151
Tue 8/914:00 -
Nonstop1h 55m
Tue 15/909:55 -
Nonstop1h 45m
Deal found 9/8£153
Mon 14/911:00 -
Nonstop2h 00m
Mon 28/907:09 -
Nonstop1h 45m
Deal found 7/8£156
Thu 10/908:50 -
Nonstop2h 03m
Wed 16/915:40 -
1 stop6h 38m
Deal found 6/8£162
Fri 18/913:00 -
Nonstop2h 05m
Sun 20/915:40 -
1 stop6h 38m
Deal found 7/8£162
Thu 3/910:15 -
Nonstop2h 06m
Tue 8/908:45 -
1 stop6h 08m
Deal found 8/8£163
Thu 24/911:00 -
Nonstop2h 00m
Mon 28/915:40 -
1 stop5h 13m
Deal found 10/8£165
Thu 10/919:43 -
1 stop4h 57m
Sun 13/917:35 -
Nonstop1h 43m
Deal found 6/8£167
Tue 8/909:44 -
1 stop7h 45m
Mon 14/914:15 -
Nonstop1h 46m
Deal found 7/8£167
Best flights from Pearson Intl to O'Hare Intl
Discover carefully curated flight deals from Pearson Intl to O'Hare Intl that have cost, travel time, and stopovers in mind to ensure you get the best travel experience. Data last updated 10 August 2026.
Thu 3/907:00 -
Nonstop2h 00m
Tue 8/921:18 -
Nonstop1h 41m
Deal found 8/8£156
Thu 17/914:24 -
1 stop7h 06m
Thu 24/913:55 -
1 stop8h 04m
Deal found 5/8£180
Thu 10/919:43 -
1 stop4h 57m
Sun 13/917:35 -
Nonstop1h 43m
Deal found 7/8£181
Thu 10/908:50 -
Nonstop2h 03m
Sun 13/917:53 -
Nonstop1h 51m
Deal found 7/8£177
Wed 9/909:45 -
1 stop4h 14m
Wed 16/917:10 -
1 stop4h 49m
Deal found 6/8£181
Thu 10/919:43 -
1 stop4h 57m
Sat 12/912:55 -
1 stop5h 07m
Deal found 8/8£182
Tue 8/916:05 -
1 stop5h 25m
Tue 15/907:05 -
1 stop3h 13m
Deal found 9/8£182
Wed 16/920:00 -
1 stop5h 28m
Mon 21/908:42 -
1 stop4h 37m
Deal found 9/8£182
Sun 30/809:45 -
1 stop4h 23m
Tue 1/911:22 -
1 stop5h 02m
Deal found 5/8£198
Fri 30/1018:40 -
1 stop6h 09m
Sat 31/1007:03 -
Nonstop1h 44m
Deal found 6/8£186
Wed 26/812:09 -
1 stop5h 08m
Tue 8/913:55 -
1 stop8h 04m
Deal found 8/8£200
Fri 4/907:00 -
Nonstop2h 00m
Mon 7/921:15 -
Nonstop1h 44m
Deal found 7/8£196
Direct flights from Pearson Intl to O'Hare Intl
Explore direct flight options from Pearson Intl to O'Hare Intl based on user searches, and compare prices and availability for your desired travel dates. Data last updated 10 August 2026.
Thu 17/908:05 -
Nonstop1h 55m
Thu 24/909:55 -
Nonstop1h 45m
Deal found 5/8£150
Wed 16/914:00 -
Nonstop1h 55m
Mon 21/915:45 -
Nonstop1h 46m
Deal found 9/8£151
Tue 8/914:00 -
Nonstop1h 55m
Tue 15/909:55 -
Nonstop1h 45m
Deal found 9/8£153
Mon 14/911:00 -
Nonstop2h 00m
Mon 28/907:09 -
Nonstop1h 45m
Deal found 7/8£156
Thu 10/908:50 -
Nonstop2h 03m
Sun 13/917:53 -
Nonstop1h 51m
Deal found 6/8£176
Mon 14/907:00 -
Nonstop2h 00m
Wed 16/917:53 -
Nonstop1h 51m
Deal found 9/8£178
Thu 10/911:00 -
Nonstop2h 00m
Sun 13/920:40 -
Nonstop1h 46m
Deal found 10/8£180
Thu 3/911:00 -
Nonstop2h 00m
Sun 6/912:59 -
Nonstop1h 47m
Deal found 7/8£196
Fri 4/907:00 -
Nonstop2h 00m
Mon 7/921:15 -
Nonstop1h 44m
Deal found 7/8£215
Sun 13/908:50 -
Nonstop2h 03m
Thu 17/907:09 -
Nonstop1h 45m
Deal found 9/8£217
Last-minute flights from Pearson Intl to O'Hare Intl
Discover last-minute flight deals from Pearson Intl to O'Hare Intl. Data last updated 10 August 2026 and is based on user searches.
