Cheap flights from Toronto Pearson Intl Airport to Chicago from C$ 224
This is the cheapest round-trip flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 31/10. Fares are subject to change and may not be available on all flights or dates of travel.
YYZ — CHI
4 Nov — 11 Nov1
Round-trip
1 adult
Economy
Round-trip
1 adult, Economy, 0 bags
Cheapflights Tip: The best prices from Toronto Pearson Intl to Chicago are usually found in March or January, booked 84 days in advance, depart on a Friday or Saturday and return on a Friday
Cheap flight deals from Pearson Intl to Chicago
Enter your travel dates to find the best prices.
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Cheapest flights from Pearson Intl to Chicago
Explore the most affordable flight options available from Pearson Intl to Chicago. Find the lowest fares from popular airlines and budget airlines, with prices last updated on 5 October 2026.
Sat 24/102:00 p.m. -
Nonstop1h 55m
Fri 30/1010:15 a.m. -
Nonstop1h 37m
Deal found 1/10C$ 312
Sat 5/128:35 a.m. -
Nonstop2h 09m
Sat 5/126:15 p.m. -
1 stop4h 37m
Deal found 4/10C$ 331
Fri 30/102:45 p.m. -
1 stop7h 59m
Sat 31/107:03 a.m. -
Nonstop1h 44m
Deal found 30/9C$ 349
Thu 5/116:55 p.m. -
Nonstop2h 03m
Mon 9/118:40 p.m. -
Nonstop1h 43m
Deal found 5/10C$ 372
Fri 27/116:20 a.m. -
1 stop5h 47m
Wed 2/128:45 a.m. -
Nonstop1h 42m
Deal found 4/10C$ 385
Fri 30/104:30 p.m. -
Nonstop2h 13m
Sat 31/108:45 a.m. -
Nonstop1h 42m
Deal found 30/9C$ 388
Thu 22/1012:25 p.m. -
Nonstop1h 58m
Sun 25/1010:15 a.m. -
Nonstop1h 37m
Deal found 1/10C$ 389
Wed 18/117:00 a.m. -
1 stop5h 07m
Wed 25/117:05 a.m. -
1 stop5h 41m
Deal found 4/10C$ 396
Fri 4/126:20 a.m. -
1 stop5h 47m
Sun 6/124:30 p.m. -
Nonstop1h 40m
Deal found 5/10C$ 398
Thu 29/107:00 a.m. -
1 stop5h 07m
Sun 1/114:30 p.m. -
Nonstop1h 40m
Deal found 4/10C$ 399
Sat 28/1112:15 p.m. -
1 stop6h 49m
Mon 7/126:41 p.m. -
1 stop3h 26m
Deal found 1/10C$ 470
Fri 23/1012:10 p.m. -
1 stop6h 50m
Fri 30/106:44 p.m. -
1 stop3h 12m
Deal found 2/10C$ 472
Best flights from Pearson Intl to Chicago
Discover carefully curated flight deals from Pearson Intl to Chicago that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated 5 October 2026.
Sat 21/1110:00 a.m. -
1 stop5h 40m
Sat 21/119:21 p.m. -
Nonstop1h 38m
Deal found 4/10C$ 349
Fri 27/113:35 p.m. -
Nonstop2h 09m
Sun 29/114:30 p.m. -
Nonstop1h 40m
Deal found 3/10C$ 464
Sat 28/1112:15 p.m. -
1 stop6h 49m
Mon 7/126:41 p.m. -
1 stop3h 26m
Deal found 4/10C$ 470
Sat 28/116:45 a.m. -
Nonstop2h 09m
Tue 8/127:02 a.m. -
Nonstop1h 45m
Deal found 4/10C$ 435
Sat 31/106:00 a.m. -
1 stop4h 32m
Sun 1/116:44 p.m. -
1 stop3h 12m
Deal found 2/10C$ 472
Sat 28/116:45 a.m. -
Nonstop2h 09m
Wed 9/121:30 p.m. -
1 stop4h 31m
Deal found 4/10C$ 464
Sat 21/116:00 a.m. -
1 stop7h 51m
Sun 29/116:44 p.m. -
1 stop3h 13m
Deal found 2/10C$ 472
Mon 30/116:45 a.m. -
Nonstop2h 09m
Mon 30/119:21 p.m. -
Nonstop1h 38m
Deal found 2/10C$ 464
