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Cheap flights from Toronto Pearson Intl Airport to Chicago O'Hare Intl Airport from C$ 170

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 1/6. Fares are subject to change and may not be available on all flights or dates of travel.
YYZ — ORD
17 May — 24 May1
1 adult
1 adult, Economy, 0 bags
Cheapflights Tip: The best prices from Toronto Pearson Intl to Chicago O'Hare Intl are usually found in January or May, booked 68 days in advance, depart on a Friday or Saturday and return on a Thursday

Cheap flight deals from Pearson Intl to O'Hare Intl

Enter your travel dates to find the best prices.

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 17 April 2026.

Tue 26/512:25 p.m.
YYZ
-
ORD
Nonstop2h 00m
Air Canada
Sun 31/59:55 a.m.
ORD
-
YYZ
Nonstop1h 40m
Air Canada
Deal found 15/4C$ 281
Fri 8/512:25 p.m.
YYZ
-
ORD
Nonstop2h 00m
Air Canada
Mon 11/55:35 p.m.
ORD
-
YYZ
Nonstop1h 42m
Air Canada
Deal found 15/4C$ 283
Sat 9/54:00 p.m.
YYZ
-
ORD
1 stop5h 08m
Air Canada
Tue 12/59:55 a.m.
ORD
-
YYZ
Nonstop1h 40m
Air Canada
Deal found 15/4C$ 292
Sat 9/510:30 a.m.
YYZ
-
ORD
1 stop5h 23m
Air Canada
Mon 11/55:35 p.m.
ORD
-
YYZ
Nonstop1h 42m
Air Canada
Deal found 15/4C$ 294
Sat 23/510:30 a.m.
YYZ
-
ORD
1 stop5h 23m
Air Canada
Wed 27/59:55 a.m.
ORD
-
YYZ
Nonstop1h 40m
Air Canada
Deal found 16/4C$ 295
Wed 27/511:00 a.m.
YYZ
-
ORD
Nonstop2h 00m
United Airlines
Sat 30/53:40 p.m.
ORD
-
YYZ
1 stop5h 43m
United Airlines
Deal found 17/4C$ 296
Sat 6/67:24 p.m.
YYZ
-
ORD
1 stop5h 34m
American Airlines
Tue 9/68:35 p.m.
ORD
-
YYZ
Nonstop1h 54m
American Airlines
Deal found 16/4C$ 303
Thu 25/62:00 p.m.
YYZ
-
ORD
Nonstop1h 55m
Air Canada
Sun 28/68:40 p.m.
ORD
-
YYZ
Nonstop1h 46m
Air Canada
Deal found 16/4C$ 304
Mon 25/58:00 a.m.
YYZ
-
ORD
Nonstop2h 00m
Air Canada
Thu 28/58:35 p.m.
ORD
-
YYZ
Nonstop1h 43m
Air Canada
Deal found 15/4C$ 311
Tue 5/54:11 p.m.
YYZ
-
ORD
1 stop3h 41m
Delta
Sun 10/57:00 a.m.
ORD
-
YYZ
1 stop5h 30m
Delta
Deal found 14/4C$ 315
Sat 9/510:59 a.m.
YYZ
-
ORD
1 stop8h 15m
American Airlines
Tue 12/56:02 a.m.
ORD
-
YYZ
1 stop4h 58m
American Airlines
Deal found 16/4C$ 317
Sun 31/58:50 a.m.
YYZ
-
ORD
Nonstop2h 00m
United Airlines
Mon 8/69:15 p.m.
ORD
-
YYZ
Nonstop1h 44m
United Airlines
Deal found 17/4C$ 321

Find 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 17 April 2026.

Round-trip from

C$ 281

One-way from

C$ 170

Popular in

December

Cheapest in

January

Average price

C$ 429

Good round-trip deal

C$ 498 or less

Good one-way deal

C$ 353 or less
Air Canada
  • Air Canada
  • 26/5-31/5
  • Nonstop
  • 3h 40m total
  • Toronto to Chicago
Search Deals
Air Canada
  • Air Canada
  • 1/6
  • Nonstop
  • 2h 00m total
  • Toronto to Chicago
Search Deals
Highest demand for flights based on searches. 0% potential increase in price (C$ 5 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 1% potential price decrease (C$ 9 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in April 2026
Search Deals
Price to beat on a round-trip flight from Toronto Pearson Intl to Chicago O'Hare Intl.
Search Deals
Price to beat on a one-way flight from Toronto Pearson Intl to Chicago O'Hare Intl.
Search Deals

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 17 April 2026.
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

Fly to

Route

Depart

Return

Price

Cheapest round-trip

TorontoChicago

YYZ - ORD

YYZORD

Toronto Pearson Intl

Thu 28/5

5:15 p.m.-6:19 p.m.

