Cheap flights from Toronto Pearson Intl Airport to Chicago from C$ 203
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 19/3. Fares are subject to change and may not be available on all flights or dates of travel.
YYZ — CHI
22 Jan — 29 Jan1
Round-trip
1 adult
Economy
The best prices from Toronto Pearson Intl to Chicago are usually found in April or July, booked 84 days in advance, depart on a Tuesday or Wednesday and return on a Tuesday
Cheap 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 17 January 2025.
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 17 January 2025.
Thu 6/27:15 a.m.YYZ - ORD
1 stop8h 37mMultiple Airlines
Sun 9/26:15 p.m.ORD - YYZ
1 stop16h 10mMultiple Airlines
Deal found 16/1C$ 344
Thu 6/29:00 a.m.YYZ - ORD
Nonstop2h 10mUnited Airlines
Mon 10/22:05 p.m.ORD - YYZ
Nonstop1h 41mUnited Airlines
Deal found 15/1C$ 356
Fri 7/22:05 p.m.YYZ - ORD
1 stop5h 33mAir Canada
Mon 10/210:53 a.m.ORD - YYZ
Nonstop1h 49mAir Canada
Deal found 16/1C$ 365
Fri 7/26:20 p.m.YYZ - ORD
Nonstop2h 00mBritish Airways
Sun 9/28:11 a.m.ORD - YYZ
Nonstop1h 40mBritish Airways
Deal found 16/1C$ 369
Thu 10/41:15 p.m.YYZ - ORD
Nonstop1h 55mAmerican Airlines
Sat 12/46:45 a.m.ORD - YYZ
1 stop7h 34mAmerican Airlines
Deal found 16/1C$ 377
Wed 19/210:10 a.m.YYZ - ORD
1 stop3h 45mDelta
Mon 24/22:35 p.m.ORD - YYZ
1 stop8h 04mDelta
Deal found 16/1C$ 385
Fri 7/26:00 a.m.YYZ - MDW
1 stop3h 51mDelta
Sun 9/25:05 p.m.MDW - YYZ
1 stop4h 44mDelta
Deal found 14/1C$ 391
Thu 6/212:20 p.m.YYZ - ORD
1 stop7h 18mLufthansa
Sun 9/24:00 p.m.ORD - YYZ
1 stop5h 15mLufthansa
Deal found 16/1C$ 397
Fri 14/22:45 p.m.YYZ - ORD
1 stop8h 13mKLM
Tue 18/27:30 a.m.ORD - YYZ
1 stop4h 56mKLM
Deal found 16/1C$ 415
Wed 12/26:30 a.m.YYZ - MDW
1 stop12h 13mWestJet
Fri 14/21:26 p.m.MDW - YYZ
1 stop8h 41mWestJet
Deal found 15/1C$ 434
Thu 13/27:45 a.m.YYZ - ORD
1 stop6h 10mWestJet
Mon 17/26:59 a.m.ORD - YYZ
1 stop3h 57mWestJet
Deal found 16/1C$ 438
Thu 30/111:05 p.m.YYZ - MDW
2 stops16h 37mMultiple Airlines
Thu 6/27:25 a.m.MDW - YYZ
1 stop9h 05mMultiple Airlines
Deal found 16/1C$ 492
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 17 January 2025.
Thu 6/27:15 a.m.YYZ - ORD
1 stop8h 37mMultiple Airlines
Sun 9/26:15 p.m.ORD - YYZ
1 stop16h 10mMultiple Airlines
Deal found 16/1C$ 344
Thu 6/29:00 a.m.YYZ - ORD
Nonstop2h 10mUnited Airlines
Mon 10/22:05 p.m.ORD - YYZ
Nonstop1h 41mUnited Airlines
Deal found 15/1C$ 356
Fri 7/22:05 p.m.YYZ - ORD
1 stop5h 33mAir Canada
Mon 10/210:53 a.m.ORD - YYZ
Nonstop1h 49mAir Canada
Deal found 16/1C$ 365
Fri 7/26:20 p.m.YYZ - ORD
Nonstop2h 00mBritish Airways
Sun 9/28:11 a.m.ORD - YYZ
Nonstop1h 40mBritish Airways
Deal found 16/1C$ 369
Thu 10/41:15 p.m.YYZ - ORD
Nonstop1h 55mAmerican Airlines
Sat 12/46:45 a.m.ORD - YYZ
1 stop7h 34mAmerican Airlines
Deal found 16/1C$ 377
Wed 19/210:10 a.m.YYZ - ORD
1 stop3h 45mDelta
Mon 24/22:35 p.m.ORD - YYZ
1 stop8h 04mDelta
Deal found 16/1C$ 385
Thu 6/212:20 p.m.YYZ - ORD
1 stop7h 18mLufthansa
Sun 9/24:00 p.m.ORD - YYZ
1 stop5h 15mLufthansa
Deal found 16/1C$ 397
Fri 14/22:45 p.m.YYZ - ORD
1 stop8h 13mKLM
Tue 18/27:30 a.m.ORD - YYZ
1 stop4h 56mKLM
Deal found 16/1C$ 415
Thu 13/27:45 a.m.YYZ - ORD
1 stop6h 10mWestJet
Mon 17/26:59 a.m.ORD - YYZ
1 stop3h 57mWestJet
Deal found 16/1C$ 438
Thu 6/27:45 a.m.YYZ - MDW
1 stop6h 20mDelta
Sat 8/25:05 p.m.MDW - YYZ
1 stop4h 44mDelta
Deal found 16/1C$ 401
Sat 22/26:30 a.m.YYZ - MDW
1 stop5h 12mWestJet
Fri 28/212:44 p.m.MDW - YYZ
1 stop10h 08mWestJet
Deal found 16/1C$ 448
Tue 1/42:45 p.m.YYZ - MDW
1 stop4h 33mMultiple Airlines
Wed 9/43:00 p.m.MDW - YYZ
1 stop7h 50mMultiple Airlines
Deal found 16/1C$ 471
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 17 January 2025.
