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Cheap flights from Toronto Pearson Intl Airport to Chicago from C$ 146

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 13/11. Fares are subject to change and may not be available on all flights or dates of travel.
YYZ — CHI
21 Aug — 28 Aug1
1 adult

Cheapflights Tip: The best prices from Toronto Pearson Intl to Chicago are usually found in May or July, booked 71 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 16 August 2025.

Round-trip from

C$ 203

One-way from

C$ 146

Popular in

December

Cheapest in

May

Average price

C$ 403

Good round-trip deal

C$ 561 or less

Good one-way deal

C$ 296 or less
Air Canada
  • Air Canada
  • 3/11-6/11
  • Nonstop
  • 3h 37m total
  • Toronto to Chicago
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American Airlines
  • American Airlines
  • 13/11
  • Nonstop
  • 2h 00m total
  • Toronto to Chicago
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Highest demand for flights based on searches. 8% potential increase in price (C$ 49 potential increase over avg. RT price).
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Cheapest flight prices on average. 1% potential price decrease (C$ 11 potential savings vs. average RT price).
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Average for round-trip flights in August 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 16 August 2025.

Mon 3/114:30 p.m.YYZ - ORD
Nonstop1h 58mAir Canada
Thu 6/118:15 p.m.ORD - YYZ
Nonstop1h 39mAir Canada
Deal found 14/8C$ 203
Sun 12/102:10 p.m.YYZ - ORD
Nonstop1h 54mAir Canada
Sun 30/118:00 a.m.ORD - YYZ
Nonstop1h 40mAir Canada
Deal found 14/8C$ 220
Thu 2/106:35 p.m.YYZ - ORD
Nonstop1h 54mAir Canada
Sun 5/108:25 p.m.ORD - YYZ
Nonstop1h 43mAir Canada
Deal found 13/8C$ 222
Wed 1/1012:20 p.m.YYZ - ORD
Nonstop1h 54mAir Canada
Sat 4/103:50 p.m.ORD - YYZ
Nonstop1h 43mAir Canada
Deal found 14/8C$ 229
Sun 5/108:20 a.m.YYZ - ORD
Nonstop1h 54mAir Canada
Fri 17/108:25 p.m.ORD - YYZ
Nonstop1h 43mAir Canada
Deal found 15/8C$ 237
Mon 24/1111:00 a.m.YYZ - ORD
Nonstop2h 05mUnited Airlines
Tue 25/119:20 p.m.ORD - YYZ
Nonstop1h 39mUnited Airlines
Deal found 13/8C$ 246
Tue 21/106:15 a.m.YYZ - MDW
1 stop7h 13mDelta
Mon 27/109:35 a.m.MDW - YYZ
1 stop6h 44mDelta
Deal found 15/8C$ 280
Wed 15/1012:15 p.m.YYZ - MDW
1 stop7h 10mDelta
Sat 18/106:23 p.m.MDW - YYZ
1 stop3h 32mDelta
Deal found 15/8C$ 293
Mon 13/1012:15 p.m.YYZ - MDW
1 stop7h 10mDelta
Sat 18/106:23 p.m.MDW - YYZ
1 stop3h 32mDelta
Deal found 15/8C$ 309
Wed 8/1012:15 p.m.YYZ - MDW
1 stop7h 10mDelta
Sun 12/109:35 a.m.MDW - YYZ
1 stop4h 10mDelta
Deal found 14/8C$ 311
Tue 23/96:00 a.m.YYZ - MDW
1 stop8h 03mDelta
Tue 30/99:35 a.m.MDW - YYZ
1 stop6h 48mDelta
Deal found 14/8C$ 327
Sun 19/1012:15 p.m.YYZ - MDW
1 stop7h 10mDelta
Wed 22/109:35 a.m.MDW - YYZ
1 stop4h 10mDelta
Deal found 15/8C$ 341

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 16 August 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

Wed 15/10

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

Nonstop1h 54m

Chicago O'Hare Intl

Sun 30/11

8:00 a.m.-10:40 a.m.

