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Cheap flights from Toronto Pearson Intl Airport to Chicago O'Hare Intl Airport from C$ 178

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 15/10. Fares are subject to change and may not be available on all flights or dates of travel.
YYZ — ORD
16 Oct — 23 Oct1
1 adult
1 adult, Economy

Cheapflights Tip: The best prices from Toronto Pearson Intl to Chicago O'Hare Intl are usually found in April or May, booked 64 days in advance, depart on a Friday or Saturday and return on a Saturday

Cheap flight deals from Pearson Intl to O'Hare Intl

Discover tips and strategies to find the most affordable flight options for your journey from Pearson Intl (YYZ) to O'Hare Intl (ORD). 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 16 September 2025.

Round-trip from

C$ 271

One-way from

C$ 178

Popular in

January

Cheapest in

April

Average price

C$ 414

Good round-trip deal

C$ 542 or less

Good one-way deal

C$ 490 or less
20/10-23/10
  • 20/10-23/10
  • 2 total stops
  • 15h 58m total
  • Toronto to Chicago
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15/10
  • 15/10
  • 1 total stop
  • 18h 15m total
  • Toronto to Chicago
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Highest demand for flights based on searches. 9% potential increase in price (C$ 59 potential increase over avg. RT price).
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Cheapest flight prices on average. 1% potential price decrease (C$ 8 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 O'Hare Intl.
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Price to beat on a one-way flight from Toronto Pearson Intl to Chicago O'Hare Intl.
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Find flight deals from Pearson Intl to O'Hare Intl

Cheapest flights from Pearson Intl to O'Hare Intl
Explore the most affordable flight options available from Pearson Intl to O'Hare Intl. Find the lowest fares from popular airlines and budget airlines, with prices last updated on 16 September 2025.

Mon 20/104:00 p.m.YYZ - ORD
1 stop8h 44mMultiple Airlines
Thu 23/1012:53 p.m.ORD - YYZ
1 stop7h 14mMultiple Airlines
Deal found 14/9C$ 271
Mon 20/104:00 p.m.YYZ - ORD
1 stop8h 44mMultiple Airlines
Wed 22/107:43 p.m.ORD - YYZ
1 stop17h 22mMultiple Airlines
Deal found 15/9C$ 275
Sun 19/104:00 p.m.YYZ - ORD
1 stop24h 49mMultiple Airlines
Thu 23/107:43 p.m.ORD - YYZ
1 stop17h 22mMultiple Airlines
Deal found 15/9C$ 279
Mon 20/104:00 p.m.YYZ - ORD
1 stop8h 44mMultiple Airlines
Thu 30/107:06 p.m.ORD - YYZ
1 stop25h 01mMultiple Airlines
Deal found 14/9C$ 282
Mon 3/114:00 p.m.YYZ - ORD
1 stop7h 39mMultiple Airlines
Thu 6/116:06 p.m.ORD - YYZ
1 stop26h 01mMultiple Airlines
Deal found 15/9C$ 283
Mon 13/104:00 p.m.YYZ - ORD
1 stop8h 44mMultiple Airlines
Thu 23/107:43 p.m.ORD - YYZ
1 stop17h 22mMultiple Airlines
Deal found 15/9C$ 285
Sun 19/104:00 p.m.YYZ - ORD
1 stop24h 49mMultiple Airlines
Fri 24/105:05 a.m.ORD - YYZ
1 stop8h 00mMultiple Airlines
Deal found 14/9C$ 290
Mon 13/104:00 p.m.YYZ - ORD
1 stop8h 44mMultiple Airlines
Thu 6/116:06 p.m.ORD - YYZ
1 stop26h 01mMultiple Airlines
Deal found 15/9C$ 291
Mon 20/104:00 p.m.YYZ - ORD
1 stop8h 44mMultiple Airlines
Sun 2/116:06 p.m.ORD - YYZ
1 stop26h 01mMultiple Airlines
Deal found 14/9C$ 296

Cheapflights Fare Finder

 
Customize your flight search to find flights from Pearson Intl to O'Hare Intl 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 16 September 2025.
Use the filters below to find and compare flights from Toronto Pearson Intl Airport to Chicago O'Hare Intl Airport that are best for you.

Fly from

Pearson Intl

Fly to

O'Hare Intl

Route

Depart

Return

Price

TorontoChicago

YYZ - ORD

YYZORD

Toronto Pearson Intl

Sat 11/10

12:15 p.m.-8:23 p.m.

1 stop9h 08m

Chicago O'Hare Intl

Mon 13/10

6:59 p.m.-11:20 a.m.

1 stop15h 21m

C$ 363

TorontoChicago

YYZ - ORD

YYZORD

Toronto Pearson Intl

Fri 17/10

11:00 a.m.-12:03 p.m.

Nonstop2h 03m

Chicago O'Hare Intl

Sun 19/10

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

Nonstop1h 43m

C$ 380

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

8:25 p.m.-11:08 p.m.

