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$129+ Cheap flights from Pearson Intl (YYZ) to Chicago (CHI)

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 10/4. Fares are subject to change and may not be available on all flights or dates of travel.
YYZ — CHI
Oct 12 — Oct 191
Sun 10/12
Sun 10/19
1 adult, Economy
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Cheapflights Tip: The best prices from Toronto Pearson Intl to Chicago are usually found in May or July, booked 71 days in advance, depart on a Saturday or Friday and return on a Thursday

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 September 12, 2025.

Round-trip from

$197
(Kiwi.com)

One-way from

$129
(Mytrip)

Popular in

December

Cheapest in

May

Average price

$286

Good round-trip deal

$390 or less

Good one-way deal

$260 or less
From Toronto Pearson Intl to Chicago (CHI)
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One-way flight from Toronto Pearson Intl to Chicago (CHI)
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Highest demand for flights based on searches. 8% potential increase in price ($27 potential increase over avg. RT price).
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Cheapest flight prices on average. 1% potential price decrease ($5 potential savings vs. average RT price).
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Average for round-trip flights in September 2025
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Price to beat on a round-trip flight from Toronto Pearson Intl to Chicago (CHI).
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Price to beat on a one-way flight from Toronto Pearson Intl to Chicago (CHI).
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Find flight deals from Pearson Intl to Chicago

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 September 12, 2025.

This Kiwi.com deal was found by Cheapflights users on 9/12. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 10/204:00 pmYYZ - ORD
1 stop8h 44mMultiple Airlines
Thu 10/2312:53 pmORD - YYZ
1 stop7h 14mMultiple Airlines
Deal found 9/12$197
This Kiwi.com deal was found by Cheapflights users on 9/11. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 10/194:00 pmYYZ - ORD
1 stop24h 49mMultiple Airlines
Wed 10/227:43 pmORD - YYZ
1 stop17h 22mMultiple Airlines
Deal found 9/11$221
This Kiwi.com deal was found by Cheapflights users on 9/12. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 10/274:00 pmYYZ - ORD
1 stop8h 44mMultiple Airlines
Mon 11/35:05 amORD - YYZ
1 stop8h 35mMultiple Airlines
Deal found 9/12$223
This Kiwi.com deal was found by Cheapflights users on 9/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 10/204:00 pmYYZ - ORD
1 stop8h 44mMultiple Airlines
Fri 10/315:25 amORD - YYZ
1 stop13h 35mMultiple Airlines
Deal found 9/10$230
This Kiwi.com deal was found by Cheapflights users on 9/12. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/167:15 amYYZ - ORD
1 stop10h 42mMultiple Airlines
Fri 10/315:25 amORD - YYZ
1 stop13h 35mMultiple Airlines
Deal found 9/12$231
This Kiwi.com deal was found by Cheapflights users on 9/11. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 10/204:00 pmYYZ - ORD
1 stop8h 44mMultiple Airlines
Wed 10/225:05 amORD - YYZ
1 stop8h 00mMultiple Airlines
Deal found 9/11$233
This Kiwi.com deal was found by Cheapflights users on 9/12. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/307:15 amYYZ - ORD
1 stop9h 57mMultiple Airlines
Thu 10/210:11 amORD - YYZ
1 stop9h 56mMultiple Airlines
Deal found 9/12$234
This Kiwi.com deal was found by Cheapflights users on 9/11. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/246:30 amYYZ - ORD
1 stop11h 13mWestJet
Mon 10/272:20 pmORD - YYZ
1 stop9h 06mWestJet
Deal found 9/11$235
This Kiwi.com deal was found by Cheapflights users on 9/12. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/267:15 amYYZ - ORD
1 stop9h 57mMultiple Airlines
Thu 10/210:11 amORD - YYZ
1 stop9h 56mMultiple Airlines
Deal found 9/12$237
This Kiwi.com deal was found by Cheapflights users on 9/12. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/49:35 amYYZ - ORD
1 stop9h 04mMultiple Airlines
Mon 10/612:43 pmORD - YYZ
1 stop7h 24mMultiple Airlines
Deal found 9/12$238
This Kiwi.com deal was found by Cheapflights users on 9/12. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/257:45 amYYZ - MDW
1 stop28h 59mMultiple Airlines
Fri 10/319:32 amMDW - YYZ
1 stop9h 28mMultiple Airlines
Deal found 9/12$240
This Trip.com deal was found by Cheapflights users on 9/12. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/111:20 pmYYZ - MDW
1 stop9h 54mWestJet
Sat 10/1810:35 amMDW - YYZ
1 stop5h 15mWestJet
Deal found 9/12$250

Cheapflights Fare Finder

 
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 2,558,603 searches. Data last updated September 12, 2025.
Use the filters below to find and compare flights from Toronto Pearson Intl Airport to Chicago that are best for you.

