HomeSearch by dateVacation packagesHotelsFlight dealsCar rentalTravel tips & news
Chicago

$118+ 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 2/1. Fares are subject to change and may not be available on all flights or dates of travel.
YYZ — CHI
ene. 11 — ene. 181
dom. 1/11
dom. 1/18
1 adult, Economy
We work with more than 300 partners to bring you better travel deals

Find cheap flights from Pearson Intl to Chicago with Cheapflights

1. Tell us where you want to go

Enter your travel information like dates, passengers, trip type (one-way or round trip), and preferred cabin class then click “Find deals”

2. Select your favorite providers

We find the providers serving your travel needs. Choose up to four travel providers to compare side-by-side for flights, hotels, or car rentals.

3. Compare prices and book

Review each provider’s pricing and select the best option for you! Book through your favorite provider’s website for a seamless experience.

Cheapflights Tip: The best prices from Toronto Pearson Intl to Chicago are usually found in September or August, booked 67 days in advance, depart on a Friday or Thursday and return on a Thursday

Cheap 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 diciembre 12, 2025.

This United Airlines deal was found by Cheapflights users on 12/10. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mié. 12/319:00 amYYZ - ORD
Nonstop2h 05mUnited Airlines
jue. 1/18:51 amORD - YYZ
1 stop13h 55mUnited Airlines
Deal found 12/10$231
This United Airlines deal was found by Cheapflights users on 12/10. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
jue. 12/257:40 pmYYZ - ORD
1 stop13h 07mUnited Airlines
jue. 1/18:51 amORD - YYZ
1 stop13h 55mUnited Airlines
Deal found 12/10$236
This United Airlines deal was found by Cheapflights users on 12/10. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
vie. 12/266:50 amYYZ - ORD
Nonstop2h 13mUnited Airlines
mié. 12/316:21 pmORD - YYZ
1 stop4h 25mUnited Airlines
Deal found 12/10$273
This United Airlines deal was found by Cheapflights users on 12/10. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
vie. 12/267:40 pmYYZ - ORD
1 stop5h 04mUnited Airlines
mar. 1/61:00 pmORD - YYZ
1 stop6h 42mUnited Airlines
Deal found 12/10$290
This United Airlines deal was found by Cheapflights users on 12/11. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
sáb. 12/279:00 amYYZ - ORD
Nonstop2h 05mUnited Airlines
mié. 12/319:20 pmORD - YYZ
Nonstop1h 39mUnited Airlines
Deal found 12/11$300
This United Airlines deal was found by Cheapflights users on 12/10. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
sáb. 12/2711:00 amYYZ - ORD
Nonstop2h 05mUnited Airlines
mar. 1/66:28 pmORD - YYZ
Nonstop1h 53mUnited Airlines
Deal found 12/10$301
This Air Canada deal was found by Cheapflights users on 12/9. 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 Air Canada is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mié. 12/249:00 amYYZ - ORD
1 stop6h 55mAir Canada
dom. 1/188:00 amORD - YYZ
Nonstop1h 40mAir Canada
Deal found 12/9$308
This United Airlines deal was found by Cheapflights users on 12/11. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
sáb. 12/279:00 amYYZ - ORD
Nonstop2h 05mUnited Airlines
mar. 12/301:24 pmORD - YYZ
1 stop9h 22mUnited Airlines
Deal found 12/11$310
This Kiwi.com deal was found by Cheapflights users on 12/10. 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.
mié. 12/317:15 amYYZ - MDW
1 stop15h 43mMultiple Airlines
dom. 1/47:44 amMDW - YYZ
2 stops31h 41mMultiple Airlines
Deal found 12/10$423
This Kiwi.com deal was found by Cheapflights users on 12/10. 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.
mar. 12/308:20 pmYYZ - MDW
2 stops26h 52mMultiple Airlines
dom. 1/46:08 pmMDW - YYZ
1 stop13h 56mMultiple Airlines
Deal found 12/10$440
This WestJet deal was found by Cheapflights users on 12/10. 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 WestJet is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mié. 12/2410:15 pmYYZ - MDW
2 stops20h 04mWestJet
mié. 12/319:50 amMDW - YYZ
1 stop24h 18mWestJet
Deal found 12/10$491
This WestJet deal was found by Cheapflights users on 12/10. 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 WestJet is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mié. 12/245:00 pmYYZ - MDW
2 stops25h 19mWestJet
vie. 12/266:08 pmMDW - YYZ
1 stop3h 42mWestJet
Deal found 12/10$495