Thu 6/29:00 a.m.YYZ - ORD
Nonstop2h 10mUnited Airlines
Mon 10/22:05 p.m.ORD - YYZ
Nonstop1h 41mUnited Airlines
Deal found 15/1C$ 356
Thu 10/41:15 p.m.YYZ - ORD
Nonstop1h 55mAmerican Airlines
Sat 12/411:55 a.m.ORD - YYZ
Nonstop1h 35mAmerican Airlines
Deal found 16/1C$ 362
Fri 7/26:20 p.m.YYZ - ORD
Nonstop2h 00mBritish Airways
Sun 9/28:11 a.m.ORD - YYZ
Nonstop1h 40mBritish Airways
Deal found 16/1C$ 369
Fri 7/29:00 a.m.YYZ - ORD
Nonstop2h 10mMultiple Airlines
Sun 23/28:30 p.m.ORD - YYZ
Nonstop1h 41mMultiple Airlines
Deal found 16/1C$ 375
Fri 21/22:00 p.m.YYZ - ORD
Nonstop1h 51mAir Canada
Sun 23/28:30 p.m.ORD - YYZ
Nonstop1h 41mAir Canada
Deal found 16/1C$ 392
Thu 20/22:00 p.m.YYZ - ORD
Nonstop1h 51mLufthansa
Sun 23/28:30 p.m.ORD - YYZ
Nonstop1h 41mLufthansa
Deal found 16/1C$ 420
Last-minute flights from Pearson Intl to Chicago
Discover last-minute flight deals from Pearson Intl to Chicago. Data last updated 17 January 2025 and is based on user searches.
Tue 21/16:30 a.m.YYZ - MDW
1 stop7h 16mWestJet
Tue 28/11:26 p.m.MDW - YYZ
1 stop8h 45mWestJet
Deal found 14/1C$ 556
Wed 22/14:20 p.m.YYZ - ORD
1 stop23h 20mAlaska Airlines
Fri 24/15:28 p.m.ORD - YYZ
1 stop20h 37mAlaska Airlines
Deal found 16/1C$ 1,774
Thu 23/110:10 a.m.YYZ - MDW
1 stop3h 58mDelta
Thu 30/19:34 a.m.MDW - YYZ
1 stop5h 38mDelta
Deal found 15/1C$ 516
Thu 23/112:20 p.m.YYZ - ORD
Nonstop1h 51mUnited Airlines
Thu 30/16:00 a.m.ORD - YYZ
1 stop4h 46mUnited Airlines
Deal found 15/1C$ 552
Thu 23/111:15 p.m.YYZ - MDW
2 stops16h 27mMultiple Airlines
Thu 30/17:25 a.m.MDW - YYZ
1 stop9h 05mMultiple Airlines
Deal found 15/1C$ 681
Sat 25/17:00 a.m.YYZ - ORD
1 stop8h 23mMultiple Airlines
Mon 27/17:26 a.m.ORD - YYZ
1 stop15h 27mMultiple Airlines
Deal found 15/1C$ 346
Sat 25/15:30 p.m.YYZ - ORD
Nonstop2h 13mAir Canada
Fri 31/18:25 p.m.ORD - YYZ
Nonstop1h 41mAir Canada
Deal found 14/1C$ 474
Sun 26/111:31 a.m.YYZ - ORD
Nonstop2h 00mAmerican Airlines
Wed 29/19:49 a.m.ORD - YYZ
Nonstop1h 41mAmerican Airlines
Deal found 15/1C$ 490
Sun 26/110:10 a.m.YYZ - ORD
1 stop3h 45mDelta
Wed 29/110:05 a.m.ORD - YYZ
1 stop6h 09mDelta
Deal found 15/1C$ 499
Sun 26/11:20 p.m.YYZ - ORD
1 stop3h 53mWestJet
Wed 29/111:50 a.m.ORD - YYZ
2 stops10h 45mWestJet
Deal found 15/1C$ 562
Thu 30/111:05 p.m.YYZ - MDW
2 stops16h 37mMultiple Airlines
Thu 6/27:25 a.m.MDW - YYZ
1 stop9h 05mMultiple Airlines
Deal found 16/1C$ 492
Sun 2/26:15 a.m.YYZ - ORD
Nonstop2h 15mAmerican Airlines
Sun 9/28:11 a.m.ORD - YYZ
Nonstop1h 40mAmerican Airlines
Deal found 16/1C$ 385
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 17 January 2025.