Nonstop2h 04m

Chicago O'Hare Intl

Sat 30/5

9:55 p.m.-10:04 a.m.

1 stop11h 09m

C$ 321

TorontoChicago

YYZ - ORD

YYZORD

Toronto Pearson Intl

Mon 1/6

4:04 p.m.-8:14 p.m.

1 stop5h 10m

Chicago O'Hare Intl

Thu 4/6

7:00 a.m.-1:30 p.m.

1 stop5h 30m

C$ 328

TorontoChicago

YYZ - ORD

YYZORD

Toronto Pearson Intl

Fri 8/5

3:00 p.m.-9:40 p.m.

1 stop7h 40m

Chicago O'Hare Intl

Thu 14/5

1:01 p.m.-3:46 p.m.

Nonstop1h 45m

C$ 328

TorontoChicago

YYZ - ORD

YYZORD

Toronto Pearson Intl

Fri 29/5

9:49 a.m.-4:29 p.m.

1 stop7h 40m

Chicago O'Hare Intl

Sun 31/5

7:00 a.m.-3:14 p.m.

1 stop7h 14m

C$ 328
Quickest round-trip

TorontoChicago

YYZ - ORD

YYZORD

Toronto Pearson Intl

Thu 4/6

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

Nonstop2h 03m

Chicago O'Hare Intl

Sun 7/6

7:09 a.m.-9:54 a.m.

Nonstop1h 45m

C$ 361

TorontoChicago

YYZ - ORD

YYZORD

Toronto Pearson Intl

Thu 7/5

2:20 p.m.-6:05 p.m.

1 stop4h 45m

Chicago O'Hare Intl

Sun 10/5

7:00 a.m.-1:30 p.m.

1 stop5h 30m

C$ 361

TorontoChicago

YYZ - ORD

YYZORD

Toronto Pearson Intl

Sat 6/6

6:10 a.m.-12:56 p.m.

1 stop7h 46m

Chicago O'Hare Intl

Tue 9/6

5:22 p.m.-11:02 p.m.

1 stop4h 40m

C$ 370

TorontoChicago

YYZ - ORD

YYZORD

Toronto Pearson Intl

Mon 15/6

12:09 p.m.-6:29 p.m.

1 stop7h 20m

Chicago O'Hare Intl

Sat 20/6

2:35 p.m.-11:02 p.m.

1 stop7h 27m

C$ 370

TorontoChicago

YYZ - ORD

YYZORD

Toronto Pearson Intl

Thu 4/6

2:20 p.m.-6:05 p.m.

1 stop4h 45m

Chicago O'Hare Intl

Sun 7/6

8:52 a.m.-5:24 p.m.

1 stop7h 32m

C$ 399

TorontoChicago

YYZ - ORD

YYZORD

Toronto Pearson Intl

Fri 12/6

12:09 p.m.-4:26 p.m.

1 stop5h 17m

Chicago O'Hare Intl

Sat 13/6

5:22 p.m.-11:02 p.m.

1 stop4h 40m

C$ 399

Flights are sorted by cheapest round-trip flights first.

Deals found on 17/4

Showing 1-10 of 22 resultsSorted by cheapest first
1
2
3

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 10 April 2026.

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 68 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$ 350). Flying from Toronto Pearson Intl Airport to Chicago O'Hare Intl Airport in December is currently the most expensive (average of C$ 454). 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 17 April 2026.

Unlike at noon, when flights are generally more expensive, you can save up to 35% 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 11 April 2026.