Nonstop1h 40m

C$ 220

TorontoChicago

YYZ - ORD

YYZORD

Toronto Pearson Intl

Mon 3/11

7:40 p.m.-11:43 p.m.

1 stop5h 03m

Chicago O'Hare Intl

Thu 6/11

1:19 p.m.-4:02 p.m.

Nonstop1h 43m

C$ 224

TorontoChicago

YYZ - ORD

YYZORD

Toronto Pearson Intl

Thu 2/10

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

Nonstop1h 54m

Chicago O'Hare Intl

Sun 5/10

8:25 p.m.-11:08 p.m.

Nonstop1h 43m

C$ 226

TorontoChicago

YYZ - ORD

YYZORD

Toronto Pearson Intl

Tue 21/10

2:10 p.m.-3:04 p.m.

Nonstop1h 54m

Chicago O'Hare Intl

Sun 26/10

10:00 a.m.-12:39 p.m.

Nonstop1h 39m

C$ 237

TorontoChicago

YYZ - ORD

YYZORD

Toronto Pearson Intl

Tue 21/10

8:20 a.m.-9:14 a.m.

Nonstop1h 54m

Chicago O'Hare Intl

Mon 27/10

8:00 a.m.-10:40 a.m.

Nonstop1h 40m

C$ 237

TorontoChicago

YYZ - ORD

YYZORD

Toronto Pearson Intl

Wed 22/10

4:40 p.m.-5:33 p.m.

Nonstop1h 53m

Chicago O'Hare Intl

Sun 26/10

2:00 p.m.-4:39 p.m.

Nonstop1h 39m

C$ 237

TorontoChicago

YYZ - ORD

YYZORD

Toronto Pearson Intl

Mon 20/10

12:20 p.m.-1:14 p.m.

Nonstop1h 54m

Chicago O'Hare Intl

Sun 26/10

8:15 p.m.-10:54 p.m.

Nonstop1h 39m

C$ 237

TorontoChicago

YYZ - ORD

YYZORD

Toronto Pearson Intl

Mon 20/10

2:10 p.m.-3:04 p.m.

Nonstop1h 54m

Chicago O'Hare Intl

Mon 27/10

10:00 a.m.-12:39 p.m.

Nonstop1h 39m

C$ 237

TorontoChicago

YYZ - ORD

YYZORD

Toronto Pearson Intl

Sat 18/10

12:20 p.m.-1:14 p.m.

Nonstop1h 54m

Chicago O'Hare Intl

Sat 25/10

9:55 a.m.-12:38 p.m.

Nonstop1h 43m

C$ 237

TorontoChicago

YYZ - ORD

YYZORD

Toronto Pearson Intl

Thu 23/10

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

Nonstop1h 54m

Chicago O'Hare Intl

Mon 27/10

3:55 p.m.-6:34 p.m.

Nonstop1h 39m

C$ 237

Flights are sorted by cheapest round-trip flights first.

Deals found on 15/8

Showing 1-10 of 41 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 8 August 2025.

Booking 71 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 16 August 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 58% 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 16 August 2025.

The most flights from YYZ to CHI are scheduled on a Thursday (61 on average). You will have fewer flight options on Tuesday, which is when the least amount of flights are scheduled (40 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 16 August 2025.
Read reviews from past customers who have flown Porter Airlines,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.
Porter Airlines
8.0
Very good
332 reviews
Check prices

Overall

8.0

Boarding

8.2

Entertainment

7.0

Food

7.6

Comfort

8.0

Crew

8.7

Reviews

1 / 20
8.0
Excellent

Anonymous,Jul 2025

LIS - YYZ

Everything was on time and easy. Crew were nice on flights and helpful. International flight, so long and typically uncomfortable but not more than most. Food and drink service were below average but you get what you pay for. Overall, good experience
Porter Airlines
8.0
Very good
332 reviews
Porter Airlines
8.0
Very good
332 reviews
Check prices