Fly from

Pearson Intl

Fly to

Chicago

Route

Depart

Return

Price

TorontoChicago

YYZ - ORD

YYZORD

Toronto Pearson Intl

Thu 10/23

8:00 am-4:43 pm

1 stop9h 43m

Chicago O'Hare Intl

Sun 10/26

2:20 pm-12:26 am

1 stop9h 06m

$245

TorontoChicago

YYZ - ORD

YYZORD

Toronto Pearson Intl

Wed 10/29

5:15 pm-12:26 pm

1 stop20h 11m

Chicago O'Hare Intl

Sun 11/2

6:06 pm-9:07 pm

1 stop26h 01m

$246

TorontoChicago

YYZ - MDW

YYZMDW

Toronto Pearson Intl

Sat 10/4

1:20 pm-9:10 pm

1 stop8h 50m

Chicago Midway

Mon 10/6

9:20 am-11:18 pm

1 stop12h 58m

$262

TorontoChicago

YYZ - MDW

YYZMDW

Toronto Pearson Intl

Fri 10/31

6:45 pm-9:45 am

2 stops16h 00m

Chicago Midway

Mon 11/3

10:30 am-4:50 pm

1 stop5h 20m

$268

TorontoChicago

YYZ - ORD

YYZORD

Toronto Pearson Intl

Sat 10/4

6:13 pm-9:34 pm

1 stop4h 21m

Chicago O'Hare Intl

Tue 10/7

10:36 am-11:05 pm

1 stop11h 29m

$272

TorontoChicago

YYZ - ORD

YYZORD

Toronto Pearson Intl

Sun 10/19

7:45 am-12:26 am

2 stops17h 41m

Chicago O'Hare Intl

Wed 10/22

5:05 am-2:05 pm

1 stop8h 00m

$274

TorontoChicago

YYZ - ORD

YYZORD

Toronto Pearson Intl

Sat 10/4

9:00 am-9:55 am

Nonstop1h 55m

Chicago O'Hare Intl

Mon 10/6

6:01 pm-8:44 pm

Nonstop1h 43m

$275

TorontoChicago

YYZ - ORD

YYZORD

Toronto Pearson Intl

Sat 10/25

11:00 am-12:03 pm

Nonstop2h 03m

Chicago O'Hare Intl

Fri 10/31

1:19 pm-4:02 pm

Nonstop1h 43m

$275

TorontoChicago

YYZ - ORD

YYZORD

Toronto Pearson Intl

Thu 11/6

9:00 am-10:05 am

Nonstop2h 05m

Chicago O'Hare Intl

Tue 11/11

4:50 pm-7:45 pm

Nonstop1h 55m

$275

TorontoChicago

YYZ - ORD

YYZORD

Toronto Pearson Intl

Wed 10/8

11:00 am-12:03 pm

Nonstop2h 03m

Chicago O'Hare Intl

Thu 10/30

10:00 am-12:39 pm

Nonstop1h 39m

$275

Flights are sorted by cheapest round-trip flights first.

Deals found on 9/12

Showing 1-10 of 39 results
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The best insider tips for Toronto Pearson Intl Airport to Chicago flights

Snippets provided in this section are AI-generated based on a summarization of Cheapflights-commissioned articles. The articles are presented as-is, for general informational purposes only, and may not be up-to-date. The opinions contained in the articles are original to the author and reflect their authentic experience, which may vary significantly from the experience of others.
Cheapflights partnered with top experts to bring you the best recommendations for your Toronto Pearson Intl Airport to Chicago trip
Airlines
British Airways

BA's Club Suite offers privacy with solo pods and a door you can close.


BA's World Traveller Plus offers extra seat width and legroom for added comfort.

