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Cheap flights from Toronto Pearson Intl Airport to Chicago from C$ 184

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 11/11. Fares are subject to change and may not be available on all flights or dates of travel.
YYZ — CHI
28 Nov — 5 Dec1
1 adult
1 adult, Economy, 0 bags

Cheapflights Tip: The best prices from Toronto Pearson Intl to Chicago are usually found in September or August, booked 84 days in advance, depart on a Friday or Saturday and return on a Thursday

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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 29 October 2025.

Fri 14/117:00 a.m.YYZ - ORD
1 stop5h 18mAir Canada
Mon 17/118:15 p.m.ORD - YYZ
Nonstop1h 39mAir Canada
Deal found 29/10C$ 253
Fri 21/116:15 p.m.YYZ - ORD
1 stop5h 41mAmerican Airlines
Tue 25/116:47 a.m.ORD - YYZ
1 stop7h 43mAmerican Airlines
Deal found 27/10C$ 257
Thu 4/126:00 a.m.YYZ - ORD
Nonstop2h 15mAmerican Airlines
Sun 7/129:39 a.m.ORD - YYZ
Nonstop1h 51mAmerican Airlines
Deal found 27/10C$ 264
Wed 26/116:00 a.m.YYZ - ORD
Nonstop2h 15mAmerican Airlines
Fri 28/117:11 a.m.ORD - YYZ
1 stop7h 46mAmerican Airlines
Deal found 27/10C$ 268
Wed 17/122:45 p.m.YYZ - ORD
1 stop4h 46mUnited Airlines
Wed 7/19:15 p.m.ORD - YYZ
Nonstop1h 44mUnited Airlines
Deal found 27/10C$ 270
Sat 15/1110:00 a.m.YYZ - ORD
1 stop5h 55mAir Canada
Mon 24/118:15 p.m.ORD - YYZ
Nonstop1h 39mAir Canada
Deal found 26/10C$ 271
Thu 27/117:00 a.m.YYZ - ORD
1 stop5h 18mAir Canada
Mon 1/123:55 p.m.ORD - YYZ
Nonstop1h 39mAir Canada
Deal found 28/10C$ 272
Tue 2/1211:59 a.m.YYZ - ORD
1 stop4h 57mAmerican Airlines
Sun 7/129:39 a.m.ORD - YYZ
Nonstop1h 51mAmerican Airlines
Deal found 28/10C$ 278
Mon 17/113:38 p.m.YYZ - ORD
1 stop3h 48mDelta
Wed 19/1112:29 p.m.ORD - YYZ
1 stop7h 00mDelta
Deal found 26/10C$ 281
Fri 14/119:00 p.m.YYZ - ORD
Nonstop2h 05mUnited Airlines
Sun 16/117:10 a.m.ORD - YYZ
Nonstop1h 48mUnited Airlines
Deal found 28/10C$ 282
Tue 2/129:52 a.m.YYZ - MDW
1 stop3h 42mDelta
Thu 4/129:34 a.m.MDW - YYZ
1 stop6h 41mDelta
Deal found 29/10C$ 295
Thu 4/1212:13 p.m.YYZ - MDW
1 stop6h 47mDelta
Sun 7/129:34 a.m.MDW - YYZ
1 stop4h 14mDelta
Deal found 27/10C$ 296

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 29 October 2025.

Round-trip from

C$ 253

One-way from

C$ 184

Popular in

December

Cheapest in

September

Average price

C$ 414

Good round-trip deal

C$ 580 or less

Good one-way deal

C$ 354 or less
Air Canada
  • Air Canada
  • 14/11-17/11
  • 1 total stop
  • 6h 57m total
  • Toronto to Chicago
Search Deals
Air Canada
  • Air Canada
  • 11/11
  • 1 total stop
  • 5h 18m total
  • Toronto to Chicago
Search Deals
Highest demand for flights based on searches. 9% potential increase in price (C$ 58 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 2% potential price decrease (C$ 13 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in October 2025
Search Deals
Price to beat on a round-trip flight from Toronto Pearson Intl to Chicago (CHI).
Search Deals
Price to beat on a one-way flight from Toronto Pearson Intl to Chicago (CHI).
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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 29 October 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

Fri 9/1

11:00 a.m.-12:08 p.m.

Nonstop2h 08m

Chicago O'Hare Intl

Sat 7/2

9:15 p.m.-11:54 p.m.

