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O'Hare Intl

$129+ Cheap flights from Pearson Intl (YYZ) to O'Hare Intl (ORD)

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 10/15. Fares are subject to change and may not be available on all flights or dates of travel.
YYZ — ORD
Oct 17 — Oct 241
Fri 10/17
Fri 10/24
1 adult, Economy
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Cheapflights Tip: The best prices from Toronto Pearson Intl to Chicago O'Hare Intl are usually found in April or May, booked 64 days in advance, depart on a Saturday or Friday and return on a Thursday

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 September 17, 2025.

Round-trip from

$196
(Kiwi.com)

One-way from

$129
(Mytrip)

Popular in

January

Cheapest in

April

Average price

$300

Good round-trip deal

$374 or less

Good one-way deal

$245 or less
From Toronto Pearson Intl to Chicago O'Hare Intl
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One-way flight from Toronto Pearson Intl to Chicago O'Hare Intl
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Highest demand for flights based on searches. 9% potential increase in price ($31 potential increase over avg. RT price).
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Cheapest flight prices on average. 1% potential price decrease ($4 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 O'Hare Intl.
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Price to beat on a one-way flight from Toronto Pearson Intl to Chicago O'Hare Intl.
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Find flight deals from Pearson Intl to O'Hare Intl

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 September 17, 2025.

This Kiwi.com deal was found by Cheapflights users on 9/14. 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 9/14$196
This Kiwi.com deal was found by Cheapflights users on 9/15. 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 10/227:43 pmORD - YYZ
1 stop17h 22mMultiple Airlines
Deal found 9/15$199
This Kiwi.com deal was found by Cheapflights users on 9/15. 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
Thu 10/237:43 pmORD - YYZ
1 stop17h 22mMultiple Airlines
Deal found 9/15$202
This Kiwi.com deal was found by Cheapflights users on 9/15. 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 11/66:06 pmORD - YYZ
1 stop26h 01mMultiple Airlines
Deal found 9/15$203
This Kiwi.com deal was found by Cheapflights users on 9/15. 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 11/34:00 pmYYZ - ORD
1 stop7h 39mMultiple Airlines
Thu 11/66:06 pmORD - YYZ
1 stop26h 01mMultiple Airlines
Deal found 9/15$205
This Kiwi.com deal was found by Cheapflights users on 9/15. 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 10/134:00 pmYYZ - ORD
1 stop8h 44mMultiple Airlines
Thu 10/237:43 pmORD - YYZ
1 stop17h 22mMultiple Airlines
Deal found 9/15$206
This Kiwi.com deal was found by Cheapflights users on 9/14. 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
Fri 10/245:05 amORD - YYZ
1 stop8h 00mMultiple Airlines
Deal found 9/14$210
This Kiwi.com deal was found by Cheapflights users on 9/15. 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 10/134:00 pmYYZ - ORD
1 stop8h 44mMultiple Airlines
Thu 11/66:06 pmORD - YYZ
1 stop26h 01mMultiple Airlines
Deal found 9/15$211
This Kiwi.com deal was found by Cheapflights users on 9/15. 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
Mon 11/35:05 amORD - YYZ
1 stop8h 35mMultiple Airlines
Deal found 9/15$215
This Kiwi.com deal was found by Cheapflights users on 9/15. 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.
Wed 10/156:30 amYYZ - ORD
1 stop13h 08mMultiple Airlines
Thu 10/235:05 amORD - YYZ
1 stop8h 00mMultiple Airlines
Deal found 9/15$216
This Kiwi.com deal was found by Cheapflights users on 9/15. 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 10/307:43 pmORD - YYZ
1 stop17h 57mMultiple Airlines
Deal found 9/15$217

Cheapflights Fare Finder

 
Customize 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 2,558,603 searches. Data last updated September 17, 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 10/17