Sat 21/119:45 a.m. -
1 stop7h 33m
Fri 27/117:05 a.m. -
1 stop3h 14m
Deal found 4/10C$ 473
Sun 22/1110:53 a.m. -
Nonstop2h 04m
Fri 27/111:57 p.m. -
Nonstop1h 50m
Deal found 4/10C$ 464
Tue 17/112:20 p.m. -
1 stop5h 10m
Tue 24/115:05 p.m. -
1 stop4h 52m
Deal found 2/10C$ 473
Tue 27/1012:55 p.m. -
1 stop5h 24m
Sun 1/115:00 a.m. -
1 stop5h 48m
Deal found 3/10C$ 470
Sun 22/119:45 a.m. -
1 stop7h 33m
Fri 27/117:05 a.m. -
1 stop3h 14m
Deal found 4/10C$ 473
Wed 4/119:40 a.m. -
1 stop4h 07m
Tue 10/111:31 p.m. -
1 stop8h 26m
Deal found 2/10C$ 473
Wed 2/126:00 a.m. -
1 stop4h 37m
Tue 8/121:41 p.m. -
1 stop8h 26m
Deal found 4/10C$ 473
Tue 24/119:45 a.m. -
1 stop4h 06m
Sat 28/116:44 p.m. -
1 stop3h 13m
Deal found 4/10C$ 473
Fri 4/122:25 p.m. -
1 stop4h 36m
Thu 10/121:41 p.m. -
1 stop8h 26m
Deal found 4/10C$ 473
Tue 3/116:00 a.m. -
1 stop4h 32m
Tue 10/111:31 p.m. -
1 stop8h 26m
Deal found 4/10C$ 473
Sat 14/116:00 a.m. -
1 stop7h 51m
Tue 17/119:30 a.m. -
1 stop3h 00m
Deal found 4/10C$ 473
Thu 29/106:00 a.m. -
1 stop7h 47m
Sun 1/116:44 p.m. -
1 stop3h 12m
Deal found 3/10C$ 473
Sat 17/1012:10 p.m. -
1 stop5h 29m
Sat 24/105:29 p.m. -
1 stop4h 27m
Deal found 2/10C$ 504
Thu 22/106:00 a.m. -
1 stop7h 47m
Sun 25/106:44 p.m. -
1 stop3h 12m
Deal found 2/10C$ 521
Sat 17/106:00 a.m. -
1 stop4h 32m
Tue 20/109:29 a.m. -
1 stop3h 07m
Deal found 1/10C$ 539
Thu 29/106:00 a.m. -
1 stop5h 29m
Sat 7/111:55 p.m. -
1 stop8h 01m
Deal found 1/10C$ 557
Direct flights from Pearson Intl to Chicago
Explore direct flight options from Pearson Intl to Chicago based on user searches, and compare prices and availability for your desired travel dates. Data last updated 5 October 2026.
Sat 24/102:00 p.m. -
Nonstop1h 55m
Fri 30/1010:15 a.m. -
Nonstop1h 37m
Deal found 1/10C$ 312
Thu 5/116:55 p.m. -
Nonstop2h 03m
Mon 9/118:40 p.m. -
Nonstop1h 43m
Deal found 5/10C$ 372
Fri 30/104:30 p.m. -
Nonstop2h 13m
Sat 31/108:45 a.m. -
Nonstop1h 42m
Deal found 30/9C$ 388
Thu 22/1012:25 p.m. -
Nonstop1h 58m
Sun 25/1010:15 a.m. -
Nonstop1h 37m
Deal found 1/10C$ 389
Wed 11/116:55 p.m. -
Nonstop2h 03m
Wed 18/118:45 a.m. -
Nonstop1h 42m
Deal found 4/10C$ 402
Wed 4/116:55 p.m. -
Nonstop2h 03m
Wed 11/1110:15 a.m. -
Nonstop1h 37m
Deal found 2/10C$ 403
Fri 23/106:50 p.m. -
Nonstop1h 58m
Sun 25/1010:15 a.m. -
Nonstop1h 37m
Deal found 2/10C$ 405
Thu 29/106:55 p.m. -
Nonstop2h 03m
Sun 1/118:40 p.m. -
Nonstop1h 43m
Deal found 5/10C$ 406
Thu 26/116:55 p.m. -
Nonstop2h 03m
Sun 29/118:40 p.m. -
Nonstop1h 43m
Deal found 3/10C$ 407
Wed 18/1112:00 p.m. -
Nonstop2h 13m
Wed 25/118:45 a.m. -
Nonstop1h 42m
Deal found 4/10C$ 409
Fri 23/102:00 p.m. -
Nonstop1h 55m
Sun 1/118:45 a.m. -
Nonstop1h 42m
Deal found 4/10C$ 413
Wed 21/102:00 p.m. -
Nonstop1h 55m
Wed 28/108:45 a.m. -
Nonstop1h 42m
Deal found 3/10C$ 416
Last-minute flights from Pearson Intl to Chicago
Discover last-minute flight deals from Pearson Intl to Chicago. Data last updated 5 October 2026 and is based on user searches.
