HomeSearch by dateVacation packagesHotelsFlight dealsCar rentalTravel tips & news
Chicago

$140+ 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 1/29. Fares are subject to change and may not be available on all flights or dates of travel.
YYZ — CHI
Dec 23 — Dec 301
Mon 12/23
Mon 12/30
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.

The best prices from Toronto Pearson Intl to Chicago are usually found in January or April, booked 84 days in advance, depart on a Wednesday or Thursday and return on a Wednesday

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 December 18, 2024.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$230
(Air Canada)

One-way from

$140
(SmartFares)

Popular in

December

Cheapest in

January

Average price

$323
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
High demand for flights, 2% potential price rise
Search Deals
Best time to find cheap flights, 1% potential price drop
Search Deals
Average for round-trip flights in December 2024
Search Deals

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 December 18, 2024.

This United Airlines deal was found by Cheapflights users on 12/17. 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.
Tue 12/3112:20 pmYYZ - ORD
Nonstop1h 51mUnited Airlines
Wed 1/810:53 amORD - YYZ
Nonstop1h 49mUnited Airlines
Deal found 12/17$273
This Air Canada deal was found by Cheapflights users on 12/17. 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.
Tue 12/3112:20 pmYYZ - ORD
Nonstop1h 51mAir Canada
Tue 1/71:55 pmORD - YYZ
1 stop5h 30mAir Canada
Deal found 12/17$274
This American Airlines deal was found by Cheapflights users on 12/18. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 12/287:35 amYYZ - ORD
1 stop5h 40mAmerican Airlines
Wed 1/83:00 pmORD - YYZ
Nonstop1h 35mAmerican Airlines
Deal found 12/18$335
This United deal was found by Cheapflights users on 12/17. 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 is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 12/309:00 pmYYZ - ORD
1 stop15h 58mMultiple Airlines
Fri 1/107:20 amORD - YYZ
1 stop6h 51mMultiple Airlines
Deal found 12/17$336
This WestJet deal was found by Cheapflights users on 12/17. 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.
Wed 12/251:00 pmYYZ - ORD
1 stop4h 40mWestJet
Mon 2/34:15 pmORD - YYZ
2 stops13h 02mWestJet
Deal found 12/17$383
This Kiwi.com deal was found by Cheapflights users on 12/17. 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 12/317:10 amYYZ - MDW
1 stop11h 44mMultiple Airlines
Wed 1/810:57 amMDW - YYZ
1 stop5h 03mMultiple Airlines
Deal found 12/17$416
This Trip.com deal was found by Cheapflights users on 12/17. 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.
Wed 12/256:30 amYYZ - MDW
1 stop5h 38mWestJet
Mon 2/31:26 pmMDW - YYZ
1 stop8h 41mWestJet
Deal found 12/17$453
This Delta deal was found by Cheapflights users on 12/18. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/1912:35 pmYYZ - MDW
1 stop6h 09mDelta
Sun 2/22:08 pmMDW - YYZ
1 stop7h 44mDelta
Deal found 12/18$456

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 2,558,603 searches. Data last updated December 18, 2024.

Fly from

Any airport

Fly to

Any airport

Route

Depart

Return

Price

TorontoChicago

YYZ - ORD

YYZORD

Toronto Pearson Intl

Thu 1/9

6:25 am-10:54 am

1 stop5h 29m

Chicago O'Hare Intl

Sun 1/12

7:20 am-1:41 pm

1 stop5h 21m

$230

TorontoChicago

YYZ - ORD

YYZORD

Toronto Pearson Intl

Fri 1/31

6:20 pm-7:20 pm

Nonstop2h 00m

Chicago O'Hare Intl

Fri 2/7

3:00 pm-5:35 pm

Nonstop1h 35m

$231

TorontoChicago

YYZ - ORD

YYZORD

Toronto Pearson Intl

Thu 1/9

11:00 am-12:13 pm

Nonstop2h 13m

Chicago O'Hare Intl

Sun 1/12

8:30 pm-11:11 pm

Nonstop1h 41m

$238

TorontoChicago

YYZ - ORD

YYZORD

Toronto Pearson Intl

Thu 1/9

2:05 pm-6:38 pm

1 stop5h 33m

Chicago O'Hare Intl

Fri 1/10

8:30 am-10:35 pm

1 stop13h 05m

$239

TorontoChicago

YYZ - ORD

YYZORD

Toronto Pearson Intl

Mon 2/17

6:20 pm-7:20 pm

Nonstop2h 00m

Chicago O'Hare Intl

Fri 2/21

9:50 am-12:30 pm

Nonstop1h 40m

$240

TorontoChicago

YYZ - ORD

YYZORD

Toronto Pearson Intl

Wed 1/15

12:20 pm-6:38 pm

1 stop7h 18m

Chicago O'Hare Intl

Sun 1/19

6:00 am-12:37 pm

1 stop5h 37m

$244

TorontoChicago

YYZ - ORD

YYZORD

Toronto Pearson Intl

Tue 1/7

2:30 pm-7:59 pm

1 stop6h 29m

Chicago O'Hare Intl

Sat 2/8

6:45 am-11:56 am

1 stop4h 11m

$246

TorontoChicago

YYZ - MDW

YYZMDW

Toronto Pearson Intl

Tue 1/7

6:00 am-8:54 am

1 stop3h 54m

Chicago Midway

Mon 2/3

6:28 pm-10:49 pm

1 stop3h 21m

$246

TorontoChicago

YYZ - MDW

YYZMDW

Toronto Pearson Intl

Thu 1/9

12:20 pm-10:12 am

1 stop22h 52m

Chicago Midway

Sun 1/12

10:19 am-11:11 pm

1 stop11h 52m

$274

TorontoChicago

YYZ - ORD

YYZORD

Toronto Pearson Intl

Tue 1/14

2:45 pm-9:58 pm

1 stop8h 13m

Chicago O'Hare Intl

Fri 1/17

10:30 am-4:12 pm

1 stop4h 42m

$284

Flights are sorted by cheapest round-trip flights first.