Read more about British Airwaysby Gabriel Leigh
Air Canada

Air Canada offers free texting via Apple iMessage, WhatsApp, and Facebook Messenger for Aeroplan Members.


Families with kids under 6 get early boarding on Air Canada flights.

Read more about Air Canadaby Jessica Macdonald
United Airlines

Basic Economy allows a personal item only; no carry-on bags unless exceptions apply.


United First offers priority perks and two free checked bags on domestic routes.

Read more about United Airlinesby Harriet Baskas
Airports
YYZ

Toronto Pearson offers fast security lines for US-bound flights. Arrive early to clear US customs before boarding.

Read more about YYZby Kaitlyn McInnis
ORD

At ORD, take the 'L' train for a quick and economical ride to downtown Chicago, avoiding traffic delays.

Read more about ORDby Ramsey Qubein
Our travel experts
Gabriel Leigh

Gabriel Leigh

Expert on British Airways

Gabriel Leigh

Gabriel Leigh

Gabriel is a writer and video creator. As senior content producer for Flightradar24 and Monocle’s transport correspondent, he keeps a close eye on aviation in particular. He has also written travel articles for the likes of The New York Times. Born in New York but raised around the world, he now lives in Sweden. He’s been to 75 countries, flying 2.3 million miles on 113 airlines and through 234 airports in the process.

Read more
Jessica Macdonald

Jessica Macdonald

Expert on Air Canada

Jessica Macdonald

Jessica Macdonald

Currently based in Scotland after living in South Africa and the United States, Jessica has been writing travel and aviation content for more than 10 years. She regularly contributes to Travel + Leisure and TripSavvy, and has had work published by Condé Nast Traveller and The Independent. She has traveled to more than 50 countries across six continents.

Read more
Harriet Baskas

Harriet Baskas

Expert on United Airlines

Harriet Baskas

Harriet Baskas

Harriet is an award-winning journalist who is happiest in an airport or an unusual museum. Her stories about airports, air travel, and the business of travel have appeared on NBC News, CNBC, USA TODAY, The Points Guy and other outlets. She is the creator of the StuckatTheAirport.com blog and the author of nine books. When not out on the road or exploring the latest airport amenities, she’s home in Seattle getting ready for the next adventure.

Read more
Ramsey Qubein

Ramsey Qubein

Expert on ORD

Ramsey Qubein

Ramsey Qubein

An avid traveler and aviation expert who has visited 173 countries, all 50 states and seven continents, Ramsey Qubein flies nearly 400,000 miles a year. As a North Carolina-based freelance journalist for publications including Conde Nast Traveler, Forbes, USA Today and Bloomberg among others, he explores the latest trends in aviation, hospitality, cruises and business.

Read more
Kaitlyn McInnis

Kaitlyn McInnis

Expert on YYZ

Kaitlyn McInnis

Kaitlyn McInnis

Kaitlyn is a guidebook author and travel writer splitting her time between Atlantic Canada and Istanbul, Türkiye. She has visited over fifty countries and all seven continents, so she is very familiar with many hotels, airports and airlines around the globe. But her favorite type of vacation is sunbathing by the sea with a good book in hand.

Read more

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.

Cheapflights Insights

Everything you need to know about your flight from Toronto Pearson Intl Airport to Chicago

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 August 29, 2025.

Booking 71 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, August is the cheapest month in which you can book a flight from Toronto Pearson Intl Airport to Chicago (average of $245). Flying from Toronto Pearson Intl Airport to Chicago in March is currently the most expensive (average of $321). 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 September 12, 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 37% on the cost of your flight, compared to a flight in the afternoon.

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 December 16, 2024.

Travelers seeking maximum savings on their Toronto Pearson Intl Airport to Chicago flight should consider departing on Saturday evenings when fares are most often at their lowest. Tuesday afternoons 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 September 12, 2025.

The most flights from YYZ to CHI are scheduled on a Friday (61 on average). You will have fewer flight options on Saturday, which is when the least amount of flights are scheduled (41 on average).

How much does it cost to fly round-trip from Toronto Pearson Intl Airport to Chicago?