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 diciembre 12, 2025.

Most accurate provider

eDreams
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$179
(Mytrip)

One-way from

$118
(Air Canada)

Popular in

December

Cheapest in

September

Average price

$366

Good round-trip deal

$324 or less

Good one-way deal

$262 or less
Provider with most accurate pricing for Toronto Pearson Intl-Chicago (CHI) flight deals.
Search Deals
Provider most trusted by Cheapflights users for Toronto Pearson Intl-Chicago (CHI) flights.
Search Deals
From Toronto Pearson Intl to Chicago (CHI)
Search Deals
One-way flight from Toronto Pearson Intl to Chicago (CHI)
Search Deals
Highest demand for flights based on searches. 10% potential increase in price ($30 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 3% potential price decrease ($9 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in December 2025
Search Deals
Price to beat on a round-trip flight from Toronto Pearson Intl to Chicago (CHI).
Search Deals
Price to beat on a one-way flight from Toronto Pearson Intl to Chicago (CHI).
Search Deals

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 diciembre 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

sáb. 1/10

5:30 pm-6:50 pm

Nonstop2h 20m

Chicago O'Hare Intl

dom. 1/11

11:15 am-2:01 pm

Nonstop1h 46m

$203

TorontoChicago

YYZ - ORD

YYZORD

Toronto Pearson Intl

vie. 2/13

9:00 pm-10:04 pm

Nonstop2h 04m

Chicago O'Hare Intl

dom. 2/15

10:55 am-5:49 pm

1 stop5h 54m

$208

TorontoChicago

YYZ - ORD

YYZORD

Toronto Pearson Intl

dom. 2/15

5:15 pm-8:44 pm

1 stop4h 29m

Chicago O'Hare Intl

jue. 2/19

6:30 am-11:18 am

1 stop3h 48m

$212

TorontoChicago

YYZ - MDW

YYZMDW

Toronto Pearson Intl

jue. 2/5

7:45 am-12:46 pm

1 stop6h 01m

Chicago Midway

dom. 2/8

1:26 pm-7:08 pm

1 stop4h 42m

$212

TorontoChicago

YYZ - ORD

YYZORD

Toronto Pearson Intl

vie. 1/16

3:30 pm-4:40 pm

Nonstop2h 10m

Chicago O'Hare Intl

lun. 1/19

6:05 am-11:48 am

1 stop4h 43m

$213

TorontoChicago

YYZ - ORD

YYZORD

Toronto Pearson Intl

jue. 2/5

6:06 am-10:55 am

1 stop5h 49m

Chicago O'Hare Intl

dom. 2/8

6:50 am-4:12 pm

1 stop8h 22m

$213

TorontoChicago

YYZ - ORD

YYZORD

Toronto Pearson Intl

lun. 1/19

9:00 pm-10:05 pm

Nonstop2h 05m

Chicago O'Hare Intl

mié. 1/21

1:00 pm-6:57 pm

1 stop4h 57m

$213

TorontoChicago

YYZ - ORD

YYZORD

Toronto Pearson Intl

jue. 1/29

6:00 am-9:41 am

1 stop4h 41m

Chicago O'Hare Intl

dom. 2/1

10:35 am-4:12 pm

1 stop4h 37m

$224

TorontoChicago

YYZ - MDW

YYZMDW

Toronto Pearson Intl

jue. 1/29

12:12 pm-5:55 pm

1 stop6h 43m

Chicago Midway

dom. 2/1

9:53 am-3:59 pm

1 stop5h 06m

$224

TorontoChicago

YYZ - ORD

YYZORD

Toronto Pearson Intl

lun. 1/12

9:00 pm-10:05 pm

Nonstop2h 05m

Chicago O'Hare Intl

mié. 1/14

9:15 pm-11:59 pm

Nonstop1h 44m

$231

Flights are sorted by cheapest round-trip flights first.

