Cheap flights from Toronto Pearson Intl Airport to Chicago from C$ 181

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 6/2. Fares are subject to change and may not be available on all flights or dates of travel.
YYZ — CHI
6 Dec — 13 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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Enter your travel dates to find the best prices.

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 6 November 2025.

Tue 2/127:30 a.m.YYZ - ORD
1 stop7h 29mAmerican Airlines
Sat 6/128:00 a.m.ORD - YYZ
1 stop7h 35mAmerican Airlines
Deal found 4/11C$ 260
Thu 11/126:00 a.m.YYZ - ORD
Nonstop2h 15mAmerican Airlines
Sun 14/128:10 a.m.ORD - YYZ
Nonstop1h 46mAmerican Airlines
Deal found 3/11C$ 265
Sun 23/116:00 a.m.YYZ - ORD
Nonstop2h 15mAmerican Airlines
Mon 1/125:00 a.m.ORD - YYZ
1 stop5h 03mAmerican Airlines
Deal found 5/11C$ 268
Fri 5/126:00 a.m.YYZ - ORD
Nonstop2h 15mAmerican Airlines
Sun 7/125:00 a.m.ORD - YYZ
1 stop5h 02mAmerican Airlines
Deal found 4/11C$ 271
Thu 20/116:20 a.m.YYZ - ORD
1 stop5h 58mAir Canada
Mon 24/118:15 p.m.ORD - YYZ
Nonstop1h 39mAir Canada
Deal found 6/11C$ 272
Thu 11/124:50 p.m.YYZ - ORD
Nonstop1h 58mAir Canada
Mon 15/122:00 p.m.ORD - YYZ
Nonstop1h 39mAir Canada
Deal found 4/11C$ 274
Thu 20/117:00 a.m.YYZ - ORD
1 stop5h 18mAir Canada
Wed 26/118:15 p.m.ORD - YYZ
Nonstop1h 39mAir Canada
Deal found 5/11C$ 275
Thu 27/112:15 p.m.YYZ - ORD
Nonstop1h 55mAir Canada
Thu 27/118:15 p.m.ORD - YYZ
Nonstop1h 39mAir Canada
Deal found 6/11C$ 282
Sat 6/129:00 a.m.YYZ - ORD
Nonstop2h 02mUnited Airlines
Sun 7/127:10 a.m.ORD - YYZ
Nonstop1h 48mUnited Airlines
Deal found 5/11C$ 284
Wed 26/113:30 p.m.YYZ - ORD
Nonstop2h 22mMultiple Airlines
Sun 30/118:00 a.m.ORD - YYZ
Nonstop1h 40mMultiple Airlines
Deal found 4/11C$ 285
Tue 2/126:30 p.m.YYZ - ORD
Nonstop2h 00mAir Canada
Tue 9/123:55 p.m.ORD - YYZ
Nonstop1h 39mAir Canada
Deal found 3/11C$ 286
Thu 4/1212:13 p.m.YYZ - MDW
1 stop6h 47mDelta
Thu 11/129:34 a.m.MDW - YYZ
1 stop6h 41mDelta
Deal found 5/11C$ 295

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 6 November 2025.

Round-trip from

C$ 260

One-way from

C$ 181

Popular in

December

Cheapest in

September

Average price

C$ 426

Good round-trip deal

C$ 567 or less

Good one-way deal

C$ 353 or less
American Airlines
  • American Airlines
  • 2/12-6/12
  • 2 total stops
  • 15h 04m total
  • Toronto to Chicago
Delta
  • Delta
  • 2/12
  • 1 total stop
  • 10h 00m total
  • Toronto to Chicago
Highest demand for flights based on searches. 10% potential increase in price (C$ 59 potential increase over avg. RT price).
Cheapest flight prices on average. 2% potential price decrease (C$ 13 potential savings vs. average RT price).
Average for round-trip flights in November 2025
Price to beat on a round-trip flight from Toronto Pearson Intl to Chicago (CHI).
Price to beat on a one-way flight from Toronto Pearson Intl to Chicago (CHI).

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 6 November 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

Mon 5/1

6:40 p.m.-11:35 p.m.

1 stop5h 55m

Chicago O'Hare Intl

Wed 14/1

1:13 p.m.-4:02 p.m.

Nonstop1h 49m

C$ 272

TorontoChicago

YYZ - ORD

YYZORD

Toronto Pearson Intl

Sun 11/1

6:00 a.m.-9:40 a.m.