Nonstop1h 43m

C$ 380

TorontoChicago

YYZ - ORD

YYZORD

Toronto Pearson Intl

Sun 12/10

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$ 380

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$ 380

TorontoChicago

YYZ - ORD

YYZORD

Toronto Pearson Intl

Wed 15/10

6:09 p.m.-8:23 p.m.

1 stop3h 14m

Chicago O'Hare Intl

Mon 20/10

6:59 p.m.-8:55 a.m.

1 stop12h 56m

C$ 380

TorontoChicago

YYZ - ORD

YYZORD

Toronto Pearson Intl

Mon 13/10

9:00 a.m.-9:55 a.m.

Nonstop1h 55m

Chicago O'Hare Intl

Wed 22/10

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

Nonstop1h 54m

C$ 380

TorontoChicago

YYZ - ORD

YYZORD

Toronto Pearson Intl

Fri 10/10

11:52 a.m.-6:49 p.m.

1 stop7h 57m

Chicago O'Hare Intl

Sun 19/10

7:10 a.m.-2:45 p.m.

1 stop6h 35m

C$ 380

TorontoChicago

YYZ - ORD

YYZORD

Toronto Pearson Intl

Sun 12/10

9:00 a.m.-9:55 a.m.

Nonstop1h 55m

Chicago O'Hare Intl

Sat 18/10

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

Nonstop1h 46m

C$ 380

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$ 380

Flights are sorted by cheapest round-trip flights first.

Deals found on 14/9

Showing 1-10 of 23 results
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Best time to book a flight from Pearson Intl to O'Hare Intl

Have a flexible travel schedule? Discover the best time to fly to O'Hare Intl 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 O'Hare Intl Airport

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

Use this chart to determine the optimal time to book a round-trip flight from Pearson Intl to O'Hare Intl. Price data was last updated on 12 September 2025.

The price you pay for your flight from Toronto Pearson Intl Airport to Chicago O'Hare Intl Airport may vary depending on when you book. For the best chance of a lower fare, look to book 64 days in advance of your trip. Fares are likely to increase a fortnight or so before your departure date.

What is the cheapest month to book a flight from Toronto Pearson Intl Airport to Chicago O'Hare Intl Airport?

Currently, January is the cheapest month in which you can book a flight from Toronto Pearson Intl Airport to Chicago O'Hare Intl Airport (average of C$ 261). Flying from Toronto Pearson Intl Airport to Chicago O'Hare Intl Airport 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 ORD?

Find hourly flight availability from Pearson Intl to O'Hare Intl. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated 16 September 2025.

Unlike in the afternoon, when flights are generally more expensive, you can save up to 52% on flights from Toronto Pearson Intl Airport to Chicago O'Hare Intl Airport by exploring options for tickets in the evening.

What is the cheapest day to fly from Toronto Pearson Intl Airport to Chicago O'Hare Intl Airport?

Use this chart to determine the cheapest time to fly round-trip from Pearson Intl to O'Hare Intl. Price data was last updated on 14 September 2025.

Travelers seeking maximum savings on their Toronto Pearson Intl Airport to Chicago O'Hare Intl Airport 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.

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

Reviews of airlines servicing O'Hare Intl

Get insights into the airlines that provide service to O'Hare Intl. 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 O'Hare Intl. Reviews last updated 16 September 2025.
Get a feel of what it's like to fly with Porter Airlines,United Airlines, andAmerican Airlines from Toronto Pearson Intl Airport to Chicago O'Hare Intl Airport by reading reviews from past customers. Users have also rated airlines in terms of entertainment options, comfort, food, crew/service, and boarding process.
Porter Airlines
7.9
Good
363 reviews
Check prices

Overall

7.9

Boarding

8.1

Food

7.6

Entertainment

7.0

Crew

8.6

Comfort

7.9

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
363 reviews
Porter Airlines
7.9
Good
363 reviews
Check prices

Overall

7.9

Boarding

8.1

Food

7.6

Entertainment

7.0

Crew

8.6

Comfort

7.9

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
8,929 reviews
Porter Airlines
7.9
Good
363 reviews
Check prices

Overall

7.9

Boarding

8.1

Food

7.6

Entertainment

7.0

Crew

8.6

Comfort

7.9

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
363 reviews
Check prices

Overall

7.9

Boarding

8.1

Food

7.6

Entertainment

7.0

Crew

8.6

Comfort

7.9

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
3,093 reviews
Porter Airlines
7.9
Good
363 reviews
Check prices

Overall

7.9

Boarding

8.1

Food

7.6

Entertainment

7.0

Crew

8.6

Comfort

7.9

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
363 reviews
Check prices

Overall

7.9

Boarding

8.1

Food

7.6

Entertainment

7.0

Crew

8.6

Comfort

7.9

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 O'Hare Intl. 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 O'Hare Intl Airport?

