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Cheap flights from Toronto Pearson Intl Airport to Chicago from C$ 185

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 1/9. Fares are subject to change and may not be available on all flights or dates of travel.
YYZ — CHI
10 Sep — 17 Sep1
1 adult
1 adult, Economy, 0 bags
Cheapflights Tip: The best prices from Toronto Pearson Intl to Chicago are usually found in March or January, booked 84 days in advance, depart on a Friday or Saturday and return on a Friday

Cheap flight deals from Pearson Intl to Chicago

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 11 August 2026.

Thu 10/96:50 p.m. -
Nonstop1h 58m
Sun 13/98:40 p.m. -
Nonstop1h 46m
Deal found 7/8C$ 278
Tue 8/96:50 p.m. -
Nonstop1h 58m
Tue 15/93:40 p.m. -
1 stop5h 13m
Deal found 11/8C$ 279
Sat 12/94:00 p.m. -
1 stop5h 12m
Tue 15/93:40 p.m. -
1 stop5h 13m
Deal found 9/8C$ 282
Sat 12/911:40 a.m. -
Nonstop2h 05m
Thu 17/92:51 p.m. -
Nonstop1h 53m
Deal found 6/8C$ 290
Tue 15/910:30 a.m. -
1 stop5h 22m
Sat 19/93:40 p.m. -
1 stop5h 13m
Deal found 10/8C$ 291
Sat 5/96:55 p.m. -
Nonstop1h 58m
Sat 12/99:55 a.m. -
Nonstop1h 45m
Deal found 6/8C$ 293
Tue 15/99:45 a.m. -
1 stop3h 54m
Wed 30/99:29 a.m. -
1 stop6h 51m
Deal found 7/8C$ 329
Mon 21/96:00 a.m. -
1 stop4h 07m
Tue 29/99:29 a.m. -
1 stop4h 46m
Deal found 9/8C$ 340
Sun 6/912:09 p.m. -
1 stop5h 50m
Sun 13/96:40 p.m. -
1 stop3h 19m
Deal found 9/8C$ 342
Sat 26/96:00 a.m. -
1 stop4h 07m
Sun 27/99:29 a.m. -
1 stop6h 51m
Deal found 10/8C$ 353
Fri 11/99:50 a.m. -
1 stop7h 32m
Sat 19/99:34 a.m. -
1 stop6h 51m
Deal found 7/8C$ 361
Mon 7/96:15 a.m. -
1 stop7h 29m
Mon 14/99:29 a.m. -
1 stop6h 56m
Deal found 8/8C$ 363

Find 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 11 August 2026.

Round-trip from

C$ 278

One-way from

C$ 185

Popular in

August

Cheapest in

March

Average price

C$ 455

Good round-trip deal

C$ 564 or less

Good one-way deal

C$ 344 or less
Air Canada
  • Air Canada
  • 10/9-13/9
  • Nonstop
  • 3h 44m total
  • Toronto to Chicago
Search Deals
Air Canada
  • Air Canada
  • 1/9
  • Nonstop
  • 1h 57m total
  • Toronto to Chicago
Search Deals
Highest demand for flights based on searches. 2% potential increase in price (C$ 15 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 1% potential price decrease (C$ 10 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in August 2026
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 11 August 2026.
Use the filters below to find and compare flights from Toronto Pearson Intl Airport to Chicago that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip

TorontoChicago

YYZ Toronto Pearson Intl - ORD Chicago O'Hare Intl

YYZORD

Toronto Pearson Intl

Mon 14/9

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

Nonstop2h 05m

Chicago O'Hare Intl

Fri 18/9

9:18 p.m.-11:59 p.m.

Nonstop1h 41m

C$ 305

TorontoChicago

YYZ Toronto Pearson Intl - ORD Chicago O'Hare Intl

YYZORD

Toronto Pearson Intl

Thu 10/9

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

Nonstop2h 00m

Chicago O'Hare Intl

Sun 13/9

8:40 p.m.-11:26 p.m.

Nonstop1h 46m

C$ 333

TorontoChicago

YYZ Toronto Pearson Intl - ORD Chicago O'Hare Intl

YYZORD

Toronto Pearson Intl

Thu 10/9

8:50 a.m.-9:53 a.m.

Nonstop2h 03m

Chicago O'Hare Intl

Sun 13/9

5:53 p.m.-8:44 p.m.

