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$144+ 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 11/27. Fares are subject to change and may not be available on all flights or dates of travel.
YYZ — CHI
Nov 3 — Nov 101
Sun 11/3
Sun 11/10
1 adult, Economy
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YYZ - CHI
Nov 3 - Nov 10

Find cheap flights from Pearson Intl to Chicago with Cheapflights

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

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 October 29, 2024.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Popular in

November

Cheapest in

January

Round-trip from

$239
(Air Canada)

One-way from

$144
(Air Canada)
Provider with most accurate pricing for Toronto Pearson Intl-Chicago (CHI) flight deals.
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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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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 October 29, 2024.

This Air Canada deal was found by Cheapflights users on 10/29. 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.
Wed 11/208:00 amYYZ - ORD
Nonstop1h 57mAir Canada
Wed 11/279:50 amORD - YYZ
Nonstop1h 41mAir Canada
Deal found 10/29$239
This United Airlines deal was found by Cheapflights users on 10/28. 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.
Wed 11/278:00 amYYZ - ORD
Nonstop1h 57mUnited Airlines
Tue 12/319:13 pmORD - YYZ
Nonstop1h 46mUnited Airlines
Deal found 10/28$240
This United deal was found by Cheapflights users on 10/28. 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.
Wed 11/278:00 amYYZ - ORD
Nonstop1h 57mMultiple Airlines
Wed 11/272:00 pmORD - YYZ
1 stop6h 35mMultiple Airlines
Deal found 10/28$245
This American Airlines deal was found by Cheapflights users on 10/28. 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.
Thu 11/216:15 amYYZ - ORD
Nonstop2h 15mAmerican Airlines
Sun 11/246:01 amORD - YYZ
1 stop4h 58mAmerican Airlines
Deal found 10/28$258
This Delta deal was found by Cheapflights users on 10/28. 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.
Mon 12/1610:05 amYYZ - ORD
1 stop3h 55mDelta
Sun 12/297:00 amORD - YYZ
1 stop8h 14mDelta
Deal found 10/28$265
This Delta deal was found by Cheapflights users on 10/28. 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.
Mon 11/252:55 pmYYZ - MDW
1 stop4h 37mDelta
Mon 12/21:30 pmMDW - YYZ
1 stop8h 06mDelta
Deal found 10/28$268
This FlightHub deal was found by Cheapflights users on 10/28. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 12/76:30 amYYZ - MDW
1 stop13h 02mWestJet
Tue 12/1012:44 pmMDW - YYZ
1 stop10h 15mWestJet
Deal found 10/28$319
This Trip.com deal was found by Cheapflights users on 10/27. 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 11/205:05 pmYYZ - ORD
1 stop6h 38mWestJet
Thu 11/2810:15 amORD - YYZ
1 stop5h 24mWestJet
Deal found 10/27$322
This Kiwi.com deal was found by Cheapflights users on 10/28. 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 11/37:00 amYYZ - MDW
1 stop26h 17mMultiple Airlines
Mon 11/410:28 pmMDW - YYZ
1 stop22h 19mMultiple Airlines
Deal found 10/28$382

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 2,539,541 searches. Data last updated October 29, 2024.