Deals found on 12/11

Showing 1-10 of 37 results
1
2
3
4

Compare providers for flights from Pearson Intl to Chicago

Provider information is updated monthly. Please note that these providers often have deals for this flight, but the availability may vary on a day-by-day basis on Cheapflights.
Use the table below to compare price accuracy, trust ratings, and cancellation policies for each provider offering flight deals from Pearson Intl to Chicago in December.
ProviderPrice AccuracyTrust Score*
FlightHubPrice Accuracy3 starsTrust Score*1 star
ExpediaPrice Accuracy2 starsTrust Score*3 stars
eDreamsPrice Accuracy3 starsTrust Score*3 stars
PricelinePrice Accuracy1 starTrust Score*3 stars

*The Trust Score is based on feedback from users after their booking experience. It measures overall satisfaction, helping us identify issues like hidden fees, problems during the ticketing process, and the quality of customer service. This score is our best indicator of the provider's quality and reliability.

  • Most accurate provider: When it comes to deals on Toronto Pearson Intl Airport-Chicago flights, users find the pricing of eDreams to be most consistent on Cheapflights vs. eDreams Users can find the same prices on Toronto Pearson Intl Airport-Chicago flight deals on Cheapflights vs. eDreams >95% of the time. Price accuracy is based on data collected from Toronto Pearson Intl Airport-Chicago flight searches over the past month and is updated monthly.
  • Most trusted provider: When it comes to deals on Toronto Pearson Intl Airport-Chicago flights, Cheapflights users trust eDreams the most. eDreams has received a user feedback score of 3 out of 3 stars (3 being the best), meaning they have been trusted the most by Cheapflights users looking for Toronto Pearson Intl Airport-Chicago flight deals. Provider user feedback score is based on Cheapflights searches over the past month and is updated monthly.

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 December 5, 2025.

Booking 67 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 $129). Flying from Toronto Pearson Intl Airport to Chicago in April is currently the most expensive (average of $212). 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 diciembre 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 23% 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 Thursday mornings when fares are most often at their lowest. Monday 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 diciembre 12, 2025.

The most flights from YYZ to CHI are scheduled on a Monday (60 on average). You will have fewer flight options on Saturday, which is when the least amount of flights are scheduled (36 on average).

How often are flights from Toronto to Chicago delayed?

About 11% of weekly flights between Toronto and Chicago have experienced delays in the past year, with the average delay time being 142 minutes.

What is the most punctual flight time for Toronto to Chicago flights?

Historically, flights departing at night 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?

Tuesday 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 last year, United Airlines have had the lowest number of delays on this route, with just 6% of flights being delayed.

The best insider tips for Toronto Pearson Intl Airport to Chicago flights

AI-powered summary based on content written by travel experts. AI can make mistakes.
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

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 diciembre 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
9,095 reviews

Entertainment

7.1

Overall

7.4

Comfort

7.3

Boarding

7.7

Crew

8.1

Food

6.6

Reviews

1 / 20
8.0
Excellent

Anonymous,Oct 2025

YUL - ORD

Crew and customer service are 5 stars. I had a lot of luggage for a very long trip and they were nothing but helpful and found solutions to every problem. It was my first time flying with United, and they really are the friendly skies. Leg room however, on 2/3 flights was terrible. Same for entertainment: There was only a seat-mounted screen on 1/3 flights. It would have been nice to have on the longest leg of the journey.
United Airlines
7.4
Good
9,095 reviews
United Airlines
7.4
Good
9,095 reviews

