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$131+ 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 3/17. Fares are subject to change and may not be available on all flights or dates of travel.
YYZ — CHI
Feb 25 — Mar 41
Tue 2/25
Tue 3/4
1 adult, Economy
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The best prices from Toronto Pearson Intl to Chicago are usually found in April or July, booked 88 days in advance, depart on a Friday or Thursday and return on a Friday

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 February 20, 2025.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$204
(123 Milhas)

One-way from

$131
(Mytrip)

Popular in

December

Cheapest in

April

Average price

$309

Good round-trip deal

$270 or less

Good one-way deal

$173 or less
Provider with most accurate pricing for Toronto Pearson Intl-Chicago (CHI) flight deals.
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Provider most trusted by Cheapflights users for Toronto Pearson Intl-Chicago (CHI) flights.
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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. 4% potential increase in price ($15 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 February 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 February 20, 2025.

This 123 Milhas deal was found by Cheapflights users on 2/20. 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 123 Milhas is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/244:00 pmYYZ - ORD
1 stop5h 12mAir Canada
Sat 6/710:40 amORD - YYZ
1 stop6h 18mAir Canada
Deal found 2/20$204
This Mytrip deal was found by Cheapflights users on 2/19. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 3/227:55 pmYYZ - ORD
1 stop13h 40mMultiple Airlines
Tue 3/256:25 pmORD - YYZ
2 stops28h 30mMultiple Airlines
Deal found 2/19$224
This Kissandfly.com deal was found by Cheapflights users on 2/19. 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 Kissandfly.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 3/205:30 pmYYZ - ORD
Nonstop2h 09mLufthansa
Mon 3/249:12 pmORD - YYZ
Nonstop1h 47mLufthansa
Deal found 2/19$236
This CheapTicketsDeal deal was found by Cheapflights users on 2/20. 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 CheapTicketsDeal is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 4/126:30 amYYZ - MDW
1 stop13h 03mWestJet
Sun 4/2010:20 amMDW - YYZ
1 stop24h 14mWestJet
Deal found 2/20$244
This United Airlines deal was found by Cheapflights users on 2/20. 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.
Sat 4/2612:45 pmYYZ - ORD
1 stop4h 59mUnited Airlines
Wed 4/3011:15 amORD - YYZ
1 stop4h 54mUnited Airlines
Deal found 2/20$246
This Delta deal was found by Cheapflights users on 2/20. 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.
Fri 4/1812:15 pmYYZ - MDW
1 stop7h 05mDelta
Tue 4/223:02 pmMDW - YYZ
1 stop6h 53mDelta
Deal found 2/20$246
This Delta deal was found by Cheapflights users on 2/20. 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.
Fri 4/189:45 amYYZ - ORD
1 stop7h 23mDelta
Sat 4/195:00 pmORD - YYZ
1 stop4h 55mDelta
Deal found 2/20$253
This American Airlines deal was found by Cheapflights users on 2/19. 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 5/31:15 pmYYZ - ORD
Nonstop1h 55mAmerican Airlines
Sat 5/109:45 amORD - YYZ
1 stop6h 35mAmerican Airlines
Deal found 2/19$258
This Vakatrip deal was found by Cheapflights users on 2/18. 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 Vakatrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 3/166:30 amYYZ - ORD
1 stop16h 17mWestJet
Sat 3/227:10 pmORD - YYZ
1 stop17h 23mWestJet
Deal found 2/18$266
This Kiwi.com deal was found by Cheapflights users on 2/20. 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 3/17:10 amYYZ - MDW
1 stop13h 19mMultiple Airlines
Tue 3/48:30 amMDW - YYZ
1 stop10h 00mMultiple Airlines
Deal found 2/20$325

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 February 20, 2025.

