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Cheap flights from Toronto Pearson Intl Airport to Chicago from C$ 166

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 28/2. Fares are subject to change and may not be available on all flights or dates of travel.
YYZ — CHI
28 Feb — 7 Mar1
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 67 days in advance, depart on a Friday or Saturday and return on a Thursday

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 29 January 2026.

Fri 19/67:00 a.m.
YYZ
-
ORD
Nonstop2h 00m
United Airlines
Sun 21/69:15 p.m.
ORD
-
YYZ
Nonstop1h 44m
United Airlines
Deal found 27/1C$ 257
Thu 19/22:15 p.m.
YYZ
-
ORD
Nonstop1h 55m
Air Canada
Mon 2/38:40 p.m.
ORD
-
YYZ
Nonstop1h 39m
Air Canada
Deal found 27/1C$ 258
Thu 19/28:45 a.m.
YYZ
-
ORD
Nonstop2h 05m
Lufthansa
Mon 23/26:28 p.m.
ORD
-
YYZ
Nonstop1h 53m
Lufthansa
Deal found 27/1C$ 261
Thu 19/28:00 a.m.
YYZ
-
ORD
1 stop7h 55m
Air Canada
Mon 23/210:00 a.m.
ORD
-
YYZ
Nonstop1h 40m
Air Canada
Deal found 26/1C$ 262
Tue 17/37:00 a.m.
YYZ
-
ORD
1 stop5h 18m
Air Canada
Tue 2/68:20 p.m.
ORD
-
YYZ
Nonstop1h 43m
Air Canada
Deal found 28/1C$ 269
Thu 5/39:00 p.m.
YYZ
-
ORD
Nonstop2h 04m
United Airlines
Wed 11/31:06 p.m.
ORD
-
YYZ
1 stop4h 51m
United Airlines
Deal found 27/1C$ 270
Tue 2/67:40 p.m.
YYZ
-
ORD
1 stop4h 41m
United Airlines
Sat 6/67:08 a.m.
ORD
-
YYZ
Nonstop1h 45m
United Airlines
Deal found 26/1C$ 277
Fri 20/212:45 p.m.
YYZ
-
ORD
1 stop5h 15m
United Airlines
Thu 26/27:07 a.m.
ORD
-
YYZ
Nonstop1h 51m
United Airlines
Deal found 27/1C$ 278
Thu 19/26:15 a.m.
YYZ
-
MDW
1 stop3h 39m
Delta
Mon 23/26:17 p.m.
MDW
-
YYZ
1 stop3h 23m
Delta
Deal found 28/1C$ 305
Wed 25/26:15 a.m.
YYZ
-
MDW
1 stop3h 39m
WestJet
Wed 4/36:20 p.m.
MDW
-
YYZ
1 stop3h 20m
WestJet
Deal found 28/1C$ 320
Mon 20/412:16 p.m.
YYZ
-
MDW
1 stop6h 42m
WestJet
Thu 23/49:27 a.m.
MDW
-
YYZ
1 stop4h 53m
WestJet
Deal found 26/1C$ 322
Tue 14/46:10 a.m.
YYZ
-
MDW
1 stop3h 37m
WestJet
Thu 30/49:27 a.m.
MDW
-
YYZ
1 stop4h 53m
WestJet
Deal found 28/1C$ 323

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 29 January 2026.

Round-trip from

C$ 257

One-way from

C$ 166

Popular in

December

Cheapest in

September

Average price

C$ 329

Good round-trip deal

C$ 551 or less

Good one-way deal

C$ 332 or less
United Airlines
  • United Airlines
  • 19/6-21/6
  • Nonstop
  • 3h 44m total
  • Toronto to Chicago
Search Deals
United Airlines
  • United Airlines
  • 28/2
  • Nonstop
  • 2h 05m total
  • Toronto to Chicago
Search Deals
Highest demand for flights based on searches. 5% potential increase in price (C$ 25 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 2% potential price decrease (C$ 12 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in January 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).
Search Deals

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 January 2026.
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 20/6

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

Nonstop2h 05m

Chicago O'Hare Intl

Tue 23/6

9:15 p.m.-11:59 p.m.

