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Cheap flights from Toronto Pearson Intl Airport to Chicago from C$ 177

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 19/10. Fares are subject to change and may not be available on all flights or dates of travel.
YYZ — CHI
18 Oct — 25 Oct1
1 adult
1 adult, Economy

Cheapflights Tip: The best prices from Toronto Pearson Intl to Chicago are usually found in August or May, 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 18 September 2025.

Round-trip from

C$ 296

One-way from

C$ 177

Popular in

December

Cheapest in

August

Average price

C$ 349

Good round-trip deal

C$ 539 or less

Good one-way deal

C$ 488 or less
15/10-22/10
  • 15/10-22/10
  • 2 total stops
  • 30h 30m total
  • Toronto to Chicago
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19/10
  • 19/10
  • 1 total stop
  • 24h 49m total
  • Toronto to Chicago
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Highest demand for flights based on searches. 10% potential increase in price (C$ 63 potential increase over avg. RT price).
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Cheapest flight prices on average. 2% potential price decrease (C$ 13 potential savings vs. average RT price).
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Average for round-trip flights in September 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 18 September 2025.

Wed 15/106:30 a.m.YYZ - ORD
1 stop13h 08mMultiple Airlines
Wed 22/107:43 p.m.ORD - YYZ
1 stop17h 22mMultiple Airlines
Deal found 17/9C$ 296
Sun 19/104:00 p.m.YYZ - ORD
1 stop24h 49mMultiple Airlines
Fri 31/105:05 a.m.ORD - YYZ
1 stop8h 35mMultiple Airlines
Deal found 16/9C$ 299
Sun 19/104:00 p.m.YYZ - ORD
1 stop24h 49mMultiple Airlines
Sat 1/116:00 a.m.ORD - YYZ
1 stop7h 20mMultiple Airlines
Deal found 16/9C$ 301
Mon 20/106:30 a.m.YYZ - ORD
1 stop13h 08mMultiple Airlines
Fri 31/105:05 a.m.ORD - YYZ
1 stop8h 35mMultiple Airlines
Deal found 16/9C$ 304
Mon 20/106:30 a.m.YYZ - ORD
1 stop18h 15mMultiple Airlines
Thu 23/107:43 p.m.ORD - YYZ
1 stop17h 22mMultiple Airlines
Deal found 16/9C$ 307
Sat 1/119:30 p.m.YYZ - ORD
1 stop18h 05mMultiple Airlines
Mon 3/115:05 a.m.ORD - YYZ
1 stop8h 35mMultiple Airlines
Deal found 15/9C$ 308
Tue 21/106:30 a.m.YYZ - ORD
1 stop13h 08mMultiple Airlines
Sat 25/105:05 a.m.ORD - YYZ
1 stop8h 00mMultiple Airlines
Deal found 16/9C$ 311
Tue 14/106:30 a.m.YYZ - ORD
1 stop18h 15mMultiple Airlines
Tue 21/107:43 p.m.ORD - YYZ
1 stop17h 22mMultiple Airlines
Deal found 16/9C$ 316
Sat 1/116:20 a.m.YYZ - MDW
1 stop5h 10mWestJet
Sat 8/113:00 p.m.MDW - YYZ
1 stop7h 18mWestJet
Deal found 17/9C$ 332
Fri 7/1112:50 p.m.YYZ - MDW
1 stop10h 30mMultiple Airlines
Mon 10/118:00 a.m.MDW - YYZ
1 stop11h 00mMultiple Airlines
Deal found 17/9C$ 347
Sat 18/106:20 a.m.YYZ - MDW
1 stop5h 10mMultiple Airlines
Fri 31/109:32 a.m.MDW - YYZ
1 stop9h 28mMultiple Airlines
Deal found 16/9C$ 351
Wed 12/115:15 p.m.YYZ - MDW
1 stop16h 57mMultiple Airlines
Mon 15/122:15 p.m.MDW - YYZ
1 stop22h 50mMultiple Airlines
Deal found 16/9C$ 352

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 18 September 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 - MDW

YYZMDW

Toronto Pearson Intl

Sat 1/11

6:20 a.m.-1:08 p.m.

1 stop7h 48m

Chicago Midway

Sat 8/11

10:35 a.m.-9:55 p.m.

1 stop10h 20m

C$ 373

TorontoChicago

YYZ - ORD

YYZORD

Toronto Pearson Intl

Thu 23/10

7:00 a.m.-7:58 a.m.

Nonstop1h 58m

Chicago O'Hare Intl

Sun 26/10

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

Nonstop1h 39m

C$ 378

TorontoChicago

YYZ - ORD

YYZORD

Toronto Pearson Intl

Sun 12/10

7:00 a.m.-7:58 a.m.

Nonstop1h 58m

Chicago O'Hare Intl

Sun 19/10

4:42 p.m.-7:37 p.m.

Nonstop1h 55m

C$ 378

TorontoChicago

YYZ - ORD

YYZORD

Toronto Pearson Intl

Sat 18/10

7:00 a.m.-7:58 a.m.