Nonstop1h 39m

C$ 257

TorontoChicago

YYZ - ORD

YYZORD

Toronto Pearson Intl

Tue 24/2

8:55 a.m.-10:02 a.m.

Nonstop2h 07m

Chicago O'Hare Intl

Sat 28/2

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

Nonstop1h 39m

C$ 257

TorontoChicago

YYZ - ORD

YYZORD

Toronto Pearson Intl

Sat 13/12

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

1 stop5h 03m

Chicago O'Hare Intl

Thu 8/1

7:10 a.m.-9:58 a.m.

Nonstop1h 48m

C$ 270

TorontoChicago

YYZ - ORD

YYZORD

Toronto Pearson Intl

Fri 12/12

7:40 p.m.-11:44 p.m.

1 stop5h 04m

Chicago O'Hare Intl

Fri 9/1

11:15 a.m.-2:01 p.m.

Nonstop1h 46m

C$ 270

TorontoChicago

YYZ - ORD

YYZORD

Toronto Pearson Intl

Fri 21/11

6:50 a.m.-7:56 a.m.

Nonstop2h 06m

Chicago O'Hare Intl

Tue 25/11

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

Nonstop1h 39m

C$ 282

TorontoChicago

YYZ - ORD

YYZORD

Toronto Pearson Intl

Fri 14/11

5:30 p.m.-6:39 p.m.

Nonstop2h 09m

Chicago O'Hare Intl

Fri 14/11

9:20 p.m.-11:59 p.m.

Nonstop1h 39m

C$ 282

TorontoChicago

YYZ - ORD

YYZORD

Toronto Pearson Intl

Tue 11/11

5:30 p.m.-6:39 p.m.

Nonstop2h 09m

Chicago O'Hare Intl

Tue 18/11

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

Nonstop1h 43m

C$ 282

TorontoChicago

YYZ - ORD

YYZORD

Toronto Pearson Intl

Wed 26/11

5:30 p.m.-6:39 p.m.

Nonstop2h 09m

Chicago O'Hare Intl

Sun 30/11

7:10 a.m.-9:58 a.m.

Nonstop1h 48m

C$ 282

TorontoChicago

YYZ - ORD

YYZORD

Toronto Pearson Intl

Wed 12/11

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

Nonstop2h 05m

Chicago O'Hare Intl

Sat 15/11

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

Nonstop1h 43m

C$ 282

TorontoChicago

YYZ - ORD

YYZORD

Toronto Pearson Intl

Fri 23/1

5:30 p.m.-6:50 p.m.

Nonstop2h 20m

Chicago O'Hare Intl

Sun 25/1

6:05 a.m.-11:48 a.m.

1 stop4h 43m

C$ 289

Flights are sorted by cheapest round-trip flights first.

Deals found on 27/10

Showing 1-10 of 46 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 24 October 2025.

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, August is the cheapest month in which you can book a flight from Toronto Pearson Intl Airport to Chicago (average of C$ 180). Flying from Toronto Pearson Intl Airport to Chicago in April is currently the most expensive (average of C$ 296). 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 29 October 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 36% on the cost of your flight, compared to a flight at noon.

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 Thursday at noon when fares are most often at their lowest. Tuesday at noon flights should be avoided if possible as fares are typically the most expensive at this time.

How much does it cost to fly round-trip from Toronto Pearson Intl Airport to Chicago?

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 29 October 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
384 reviews
Check prices

Overall

8.0

Comfort

8.0

Entertainment

7.0

Food

7.6

Boarding

8.2

Crew

8.6

Reviews

1 / 20
2.0
Mediocre

Anonymous,Sep 2025

YYZ - OPO

Very disappointing, booked with Porter airlines and changed to Air Transit last minute. Old plane, cramped seating, even the aisle was the narrowest I’ve ever seen. Very uncomfortable flight. Full meal at 130 am and only a small piece of banana bread in the morning… should be opposite.
Porter Airlines
8.0
Very good
384 reviews
Porter Airlines
8.0
Very good
384 reviews
Check prices