Tue 11/28:00 p.m.YYZ - ORD
1 stop11h 07mMultiple Airlines
Deal found 16/1C$ 213
Thu 6/29:00 a.m.YYZ - ORD
1 stop6h 45mAir Canada
Deal found 16/1C$ 221
Wed 19/210:55 a.m.YYZ - ORD
1 stop6h 56mAmerican Airlines
Deal found 16/1C$ 227
Wed 12/29:00 p.m.YYZ - ORD
Nonstop2h 13mUnited Airlines
Deal found 15/1C$ 231
Sun 9/27:40 a.m.YYZ - MDW
1 stop8h 41mMultiple Airlines
Deal found 15/1C$ 233
Thu 13/26:30 a.m.YYZ - ORD
1 stop10h 00mDelta
Deal found 16/1C$ 236
Thu 6/27:45 a.m.YYZ - MDW
1 stop6h 20mDelta
Deal found 16/1C$ 240
Tue 11/22:45 p.m.YYZ - MDW
1 stop22h 57mWestJet
Deal found 16/1C$ 270
Fri 4/46:00 a.m.YYZ - ORD
1 stop4h 12mWestJet
Deal found 16/1C$ 279
Wed 29/110:54 a.m.YYZ - ORD
1 stop6h 41mBritish Airways
Deal found 16/1C$ 407
Find flights from Pearson Intl to Chicago within your budget
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 629,999 searches. Data last updated 17 January 2025.
Fly from
Any airport
Fly to
Any airport
Route
Depart
Return
Price
TorontoChicago
YYZ - ORD
YYZORD
Toronto Pearson Intl
Thu 6/2
7:15 a.m.-2:52 p.m.
1 stop8h 37m
Chicago O'Hare Intl
Sun 9/2
6:15 p.m.-11:25 a.m.
1 stop16h 10m
C$ 344
TorontoChicago
YYZ - ORD
YYZORD
Toronto Pearson Intl
Wed 5/2
6:20 p.m.-7:20 p.m.
Nonstop2h 00m
Chicago O'Hare Intl
Wed 12/2
8:11 a.m.-10:51 a.m.
Nonstop1h 40m
C$ 346
TorontoChicago
YYZ - ORD
YYZORD
Toronto Pearson Intl
Fri 7/2
8:00 a.m.-2:45 p.m.
1 stop7h 45m
Chicago O'Hare Intl
Mon 10/2
10:53 a.m.-1:42 p.m.
Nonstop1h 49m
C$ 352
TorontoChicago
YYZ - ORD
YYZORD
Toronto Pearson Intl
Thu 6/2
9:00 a.m.-10:10 a.m.
Nonstop2h 10m
Chicago O'Hare Intl
Mon 10/2
2:05 p.m.-4:46 p.m.
Nonstop1h 41m
C$ 356
TorontoChicago
YYZ - ORD
YYZORD
Toronto Pearson Intl
Thu 13/2
7:45 a.m.-12:55 p.m.
1 stop6h 10m
Chicago O'Hare Intl
Mon 17/2
6:59 a.m.-4:09 p.m.
1 stop8h 10m
C$ 391
TorontoChicago
YYZ - MDW
YYZMDW
Toronto Pearson Intl
Fri 7/2
6:00 a.m.-8:51 a.m.
1 stop3h 51m
Chicago Midway
Sun 9/2
5:05 p.m.-10:49 p.m.
1 stop4h 44m
C$ 391
TorontoChicago
YYZ - ORD
YYZORD
Toronto Pearson Intl
Thu 6/2
12:20 p.m.-6:38 p.m.
1 stop7h 18m
Chicago O'Hare Intl
Sun 9/2
4:00 p.m.-10:15 p.m.