Thu 3/910:15 -
Nonstop2h 06m
Tue 8/908:45 -
1 stop6h 08m
Deal found 8/8£163
Tue 8/914:00 -
Nonstop1h 55m
Tue 15/909:55 -
Nonstop1h 45m
Deal found 9/8£153
Tue 8/909:44 -
1 stop7h 45m
Mon 14/914:15 -
Nonstop1h 46m
Deal found 7/8£167
Thu 10/908:50 -
Nonstop2h 03m
Wed 16/915:40 -
1 stop6h 38m
Deal found 6/8£162
Thu 10/919:43 -
1 stop4h 57m
Sun 13/917:35 -
Nonstop1h 43m
Deal found 6/8£167
Mon 14/908:50 -
Nonstop2h 03m
Sat 26/907:09 -
Nonstop1h 45m
Deal found 7/8£156
Wed 16/914:00 -
Nonstop1h 55m
Mon 21/915:45 -
Nonstop1h 46m
Deal found 9/8£151
Thu 17/908:05 -
Nonstop1h 55m
Thu 24/909:55 -
Nonstop1h 45m
Deal found 5/8£150
Fri 18/913:00 -
Nonstop2h 05m
Sun 20/915:40 -
1 stop6h 38m
Deal found 7/8£162
Thu 24/911:00 -
Nonstop2h 00m
Mon 28/915:40 -
1 stop5h 13m
Deal found 10/8£165
One-way flights from Pearson Intl to O'Hare Intl
Search for one-way flight options from Pearson Intl to O'Hare Intl. Find affordable one-way fares based on user searches. Data last updated 10 August 2026.
Sat 29/814:00 -
Nonstop1h 55m
Deal found 6/8£107
Sun 13/908:50 -
Nonstop2h 03m
Deal found 7/8£108
Mon 7/906:10 -
1 stop7h 58m
Deal found 10/8£109
Tue 1/909:45 -
1 stop4h 23m
Deal found 6/8£112
Tue 15/909:45 -
1 stop7h 28m
Deal found 8/8£113
Sun 30/808:05 -
Nonstop1h 55m
Deal found 6/8£114
Thu 27/821:00 -
Nonstop2h 05m
Deal found 6/8£116
Sun 30/810:15 -
Nonstop2h 06m
Deal found 9/8£116
Mon 31/815:00 -
1 stop6h 05m
Deal found 6/8£119
Fri 28/808:50 -
Nonstop2h 03m
Deal found 5/8£124
Find 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 10 August 2026.
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 10 August 2026.
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
Fly to
Route
Depart
Return
Price
Cheapest return flight
Fastest return journey
TorontoChicago
YYZ Toronto Pearson Intl - ORD Chicago O'Hare Intl
YYZORD
Toronto Pearson Intl
Thu 3/9
07:00-08:00
Nonstop2h 00m
Chicago O'Hare Intl
Tue 8/9
21:18-23:59
Nonstop1h 41m
£156
TorontoChicago
YYZ Toronto Pearson Intl - ORD Chicago O'Hare Intl
YYZORD
Toronto Pearson Intl
Thu 10/9
08:50-09:53
Nonstop2h 03m
Chicago O'Hare Intl
Sun 13/9
17:53-20:44
Nonstop1h 51m
£177
TorontoChicago
YYZ Toronto Pearson Intl - ORD Chicago O'Hare Intl
YYZORD
Toronto Pearson Intl
Thu 17/9
14:24-20:30
1 stop7h 06m
Chicago O'Hare Intl
Thu 24/9
13:55-22:59
1 stop8h 04m
£180
TorontoChicago
YYZ Toronto Pearson Intl - ORD Chicago O'Hare Intl
YYZORD
Toronto Pearson Intl
Thu 10/9
19:43-23:40
1 stop4h 57m
Chicago O'Hare Intl
Sun 13/9
17:35-20:18
Nonstop1h 43m
£181
TorontoChicago
YYZ Toronto Pearson Intl - ORD Chicago O'Hare Intl
YYZORD
Toronto Pearson Intl
Wed 9/9
09:45-12:59
1 stop4h 14m
Chicago O'Hare Intl
Wed 16/9
17:10-22:59
1 stop4h 49m
£181
TorontoChicago
YYZ Toronto Pearson Intl - ORD Chicago O'Hare Intl
YYZORD
Toronto Pearson Intl
Thu 10/9
19:43-23:40
1 stop4h 57m
Chicago O'Hare Intl
Sat 12/9
12:55-19:02
1 stop5h 07m
£182
TorontoChicago
YYZ Toronto Pearson Intl - ORD Chicago O'Hare Intl
YYZORD
Toronto Pearson Intl
Tue 8/9
16:05-20:30
1 stop5h 25m
Chicago O'Hare Intl
Tue 15/9
07:05-11:18
1 stop3h 13m
£182
TorontoChicago
YYZ Toronto Pearson Intl - ORD Chicago O'Hare Intl
YYZORD
Toronto Pearson Intl
Wed 16/9
20:00-00:28
1 stop5h 28m
Chicago O'Hare Intl
Mon 21/9
08:42-14:19
1 stop4h 37m
£182
TorontoChicago
YYZ Toronto Pearson Intl - ORD Chicago O'Hare Intl
YYZORD
Toronto Pearson Intl
Fri 30/10
18:40-23:49
1 stop6h 09m
Chicago O'Hare Intl
Sat 31/10
07:03-09:47
Nonstop1h 44m
£186
TorontoChicago
YYZ Toronto Pearson Intl - ORD Chicago O'Hare Intl
YYZORD
Toronto Pearson Intl
Fri 4/9
07:00-08:00
Nonstop2h 00m
Chicago O'Hare Intl
Mon 7/9
21:15-23:59
Nonstop1h 44m
£196
Flights are sorted by cheapest return flights first.