Fly from

Pearson Intl

Fly to

Chicago

Route

Depart

Return

Price

TorontoChicago

YYZ - ORD

YYZORD

Toronto Pearson Intl

Sat 5/24

4:00 pm-8:12 pm

1 stop5h 12m

Chicago O'Hare Intl

Sat 6/7

10:40 am-5:58 pm

1 stop6h 18m

$204

TorontoChicago

YYZ - ORD

YYZORD

Toronto Pearson Intl

Sat 3/22

7:55 pm-8:35 am

1 stop13h 40m

Chicago O'Hare Intl

Tue 3/25

6:25 pm-11:55 pm

2 stops28h 30m

$224

TorontoChicago

YYZ - MDW

YYZMDW

Toronto Pearson Intl

Sat 4/12

6:30 am-6:33 pm

1 stop13h 03m

Chicago Midway

Mon 4/21

1:16 pm-11:34 am

1 stop21h 18m

$244

TorontoChicago

YYZ - ORD

YYZORD

Toronto Pearson Intl

Sat 4/26

12:45 pm-4:44 pm

1 stop4h 59m

Chicago O'Hare Intl

Wed 4/30

11:15 am-5:09 pm

1 stop4h 54m

$246

TorontoChicago

YYZ - MDW

YYZMDW

Toronto Pearson Intl

Thu 3/20

10:20 am-12:36 pm

1 stop3h 16m

Chicago Midway

Mon 3/24

2:55 pm-10:38 pm

1 stop6h 43m

$247

TorontoChicago

YYZ - ORD

YYZORD

Toronto Pearson Intl

Fri 4/18

9:45 am-4:08 pm

1 stop7h 23m

Chicago O'Hare Intl

Sat 4/19

5:00 pm-10:55 pm

1 stop4h 55m

$253

TorontoChicago

YYZ - ORD

YYZORD

Toronto Pearson Intl

Sat 5/3

1:15 pm-2:10 pm

Nonstop1h 55m

Chicago O'Hare Intl

Sat 5/10

9:45 am-5:20 pm

1 stop6h 35m

$258

TorontoChicago

YYZ - ORD

YYZORD

Toronto Pearson Intl

Sun 3/16

6:30 am-9:47 pm

1 stop16h 17m

Chicago O'Hare Intl

Sat 3/22

7:10 pm-1:33 pm

1 stop17h 23m

$266

TorontoChicago

YYZ - MDW

YYZMDW

Toronto Pearson Intl

Thu 3/20

8:00 pm-5:31 am

1 stop10h 31m

Chicago Midway

Mon 3/24

8:44 pm-9:11 pm

2 stops23h 27m

$328

TorontoChicago

YYZ - ORD

YYZORD

Toronto Pearson Intl

Mon 3/17

10:15 am-9:28 am

1 stop24h 13m

$131

Flights are sorted by cheapest round-trip flights first.

Deals found on 2/20

Showing 1-10 of 19 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 February.
ProviderPrice AccuracyTrust Score*
FlightHubPrice Accuracy3 starsTrust Score*3 stars
ExpediaPrice Accuracy1 starTrust 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 February 14, 2025.

Booking 88 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 February 20, 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 56% 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 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 February 20, 2025.

The most flights from YYZ to CHI are scheduled on a Thursday (53 on average). You will have fewer flight options on Saturday, which is when the least amount of flights are scheduled (38 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 February 20, 2025.
Get a feel of what it's like to fly with Delta, KLM and United Airlines 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
8,219 reviews

Boarding

8.2

Entertainment

7.9

Comfort

8.0

Crew

8.5

Food

7.3

Overall

8.0

Reviews

1 / 20

10.0
Excellent

Aaron,Oct 2024

TUS - LAX

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

Delta
8.0
Very good
8,219 reviews
Delta
8.0
Very good
8,219 reviews

Boarding

8.2

Entertainment

7.9

Comfort

8.0

Crew

8.5

Food

7.3

Overall

8.0

Reviews

1 / 20

10.0
Excellent

Aaron,Oct 2024

TUS - LAX

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

KLM
7.8
Good
1,333 reviews
Delta
8.0
Very good
8,219 reviews

Boarding

8.2

Entertainment

7.9

Comfort

8.0

Crew

8.5

Food

7.3

Overall

8.0

Reviews

1 / 20

10.0
Excellent

Aaron,Oct 2024

TUS - LAX

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

United Airlines
7.4
Good
8,765 reviews
Delta
8.0
Very good
8,219 reviews

Boarding

8.2

Entertainment

7.9

Comfort

8.0

Crew

8.5

Food

7.3

Overall

8.0

Reviews

1 / 20

10.0
Excellent

Aaron,Oct 2024

TUS - LAX

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
8,219 reviews

Boarding

8.2

Entertainment

7.9

Comfort

8.0

Crew

8.5

Food

7.3

Overall

8.0

Reviews

1 / 20

10.0
Excellent

Aaron,Oct 2024

TUS - LAX

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

WestJet
7.2
Good
2,801 reviews
Delta
8.0
Very good
8,219 reviews

Boarding

8.2

Entertainment

7.9

Comfort

8.0

Crew

8.5

Food

7.3

Overall

8.0

Reviews

1 / 20

10.0
Excellent

Aaron,Oct 2024

TUS - LAX

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 $204, 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 WestJet and United Airlines - these airlines can fly you to your destination from $244 and $246, respectively. Air Canada is 31% 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 Air Canada ($132), United Airlines ($136), and American Airlines ($148).

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

    Consider Emirates (90%), Republic Airways (89%) or ANA (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 $858, our data shows the cheapest flight currently is $129. When looking at the most popular route, (Toronto Pearson Intl - Chicago O'Hare Intl), you can expect to pay $221 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 Toronto Pearson Intl Airport?

Book flights to Toronto Pearson Intl Airport if you plan to visit one of these locations
Merrillville
New Buffalo
Hammond
Benton Harbor
Porter
Lansing
Valparaiso
Chesterton

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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 February 20, 2025.
AirlineCheapestAverageFlexibilityOn-time
Porter AirlinesCheapest$194Average$229FlexibilityNo cancel feeOn-time52%
Air CanadaCheapest$210Average$296FlexibilityNo cancel feeOn-time67%
United AirlinesCheapest$233Average$319FlexibilityNo cancel feeOn-time69%
American AirlinesCheapest$236Average$323FlexibilityNo cancel feeOn-time71%
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