1 stop5h 15m
C$ 397
TorontoChicago
YYZ - MDW
YYZMDW
Toronto Pearson Intl
Wed 12/2
6:30 a.m.-5:43 p.m.
1 stop12h 13m
Chicago Midway
Fri 14/2
1:26 p.m.-11:07 p.m.
1 stop8h 41m
C$ 434
TorontoChicago
YYZ - ORD
YYZORD
Toronto Pearson Intl
Mon 27/1
2:30 p.m.-10:36 p.m.
1 stop9h 06m
Chicago O'Hare Intl
Wed 29/1
1:40 p.m.-7:09 p.m.
1 stop4h 29m
C$ 454
TorontoChicago
YYZ - MDW
YYZMDW
Toronto Pearson Intl
Thu 30/1
11:05 p.m.-2:42 p.m.
2 stops16h 37m
Chicago Midway
Thu 6/2
7:25 a.m.-5:30 p.m.
1 stop9h 05m
C$ 492
Flights are sorted by cheapest round-trip flights first.
Deals found on 15/1
Showing 1-10 of 19 results
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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.
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.
Travel insights for flights from Pearson Intl to Chicago
Get recent, data-driven insights about flights from Pearson Intl to Chicago including ideal travel times, pricing trends, and more.
How far ahead should I book a flight from Toronto Pearson Intl Airport to Chicago?
Use this chart to determine the optimal time to book a round-trip flight from Pearson Intl to Chicago. Price data was last updated on 10 January 2025.
Booking 84 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 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$ 261). Flying from Toronto Pearson Intl Airport to Chicago in March is currently the most expensive (average of C$ 355). 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 17 January 2025.
It’s optimal to fly from Toronto Pearson Intl Airport to Chicago in the evening. By choosing this option you can save up to 4% on the cost of your flight, compared to a flight at noon.
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 16 December 2024.
Travelers seeking maximum savings on their Toronto Pearson Intl Airport to Chicago flight should consider departing on Thursday at noon 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.
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 17 January 2025.
The most flights from YYZ to CHI are scheduled on a Monday (52 on average). You will have fewer flight options on Saturday, which is when the least amount of flights are scheduled (30 on average).
Rainfall in Chicago by month
Plan your trip to Chicago by taking into account the average rainfall totals by month.
In terms of precipitation, rainfall in Chicago ranges from 43.0 - 125.0 mm per month. August is typically the wettest month, when rainfall can reach 125.0 mm. January is typically the driest time to visit Chicago when rainfall is around 43.0 mm.
Temperature in Chicago by month
Plan your trip to Chicago by taking into account the average temperature totals by month.
If weather is an important factor for your trip to Chicago, use this chart to help with planning. For those seeking warmer temperatures, July is the ideal time of year to visit, when temperatures reach an average of 23.0 C. Travellers hoping to avoid the cold should look outside of January, when temperatures are typically at their lowest (around -5.0 C).
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 17 January 2025.
To help decide which airline to fly from Toronto to Chicago, see what other customers have to say about Air Canada, United Airlines and American Airlines. You can also see how each airline stacks up in terms of entertainment options, comfort, food, crew/service, and boarding process.
Delta has consistently been the best U.S. airline for my travels and this flight was no exception
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.
What are the cheapest airlines flying from Toronto Pearson Intl Airport to Chicago round-trip?
Currently priced at C$ 356, United Airlines will fly you from Toronto Pearson Intl Airport to Chicago and back. In addition to United Airlines, many other airlines offer competitively priced options for your trip. Search Cheapflights for deals from Air Canada and British Airways - these airlines can fly you to your destination from C$ 365 and C$ 369, respectively. Users have found that United Airlines is 15% 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$ 221 on Air Canada. Other airlines that offer cheap prices include American Airlines from C$ 227 and United Airlines from C$ 231 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: Emirates (92%), Japan Airlines (92%), Republic Airways( 90%).
What are the cheapest flights from Toronto Pearson Intl Airport to Chicago?
On average you can expect to pay C$ 1,477 for a flight from Toronto Pearson Intl Airport to Chicago. The cheapest flight overall is C$ 219 while the most popular route, (Toronto Pearson Intl - Chicago O'Hare Intl) is currently priced at C$ 356.
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$ 261). Flying from Toronto Pearson Intl Airport to Chicago in March is currently the most expensive (average of C$ 355). 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
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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 17 January 2025.
Explore flights to Chicago departing from other origins. Flights are based on user searches made on Cheapflights and were last updated on 17 January 2025.
Browse through other flights departing from Pearson Intl. Flights are based on user searches made on Cheapflights and were last updated on 17 January 2025.
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 629,999 searches. Data last updated 17 January 2025.
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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