1 stop4h 40m

Chicago O'Hare Intl

Thu 15/1

11:05 a.m.-4:12 p.m.

1 stop4h 07m

C$ 284

TorontoChicago

YYZ - MDW

YYZMDW

Toronto Pearson Intl

Mon 5/1

7:45 a.m.-12:48 p.m.

1 stop6h 03m

Chicago Midway

Fri 9/1

6:30 p.m.-10:41 p.m.

1 stop3h 11m

C$ 284

TorontoChicago

YYZ - MDW

YYZMDW

Toronto Pearson Intl

Sun 11/1

6:00 a.m.-8:54 a.m.

1 stop3h 54m

Chicago Midway

Mon 12/1

6:14 p.m.-10:41 p.m.

1 stop3h 27m

C$ 284

TorontoChicago

YYZ - MDW

YYZMDW

Toronto Pearson Intl

Sun 11/1

6:00 a.m.-8:54 a.m.

1 stop3h 54m

Chicago Midway

Thu 15/1

9:50 a.m.-3:59 p.m.

1 stop5h 09m

C$ 284

TorontoChicago

YYZ - MDW

YYZMDW

Toronto Pearson Intl

Mon 5/1

7:45 a.m.-12:48 p.m.

1 stop6h 03m

Chicago Midway

Tue 13/1

6:14 p.m.-10:41 p.m.

1 stop3h 27m

C$ 284

TorontoChicago

YYZ - ORD

YYZORD

Toronto Pearson Intl

Fri 21/11

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

Nonstop2h 09m

Chicago O'Hare Intl

Mon 24/11

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

Nonstop1h 39m

C$ 285

TorontoChicago

YYZ - ORD

YYZORD

Toronto Pearson Intl

Fri 28/11

11:00 a.m.-12:05 p.m.

Nonstop2h 05m

Chicago O'Hare Intl

Sun 30/11

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

Nonstop1h 39m

C$ 285

TorontoChicago

YYZ - ORD

YYZORD

Toronto Pearson Intl

Fri 21/11

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

Nonstop2h 05m

Chicago O'Hare Intl

Sat 29/11

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

Nonstop1h 40m

C$ 285

TorontoChicago

YYZ - ORD

YYZORD

Toronto Pearson Intl

Tue 30/12

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

Nonstop2h 05m

Chicago O'Hare Intl

Thu 1/1

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

Nonstop1h 39m

C$ 285

Flights are sorted by cheapest round-trip flights first.

Deals found on 5/11

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 31 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$ 182). Flying from Toronto Pearson Intl Airport to Chicago in April is currently the most expensive (average of C$ 299). 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 6 November 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 38% 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.

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 6 November 2025.

The most flights from YYZ to CHI are scheduled on a Monday (58 on average). You will have fewer flight options on Saturday, which is when the least amount of flights are scheduled (39 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 6 November 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.

Overall

8.0

Crew

8.6

Entertainment

7.0

Food

7.6

Comfort

8.0

Boarding

8.2

Reviews

1 / 20
2.0
Mediocre

Kelly,Nov 2025

YVR - YUL

I recently flew with Porter Airlines on Flight PD372 on October 30th, and unfortunately, had a very disappointing experience. At the gate, one of their attendants gave me two boarding passes. I assumed these were for my itinerary from Vancouver to Montreal and back, but one of the boarding passes unexpectedly included a connecting flight to Toronto, which was never part of my booking or invoice. As a result of this error, my checked baggage was mistakenly routed to Toronto. When I contacted Porter’s customer service, I spoke to an agent who apologized on behalf of the attendant (employee number 13209961) and promised to have my luggage flown back to Montreal. However, shortly after, I was told there was nothing they could do except for me to travel to Toronto myself to pick up my bag. This is highly unreasonable and unfair, considering the issue was caused by their staff printing the wrong boarding pass. This entire situation caused me significant inconvenience and stress. I expected Porter to correct the mistake and deliver my luggage as originally planned, but instead, I was left with the burden of fixing an error that was not mine. I even have a photo of the staff badge of the employee who made the promise, yet the company still failed to honor it. I hope Porter Airlines reviews their internal communication and baggage handling procedures to prevent this from happening to other passengers. Customer care and responsibility fell short in this experience, and I am still waiting for a satisfactory resolution.