Entertainment

7.1

Overall

7.4

Comfort

7.3

Boarding

7.7

Crew

8.1

Food

6.6

Reviews

1 / 20
8.0
Excellent

Anonymous,Oct 2025

YUL - ORD

Crew and customer service are 5 stars. I had a lot of luggage for a very long trip and they were nothing but helpful and found solutions to every problem. It was my first time flying with United, and they really are the friendly skies. Leg room however, on 2/3 flights was terrible. Same for entertainment: There was only a seat-mounted screen on 1/3 flights. It would have been nice to have on the longest leg of the journey.
American Airlines
7.2
Good
11,048 reviews
United Airlines
7.4
Good
9,095 reviews

Entertainment

7.1

Overall

7.4

Comfort

7.3

Boarding

7.7

Crew

8.1

Food

6.6

Reviews

1 / 20
8.0
Excellent

Anonymous,Oct 2025

YUL - ORD

Crew and customer service are 5 stars. I had a lot of luggage for a very long trip and they were nothing but helpful and found solutions to every problem. It was my first time flying with United, and they really are the friendly skies. Leg room however, on 2/3 flights was terrible. Same for entertainment: There was only a seat-mounted screen on 1/3 flights. It would have been nice to have on the longest leg of the journey.
Air Canada
7.1
Good
10,514 reviews
United Airlines
7.4
Good
9,095 reviews

Entertainment

7.1

Overall

7.4

Comfort

7.3

Boarding

7.7

Crew

8.1

Food

6.6

Reviews

1 / 20
8.0
Excellent

Anonymous,Oct 2025

YUL - ORD

Crew and customer service are 5 stars. I had a lot of luggage for a very long trip and they were nothing but helpful and found solutions to every problem. It was my first time flying with United, and they really are the friendly skies. Leg room however, on 2/3 flights was terrible. Same for entertainment: There was only a seat-mounted screen on 1/3 flights. It would have been nice to have on the longest leg of the journey.

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?

    United Airlines and Delta can get you from Toronto Pearson Intl Airport to Chicago in just under 2h 20m. Your travel time can differ by up to 2h 09m. 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 $140, 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 Porter Airlines - these airlines can fly you to your destination from $165 and $180, respectively. Air Canada is 48% cheaper than the average price of flights available within the next 90 days to this destination.

  • What are the cheapest airlines to fly from Toronto Pearson Intl Airport to Chicago one-way?

    The cheapest airlines for a one-way flight from Toronto Pearson Intl Airport to Chicago are Porter Airlines ($103), United Airlines ($109), and Air Canada ($110).

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

    Consider Qatar Airways (86%), EVA Air (85%) or SkyWest Airlines (84%) 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 $1,207, our data shows the cheapest flight currently is $126. When looking at the most popular route, (Toronto Pearson Intl - Chicago O'Hare Intl), you can expect to pay $155 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 $129). Flying from Toronto Pearson Intl Airport to Chicago in April is currently the most expensive (average of $212). 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
Lansing
Merrillville
Hammond
Porter
Benton Harbor

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.

Top 4 airlines flying from Pearson Intl to Chicago

Discover the top 4 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 diciembre 12, 2025.
AirlineCheapestAverageFlexibilityOn-time
Air CanadaCheapest$149Average$269FlexibilityNo cancel feeOn-time67%
United AirlinesCheapest$165Average$282FlexibilityNo cancel feeOn-time69%
Porter AirlinesCheapest$180Average$423FlexibilityNo cancel feeOn-time52%
American AirlinesCheapest$195Average$345FlexibilityNo cancel feeOn-time71%

100% Free

Cheapflights is completely free to use, so you can start saving the moment you arrive.

Book with Flexibility

Our users can plan ahead with confidence and find flights with no change fees

Travel Smart

Millions of people come to us for their flight needs every year. We help make travel planning easy by providing useful insights and data-driven graphs that can inform your decisions.