    Airlines like WestJet and United Airlines fly from Toronto Pearson Intl Airport to Chicago O'Hare Intl Airport in about 2h 03m. The time it takes to get you to your destination can typically vary by up to 7h 05m. Toronto Pearson Intl Airport and Chicago O'Hare Intl Airport are separated by a distance of 702 km. Both multi-stop and direct flights can be found to your destination and back.

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

    According to our current data, Porter Airlines (C$ 196), Air Canada (C$ 264), and American Airlines (C$ 267) offers the cheapest pricing from Toronto Pearson Intl Airport to Chicago O'Hare Intl Airport. These flights start at 51% lower than the current average price 3 months from now.

  • What are the most reliable airlines from Toronto Pearson Intl Airport to Chicago O'Hare Intl Airport?

    Consider EVA Air (83%), SkyWest Airlines (83%) or ANA (83%) when booking your flight. These represent the most reliable airlines when flying from Toronto Pearson Intl Airport to Chicago O'Hare Intl Airport.

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

    Looking at all options, your cheapest flight can be booked for C$ 240. While the most popular route (Toronto Pearson Intl - Chicago O'Hare Intl) can be booked for C$ 275 on average, our data indicates C$ 1,703 when flying from Toronto Pearson Intl Airport to Chicago O'Hare Intl Airport.

  • Can I find deals for flights from Pearson Intl to O'Hare Intl that include hotel bookings?

    Yes. In addition to deals on Pearson Intl to O'Hare Intl flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from Pearson Intl to O'Hare Intl?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Pearson Intl to O'Hare Intl.

  • Can I find deals for business class flights from Pearson Intl to O'Hare Intl?

    Yes. Cheapflights offers flight deals from Pearson Intl to O'Hare Intl 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 O'Hare Intl Airport?

    Currently, January is the cheapest month in which you can book a flight from Toronto Pearson Intl Airport to Chicago O'Hare Intl Airport (average of C$ 261). Flying from Toronto Pearson Intl Airport to Chicago O'Hare Intl Airport 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

Travelling to a place near Chicago O'Hare Intl Airport?

Book flights to Chicago O'Hare Intl Airport if you plan to visit one of these locations
Evanston
Des Plaines
Elk Grove Village
Skokie
Downers Grove
Naperville
Bolingbrook
Romeoville

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Fly from Pearson Intl to O'Hare Intl on these airlines

Choose from the following airlines for your flight from Pearson Intl to O'Hare Intl. Flights are based on user searches made on Cheapflights and were last updated on 16 September 2025.
Air Canada flights from Toronto Pearson Intl to Chicago O'Hare Intl
United Airlines flights from Toronto Pearson Intl to Chicago O'Hare Intl
American Airlines flights from Toronto Pearson Intl to Chicago O'Hare Intl

Top 5 airlines flying from Pearson Intl to O'Hare Intl

Discover the top 5 airlines that operate flights from Pearson Intl to O'Hare Intl. 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 16 September 2025.
AirlineCheapestAverageFlexibilityOn-time
Porter AirlinesCheapestC$ 196AverageC$ 263FlexibilityNo cancel feeOn-time52%
Search Porter Airlines flights
Air CanadaCheapestC$ 264AverageC$ 394FlexibilityNo cancel feeOn-time67%
Search Air Canada flights
American AirlinesCheapestC$ 267AverageC$ 496FlexibilityNo cancel feeOn-time71%
Search American Airlines flights
United AirlinesCheapestC$ 278AverageC$ 418FlexibilityNo cancel feeOn-time69%
Search United Airlines flights
WestJetCheapestC$ 382AverageC$ 584FlexibilityNo cancel feeOn-time60%
Search WestJet flights

Fly with Cheapflights

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How does Cheapflights help users find flights from Pearson Intl to O'Hare Intl?

Deals for Pearson Intl to O'Hare Intl flights are sourced from 900+ travel sites when you use Cheapflights. When all flight results come back, Cheapflights lets you sort and filter flights using different criteria to choose better, like price, airport, cabin class, and plenty of other options.

Why should you use Cheapflights to find cheap flight tickets from Pearson Intl to O'Hare Intl?

Millions of users choose and trust Cheapflights to book the best flight deals from Pearson Intl to O'Hare Intl for free. We help you search and compare prices from hundreds of airlines for the right flight just for you.

Can Cheapflights find flights from Pearson Intl to O'Hare Intl with no change fees?

Cheapflights does show flights with no change fees to all users. To see these options for flights from Pearson Intl to O'Hare Intl, users can toggle the no change fees filter when performing a flight search.

Can Cheapflights notify me if prices for flights from Pearson Intl to O'Hare Intl become cheaper?

Not ready to book yet? You can track prices for flights from Pearson Intl to O'Hare Intl on Cheapflights with our Price Alert feature and get notified when better prices are available.

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