Deals found on 12/18

Showing 1-10 of 20 results
1
2

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*3 stars
ExpediaPrice Accuracy1 starTrust 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 FlightHub to be most consistent on Cheapflights vs. FlightHub Users can find the same prices on Toronto Pearson Intl Airport-Chicago flight deals on Cheapflights vs. FlightHub >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 FlightHub the most. FlightHub 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.

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 December 13, 2024.

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, September is the cheapest month in which you can book a flight from Toronto Pearson Intl Airport to Chicago (average of $232). Flying from Toronto Pearson Intl Airport to Chicago in June is currently the most expensive (average of $308). 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 December 18, 2024.

It’s optimal to fly from Toronto Pearson Intl Airport to Chicago in the morning. By choosing this option you can save up to 17% 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 June 30, 2024.

Travelers seeking maximum savings on their Toronto Pearson Intl Airport to Chicago flight should consider departing on Wednesday mornings when fares are most often at their lowest. Friday evenings 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 December 18, 2024.

The most flights from YYZ to CHI are scheduled on a Monday (51 on average). You will have fewer flight options on Friday, which is when the least amount of flights are scheduled (9 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 1.7 - 4.9 inches per month. August is typically the wettest month, when rainfall can reach 4.9 in. January is typically the driest time to visit Chicago when rainfall is around 1.7 in.

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 73.4 F. Travelers looking to avoid the cold should look outside of January, when temperatures are typically at their lowest (around 23.0 F).

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 December 18, 2024.
Get a feel of what it's like to fly with Air Canada, Delta and WestJet from Toronto to Chicago by reading reviews from past customers. You can also see how each airline stacks up in terms of entertainment options, comfort, food, crew/service, and boarding process.
Delta
8.0
Very good
8,604 reviews

Food

7.3

Entertainment

7.9

Crew

8.6

Overall

8.0

Boarding

8.2

Comfort

7.9

Reviews

1 / 10

Delta has consistently been the best U.S. airline for my travels and this flight was no exception

Delta
8.0
Very good
8,604 reviews
Delta
8.0
Very good
8,604 reviews

Food

7.3

Entertainment

7.9

Crew

8.6

Overall

8.0

Boarding

8.2

Comfort

7.9

Reviews

1 / 10

Delta has consistently been the best U.S. airline for my travels and this flight was no exception

Finnair
7.7
Good
1,285 reviews
Delta
8.0
Very good
8,604 reviews

Food

7.3

Entertainment

7.9

Crew

8.6

Overall

8.0

Boarding

8.2

Comfort

7.9

Reviews

1 / 10

Delta has consistently been the best U.S. airline for my travels and this flight was no exception

United Airlines
7.4
Good
9,059 reviews
Delta
8.0
Very good
8,604 reviews

Food

7.3

Entertainment

7.9

Crew

8.6

Overall

8.0

Boarding

8.2

Comfort

7.9

Reviews

1 / 10

Delta has consistently been the best U.S. airline for my travels and this flight was no exception

WestJet
7.3
Good
2,818 reviews
Delta
8.0
Very good
8,604 reviews

Food

7.3

Entertainment

7.9

Crew

8.6

Overall

8.0

Boarding

8.2

Comfort

7.9

Reviews

1 / 10

Delta has consistently been the best U.S. airline for my travels and this flight was no exception

American Airlines
7.2
Good
10,000 reviews
Delta
8.0
Very good
8,604 reviews

Food

7.3

Entertainment

7.9

Crew

8.6

Overall

8.0

Boarding

8.2

Comfort

7.9

Reviews

1 / 10

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 $230, 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 Finnair and Lufthansa - these airlines can fly you to your destination from $231 and $238, respectively. Air Canada is 20% 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 Delta ($140), Air Canada ($146), and United Airlines ($147).

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

    Consider Lufthansa (100%), Royal Jordanian (97%) or SkyWest Airlines (97%) 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 $1,064, our data shows the cheapest flight currently is $158. When looking at the most popular route, (Toronto Pearson Intl - Chicago O'Hare Intl), you can expect to pay $220 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, September is the cheapest month in which you can book a flight from Toronto Pearson Intl Airport to Chicago (average of $232). Flying from Toronto Pearson Intl Airport to Chicago in June is currently the most expensive (average of $308). 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

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 December 18, 2024.
AirlineCheapestAverageFlexibilityOn-time
Air CanadaCheapest$204Average$281FlexibilityNo cancel feeOn-time67%
United AirlinesCheapest$219Average$303FlexibilityNo cancel feeOn-time69%
Porter AirlinesCheapest$221Average$261FlexibilityNo cancel feeOn-time52%
American AirlinesCheapest$236Average$325FlexibilityNo 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.