11:00 am-12:03 pm

Nonstop2h 03m

Chicago O'Hare Intl

Sun 10/19

6:01 pm-8:44 pm

Nonstop1h 43m

$275

TorontoChicago

YYZ - ORD

YYZORD

Toronto Pearson Intl

Thu 10/23

7:00 am-7:58 am

Nonstop1h 58m

Chicago O'Hare Intl

Sun 10/26

10:00 am-12:39 pm

Nonstop1h 39m

$275

TorontoChicago

YYZ - ORD

YYZORD

Toronto Pearson Intl

Sat 10/25

9:45 am-4:11 pm

1 stop7h 26m

Chicago O'Hare Intl

Sun 11/2

7:10 am-2:45 pm

1 stop6h 35m

$275

TorontoChicago

YYZ - ORD

YYZORD

Toronto Pearson Intl

Sun 10/12

7:00 am-7:58 am

Nonstop1h 58m

Chicago O'Hare Intl

Fri 10/24

6:01 pm-8:44 pm

Nonstop1h 43m

$275

TorontoChicago

YYZ - ORD

YYZORD

Toronto Pearson Intl

Wed 10/15

6:09 pm-8:23 pm

1 stop3h 14m

Chicago O'Hare Intl

Mon 10/20

6:59 pm-8:55 am

1 stop12h 56m

$275

TorontoChicago

YYZ - ORD

YYZORD

Toronto Pearson Intl

Mon 10/13

9:00 am-9:55 am

Nonstop1h 55m

Chicago O'Hare Intl

Wed 10/22

8:55 am-11:49 am

Nonstop1h 54m

$275

TorontoChicago

YYZ - ORD

YYZORD

Toronto Pearson Intl

Fri 10/17

9:00 pm-10:07 pm

Nonstop2h 07m

Chicago O'Hare Intl

Fri 10/24

9:12 pm-11:58 pm

Nonstop1h 46m

$275

TorontoChicago

YYZ - ORD

YYZORD

Toronto Pearson Intl

Sun 10/12

7:00 am-7:58 am

Nonstop1h 58m

Chicago O'Hare Intl

Sun 10/19

4:42 pm-7:37 pm

Nonstop1h 55m

$275

TorontoChicago

YYZ - ORD

YYZORD

Toronto Pearson Intl

Sat 10/18

7:00 am-7:58 am

Nonstop1h 58m

Chicago O'Hare Intl

Sun 10/19

4:42 pm-7:37 pm

Nonstop1h 55m

$275

TorontoChicago

YYZ - ORD

YYZORD

Toronto Pearson Intl

Tue 10/14

9:00 pm-10:07 pm

Nonstop2h 07m

Chicago O'Hare Intl

Wed 10/22

8:55 am-11:49 am

Nonstop1h 54m

$275

Flights are sorted by cheapest round-trip flights first.

Deals found on 9/16

Showing 1-10 of 24 results
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The best insider tips for Toronto Pearson Intl Airport to Chicago O'Hare Intl Airport 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 O'Hare Intl Airport trip
Airlines
Qatar Airways

Qatar Airways allows only one carry-on item in economy, plan ahead to avoid extra fees.


Qatar Airways' business class offers luxury with pajamas, fresh flowers, and anytime dining.

Read more about Qatar Airwaysby Brandon Schultz
Air Canada

Air Canada offers Preferred Seats with up to four inches extra space, ideal for taller travelers.


Air Canada's Economy Flex includes a checked bag and free advanced seat selection.

Read more about Air Canadaby Jessica Macdonald
United Airlines

United's Basic Economy restricts carry-ons; exceptions for Premier members and select routes.


United's Economy Plus offers extra legroom and priority boarding for MileagePlus Premier members.

Read more about United Airlinesby Harriet Baskas
Airports
YYZ

Security lines at YYZ are efficient, moving quickly even for US-bound flights. Arrive early to clear US customs before boarding.

Read more about YYZby Kaitlyn McInnis
ORD

For arrivals at ORD, take the 'L' train for a reliable and efficient trip to downtown Chicago, avoiding traffic delays.

Read more about ORDby Ramsey Qubein
Our travel experts
Brandon Schultz

Brandon Schultz

Expert on Qatar Airways

Brandon Schultz

Brandon Schultz

Brandon Schultz is an award-winning food and travel writer based in New York City. His work has appeared in Forbes, AAA, Thrillist, Travel + Leisure, and The Daily Meal, among many others, and he is the author of 6 books, including 3 cookbooks.

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 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 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 O'Hare Intl Airport

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 round-trip flight from Pearson Intl to O'Hare Intl. Price data was last updated on September 12, 2025.