Overall

8.0

Crew

8.6

Entertainment

7.0

Food

7.6

Comfort

8.0

Boarding

8.2

Reviews

1 / 20
2.0
Mediocre

Kelly,Nov 2025

YVR - YUL

I recently flew with Porter Airlines on Flight PD372 on October 30th, and unfortunately, had a very disappointing experience. At the gate, one of their attendants gave me two boarding passes. I assumed these were for my itinerary from Vancouver to Montreal and back, but one of the boarding passes unexpectedly included a connecting flight to Toronto, which was never part of my booking or invoice. As a result of this error, my checked baggage was mistakenly routed to Toronto. When I contacted Porter’s customer service, I spoke to an agent who apologized on behalf of the attendant (employee number 13209961) and promised to have my luggage flown back to Montreal. However, shortly after, I was told there was nothing they could do except for me to travel to Toronto myself to pick up my bag. This is highly unreasonable and unfair, considering the issue was caused by their staff printing the wrong boarding pass. This entire situation caused me significant inconvenience and stress. I expected Porter to correct the mistake and deliver my luggage as originally planned, but instead, I was left with the burden of fixing an error that was not mine. I even have a photo of the staff badge of the employee who made the promise, yet the company still failed to honor it. I hope Porter Airlines reviews their internal communication and baggage handling procedures to prevent this from happening to other passengers. Customer care and responsibility fell short in this experience, and I am still waiting for a satisfactory resolution.

Overall

8.0

Crew

8.6

Entertainment

7.0

Food

7.6

Comfort

8.0

Boarding

8.2

Reviews

1 / 20
2.0
Mediocre

Kelly,Nov 2025

YVR - YUL

I recently flew with Porter Airlines on Flight PD372 on October 30th, and unfortunately, had a very disappointing experience. At the gate, one of their attendants gave me two boarding passes. I assumed these were for my itinerary from Vancouver to Montreal and back, but one of the boarding passes unexpectedly included a connecting flight to Toronto, which was never part of my booking or invoice. As a result of this error, my checked baggage was mistakenly routed to Toronto. When I contacted Porter’s customer service, I spoke to an agent who apologized on behalf of the attendant (employee number 13209961) and promised to have my luggage flown back to Montreal. However, shortly after, I was told there was nothing they could do except for me to travel to Toronto myself to pick up my bag. This is highly unreasonable and unfair, considering the issue was caused by their staff printing the wrong boarding pass. This entire situation caused me significant inconvenience and stress. I expected Porter to correct the mistake and deliver my luggage as originally planned, but instead, I was left with the burden of fixing an error that was not mine. I even have a photo of the staff badge of the employee who made the promise, yet the company still failed to honor it. I hope Porter Airlines reviews their internal communication and baggage handling procedures to prevent this from happening to other passengers. Customer care and responsibility fell short in this experience, and I am still waiting for a satisfactory resolution.

Overall

8.0

Crew

8.6

Entertainment

7.0

Food

7.6

Comfort

8.0

Boarding

8.2

Reviews

1 / 20
2.0
Mediocre

Kelly,Nov 2025

YVR - YUL

I recently flew with Porter Airlines on Flight PD372 on October 30th, and unfortunately, had a very disappointing experience. At the gate, one of their attendants gave me two boarding passes. I assumed these were for my itinerary from Vancouver to Montreal and back, but one of the boarding passes unexpectedly included a connecting flight to Toronto, which was never part of my booking or invoice. As a result of this error, my checked baggage was mistakenly routed to Toronto. When I contacted Porter’s customer service, I spoke to an agent who apologized on behalf of the attendant (employee number 13209961) and promised to have my luggage flown back to Montreal. However, shortly after, I was told there was nothing they could do except for me to travel to Toronto myself to pick up my bag. This is highly unreasonable and unfair, considering the issue was caused by their staff printing the wrong boarding pass. This entire situation caused me significant inconvenience and stress. I expected Porter to correct the mistake and deliver my luggage as originally planned, but instead, I was left with the burden of fixing an error that was not mine. I even have a photo of the staff badge of the employee who made the promise, yet the company still failed to honor it. I hope Porter Airlines reviews their internal communication and baggage handling procedures to prevent this from happening to other passengers. Customer care and responsibility fell short in this experience, and I am still waiting for a satisfactory resolution.