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 September 12, 2025.
See what other customers who have flown with United Airlines, American Airlines, and Air Canada from Toronto Pearson Intl Airport to Chicago have to say. You can also see how each airline compares in terms of entertainment options, comfort, food, crew/service, and boarding process.
United Airlines
7.4
Good
8,936 reviews

Entertainment

7.1

Crew

8.1

Comfort

7.3

Overall

7.4

Food

6.6

Boarding

7.7

Reviews

1 / 20
2.0
Mediocre

Deb,Jan 2025

MKE - ORD

It was terrible! So much to say, but in a nutshell we used vouchers from United because our last trip with them was awful with many mishaps and errors made. Unfortunately, this trip was even worse!
United Airlines
7.4
Good
8,936 reviews
United Airlines
7.4
Good
8,936 reviews

Entertainment

7.1

Crew

8.1

Comfort

7.3

Overall

7.4

Food

6.6

Boarding

7.7

Reviews

1 / 20
2.0
Mediocre

Deb,Jan 2025

MKE - ORD

It was terrible! So much to say, but in a nutshell we used vouchers from United because our last trip with them was awful with many mishaps and errors made. Unfortunately, this trip was even worse!
American Airlines
7.2
Good
10,000 reviews
United Airlines
7.4
Good
8,936 reviews

Entertainment

7.1

Crew

8.1

Comfort

7.3

Overall

7.4

Food

6.6

Boarding

7.7

Reviews

1 / 20
2.0
Mediocre

Deb,Jan 2025

MKE - ORD

It was terrible! So much to say, but in a nutshell we used vouchers from United because our last trip with them was awful with many mishaps and errors made. Unfortunately, this trip was even worse!
Air Canada
7.1
Good
10,000 reviews
United Airlines
7.4
Good
8,936 reviews

Entertainment

7.1

Crew

8.1

Comfort

7.3

Overall

7.4

Food

6.6

Boarding

7.7

Reviews

1 / 20
2.0
Mediocre

Deb,Jan 2025

MKE - ORD

It was terrible! So much to say, but in a nutshell we used vouchers from United because our last trip with them was awful with many mishaps and errors made. Unfortunately, this trip was even worse!

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?

    WestJet and United Airlines can get you from Toronto Pearson Intl Airport to Chicago in just under 1h 55m. Your travel time can differ by up to 6h 55m. The distance from Toronto Pearson Intl Airport to Chicago is about 436 mi. 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 $145, Air Canada will fly you from Toronto Pearson Intl Airport to Chicago and back. In addition to Air Canada, many other airlines offer competitively priced options for your trip. Search Cheapflights for deals from United Airlines and American Airlines - these airlines can fly you to your destination from $165 and $196, respectively. Air Canada is 49% cheaper than the average price of flights available within the next 90 days to this destination.

  • What are the most reliable airlines from Toronto Pearson Intl Airport to Chicago?

    Consider EVA Air (83%), SkyWest Airlines (83%) or ANA (83%) when booking your flight. These represent the most reliable airlines when flying from Toronto Pearson Intl Airport to Chicago.

  • What are the cheapest flights from Toronto Pearson Intl Airport to Chicago?

    While on average a flight from Toronto Pearson Intl Airport to Chicago is generally $1,182, our data shows the cheapest flight currently is $127. When looking at the most popular route, (Toronto Pearson Intl - Chicago O'Hare Intl), you can expect to pay $214 for that flight.

  • Can I find deals for flights from Pearson Intl to Chicago that include hotel bookings?

    Yes. In addition to deals on Pearson Intl to Chicago flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from Pearson Intl to Chicago?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Pearson Intl to Chicago.

  • 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, August is the cheapest month in which you can book a flight from Toronto Pearson Intl Airport to Chicago (average of $245). Flying from Toronto Pearson Intl Airport to Chicago in March is currently the most expensive (average of $321). 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.

See more FAQs

Traveling to a place near Chicago?

Book flights to Chicago if you plan to visit one of these locations
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Lansing
Hammond
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Porter
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Top 3 airlines flying from Pearson Intl to Chicago

Discover the top 3 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 2,558,603 searches. Data last updated September 12, 2025.
AirlineCheapestAverageFlexibilityOn-time
Air CanadaCheapest$145Average$272FlexibilityNo cancel feeOn-time67%
United AirlinesCheapest$165Average$286FlexibilityNo cancel feeOn-time69%
American AirlinesCheapest$196Average$340FlexibilityNo cancel feeOn-time71%

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