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Cheap flights from Toronto Pearson Intl Airport to Chicago O'Hare Intl Airport from C$ 180

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 18/11. Fares are subject to change and may not be available on all flights or dates of travel.
YYZ — ORD
21 Nov — 28 Nov1
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 41 days in advance, depart on a Friday or Saturday and return on a Thursday

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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 22 October 2025.

Wed 3/123:56 p.m.YYZ - ORD
1 stop5h 54mAmerican Airlines
Wed 10/122:47 p.m.ORD - YYZ
1 stop5h 43mAmerican Airlines
Deal found 20/10C$ 257
Sat 6/1211:36 a.m.YYZ - ORD
Nonstop1h 55mAmerican Airlines
Sat 13/125:00 a.m.ORD - YYZ
1 stop5h 00mAmerican Airlines
Deal found 22/10C$ 264
Thu 4/1211:36 a.m.YYZ - ORD
Nonstop1h 55mAmerican Airlines
Mon 8/128:10 a.m.ORD - YYZ
Nonstop1h 46mAmerican Airlines
Deal found 20/10C$ 265
Tue 18/116:00 a.m.YYZ - ORD
Nonstop2h 15mAmerican Airlines
Thu 20/116:47 a.m.ORD - YYZ
1 stop7h 43mAmerican Airlines
Deal found 20/10C$ 271
Tue 2/125:15 p.m.YYZ - ORD
1 stop4h 50mAmerican Airlines
Thu 4/128:10 a.m.ORD - YYZ
Nonstop1h 46mAmerican Airlines
Deal found 21/10C$ 278
Fri 5/1211:59 a.m.YYZ - ORD
1 stop8h 45mAmerican Airlines
Fri 12/126:34 p.m.ORD - YYZ
Nonstop1h 55mAmerican Airlines
Deal found 20/10C$ 279
Tue 25/116:05 a.m.YYZ - ORD
1 stop4h 56mDelta
Fri 5/128:55 a.m.ORD - YYZ
1 stop7h 20mDelta
Deal found 21/10C$ 282
Mon 17/114:30 p.m.YYZ - ORD
1 stop8h 07mAmerican Airlines
Wed 19/116:50 a.m.ORD - YYZ
1 stop7h 40mAmerican Airlines
Deal found 20/10C$ 285
Wed 12/117:00 a.m.YYZ - ORD
1 stop6h 18mAmerican Airlines
Sat 15/117:10 a.m.ORD - YYZ
1 stop7h 49mAmerican Airlines
Deal found 22/10C$ 286
Fri 5/126:30 p.m.YYZ - ORD
Nonstop2h 00mAir Canada
Mon 5/18:15 p.m.ORD - YYZ
Nonstop1h 39mAir Canada
Deal found 21/10C$ 288
Thu 4/126:05 a.m.YYZ - ORD
1 stop4h 55mKLM
Mon 8/125:42 p.m.ORD - YYZ
1 stop4h 45mKLM
Deal found 20/10C$ 291

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 22 October 2025.

Round-trip from

C$ 243

One-way from

C$ 180

Popular in

October

Cheapest in

April

Average price

C$ 467

Good round-trip deal

C$ 560 or less

Good one-way deal

C$ 347 or less
American Airlines
  • American Airlines
  • 24/3-31/3
  • 1 total stop
  • 9h 33m total
  • Toronto to Chicago
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Delta
  • Delta
  • 18/11
  • 1 total stop
  • 9h 44m total
  • Toronto to Chicago
Search Deals
Highest demand for flights based on searches. 4% potential increase in price (C$ 27 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 1% potential price decrease (C$ 8 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in October 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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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 22 October 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

Wed 26/11

12:08 p.m.-4:24 p.m.

1 stop5h 16m

Chicago O'Hare Intl

Sat 6/12

6:00 a.m.-4:15 p.m.

1 stop9h 15m

C$ 282

TorontoChicago

YYZ - ORD

YYZORD

Toronto Pearson Intl

Mon 24/11

6:05 a.m.-10:01 a.m.

1 stop4h 56m

Chicago O'Hare Intl

Tue 9/12

7:00 a.m.-5:48 p.m.

1 stop9h 48m

C$ 282

TorontoChicago

YYZ - ORD

YYZORD

Toronto Pearson Intl

Mon 24/11

7:50 a.m.-1:17 p.m.

1 stop6h 27m

Chicago O'Hare Intl

Thu 11/12

10:45 a.m.-5:15 p.m.

1 stop5h 30m

C$ 282

TorontoChicago

YYZ - ORD

YYZORD

Toronto Pearson Intl

Wed 3/12

2:09 p.m.-8:38 p.m.

1 stop7h 29m

Chicago O'Hare Intl

Sat 13/12

6:45 a.m.-11:25 a.m.

1 stop3h 40m

C$ 282

TorontoChicago

YYZ - ORD

YYZORD

Toronto Pearson Intl

Tue 2/12

6:05 a.m.-10:00 a.m.