Nonstop1h 58m

Chicago O'Hare Intl

Sun 19/10

4:42 p.m.-7:37 p.m.

Nonstop1h 55m

C$ 378

TorontoChicago

YYZ - MDW

YYZMDW

Toronto Pearson Intl

Mon 13/10

7:45 a.m.-10:14 p.m.

1 stop15h 29m

Chicago Midway

Sat 18/10

10:35 a.m.-9:55 p.m.

1 stop10h 20m

C$ 378

TorontoChicago

YYZ - ORD

YYZORD

Toronto Pearson Intl

Sat 18/10

7:00 a.m.-7:58 a.m.

Nonstop1h 58m

Chicago O'Hare Intl

Fri 24/10

6:01 p.m.-8:44 p.m.

Nonstop1h 43m

C$ 378

TorontoChicago

YYZ - MDW

YYZMDW

Toronto Pearson Intl

Thu 16/10

7:45 a.m.-10:14 p.m.

1 stop15h 29m

Chicago Midway

Sat 18/10

10:35 a.m.-9:55 p.m.

1 stop10h 20m

C$ 378

TorontoChicago

YYZ - ORD

YYZORD

Toronto Pearson Intl

Tue 14/10

9:00 p.m.-10:07 p.m.

Nonstop2h 07m

Chicago O'Hare Intl

Wed 22/10

8:55 a.m.-11:49 a.m.

Nonstop1h 54m

C$ 378

TorontoChicago

YYZ - MDW

YYZMDW

Toronto Pearson Intl

Fri 7/11

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

1 stop16h 40m

Chicago Midway

Sun 9/11

10:47 a.m.-5:00 p.m.

1 stop5h 13m

C$ 378

TorontoChicago

YYZ - ORD

YYZORD

Toronto Pearson Intl

Sat 11/10

5:15 p.m.-6:22 p.m.

Nonstop2h 07m

Chicago O'Hare Intl

Wed 15/10

9:12 p.m.-11:58 p.m.

Nonstop1h 46m

C$ 378

Flights are sorted by cheapest round-trip flights first.

Deals found on 17/9

Showing 1-10 of 43 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 12 September 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$ 348). 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 18 September 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 51% 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. 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 18 September 2025.

The most flights from YYZ to CHI are scheduled on a Thursday (61 on average). You will have fewer flight options on Saturday, which is when the least amount of flights are scheduled (41 on average).

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 18 September 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
7.9
Good
365 reviews
Check prices

Crew

8.6

Comfort

7.9

Entertainment

7.0

Overall

7.9

Boarding

8.2

Food

7.6

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
7.9
Good
365 reviews
Porter Airlines
7.9
Good
365 reviews
Check prices

Crew

8.6

Comfort

7.9

Entertainment

7.0

Overall

7.9

Boarding

8.2

Food

7.6

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
8,926 reviews
Porter Airlines
7.9
Good
365 reviews
Check prices

Crew

8.6

Comfort

7.9

Entertainment

7.0

Overall

7.9

Boarding

8.2

Food

7.6

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
10,000 reviews
Porter Airlines
7.9
Good
365 reviews
Check prices

Crew

8.6

Comfort

7.9

Entertainment

7.0

Overall

7.9

Boarding

8.2

Food

7.6

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
3,095 reviews
Porter Airlines
7.9
Good
365 reviews
Check prices

Crew

8.6

Comfort

7.9

Entertainment

7.0

Overall

7.9

Boarding

8.2

Food

7.6

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
10,000 reviews
Porter Airlines
7.9
Good
365 reviews
Check prices

Crew

8.6

Comfort

7.9

Entertainment

7.0

Overall

7.9

Boarding

8.2

Food

7.6

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 WestJet and United Airlines fly from Toronto Pearson Intl Airport to Chicago in about 1h 58m. The time it takes to get you to your destination can typically vary by up to 5h 50m. 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$ 195, 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 American Airlines - these airlines can fly you to your destination from C$ 263 and C$ 266, respectively. Users have found that Porter Airlines is 48% 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 (88%), Egyptair (85%), Copa Airlines( 85%).

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

    On average you can expect to pay C$ 1,696 for a flight from Toronto Pearson Intl Airport to Chicago. The cheapest flight overall is C$ 239 while the most popular route, (Toronto Pearson Intl - Chicago O'Hare Intl) is currently priced at C$ 316.

  • 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$ 348). 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 18 September 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 18 September 2025.
AirlineCheapestAverageFlexibilityOn-time
Porter AirlinesCheapestC$ 195AverageC$ 305FlexibilityNo cancel feeOn-time52%
Search Porter Airlines flights
Air CanadaCheapestC$ 263AverageC$ 393FlexibilityNo cancel feeOn-time67%
Search Air Canada flights
American AirlinesCheapestC$ 266AverageC$ 494FlexibilityNo cancel feeOn-time71%
Search American Airlines flights
United AirlinesCheapestC$ 277AverageC$ 416FlexibilityNo cancel feeOn-time69%
Search United Airlines flights
WestJetCheapestC$ 380AverageC$ 628FlexibilityNo cancel feeOn-time60%
Search WestJet flights

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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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