Overall

8.0

Boarding

8.2

Entertainment

7.0

Food

7.6

Comfort

8.0

Crew

8.7

Reviews

1 / 20
8.0
Excellent

Anonymous,Jul 2025

LIS - YYZ

Everything was on time and easy. Crew were nice on flights and helpful. International flight, so long and typically uncomfortable but not more than most. Food and drink service were below average but you get what you pay for. Overall, good experience
United Airlines
7.4
Good
8,916 reviews
Porter Airlines
8.0
Very good
332 reviews
Check prices

Overall

8.0

Boarding

8.2

Entertainment

7.0

Food

7.6

Comfort

8.0

Crew

8.7

Reviews

1 / 20
8.0
Excellent

Anonymous,Jul 2025

LIS - YYZ

Everything was on time and easy. Crew were nice on flights and helpful. International flight, so long and typically uncomfortable but not more than most. Food and drink service were below average but you get what you pay for. Overall, good experience
American Airlines
7.2
Good
10,000 reviews
Porter Airlines
8.0
Very good
332 reviews
Check prices

Overall

8.0

Boarding

8.2

Entertainment

7.0

Food

7.6

Comfort

8.0

Crew

8.7

Reviews

1 / 20
8.0
Excellent

Anonymous,Jul 2025

LIS - YYZ

Everything was on time and easy. Crew were nice on flights and helpful. International flight, so long and typically uncomfortable but not more than most. Food and drink service were below average but you get what you pay for. Overall, good experience
WestJet
7.2
Good
3,016 reviews
Porter Airlines
8.0
Very good
332 reviews
Check prices

Overall

8.0

Boarding

8.2

Entertainment

7.0

Food

7.6

Comfort

8.0

Crew

8.7

Reviews

1 / 20
8.0
Excellent

Anonymous,Jul 2025

LIS - YYZ

Everything was on time and easy. Crew were nice on flights and helpful. International flight, so long and typically uncomfortable but not more than most. Food and drink service were below average but you get what you pay for. Overall, good experience
Air Canada
7.1
Good
9,966 reviews
Porter Airlines
8.0
Very good
332 reviews
Check prices

Overall

8.0

Boarding

8.2

Entertainment

7.0

Food

7.6

Comfort

8.0

Crew

8.7

Reviews

1 / 20
8.0
Excellent

Anonymous,Jul 2025

LIS - YYZ

Everything was on time and easy. Crew were nice on flights and helpful. International flight, so long and typically uncomfortable but not more than most. Food and drink service were below average but you get what you pay for. Overall, good experience

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$ 228, Porter Airlines will fly you from Toronto Pearson Intl Airport to Chicago and back. In addition to Porter 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$ 266 and C$ 282, respectively. Users have found that Porter Airlines is 42% 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 American Airlines. Other airlines that offer cheap prices include Air Canada from C$ 153 and Delta from C$ 185 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: SkyWest Airlines (89%), Egyptair (87%), Copa Airlines( 87%).

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

    On average you can expect to pay C$ 1,512 for a flight from Toronto Pearson Intl Airport to Chicago. The cheapest flight overall is C$ 194 while the most popular route, (Toronto Pearson Intl - Chicago O'Hare Intl) is currently priced at C$ 203.

  • 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 16 August 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 16 August 2025.
AirlineCheapestAverageFlexibilityOn-time
Porter AirlinesCheapestC$ 228AverageC$ 334FlexibilityNo cancel feeOn-time52%
Search Porter Airlines flights
Air CanadaCheapestC$ 266AverageC$ 395FlexibilityNo cancel feeOn-time67%
Search Air Canada flights
United AirlinesCheapestC$ 282AverageC$ 426FlexibilityNo cancel feeOn-time69%
Search United Airlines flights
American AirlinesCheapestC$ 289AverageC$ 495FlexibilityNo cancel feeOn-time71%
Search American Airlines flights
WestJetCheapestC$ 422AverageC$ 592FlexibilityNo 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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