Nonstop1h 44m

C$ 257

TorontoChicago

YYZ - ORD

YYZORD

Toronto Pearson Intl

Tue 17/2

8:45 a.m.-9:50 a.m.

Nonstop2h 05m

Chicago O'Hare Intl

Tue 24/2

1:12 p.m.-4:02 p.m.

Nonstop1h 50m

C$ 257

TorontoChicago

YYZ - ORD

YYZORD

Toronto Pearson Intl

Tue 10/3

9:00 p.m.-10:04 p.m.

Nonstop2h 04m

Chicago O'Hare Intl

Tue 31/3

1:00 p.m.-7:02 p.m.

1 stop5h 02m

C$ 270

TorontoChicago

YYZ - ORD

YYZORD

Toronto Pearson Intl

Fri 20/2

3:30 p.m.-4:39 p.m.

Nonstop2h 09m

Chicago O'Hare Intl

Thu 26/2

6:00 a.m.-11:48 a.m.

1 stop4h 48m

C$ 270

TorontoChicago

YYZ - ORD

YYZORD

Toronto Pearson Intl

Sat 6/6

2:50 p.m.-11:12 p.m.

1 stop9h 22m

Chicago O'Hare Intl

Tue 9/6

3:00 p.m.-5:58 p.m.

Nonstop1h 58m

C$ 278

TorontoChicago

YYZ - ORD

YYZORD

Toronto Pearson Intl

Wed 25/2

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

1 stop5h 03m

Chicago O'Hare Intl

Thu 26/2

6:00 a.m.-11:48 a.m.

1 stop4h 48m

C$ 291

TorontoChicago

YYZ - ORD

YYZORD

Toronto Pearson Intl

Fri 27/2

8:45 a.m.-9:50 a.m.

Nonstop2h 05m

Chicago O'Hare Intl

Mon 2/3

1:02 p.m.-6:57 p.m.

1 stop4h 55m

C$ 297

TorontoChicago

YYZ - ORD

YYZORD

Toronto Pearson Intl

Wed 11/3

5:30 p.m.-6:40 p.m.

Nonstop2h 10m

Chicago O'Hare Intl

Fri 13/3

12:35 p.m.-11:46 p.m.

1 stop10h 11m

C$ 297

TorontoChicago

YYZ - ORD

YYZORD

Toronto Pearson Intl

Tue 10/3

5:30 p.m.-6:40 p.m.

Nonstop2h 10m

Chicago O'Hare Intl

Sat 14/3

6:25 p.m.-9:18 p.m.

Nonstop1h 53m

C$ 297

TorontoChicago

YYZ - ORD

YYZORD

Toronto Pearson Intl

Sat 7/3

5:30 p.m.-6:40 p.m.

Nonstop2h 10m

Chicago O'Hare Intl

Wed 11/3

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

Nonstop1h 50m

C$ 297

Flights are sorted by cheapest round-trip flights first.

Deals found on 27/1

Showing 1-10 of 44 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 23 January 2026.

Booking 67 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$ 175). Flying from Toronto Pearson Intl Airport to Chicago in April is currently the most expensive (average of C$ 288). 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 January 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 43% 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 24 January 2026.

Travelers seeking maximum savings on their Toronto Pearson Intl Airport to Chicago flight should consider departing on Thursday evenings when fares are most often at their lowest. Tuesday 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 29 January 2026.

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 (47 on average).

How often are flights from Toronto to Chicago delayed?

About 11% of weekly flights between Toronto and Chicago have experienced delays in the past year, with the average delay time being 141 minutes.

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

Historically, flights departing at night 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?

Tuesday 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 7% of flights being delayed.