Thu 22/1012:25 p.m. -
Nonstop1h 58m
Sun 25/1010:15 a.m. -
Nonstop1h 37m
Deal found 1/10C$ 389
Fri 23/104:00 p.m. -
1 stop5h 12m
Mon 26/104:30 p.m. -
Nonstop1h 40m
Deal found 2/10C$ 398
Fri 23/104:00 p.m. -
1 stop5h 12m
Fri 30/108:45 a.m. -
Nonstop1h 42m
Deal found 30/9C$ 400
Fri 23/1012:10 p.m. -
1 stop6h 50m
Fri 30/106:44 p.m. -
1 stop3h 12m
Deal found 2/10C$ 472
Sat 24/102:00 p.m. -
Nonstop1h 55m
Fri 30/1010:15 a.m. -
Nonstop1h 37m
Deal found 1/10C$ 312
Thu 29/107:00 a.m. -
1 stop5h 07m
Sun 1/114:30 p.m. -
Nonstop1h 40m
Deal found 4/10C$ 399
Fri 30/102:45 p.m. -
1 stop7h 59m
Sat 31/107:03 a.m. -
Nonstop1h 44m
Deal found 30/9C$ 349
Fri 30/104:30 p.m. -
Nonstop2h 13m
Sat 31/108:45 a.m. -
Nonstop1h 42m
Deal found 30/9C$ 388
Thu 5/116:55 p.m. -
Nonstop2h 03m
Mon 9/118:40 p.m. -
Nonstop1h 43m
Deal found 5/10C$ 372
Wed 18/117:00 a.m. -
1 stop5h 07m
Wed 25/117:05 a.m. -
1 stop5h 41m
Deal found 4/10C$ 396
Fri 27/116:20 a.m. -
1 stop5h 47m
Mon 7/124:30 p.m. -
Nonstop1h 40m
Deal found 2/10C$ 385
Sat 28/1112:15 p.m. -
1 stop6h 49m
Mon 7/126:41 p.m. -
1 stop3h 26m
Deal found 1/10C$ 470
One-way flights from Pearson Intl to Chicago
Search for one-way flight options from Pearson Intl to Chicago. Find affordable one-way fares based on user searches. Data last updated 5 October 2026.
Sat 31/104:30 p.m. -
Nonstop2h 13m
Wed 31/1212:00 a.m. -
Nonstop0h 00m
Deal found 5/10C$ 224
Sat 24/102:00 p.m. -
Nonstop1h 55m
Wed 31/1212:00 a.m. -
Nonstop0h 00m
Deal found 30/9C$ 231
Wed 28/102:35 p.m. -
Nonstop2h 03m
Wed 31/1212:00 a.m. -
Nonstop0h 00m
Deal found 1/10C$ 232
Wed 18/116:55 p.m. -
Nonstop2h 03m
Wed 31/1212:00 a.m. -
Nonstop0h 00m
Deal found 5/10C$ 239
Tue 1/1210:00 a.m. -
1 stop5h 52m
Wed 31/1212:00 a.m. -
Nonstop0h 00m
Deal found 1/10C$ 244
Sat 21/117:35 a.m. -
1 stop16h 59m
Wed 31/1212:00 a.m. -
Nonstop0h 00m
Deal found 2/10C$ 246
Sat 12/127:10 a.m. -
2 stops8h 42m
Wed 31/1212:00 a.m. -
Nonstop0h 00m
Deal found 1/10C$ 251
Mon 9/116:00 a.m. -
1 stop7h 51m
Wed 31/1212:00 a.m. -
Nonstop0h 00m
Deal found 1/10C$ 278
Sat 12/1212:15 p.m. -
1 stop6h 46m
Wed 31/1212:00 a.m. -
Nonstop0h 00m
Deal found 2/10C$ 285
Wed 18/116:00 a.m. -
1 stop4h 46m
Wed 31/1212:00 a.m. -
Nonstop0h 00m
Deal found 5/10C$ 286
Mon 2/117:35 a.m. -
2 stops41h 12m
Wed 31/1212:00 a.m. -
Nonstop0h 00m
Deal found 30/9C$ 299
Fri 30/107:35 a.m. -
2 stops35h 12m
Wed 31/1212:00 a.m. -
Nonstop0h 00m
Deal found 30/9C$ 302
Find flight deals from Pearson Intl to Chicago
Discover tips and strategies to find the most affordable flight options for your journey from Pearson Intl (YYZ) to Chicago (CHI). 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 5 October 2026.