Booking 64 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, August is the cheapest month in which you can book a flight from Toronto Pearson Intl Airport to Chicago O'Hare Intl Airport (average of $245). Flying from Toronto Pearson Intl Airport to Chicago O'Hare Intl Airport 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 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 September 17, 2025.

When flying from Toronto Pearson Intl Airport to Chicago O'Hare Intl Airport, the time of day you fly usually plays a role in the price. Save by searching for a flight in the evening, which can drop the price by up to 36% versus a flight in the afternoon.

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 round-trip from Pearson Intl to O'Hare Intl. Price data was last updated on September 14, 2025.

Travelers seeking maximum savings on their Toronto Pearson Intl Airport to Chicago O'Hare Intl Airport 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.

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

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 September 17, 2025.
Peruse reviews from past customers who have flown with United Airlines, American Airlines, and Air Canada from Toronto Pearson Intl Airport to Chicago O'Hare Intl Airport to help guide your decision. You can also see how each airline stacks up in terms of entertainment options, comfort, food, crew/service, and boarding process.
United Airlines
7.4
Good
8,926 reviews

Overall

7.4

Boarding

7.7

Crew

8.1

Comfort

7.3

Food

6.6

Entertainment

7.1

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
8,926 reviews
United Airlines
7.4
Good
8,926 reviews

Overall

7.4

Boarding

7.7

Crew

8.1

Comfort

7.3

Food

6.6

Entertainment

7.1

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
8,926 reviews

Overall

7.4

Boarding

7.7

Crew

8.1

Comfort

7.3

Food

6.6

Entertainment

7.1

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
8,926 reviews

Overall

7.4

Boarding

7.7

Crew

8.1

Comfort

7.3

Food

6.6

Entertainment

7.1

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 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 $275, United Airlines can have you in Chicago O'Hare Intl Airport from Toronto Pearson Intl Airport in 2h 03m. The distance from Toronto Pearson Intl Airport to Chicago O'Hare Intl Airport is about 436 mi. All flights are typically nonstop.

  • What are the cheapest airlines flying from Toronto Pearson Intl Airport to Chicago O'Hare Intl Airport round-trip?

    Flying on Air Canada is currently your cheapest option to Chicago O'Hare Intl Airport, with prices starting at $146. Additional round-trip tickets that might be worth considering are offered by United Airlines and American Airlines, with the lowest prices starting at $165 and $196, respectively. Users have found that Air Canada is 50% cheaper than the other options available to this destination.

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

    The top 3 most reliable airlines when flying from Toronto Pearson Intl Airport to Chicago O'Hare Intl Airport are EVA Air (88%), Egyptair (85%) and Copa Airlines (85%).

  • 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 $1,139, our data indicates the cheapest price to be $126. The most popular route (Toronto Pearson Intl - Chicago O'Hare Intl), is priced around $217.

  • 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 vacation 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, August is the cheapest month in which you can book a flight from Toronto Pearson Intl Airport to Chicago O'Hare Intl Airport (average of $245). Flying from Toronto Pearson Intl Airport to Chicago O'Hare Intl Airport 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 O'Hare Intl Airport?

Book flights to Chicago O'Hare Intl Airport if you plan to visit one of these locations
Schaumburg
Rosemont
Skokie
Gurnee
Hoffman Estates
Des Plaines
Elgin
Arlington Heights
Orland Park
Beloit
Racine
Rockford
Oak Brook
Elk Grove Village
Downers Grove
Naperville
Evanston
Merrillville
Bridgeview
Warrenville

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Alternative routes for Pearson Intl to O'Hare Intl

See prices for flight routes from nearby airports that may be better suited for you.
Toronto Island to Midway flights
Pearson Intl to Midway flights
Toronto Island to O'Hare Intl flights
Hamilton to O'Hare Intl flights

Top 3 airlines flying from Pearson Intl to O'Hare Intl

Discover the top 3 airlines 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 2,558,603 searches. Data last updated September 17, 2025.
AirlineCheapestAverageFlexibilityOn-time
Air CanadaCheapest$146Average$271FlexibilityNo cancel feeOn-time67%
United AirlinesCheapest$165Average$286FlexibilityNo cancel feeOn-time69%
American AirlinesCheapest$196Average$341FlexibilityNo cancel feeOn-time71%

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