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Cheap flights from Toronto Pearson Intl Airport to Chicago from C$ 143

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 16/8. Fares are subject to change and may not be available on all flights or dates of travel.
YYZ — CHI
7 Jul — 14 Jul1
1 adult

Cheapflights Tip: The best prices from Toronto Pearson Intl to Chicago are usually found in May or July, booked 88 days in advance, depart on a Friday or Saturday and return on a Saturday

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 2 July 2025.

Round-trip from

C$ 222

One-way from

C$ 146

Popular in

December

Cheapest in

May

Average price

C$ 352

Good round-trip deal

C$ 505 or less

Good one-way deal

C$ 309 or less
American Airlines
  • American Airlines
  • 30/8-5/9
  • Nonstop
  • 3h 38m total
  • Toronto to Chicago
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Air Canada
  • Air Canada
  • 23/8
  • 1 total stop
  • 4h 37m total
  • Toronto to Chicago
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Highest demand for flights based on searches. 7% potential increase in price (C$ 44 potential increase over avg. RT price).
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Cheapest flight prices on average. 1% potential price decrease (C$ 10 potential savings vs. average RT price).
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Average for round-trip flights in July 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 2 July 2025.

Sat 30/83:14 p.m.YYZ - ORD
Nonstop1h 56mAmerican Airlines
Fri 5/93:05 p.m.ORD - YYZ
Nonstop1h 42mAmerican Airlines
Deal found 30/6C$ 222
Fri 15/86:35 p.m.YYZ - ORD
Nonstop1h 54mAir Canada
Sat 16/88:25 p.m.ORD - YYZ
Nonstop1h 45mAir Canada
Deal found 1/7C$ 224
Thu 10/77:00 a.m.YYZ - ORD
Nonstop1h 59mUnited Airlines
Sun 13/79:14 p.m.ORD - YYZ
Nonstop1h 44mUnited Airlines
Deal found 30/6C$ 226
Thu 10/79:00 a.m.YYZ - ORD
Nonstop1h 59mLufthansa
Sun 13/79:14 p.m.ORD - YYZ
Nonstop1h 44mLufthansa
Deal found 30/6C$ 240
Sat 4/1012:14 p.m.YYZ - MDW
1 stop7h 21mDelta
Wed 15/102:00 p.m.MDW - YYZ
1 stop7h 55mDelta
Deal found 1/7C$ 292
Fri 15/87:21 p.m.YYZ - MDW
1 stop18h 42mWestJet
Fri 22/812:43 p.m.MDW - YYZ
1 stop8h 15mWestJet
Deal found 2/7C$ 349

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 629,999 searches. Data last updated 2 July 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

Sat 30/8

3:14 p.m.-4:10 p.m.

Nonstop1h 56m

Chicago O'Hare Intl

Fri 5/9

3:05 p.m.-5:47 p.m.

Nonstop1h 42m

C$ 222

TorontoChicago

YYZ - ORD

YYZORD

Toronto Pearson Intl

Fri 15/8

6:35 p.m.-7:29 p.m.

Nonstop1h 54m

Chicago O'Hare Intl

Sat 16/8

8:25 p.m.-11:10 p.m.

Nonstop1h 45m

C$ 224

TorontoChicago

YYZ - ORD

YYZORD

Toronto Pearson Intl

Thu 17/7

7:00 a.m.-7:59 a.m.

Nonstop1h 59m

Chicago O'Hare Intl

Sat 19/7

7:40 p.m.-8:33 a.m.

1 stop11h 53m

C$ 237

TorontoChicago

YYZ - MDW

YYZMDW

Toronto Pearson Intl

Sat 4/10

12:14 p.m.-6:35 p.m.

1 stop7h 21m

Chicago Midway

Wed 15/10

2:00 p.m.-10:55 p.m.

1 stop7h 55m

C$ 292

TorontoChicago

YYZ - MDW

YYZMDW

Toronto Pearson Intl

Fri 15/8

7:21 p.m.-1:03 p.m.