Customize your flight search to find flights from Pearson Intl to Chicago 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 7,457,451 searches. Data last updated 5 October 2026.
Use the filters below to find and compare flights from Toronto Pearson Intl Airport to Chicago that are best for you.
Fly from
Fly to
Route
Depart
Return
Price
Cheapest round-trip
TorontoChicago
YYZ Toronto Pearson Intl - ORD Chicago O'Hare Intl
YYZORD
Toronto Pearson Intl
Sat 31/10
5:55 p.m.-7:05 p.m.
Nonstop2h 10m
Chicago O'Hare Intl
Wed 31/12
12:00 a.m.-1:00 a.m.
Nonstop0h 00m
C$ 254
TorontoChicago
YYZ Toronto Pearson Intl - ORD Chicago O'Hare Intl
YYZORD
Toronto Pearson Intl
Sat 14/11
5:55 p.m.-7:05 p.m.
Nonstop2h 10m
Chicago O'Hare Intl
Wed 31/12
12:00 a.m.-1:00 a.m.
Nonstop0h 00m
C$ 255
Quickest round-trip
TorontoChicago
YYZ Toronto Pearson Intl - ORD Chicago O'Hare Intl
YYZORD
Toronto Pearson Intl
Sun 29/11
6:45 a.m.-7:54 a.m.
Nonstop2h 09m
Chicago O'Hare Intl
Wed 31/12
12:00 a.m.-1:00 a.m.
Nonstop0h 00m
C$ 255
TorontoChicago
YYZ Toronto Pearson Intl - ORD Chicago O'Hare Intl
YYZORD
Toronto Pearson Intl
Sun 8/11
7:26 p.m.-8:48 p.m.
Nonstop2h 22m
Chicago O'Hare Intl
Wed 31/12
12:00 a.m.-1:00 a.m.
Nonstop0h 00m
C$ 269
TorontoChicago
YYZ Toronto Pearson Intl - ORD Chicago O'Hare Intl
YYZORD
Toronto Pearson Intl
Wed 28/10
7:43 a.m.-3:14 p.m.
1 stop8h 31m
Chicago O'Hare Intl
Wed 31/12
12:00 a.m.-1:00 a.m.
Nonstop0h 00m
C$ 276
TorontoChicago
YYZ Toronto Pearson Intl - ORD Chicago O'Hare Intl
YYZORD
Toronto Pearson Intl
Thu 5/11
7:44 p.m.-12:01 a.m.
1 stop5h 17m
Chicago O'Hare Intl
Wed 31/12
12:00 a.m.-1:00 a.m.
Nonstop0h 00m
C$ 276
TorontoChicago
YYZ Toronto Pearson Intl - ORD Chicago O'Hare Intl
YYZORD
Toronto Pearson Intl
Tue 24/11
7:44 p.m.-12:01 a.m.
1 stop5h 17m
Chicago O'Hare Intl
Wed 31/12
12:00 a.m.-1:00 a.m.
Nonstop0h 00m
C$ 276
TorontoChicago
YYZ Toronto Pearson Intl - MDW Chicago Midway
YYZMDW
Toronto Pearson Intl
Sat 31/10
6:00 a.m.-9:32 a.m.
1 stop4h 32m
Chicago Midway
Wed 31/12
12:00 a.m.-1:00 a.m.