Overall

8.0

Comfort

8.0

Entertainment

7.0

Food

7.6

Boarding

8.2

Crew

8.6

Reviews

1 / 20
2.0
Mediocre

Anonymous,Sep 2025

YYZ - OPO

Very disappointing, booked with Porter airlines and changed to Air Transit last minute. Old plane, cramped seating, even the aisle was the narrowest I’ve ever seen. Very uncomfortable flight. Full meal at 130 am and only a small piece of banana bread in the morning… should be opposite.
United Airlines
7.4
Good
9,001 reviews
Porter Airlines
8.0
Very good
384 reviews
Check prices

Overall

8.0

Comfort

8.0

Entertainment

7.0

Food

7.6

Boarding

8.2

Crew

8.6

Reviews

1 / 20
2.0
Mediocre

Anonymous,Sep 2025

YYZ - OPO

Very disappointing, booked with Porter airlines and changed to Air Transit last minute. Old plane, cramped seating, even the aisle was the narrowest I’ve ever seen. Very uncomfortable flight. Full meal at 130 am and only a small piece of banana bread in the morning… should be opposite.
American Airlines
7.2
Good
11,032 reviews
Porter Airlines
8.0
Very good
384 reviews
Check prices

Overall

8.0

Comfort

8.0

Entertainment

7.0

Food

7.6

Boarding

8.2

Crew

8.6

Reviews

1 / 20
2.0
Mediocre

Anonymous,Sep 2025

YYZ - OPO

Very disappointing, booked with Porter airlines and changed to Air Transit last minute. Old plane, cramped seating, even the aisle was the narrowest I’ve ever seen. Very uncomfortable flight. Full meal at 130 am and only a small piece of banana bread in the morning… should be opposite.
WestJet
7.2
Good
3,148 reviews
Porter Airlines
8.0
Very good
384 reviews
Check prices

Overall

8.0

Comfort

8.0

Entertainment

7.0

Food

7.6

Boarding

8.2

Crew

8.6

Reviews

1 / 20
2.0
Mediocre

Anonymous,Sep 2025

YYZ - OPO

Very disappointing, booked with Porter airlines and changed to Air Transit last minute. Old plane, cramped seating, even the aisle was the narrowest I’ve ever seen. Very uncomfortable flight. Full meal at 130 am and only a small piece of banana bread in the morning… should be opposite.
Air Canada
7.1
Good
10,371 reviews
Porter Airlines
8.0
Very good
384 reviews
Check prices

Overall

8.0

Comfort

8.0

Entertainment

7.0

Food

7.6

Boarding

8.2

Crew

8.6

Reviews

1 / 20
2.0
Mediocre

Anonymous,Sep 2025

YYZ - OPO

Very disappointing, booked with Porter airlines and changed to Air Transit last minute. Old plane, cramped seating, even the aisle was the narrowest I’ve ever seen. Very uncomfortable flight. Full meal at 130 am and only a small piece of banana bread in the morning… should be opposite.

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.

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

    Airlines like United Airlines and Delta fly from Toronto Pearson Intl Airport to Chicago in about 2h 08m. The time it takes to get you to your destination can typically vary by up to 5h 21m. The distance between Toronto Pearson Intl Airport and Chicago is about 702 km. This flight may include one or multiple stops.

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

    Currently priced at C$ 225, 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$ 264 and C$ 283, respectively. Users have found that Porter Airlines is 41% cheaper than the other options available to this destination.

  • 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: EVA Air (94%), Egyptair (90%), Copa Airlines( 90%).

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

    On average you can expect to pay C$ 2,049 for a flight from Toronto Pearson Intl Airport to Chicago. The cheapest flight overall is C$ 221 while the most popular route, (Toronto Pearson Intl - Chicago O'Hare Intl) is currently priced at C$ 214.

  • 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 C$ 180). Flying from Toronto Pearson Intl Airport to Chicago in April is currently the most expensive (average of C$ 296). 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 29 October 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 29 October 2025.
AirlineCheapestAverageFlexibilityOn-time
Porter AirlinesCheapestC$ 225AverageC$ 315FlexibilityNo cancel feeOn-time52%
Search Porter Airlines flights
Air CanadaCheapestC$ 264AverageC$ 400FlexibilityNo cancel feeOn-time67%
Search Air Canada flights
United AirlinesCheapestC$ 283AverageC$ 425FlexibilityNo cancel feeOn-time69%
Search United Airlines flights
American AirlinesCheapestC$ 284AverageC$ 464FlexibilityNo cancel feeOn-time71%
Search American Airlines flights
WestJetCheapestC$ 373AverageC$ 596FlexibilityNo 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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