1 stop18h 42m

Chicago Midway

Fri 22/8

12:43 p.m.-9:58 p.m.

1 stop8h 15m

C$ 349

TorontoChicago

YYZ - ORD

YYZORD

Toronto Pearson Intl

Sat 16/8

6:15 a.m.-9:52 a.m.

1 stop4h 37m

C$ 143

TorontoChicago

YYZ - ORD

YYZORD

Toronto Pearson Intl

Wed 1/10

11:44 a.m.-12:39 p.m.

Nonstop1h 55m

C$ 144

TorontoChicago

YYZ - ORD

YYZORD

Toronto Pearson Intl

Fri 18/7

7:00 a.m.-7:59 a.m.

Nonstop1h 59m

C$ 147

TorontoChicago

YYZ - ORD

YYZORD

Toronto Pearson Intl

Fri 11/7

9:00 p.m.-10:05 p.m.

Nonstop2h 05m

C$ 162

TorontoChicago

YYZ - ORD

YYZORD

Toronto Pearson Intl

Fri 11/7

10:44 a.m.-4:14 p.m.

1 stop6h 30m

C$ 170

Flights are sorted by cheapest round-trip flights first.

Deals found on 2/7

Showing 1-10 of 16 results
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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 27 June 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, January is the cheapest month in which you can book a flight from Toronto Pearson Intl Airport to Chicago (average of C$ 261). Flying from Toronto Pearson Intl Airport to Chicago in March is currently the most expensive (average of C$ 352). 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 2 July 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 61% 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 16 December 2024.

Travelers seeking maximum savings on their Toronto Pearson Intl Airport to Chicago flight should consider departing on Friday evenings when fares are most often at their lowest. Wednesday 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 2 July 2025.

The most flights from YYZ to CHI are scheduled on a Monday (62 on average). You will have fewer flight options on Saturday, which is when the least amount of flights are scheduled (31 on average).

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 2 July 2025.
Read reviews from past customers who have flown Delta,United Airlines, andAmerican Airlines from Toronto Pearson Intl Airport to Chicago. Users can see the overall rating for each airline as well as how each is rated in terms of entertainment options, comfort, food, crew/service, and boarding process.
Delta
8.0
Very good
7,983 reviews
Check prices

Boarding

8.2

Food

7.3

Overall

8.0

Crew

8.5

Entertainment

7.9

Comfort

7.9

Reviews

1 / 20
10.0
Excellent

Kim,May 2025

PIH - SLC

This trip was fine even with delay I had plenty of time to get connection flight!
Delta
8.0
Very good
7,983 reviews
Delta
8.0
Very good
7,983 reviews
Check prices

Boarding

8.2

Food

7.3

Overall

8.0

Crew

8.5

Entertainment

7.9

Comfort

7.9

Reviews

1 / 20
10.0
Excellent

Kim,May 2025

PIH - SLC

This trip was fine even with delay I had plenty of time to get connection flight!
United Airlines
7.4
Good
8,861 reviews
Delta
8.0
Very good
7,983 reviews
Check prices

Boarding

8.2

Food

7.3

Overall

8.0

Crew

8.5

Entertainment

7.9

Comfort

7.9

Reviews

1 / 20
10.0
Excellent

Kim,May 2025

PIH - SLC

This trip was fine even with delay I had plenty of time to get connection flight!
American Airlines
7.2
Good
10,000 reviews
Delta
8.0
Very good
7,983 reviews
Check prices

Boarding

8.2

Food

7.3

Overall

8.0

Crew

8.5

Entertainment

7.9

Comfort

7.9

Reviews

1 / 20
10.0
Excellent

Kim,May 2025

PIH - SLC

This trip was fine even with delay I had plenty of time to get connection flight!
WestJet
7.2
Good
2,912 reviews
Delta
8.0
Very good
7,983 reviews
Check prices