Nonstop1h 51m

C$ 333
Quickest round-trip

TorontoChicago

YYZ Toronto Pearson Intl - ORD Chicago O'Hare Intl

YYZORD

Toronto Pearson Intl

Thu 10/9

5:15 p.m.-6:18 p.m.

Nonstop2h 03m

Chicago O'Hare Intl

Sat 19/9

9:18 p.m.-11:59 p.m.

Nonstop1h 41m

C$ 335

TorontoChicago

YYZ Toronto Pearson Intl - MDW Chicago Midway

YYZMDW

Toronto Pearson Intl

Wed 23/9

4:05 p.m.-6:33 p.m.

1 stop3h 28m

Chicago Midway

Tue 29/9

9:29 a.m.-3:15 p.m.

1 stop4h 46m

C$ 340

TorontoChicago

YYZ Toronto Pearson Intl - MDW Chicago Midway

YYZMDW

Toronto Pearson Intl

Tue 8/9

9:45 a.m.-4:57 p.m.

1 stop8h 12m

Chicago Midway

Mon 14/9

9:24 a.m.-5:20 p.m.

1 stop6h 56m

C$ 340

TorontoChicago

YYZ Toronto Pearson Intl - MDW Chicago Midway

YYZMDW

Toronto Pearson Intl

Mon 21/9

4:05 p.m.-6:33 p.m.

1 stop3h 28m

Chicago Midway

Mon 28/9

9:29 a.m.-5:20 p.m.

1 stop6h 51m

C$ 340

TorontoChicago

YYZ Toronto Pearson Intl - MDW Chicago Midway

YYZMDW

Toronto Pearson Intl

Tue 15/9

9:45 a.m.-12:39 p.m.

1 stop3h 54m

Chicago Midway

Wed 23/9

9:29 a.m.-5:20 p.m.

1 stop6h 51m

C$ 340

TorontoChicago

YYZ Toronto Pearson Intl - ORD Chicago O'Hare Intl

YYZORD

Toronto Pearson Intl

Sat 5/9

9:44 a.m.-2:27 p.m.

1 stop5h 43m

Chicago O'Hare Intl

Tue 8/9

6:30 a.m.-2:19 p.m.

1 stop6h 49m

C$ 342

TorontoChicago

YYZ Toronto Pearson Intl - ORD Chicago O'Hare Intl

YYZORD

Toronto Pearson Intl

Fri 25/9

2:24 p.m.-8:30 p.m.

1 stop7h 06m

Chicago O'Hare Intl

Mon 28/9

8:55 a.m.-5:20 p.m.

1 stop7h 25m

C$ 342

Flights are sorted by cheapest round-trip flights first.

Deals found on 9/8

Showing 1-10 of 39 resultsSorted by cheapest first
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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

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$ 346). Flying from Toronto Pearson Intl Airport to Chicago in December is currently the most expensive (average of C$ 457). 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 11 August 2026.

It’s optimal to fly from Toronto Pearson Intl Airport to Chicago in the evening. By choosing this option you can save up to 32% on the cost of your flight, compared to a flight in the afternoon.

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 11 August 2026.

The most flights from YYZ to CHI are scheduled on a Sunday (70 on average). You will have fewer flight options on Wednesday, which is when the least amount of flights are scheduled (42 on average).

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

Airfare is below average for this route at the moment.
Toronto Pearson Intl Airport to Chicago flights typically cost between C$ 357 and C$ 594 in September.
The cheapest round-trip price found within the last 5 days was C$ 278 on Air Canada (10 Sep-13 Sep).

How often are flights from Toronto to Chicago delayed?

About 13% of weekly flights between Toronto and Chicago have experienced delays in the past year, with the average delay time being 139 minutes.

What is the most punctual flight time for Toronto to Chicago flights?

Historically, flights departing in the morning are less likely to be delayed, whereas flights leaving in the evening tend to experience delays more often.

What day of the week experiences the fewest flight delays on this route?

Thursday tends to have the lowest number of delays on this route, whereas Saturday has historically faced a higher average of delays compared to other days of the week.

Which airline has the best punctuality record on Toronto to Chicago flights?

Over the past year, United Airlines has had the lowest number of delays on this route, with just 9% of flights being delayed.

How far ahead should I book a flight from Toronto Pearson Intl Airport to Chicago?

Booking 83 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 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 8 August 2026.