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 January 2026.
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
7.9
Good
412 reviews
Check prices

Comfort

7.9

Entertainment

6.9

Food

7.5

Boarding

8.2

Crew

8.6

Overall

7.9

Reviews

1 / 20
8.0
Excellent

Mohameed,Nov 2025

LAS - YYZ

It's good. Planes are new and fresh. WiFi is best and stands out
Porter Airlines
7.9
Good
412 reviews
Porter Airlines
7.9
Good
412 reviews
Check prices

Comfort

7.9

Entertainment

6.9

Food

7.5

Boarding

8.2

Crew

8.6

Overall

7.9

Reviews

1 / 20
8.0
Excellent

Mohameed,Nov 2025

LAS - YYZ

It's good. Planes are new and fresh. WiFi is best and stands out
United Airlines
7.4
Good
9,215 reviews
Porter Airlines
7.9
Good
412 reviews
Check prices

Comfort

7.9

Entertainment

6.9

Food

7.5

Boarding

8.2

Crew

8.6

Overall

7.9

Reviews

1 / 20
8.0
Excellent

Mohameed,Nov 2025

LAS - YYZ

It's good. Planes are new and fresh. WiFi is best and stands out
American Airlines
7.2
Good
11,206 reviews
Porter Airlines
7.9
Good
412 reviews
Check prices

Comfort

7.9

Entertainment

6.9

Food

7.5

Boarding

8.2

Crew

8.6

Overall

7.9

Reviews

1 / 20
8.0
Excellent

Mohameed,Nov 2025

LAS - YYZ

It's good. Planes are new and fresh. WiFi is best and stands out
WestJet
7.2
Good
3,253 reviews
Porter Airlines
7.9
Good
412 reviews
Check prices

Comfort

7.9

Entertainment

6.9

Food

7.5

Boarding

8.2

Crew

8.6

Overall

7.9

Reviews

1 / 20
8.0
Excellent

Mohameed,Nov 2025

LAS - YYZ

It's good. Planes are new and fresh. WiFi is best and stands out
Air Canada
7.1
Good
10,667 reviews
Porter Airlines
7.9
Good
412 reviews
Check prices

Comfort

7.9

Entertainment

6.9

Food

7.5

Boarding

8.2

Crew

8.6

Overall

7.9

Reviews

1 / 20
8.0
Excellent

Mohameed,Nov 2025

LAS - YYZ

It's good. Planes are new and fresh. WiFi is best and stands out

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 34m. 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$ 111, 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$ 220 and C$ 243, respectively. Users have found that Porter Airlines is 68% 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$ 126 on Porter Airlines. Other airlines that offer cheap prices include United Airlines from C$ 158 and Air Canada from C$ 160 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: Japan Airlines (79%), Copa Airlines (76%), Republic Airways( 72%).

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

    On average you can expect to pay C$ 1,658 for a flight from Toronto Pearson Intl Airport to Chicago. The cheapest flight overall is C$ 209 while the most popular route, (Toronto Pearson Intl - Chicago O'Hare Intl) is currently priced at C$ 255.

  • 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$ 175). Flying from Toronto Pearson Intl Airport to Chicago in April is currently the most expensive (average of C$ 288). 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

Browse thousands of different options on Cheapflights for your next trip

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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 January 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 29 January 2026.
AirlineCheapestAverageFlexibilityOn-time
Porter AirlinesCheapestC$ 111AverageC$ 306FlexibilityNo cancel feeOn-time52%
Search Porter Airlines flights
American AirlinesCheapestC$ 220AverageC$ 405FlexibilityNo cancel feeOn-time71%
Search American Airlines flights
Air CanadaCheapestC$ 243AverageC$ 383FlexibilityNo cancel feeOn-time67%
Search Air Canada flights
United AirlinesCheapestC$ 256AverageC$ 391FlexibilityNo cancel feeOn-time69%
Search United Airlines flights
WestJetCheapestC$ 362AverageC$ 466FlexibilityNo 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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