1 stop4h 55m

Chicago O'Hare Intl

Thu 11/12

8:55 a.m.-5:15 p.m.

1 stop7h 20m

C$ 282

TorontoChicago

YYZ - ORD

YYZORD

Toronto Pearson Intl

Mon 24/11

9:52 a.m.-4:24 p.m.

1 stop7h 32m

Chicago O'Hare Intl

Fri 5/12

6:00 a.m.-4:15 p.m.

1 stop9h 15m

C$ 282

TorontoChicago

YYZ - ORD

YYZORD

Toronto Pearson Intl

Wed 3/12

6:05 a.m.-10:00 a.m.

1 stop4h 55m

Chicago O'Hare Intl

Mon 8/12

5:42 p.m.-11:27 p.m.

1 stop4h 45m

C$ 282

TorontoChicago

YYZ - ORD

YYZORD

Toronto Pearson Intl

Tue 2/12

10:20 a.m.-6:27 p.m.

1 stop9h 07m

Chicago O'Hare Intl

Fri 12/12

6:45 a.m.-2:48 p.m.

1 stop7h 03m

C$ 282

TorontoChicago

YYZ - ORD

YYZORD

Toronto Pearson Intl

Thu 27/11

6:05 a.m.-8:57 a.m.

1 stop3h 52m

Chicago O'Hare Intl

Wed 10/12

6:00 a.m.-1:19 p.m.

1 stop6h 19m

C$ 282

TorontoChicago

YYZ - ORD

YYZORD

Toronto Pearson Intl

Fri 5/12

12:13 p.m.-6:27 p.m.

1 stop7h 14m

Chicago O'Hare Intl

Thu 11/12

6:45 a.m.-2:48 p.m.

1 stop7h 03m

C$ 282

Flights are sorted by cheapest round-trip flights first.

Deals found on 20/10

Showing 1-10 of 22 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 17 October 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 41 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$ 192). Flying from Toronto Pearson Intl Airport to Chicago O'Hare Intl Airport in February is currently the most expensive (average of C$ 330). 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 22 October 2025.

Unlike in the afternoon, when flights are generally more expensive, you can save up to 42% 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 19 October 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 22 October 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
8.0
Very good
382 reviews
Check prices

Comfort

8.0

Overall

8.0

Entertainment

7.0

Crew

8.6

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
8.0
Very good
382 reviews
Porter Airlines
8.0
Very good
382 reviews
Check prices

Comfort

8.0

Overall

8.0

Entertainment

7.0

Crew

8.6

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
8,988 reviews
Porter Airlines
8.0
Very good
382 reviews
Check prices

Comfort

8.0

Overall

8.0

Entertainment

7.0

Crew

8.6

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
11,028 reviews
Porter Airlines
8.0
Very good
382 reviews
Check prices

Comfort

8.0

Overall

8.0

Entertainment

7.0

Crew

8.6

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
3,132 reviews
Porter Airlines
8.0
Very good
382 reviews
Check prices

Comfort

8.0

Overall

8.0

Entertainment

7.0

Crew

8.6

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
10,335 reviews
Porter Airlines
8.0
Very good
382 reviews
Check prices

Comfort

8.0

Overall

8.0

Entertainment

7.0

Crew

8.6

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 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 Delta fly from Toronto Pearson Intl Airport to Chicago O'Hare Intl Airport in about 5h 16m. The time it takes to get you to your destination can typically vary by up to . Toronto Pearson Intl Airport and Chicago O'Hare Intl Airport are separated by a distance of 702 km.

  • 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$ 226), Air Canada (C$ 263), and United Airlines (C$ 285) offers the cheapest pricing from Toronto Pearson Intl Airport to Chicago O'Hare Intl Airport. These flights start at 44% 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 (94%), Egyptair (90%) or Copa Airlines (90%) 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$ 213. While the most popular route (Toronto Pearson Intl - Chicago O'Hare Intl) can be booked for C$ 215 on average, our data indicates C$ 1,894 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$ 192). Flying from Toronto Pearson Intl Airport to Chicago O'Hare Intl Airport in February is currently the most expensive (average of C$ 330). 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 22 October 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 22 October 2025.
AirlineCheapestAverageFlexibilityOn-time
Porter AirlinesCheapestC$ 226AverageC$ 275FlexibilityNo cancel feeOn-time52%
Search Porter Airlines flights
Air CanadaCheapestC$ 263AverageC$ 400FlexibilityNo cancel feeOn-time67%
Search Air Canada flights
United AirlinesCheapestC$ 285AverageC$ 426FlexibilityNo cancel feeOn-time69%
Search United Airlines flights
American AirlinesCheapestC$ 285AverageC$ 475FlexibilityNo cancel feeOn-time71%
Search American Airlines flights
WestJetCheapestC$ 375AverageC$ 514FlexibilityNo 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 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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