Nonstop0h 00m
C$ 278
TorontoChicago
YYZ Toronto Pearson Intl - MDW Chicago Midway
YYZMDW
Toronto Pearson Intl
Tue 24/11
2:20 p.m.-6:04 p.m.
1 stop4h 44m
Chicago Midway
Wed 31/12
12:00 a.m.-1:00 a.m.
Nonstop0h 00m
C$ 278
TorontoChicago
YYZ Toronto Pearson Intl - MDW Chicago Midway
YYZMDW
Toronto Pearson Intl
Sat 14/11
6:00 a.m.-12:51 p.m.
1 stop7h 51m
Chicago Midway
Wed 31/12
12:00 a.m.-1:00 a.m.
Nonstop0h 00m
C$ 278
Flights are sorted by cheapest round-trip flights first.
Deals found on 4/10
Showing 1-10 of 44 resultsSorted by cheapest first
1
2
3
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5
Best time to book a flight from Pearson Intl to Chicago
Have a flexible travel schedule? Discover the best time to fly to Chicago from Pearson Intl with our price prediction graph.
YYZ-CHI
YYZ-ORD
YYZ-MDW
Estimated round-trip 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
YYZ-CHI
YYZ-ORD
YYZ-MDW
What is the cheapest month to book a flight from Toronto Pearson Intl Airport to Chicago?
Currently, January is the cheapest month in which you can book a flight from Toronto Pearson Intl Airport to Chicago (average of C$ 358). Flying from Toronto Pearson Intl Airport to Chicago in December is currently the most expensive (average of C$ 489). 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 CHI?
Find hourly flight availability from Pearson Intl to Chicago. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated 5 October 2026.
It’s optimal to fly from Toronto Pearson Intl Airport to Chicago in the evening. By choosing this option you can save up to 34% on the cost of your flight, compared to a flight in the afternoon.
Weekly flight availability from Toronto Pearson Intl Airport to Chicago
Explore weekly flight availability from Pearson Intl to Chicago. 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 5 October 2026.
The most flights from YYZ to CHI are scheduled on a Sunday (69 on average). You will have fewer flight options on Tuesday, which is when the least amount of flights are scheduled (42 on average).
How much does it cost to fly round-trip from Toronto Pearson Intl Airport to Chicago?
Airfare is below average for this route at the moment.
Toronto Pearson Intl Airport to Chicago flights typically cost between C$ 332 and C$ 571 in October.The cheapest round-trip price found within the last 5 days was C$ 312 on Air Canada (24 Oct-30 Oct).
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 has had the lowest number of delays on this route, with just 9% of flights being delayed.
How far ahead should I book a flight from Toronto Pearson Intl Airport to Chicago?
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. The general trend is that the closer you book to the departure date, the more expensive your flight will be.
What is the cheapest day to fly from Toronto Pearson Intl Airport to Chicago?
Use this chart to determine the cheapest time to fly round-trip from Pearson Intl to Chicago. Price data was last updated on 3 October 2026.
Travelers seeking maximum savings on their Toronto Pearson Intl Airport to Chicago flight should consider departing on Friday evenings when fares are most often at their lowest. Sunday at noon flights should be avoided if possible as fares are typically the most expensive at this time.
Reviews of airlines servicing Chicago
Get insights into the airlines that provide service to Chicago. 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 Chicago. Reviews last updated 5 October 2026.
Read reviews from past customers who have flown Porter Airlines,United Airlines, andWestJet
from Toronto Pearson Intl Airport to Chicago. Users can see the overall rating for each airline as well as how each is rated in terms of entertainment options, comfort, food, crew/service, and boarding process.
The flight including check-in, checked baggage, boarding, flight and timing were great. My checked bag was delayed two days which was concerning. They did deliver it to my door though which was great.
The flight including check-in, checked baggage, boarding, flight and timing were great. My checked bag was delayed two days which was concerning. They did deliver it to my door though which was great.
The flight including check-in, checked baggage, boarding, flight and timing were great. My checked bag was delayed two days which was concerning. They did deliver it to my door though which was great.
The flight including check-in, checked baggage, boarding, flight and timing were great. My checked bag was delayed two days which was concerning. They did deliver it to my door though which was great.
The flight including check-in, checked baggage, boarding, flight and timing were great. My checked bag was delayed two days which was concerning. They did deliver it to my door though which was great.