Deals found on 9/8
Showing 1-10 of 23 resultsSorted by cheapest first
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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.
YYZ-ORD
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
Airlines
Delays
How far ahead should I book a flight from Toronto Pearson Intl Airport to Chicago O'Hare Intl Airport?
Booking 83 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 £193). Flying from Toronto Pearson Intl Airport to Chicago O'Hare Intl Airport in October is currently the most expensive (average of £245). 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 10 August 2026.
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 in the afternoon tend to be the most expensive. A flight in the evening could potentially save you up to 60% 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 8 August 2026.
Travellers seeking maximum savings on their Toronto Pearson Intl Airport to Chicago O'Hare Intl Airport flight should consider departing on Friday evenings when fares are most often at their lowest. Monday mornings flights should be avoided if possible as fares are typically the most expensive at this time.
How much does it cost for a return flight from Toronto Pearson Intl Airport to Chicago O'Hare Intl Airport?
Airfare is below average for this route at the moment.
Toronto Pearson Intl Airport to Chicago O'Hare Intl Airport flights typically cost between £190 and £303 in September.The cheapest return price found within the last 5 days was £150 on Air Canada (17 Sept–24 Sept).
Weekly flight availability from Toronto Pearson Intl Airport to Chicago O'Hare Intl Airport
Explore weekly flight availability from Pearson Intl to O'Hare Intl. Discover flights operating on different days of the week, giving you the flexibility to choose a travel day that best fits your plans. Compare info to find the most convenient option for your journey. Data last updated 10 August 2026.
The most flights from YYZ to ORD are scheduled on a Sunday (70 on average). You will have fewer flight options on Wednesday, which is when the least amount of flights are scheduled (42 on average).
How often are flights from Toronto to Chicago delayed?
About 13% of weekly flights between Toronto and Chicago have experienced delays in the past year, with the average delay time being 139 minutes.
What is the most punctual flight time for Toronto to Chicago flights?
Historically, flights departing in the morning 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?
Thursday tends to have the lowest number of delays on this route, whereas Saturday 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, United Airlines have had the lowest number of delays on this route, with just 9% of flights being delayed.
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.
How long is the flight from Toronto Pearson Intl Airport to Chicago O'Hare Intl Airport?
For as low as £150, Air Canada can have you in Chicago O'Hare Intl Airport from Toronto Pearson Intl Airport in 1h 55m. There are 436 mi between Toronto Pearson Intl Airport and Chicago O'Hare Intl Airport. Most flights are nonstop.
What are the most reliable airlines from Toronto Pearson Intl Airport to Chicago O'Hare Intl Airport?
Looking for the most reliable airlines to get you to your destination on time? Our data shows these are most likely to get you from Toronto Pearson Intl Airport to Chicago O'Hare Intl Airport on time: Egyptair (95%), Envoy Air (89%), Japan Airlines (84%).
What are the cheapest flights from Toronto Pearson Intl Airport to Chicago O'Hare Intl Airport?
Looking for the cheapest flight from Toronto Pearson Intl Airport to Chicago O'Hare Intl Airport? While on average our users pay £272, our data indicates the cheapest price to be £107. The most popular route (Toronto Pearson Intl - Chicago O'Hare Intl), is priced around £172.
Can I find deals for flights from Pearson Intl to O'Hare Intl that include hotel bookings?
Yes. In addition to deals on Pearson Intl to O'Hare Intl flights, Cheapflights offers holiday packages that include both flights and hotel.
How can I find direct flights from Pearson Intl to O'Hare Intl?
After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Pearson Intl to O'Hare Intl.
Can I find deals for business class flights from Pearson Intl to O'Hare Intl?
Yes. Cheapflights offers flight deals from Pearson Intl to O'Hare Intl by cabin class. In addition to browsing deals, you can also filter by cabin class on the search results page after making a search.
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 £193). Flying from Toronto Pearson Intl Airport to Chicago O'Hare Intl Airport in October is currently the most expensive (average of £245). 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.
Explore flights to O'Hare Intl departing from other origins. Flights are based on user searches made on Cheapflights and were last updated on 10 August 2026.
Browse through other flights departing from Pearson Intl. Flights are based on user searches made on Cheapflights and were last updated on 10 August 2026.
Find the best flight deals on Cheapflights, where travellers can enjoy low prices and a wide availability of flights to their desired destinations.
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.
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