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

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 11 August 2026.
Read reviews from past customers who have flown Porter Airlines,United Airlines, andWestJet 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
454 reviews
Check prices

Crew

8.6

Food

7.6

Entertainment

6.9

Overall

8.0

Boarding

8.2

Comfort

8.0

Reviews

1 / 20
10.0
Excellent

Regan,Aug 2026

YYZ - YVR

My first flight with an all female flight crew who were the best ever.
Porter Airlines
8.0
Very good
454 reviews
Porter Airlines
8.0
Very good
454 reviews
Check prices

Crew

8.6

Food

7.6

Entertainment

6.9

Overall

8.0

Boarding

8.2

Comfort

8.0

Reviews

1 / 20
10.0
Excellent

Regan,Aug 2026

YYZ - YVR

My first flight with an all female flight crew who were the best ever.
United Airlines
7.4
Good
10,101 reviews
Porter Airlines
8.0
Very good
454 reviews
Check prices

Crew

8.6

Food

7.6

Entertainment

6.9

Overall

8.0

Boarding

8.2

Comfort

8.0

Reviews

1 / 20
10.0
Excellent

Regan,Aug 2026

YYZ - YVR

My first flight with an all female flight crew who were the best ever.
WestJet
7.2
Good
3,430 reviews
Porter Airlines
8.0
Very good
454 reviews
Check prices

Crew

8.6

Food

7.6

Entertainment

6.9

Overall

8.0

Boarding

8.2

Comfort

8.0

Reviews

1 / 20
10.0
Excellent

Regan,Aug 2026

YYZ - YVR

My first flight with an all female flight crew who were the best ever.
American Airlines
7.1
Good
11,899 reviews
Porter Airlines
8.0
Very good
454 reviews
Check prices

Crew

8.6

Food

7.6

Entertainment

6.9

Overall

8.0

Boarding

8.2

Comfort

8.0

Reviews

1 / 20
10.0
Excellent

Regan,Aug 2026

YYZ - YVR

My first flight with an all female flight crew who were the best ever.
Air Canada
7.1
Good
11,460 reviews
Porter Airlines
8.0
Very good
454 reviews
Check prices

Crew

8.6

Food

7.6

Entertainment

6.9

Overall

8.0

Boarding

8.2

Comfort

8.0

Reviews

1 / 20
10.0
Excellent

Regan,Aug 2026

YYZ - YVR

My first flight with an all female flight crew who were the best ever.

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 05m. The time it takes to get you to your destination can typically vary by up to 1h 23m. 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 American Airlines and Air Canada - these airlines can fly you to your destination from C$ 252 and C$ 284, 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$ 157 on United Airlines. Other airlines that offer cheap prices include Air Canada from C$ 163 and American Airlines from C$ 166 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: Egyptair (95%), Envoy Air (89%), Japan Airlines( 84%).

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

    On average you can expect to pay C$ 1,541 for a flight from Toronto Pearson Intl Airport to Chicago. The cheapest flight overall is C$ 252 while the most popular route, (Toronto Pearson Intl - Chicago O'Hare Intl) is currently priced at C$ 294.

  • 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$ 346). Flying from Toronto Pearson Intl Airport to Chicago in December is currently the most expensive (average of C$ 457). 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 11 August 2026.
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 11 August 2026.
AirlineCheapestAverageFlexibilityOn-time
Porter AirlinesCheapestC$ 225AverageC$ 517FlexibilityNo cancel feeOn-time52%
Search Porter Airlines flights
American AirlinesCheapestC$ 252AverageC$ 421FlexibilityNo cancel feeOn-time71%
Search American Airlines flights
Air CanadaCheapestC$ 284AverageC$ 453FlexibilityNo cancel feeOn-time67%
Search Air Canada flights
United AirlinesCheapestC$ 286AverageC$ 412FlexibilityNo cancel feeOn-time69%
Search United Airlines flights
WestJetCheapestC$ 354AverageC$ 462FlexibilityNo cancel feeOn-time60%
Search WestJet flights

Fly with Cheapflights

Find the best flight deals on Cheapflights, where travelers can enjoy low prices and a wide availability of flights to their desired destinations.

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

Cheapflights makes it easy to find Pearson Intl to Chicago flights by helping our users search from 900+ travel sites for deals. We also provide you with filters for cabin, price, airline, airports, number of stops, and many more to narrow down that perfect flight.

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

Cheapflights simply makes it quick and affordable to book flights from Pearson Intl to Chicago by bringing together all flight options from hundreds of airlines and agencies online — and put it in one place for you to choose from. Plus, Cheapflights is 100% free to use for all.

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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