Fly from

Any airport

Fly to

Any airport

Budget

$239 - $461

Route

Depart

Return

Price

Toronto Pearson IntlChicago O'Hare Intl

YYZ - ORD

YYZORD

Toronto Pearson Intl

Wed 11/20

Nonstop1h 57m

Chicago O'Hare Intl

Wed 11/27

Nonstop1h 41m

$239

Toronto Pearson IntlChicago O'Hare Intl

YYZ - ORD

YYZORD

Toronto Pearson Intl

Wed 11/27

Nonstop1h 57m

Chicago O'Hare Intl

Tue 12/31

Nonstop1h 46m

$240

Toronto Pearson IntlChicago O'Hare Intl

YYZ - ORD

YYZORD

Toronto Pearson Intl

Wed 11/27

Nonstop1h 57m

Chicago O'Hare Intl

Wed 11/27

1 stop6h 35m

$245

Toronto Pearson IntlChicago O'Hare Intl

YYZ - ORD

YYZORD

Toronto Pearson Intl

Thu 11/21

Nonstop2h 15m

Chicago O'Hare Intl

Sun 11/24

1 stop4h 58m

$258

Toronto Pearson IntlChicago O'Hare Intl

YYZ - ORD

YYZORD

Toronto Pearson Intl

Mon 12/16

1 stop3h 55m

Chicago O'Hare Intl

Sun 12/29

1 stop8h 14m

$265

Toronto Pearson IntlChicago Midway

YYZ - MDW

YYZMDW

Toronto Pearson Intl

Mon 11/25

1 stop7h 49m

Chicago Midway

Mon 12/2

1 stop8h 06m

$268

Toronto Pearson IntlChicago Midway

YYZ - MDW

YYZMDW

Toronto Pearson Intl

Sat 12/7

1 stop13h 02m

Chicago Midway

Tue 12/10

1 stop10h 15m

$319

Toronto Pearson IntlChicago O'Hare Intl

YYZ - ORD

YYZORD

Toronto Pearson Intl

Wed 11/20

1 stop6h 38m

Chicago O'Hare Intl

Thu 11/28

1 stop5h 24m

$322

Toronto Pearson IntlChicago Midway

YYZ - MDW

YYZMDW

Toronto Pearson Intl

Fri 12/6

1 stop10h 37m

Chicago Midway

Sun 12/8

1 stop8h 27m

$461

Flights are sorted by cheapest first

Deals found on 10/29

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 October.
ProviderPrice AccuracyTrust Score*Cancellation Policy
FlightHubPrice Accuracy3 starsTrust Score*3 starsCancellation PolicyAirline Policy
ExpediaPrice Accuracy1 starTrust Score*3 starsCancellation PolicyAirline Policy
eDreamsPrice Accuracy3 starsTrust Score*3 starsCancellation PolicyAirline Policy
PricelinePrice Accuracy1 starTrust Score*3 starsCancellation PolicyAirline Policy

*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 October 25, 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.

Find deals

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 October 29, 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 16% on the cost of your flight, compared to a flight in the evening.

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. Tuesday evenings flights should be avoided if possible as fares are typically the most expensive at this time.

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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 October 29, 2024.
Get a feel of what it's like to fly with Air Canada, United Airlines and Delta 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
8,845 reviews

Overall

8.0

Food

7.3

Crew

8.5

Entertainment

7.9

Boarding

8.2

Comfort

7.9

Reviews

1 / 10

Overall it was good on the flight. Before the flight with checking the bag at JFK was a nightmare. It took way too long and the Delta concierge was very rude to everyone. But other than that it was fine.

Delta
8.0
Very good
8,845 reviews
Delta
8.0
Very good
8,845 reviews

Overall

8.0

Food

7.3

Crew

8.5

Entertainment

7.9

Boarding

8.2

Comfort

7.9

Reviews

1 / 10

Overall it was good on the flight. Before the flight with checking the bag at JFK was a nightmare. It took way too long and the Delta concierge was very rude to everyone. But other than that it was fine.

KLM
7.8
Good
1,351 reviews
Delta
8.0
Very good
8,845 reviews

Overall

8.0

Food

7.3

Crew

8.5

Entertainment

7.9

Boarding

8.2

Comfort

7.9

Reviews

1 / 10

Overall it was good on the flight. Before the flight with checking the bag at JFK was a nightmare. It took way too long and the Delta concierge was very rude to everyone. But other than that it was fine.

United Airlines
7.4
Good
9,249 reviews
Delta
8.0
Very good
8,845 reviews

Overall

8.0

Food

7.3

Crew

8.5

Entertainment

7.9

Boarding

8.2

Comfort

7.9

Reviews

1 / 10

Overall it was good on the flight. Before the flight with checking the bag at JFK was a nightmare. It took way too long and the Delta concierge was very rude to everyone. But other than that it was fine.

WestJet
7.3
Good
2,801 reviews
Delta
8.0
Very good
8,845 reviews

Overall

8.0

Food

7.3

Crew

8.5

Entertainment

7.9

Boarding

8.2

Comfort

7.9

Reviews

1 / 10

Overall it was good on the flight. Before the flight with checking the bag at JFK was a nightmare. It took way too long and the Delta concierge was very rude to everyone. But other than that it was fine.

American Airlines
7.3
Good
10,000 reviews
Delta
8.0
Very good
8,845 reviews

Overall

8.0

Food

7.3

Crew

8.5

Entertainment

7.9

Boarding

8.2

Comfort

7.9

Reviews

1 / 10

Overall it was good on the flight. Before the flight with checking the bag at JFK was a nightmare. It took way too long and the Delta concierge was very rude to everyone. But other than that it was fine.

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.

  • Can I find flights from Toronto Pearson Intl Airport to Chicago for under $300 on Cheapflights?

    Yes, there are multiple flights from Toronto Pearson Intl Airport to Chicago for under $300. The cheapest flight booked recently is on Air Canada for just $239, but on average you can expect to pay $290.