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

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 17 April 2026.
Get a feel of what it's like to fly with Porter Airlines,United Airlines, andWestJet 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
435 reviews
Check prices

Overall

8.0

Crew

8.6

Entertainment

7.0

Food

7.6

Boarding

8.2

Comfort

8.0

Reviews

1 / 20
10.0
Excellent

John,Mar 2026

YYZ - PVR

I'm 6ft 4in. The seats don't have enough room. But was a good flight.
Porter Airlines
8.0
Very good
435 reviews
Porter Airlines
8.0
Very good
435 reviews
Check prices

Overall

8.0

Crew

8.6

Entertainment

7.0

Food

7.6

Boarding

8.2

Comfort

8.0

Reviews

1 / 20
10.0
Excellent

John,Mar 2026

YYZ - PVR

I'm 6ft 4in. The seats don't have enough room. But was a good flight.
United Airlines
7.4
Good
9,604 reviews
Porter Airlines
8.0
Very good
435 reviews
Check prices

Overall

8.0

Crew

8.6

Entertainment

7.0

Food

7.6

Boarding

8.2

Comfort

8.0

Reviews

1 / 20
10.0
Excellent

John,Mar 2026

YYZ - PVR

I'm 6ft 4in. The seats don't have enough room. But was a good flight.
WestJet
7.2
Good
3,321 reviews
Porter Airlines
8.0
Very good
435 reviews
Check prices

Overall

8.0

Crew

8.6

Entertainment

7.0

Food

7.6

Boarding

8.2

Comfort

8.0

Reviews

1 / 20
10.0
Excellent

John,Mar 2026

YYZ - PVR

I'm 6ft 4in. The seats don't have enough room. But was a good flight.
American Airlines
7.1
Good
11,601 reviews
Porter Airlines
8.0
Very good
435 reviews
Check prices

Overall

8.0

Crew

8.6

Entertainment

7.0

Food

7.6

Boarding

8.2

Comfort

8.0

Reviews

1 / 20
10.0
Excellent

John,Mar 2026

YYZ - PVR

I'm 6ft 4in. The seats don't have enough room. But was a good flight.
Air Canada
7.1
Good
10,935 reviews
Porter Airlines
8.0
Very good
435 reviews
Check prices

Overall

8.0

Crew

8.6

Entertainment

7.0

Food

7.6

Boarding

8.2

Comfort

8.0

Reviews

1 / 20
10.0
Excellent

John,Mar 2026

YYZ - PVR

I'm 6ft 4in. The seats don't have enough room. But was a good flight.

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 United Airlines and Delta fly from Toronto Pearson Intl Airport to Chicago O'Hare Intl Airport in about 2h 04m. The time it takes to get you to your destination can typically vary by up to 3h 06m. 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$ 221), American Airlines (C$ 223), and Air Canada (C$ 243) 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 cheapest airlines to fly from Toronto Pearson Intl Airport to Chicago O'Hare Intl Airport one-way?

    The cheapest airline one-way is Air Canada, with whom users have recently found tickets for as low as C$ 145. However, be on the lookout for offers from United Airlines and American Airlines, as they are both options that can get you from Toronto Pearson Intl Airport to Chicago O'Hare Intl Airport for a low price.

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

    Consider Copa Airlines (91%), EVA Air (78%) or Republic Airways (73%) 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$ 223. While the most popular route (Toronto Pearson Intl - Chicago O'Hare Intl) can be booked for C$ 281 on average, our data indicates C$ 1,278 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$ 350). Flying from Toronto Pearson Intl Airport to Chicago O'Hare Intl Airport in December is currently the most expensive (average of C$ 454). 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
Skokie
Downers Grove
Elk Grove Village
Racine
Naperville
Bolingbrook
Romeoville
Schaumburg

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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 17 April 2026.
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 17 April 2026.
AirlineCheapestAverageFlexibilityOn-time
Porter AirlinesCheapestC$ 221AverageC$ 290FlexibilityNo cancel feeOn-time52%
Search Porter Airlines flights
American AirlinesCheapestC$ 223AverageC$ 408FlexibilityNo cancel feeOn-time71%
Search American Airlines flights
Air CanadaCheapestC$ 243AverageC$ 407FlexibilityNo cancel feeOn-time67%
Search Air Canada flights
United AirlinesCheapestC$ 264AverageC$ 394FlexibilityNo cancel feeOn-time69%
Search United Airlines flights
WestJetCheapestC$ 366AverageC$ 471FlexibilityNo 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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