The flight including check-in, checked baggage, boarding, flight and timing were great. My checked bag was delayed two days which was concerning. They did deliver it to my door though which was great.
Related info for your journey
Find useful and relevant information for your journey from Pearson Intl to Chicago. 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?
Airlines like United Airlines and Delta fly from Toronto Pearson Intl Airport to Chicago in about 5h 40m. The time it takes to get you to your destination can typically vary by up to 1h 09m. The distance between Toronto Pearson Intl Airport and Chicago is about 702 km. This flight may include one or multiple stops.
What are the cheapest airlines flying from Toronto Pearson Intl Airport to Chicago round-trip?
Currently priced at C$ 268, American Airlines will fly you from Toronto Pearson Intl Airport to Chicago and back. In addition to American Airlines, many other airlines offer competitively priced options for your trip. Search Cheapflights for deals from United Airlines and Air Canada - these airlines can fly you to your destination from C$ 301 and C$ 307, respectively. Users have found that American Airlines is 35% cheaper than the other options available to this destination.
What are the cheapest airlines to fly from Toronto Pearson Intl Airport to Chicago one-way?
One-way options have recently been found by users for as low as C$ 161 on United Airlines. Other airlines that offer cheap prices include Air Canada from C$ 167 and American Airlines from C$ 170 one-way.
What are the most reliable airlines from Toronto Pearson Intl Airport to Chicago?
Before booking your flight to Chicago from Toronto Pearson Intl Airport, check out the most reliable airlines to get you to your destination on time: Sun Country Air (100%), Copa Airlines (86%), Egyptair( 76%).
What are the cheapest flights from Toronto Pearson Intl Airport to Chicago?
On average you can expect to pay C$ 1,461 for a flight from Toronto Pearson Intl Airport to Chicago. The cheapest flight overall is C$ 251 while the most popular route, (Toronto Pearson Intl - Chicago O'Hare Intl) is currently priced at C$ 426.
Can I find deals for business class flights from Pearson Intl to Chicago?
Yes. Cheapflights offers flight deals from Pearson Intl to Chicago 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?
Currently, January is the cheapest month in which you can book a flight from Toronto Pearson Intl Airport to Chicago (average of C$ 358). Flying from Toronto Pearson Intl Airport to Chicago in December is currently the most expensive (average of C$ 489). 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.
Browse thousands of different options on Cheapflights for your next trip
Toggle through the tabs below to find thousands of options on Cheapflights for your next trip.
Airlines
Alternative routes
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Complete your trip
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Popular flights
Fly from Pearson Intl to Chicago on these airlines
Choose from the following airlines for your flight from Pearson Intl to Chicago. Flights are based on user searches made on Cheapflights and were last updated on 5 October 2026.
Explore flights to Chicago departing from other origins. Flights are based on user searches made on Cheapflights and were last updated on 5 October 2026.
Browse through other flights departing from Pearson Intl. Flights are based on user searches made on Cheapflights and were last updated on 5 October 2026.
Top 5 airlines flying from Pearson Intl to Chicago
Discover the top 5 airlines that operate flights from Pearson Intl to Chicago. 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 7,457,451 searches. Data last updated 5 October 2026.
Find the best flight deals on Cheapflights, where travelers 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 Chicago?
Cheapflights makes it easy to find Pearson Intl to Chicago flights by helping our users search from 900+ travel sites for deals. We also provide you with filters for cabin, price, airline, airports, number of stops, and many more to narrow down that perfect flight.
Why should you use Cheapflights to find cheap flight tickets from Pearson Intl to Chicago?
Cheapflights simply makes it quick and affordable to book flights from Pearson Intl to Chicago by bringing together all flight options from hundreds of airlines and agencies online — and put it in one place for you to choose from. Plus, Cheapflights is 100% free to use for all.
Can Cheapflights find flights from Pearson Intl to Chicago with no change fees?
Certainly. Search results for flights to Chicago from Pearson Intl shown to you on Cheapflights can be narrowed down with different useful search filters, which includes flexible booking options.
Can Cheapflights notify me if prices for flights from Pearson Intl to Chicago become cheaper?
Yes, and it’s super simple to set up. Click the bell icon next to the flight deals above and provide a valid email address to enable Price Alerts. That’s it!
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