Boarding

8.2

Food

7.3

Overall

8.0

Crew

8.5

Entertainment

7.9

Comfort

7.9

Reviews

1 / 20
10.0
Excellent

Kim,May 2025

PIH - SLC

This trip was fine even with delay I had plenty of time to get connection flight!
Air Canada
7.1
Good
9,669 reviews
Delta
8.0
Very good
7,983 reviews
Check prices

Boarding

8.2

Food

7.3

Overall

8.0

Crew

8.5

Entertainment

7.9

Comfort

7.9

Reviews

1 / 20
10.0
Excellent

Kim,May 2025

PIH - SLC

This trip was fine even with delay I had plenty of time to get connection flight!

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 C$ 222, American Airlines will fly you from Toronto Pearson Intl Airport to Chicago and back. In addition to American Airlines, many other airlines offer competitively priced options for your trip. Search Cheapflights for deals from Air Canada and United Airlines - these airlines can fly you to your destination from C$ 224 and C$ 237, respectively. Users have found that American Airlines is 43% cheaper than the other options available to this destination.

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

    One-way options have recently been found by users for as low as C$ 146 on Air Canada. Other airlines that offer cheap prices include United Airlines from C$ 147 and Lufthansa from C$ 162 one-way.

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

    Before booking your flight to Chicago from Toronto Pearson Intl Airport, check out the most reliable airlines to get you to your destination on time: Cathay Pacific (100%), Copa Airlines (93%), Egyptair( 92%).

  • What are the cheapest flights from Toronto Pearson Intl Airport to Chicago?

    On average you can expect to pay C$ 1,980 for a flight from Toronto Pearson Intl Airport to Chicago. The cheapest flight overall is C$ 187 while the most popular route, (Toronto Pearson Intl - Chicago O'Hare Intl) is currently priced at C$ 210.

  • 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, January is the cheapest month in which you can book a flight from Toronto Pearson Intl Airport to Chicago (average of C$ 261). Flying from Toronto Pearson Intl Airport to Chicago in March is currently the most expensive (average of C$ 352). 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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Fly from Pearson Intl to Chicago on these airlines

Choose from the following airlines for your flight from Pearson Intl to Chicago. Flights are based on user searches made on Cheapflights and were last updated on 2 July 2025.
Air Canada flights from Toronto Pearson Intl to Chicago
United Airlines flights from Toronto Pearson Intl to Chicago

Top 5 airlines flying from Pearson Intl to Chicago

Discover the top 5 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 629,999 searches. Data last updated 2 July 2025.
AirlineCheapestAverageFlexibilityOn-time
American AirlinesCheapestC$ 221AverageC$ 493FlexibilityNo cancel feeOn-time71%
Search American Airlines flights
Porter AirlinesCheapestC$ 231AverageC$ 338FlexibilityNo cancel feeOn-time52%
Search Porter Airlines flights
Air CanadaCheapestC$ 276AverageC$ 393FlexibilityNo cancel feeOn-time67%
Search Air Canada flights
United AirlinesCheapestC$ 292AverageC$ 435FlexibilityNo cancel feeOn-time69%
Search United Airlines flights
WestJetCheapestC$ 422AverageC$ 608FlexibilityNo cancel feeOn-time60%
Search WestJet flights

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How does Cheapflights help users find flights from Pearson Intl to Chicago?

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Why should you use Cheapflights to find cheap flight tickets from Pearson Intl to Chicago?

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Can Cheapflights find flights from Pearson Intl to Chicago with no change fees?

Certainly. Search results for flights to Chicago from Pearson Intl shown to you on Cheapflights can be narrowed down with different useful search filters, which includes flexible booking options.

Can Cheapflights notify me if prices for flights from Pearson Intl to Chicago become cheaper?

Yes, and it’s super simple to set up. Click the bell icon next to the flight deals above and provide a valid email address to enable Price Alerts. That’s it!

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