Overall

8.0

Crew

8.6

Entertainment

7.0

Food

7.6

Comfort

8.0

Boarding

8.2

Reviews

1 / 20
2.0
Mediocre

Kelly,Nov 2025

YVR - YUL

I recently flew with Porter Airlines on Flight PD372 on October 30th, and unfortunately, had a very disappointing experience. At the gate, one of their attendants gave me two boarding passes. I assumed these were for my itinerary from Vancouver to Montreal and back, but one of the boarding passes unexpectedly included a connecting flight to Toronto, which was never part of my booking or invoice. As a result of this error, my checked baggage was mistakenly routed to Toronto. When I contacted Porter’s customer service, I spoke to an agent who apologized on behalf of the attendant (employee number 13209961) and promised to have my luggage flown back to Montreal. However, shortly after, I was told there was nothing they could do except for me to travel to Toronto myself to pick up my bag. This is highly unreasonable and unfair, considering the issue was caused by their staff printing the wrong boarding pass. This entire situation caused me significant inconvenience and stress. I expected Porter to correct the mistake and deliver my luggage as originally planned, but instead, I was left with the burden of fixing an error that was not mine. I even have a photo of the staff badge of the employee who made the promise, yet the company still failed to honor it. I hope Porter Airlines reviews their internal communication and baggage handling procedures to prevent this from happening to other passengers. Customer care and responsibility fell short in this experience, and I am still waiting for a satisfactory resolution.

Overall

8.0

Crew

8.6

Entertainment

7.0

Food

7.6

Comfort

8.0

Boarding

8.2

Reviews

1 / 20
2.0
Mediocre

Kelly,Nov 2025

YVR - YUL

I recently flew with Porter Airlines on Flight PD372 on October 30th, and unfortunately, had a very disappointing experience. At the gate, one of their attendants gave me two boarding passes. I assumed these were for my itinerary from Vancouver to Montreal and back, but one of the boarding passes unexpectedly included a connecting flight to Toronto, which was never part of my booking or invoice. As a result of this error, my checked baggage was mistakenly routed to Toronto. When I contacted Porter’s customer service, I spoke to an agent who apologized on behalf of the attendant (employee number 13209961) and promised to have my luggage flown back to Montreal. However, shortly after, I was told there was nothing they could do except for me to travel to Toronto myself to pick up my bag. This is highly unreasonable and unfair, considering the issue was caused by their staff printing the wrong boarding pass. This entire situation caused me significant inconvenience and stress. I expected Porter to correct the mistake and deliver my luggage as originally planned, but instead, I was left with the burden of fixing an error that was not mine. I even have a photo of the staff badge of the employee who made the promise, yet the company still failed to honor it. I hope Porter Airlines reviews their internal communication and baggage handling procedures to prevent this from happening to other passengers. Customer care and responsibility fell short in this experience, and I am still waiting for a satisfactory resolution.

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 4h 40m. The time it takes to get you to your destination can typically vary by up to 1h 15m. 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$ 227, 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 American Airlines and Air Canada - these airlines can fly you to your destination from C$ 266 and C$ 266, respectively. Users have found that Porter Airlines is 41% 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$ 181 on Delta. Other airlines that offer cheap prices include American Airlines from C$ 182 and Air Canada from C$ 183 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: EVA Air (94%), Egyptair (92%), ANA( 88%).

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

    On average you can expect to pay C$ 2,105 for a flight from Toronto Pearson Intl Airport to Chicago. The cheapest flight overall is C$ 222 while the most popular route, (Toronto Pearson Intl - Chicago O'Hare Intl) is currently priced at C$ 216.

  • 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$ 182). Flying from Toronto Pearson Intl Airport to Chicago in April is currently the most expensive (average of C$ 299). 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 6 November 2025.

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 6 November 2025.
AirlineCheapestAverageFlexibilityOn-time
Porter AirlinesCheapestC$ 227AverageC$ 318FlexibilityNo cancel feeOn-time52%
Search Porter Airlines flights
American AirlinesCheapestC$ 266AverageC$ 456FlexibilityNo cancel feeOn-time71%
Search American Airlines flights
Air CanadaCheapestC$ 266AverageC$ 404FlexibilityNo cancel feeOn-time67%
Search Air Canada flights
United AirlinesCheapestC$ 285AverageC$ 427FlexibilityNo cancel feeOn-time69%
Search United Airlines flights
WestJetCheapestC$ 377AverageC$ 604FlexibilityNo cancel feeOn-time60%
Search WestJet flights

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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.

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