  • Are there nonstop flights from Toronto Pearson Intl Airport to Chicago for under $300 on Cheapflights?

    Cheapflights has at least 4 direct flights from Toronto Pearson Intl Airport to Chicago under $300. A good price for a nonstop flight from Toronto Pearson Intl Airport to Chicago is less than $249.

  • Are there last-minute flights available from Toronto Pearson Intl Airport to Chicago for under $400?

    There are currently 9+ open flights from Toronto Pearson Intl Airport to Chicago within the next 7 days for less than $400.

  • What days are nonstop flights available from Toronto Pearson Intl Airport to Chicago?

    Nonstop flights are available for this route on the following days: Sunday, Tuesday, Wednesday, Thursday, Friday, Saturday.

  • How many flights depart from Toronto Pearson Intl Airport to Chicago on average per day?

    Per day, 46 flights depart from Toronto Pearson Intl Airport to Chicago on average.
    Early Morning (Midnight to 6am) - 11% of flight departures
    Morning (6am - Noon) - 28% of flight departures
    Afternoon (Noon - 6pm) - 52% of flight departures
    Evening (6pm - Midnight) - 9% of flight departures

  • How long is the flight from Toronto Pearson Intl Airport to Chicago?

    Air Canada, United Airlines, and American Airlines can get you from Toronto Pearson Intl Airport to Chicago in just under 1h 57m. Your travel time will be generally consistent. The distance from Toronto Pearson Intl Airport to Chicago is about 437 mi. All flights are typically nonstop.

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

    Currently priced at $239, Air Canada will fly you from Toronto Pearson Intl Airport to Chicago and back. In addition to Air Canada, many other airlines offer competitively priced options for your trip. Search Cheapflights for deals from United Airlines and American Airlines - these airlines can fly you to your destination from $240 and $258, respectively. Air Canada is 16% 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 ($144), United Airlines ($145), and American Airlines ($156).

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

    Consider SkyWest Airlines (93%), Japan Airlines (91%) or Royal Jordanian (91%) 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 $1,019, our data shows the cheapest flight currently is $146. When looking at the most popular route, (Toronto Pearson Intl - Chicago O'Hare Intl), you can expect to pay $240 for that flight.

  • What does YYZ to ORD mean?

    YYZ and ORD are unique codes to identify airports used in the aviation industry. They are defined by IATA (International Air Transport Association) and are commonly called IATA codes. YYZ to ORD refers to a flight route from Toronto Pearson Intl Airport to Chicago O'Hare Intl Airport. This flight route has multiple associated airports, so we think it might be helpful to learn the name and codes of them as well. They are Chicago Midway Airport (MDW), Chicago Greater Rockford Airport (RFD).

  • Can I find deals for flights from Pearson Intl to Chicago that include extra baggage allowance?

    The amount of baggage you can bring on your Pearson Intl to Chicago flight depends on the airline and the type of fare you've chosen. After entering your flight details, you'll be able to view the specific baggage policies for each deal in the search results. Keep in mind that certain deals may offer additional baggage allowance.

  • Can I find deals on flights from Pearson Intl to Chicago with specific airlines?

    Yes, Cheapflights allows you to browse and filter Pearson Intl to Chicago flight deals by airline. After entering your origin and destination, use the available filters to view flights offered by airlines.

  • 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.

  • Can I find deals for flights from Pearson Intl to Chicago that allow pets onboard?

    Many airlines flying from Pearson Intl to Chicago offer the option to travel with pets. After selecting a flight deal, you can find more information about the airline's pet policy on their official website or by contacting the airline directly. Please note that additional fees and restrictions may apply.

  • Can I find deals on last-minute flights from Pearson Intl to Chicago?

    Yes, you can often find last-minute deals on Pearson Intl to Chicago flights on Cheapflights. However, these deals can vary and may not always be available. We recommend checking back frequently or signing up for price alerts for the most up-to-date deals.

  • How recently were the Toronto Pearson Intl Airport to Chicago flight deals updated?

    The Toronto Pearson Intl Airport to Chicago flight deals you see on this page were last updated on 10/29.

  • 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

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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 2,539,541 searches. Data last updated October 29, 2024.
AirlineCheapestAverageFlexibilityOn-time
Air CanadaCheapest$207Average$284FlexibilityNo cancel feeOn-time67%
United AirlinesCheapest$219Average$290FlexibilityNo cancel feeOn-time69%
Porter AirlinesCheapest$221Average$257FlexibilityNo cancel feeOn-time52%
American AirlinesCheapest$236Average$326FlexibilityNo cancel feeOn-time71%
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