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Cheap flights from Toronto Pearson Intl Airport to Chicago O'Hare Intl Airport from C$ 168

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 14/4. Fares are subject to change and may not be available on all flights or dates of travel.
YYZ — ORD
29 Mar — 5 Apr1
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 May or January, booked 84 days in advance, depart on a Friday or Saturday and return on a Friday

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 27 February 2026.

Sat 6/68:05 a.m.
YYZ
-
ORD
Nonstop2h 00m
Air Canada
Wed 10/68:20 p.m.
ORD
-
YYZ
Nonstop1h 43m
Air Canada
Deal found 26/2C$ 258
Fri 10/48:50 a.m.
YYZ
-
ORD
Nonstop2h 00m
United Airlines
Sun 12/49:20 p.m.
ORD
-
YYZ
Nonstop1h 39m
United Airlines
Deal found 27/2C$ 259
Tue 7/410:15 a.m.
YYZ
-
ORD
Nonstop2h 03m
United Airlines
Tue 7/44:43 p.m.
ORD
-
YYZ
Nonstop1h 54m
United Airlines
Deal found 24/2C$ 261
Thu 26/37:00 a.m.
YYZ
-
ORD
1 stop5h 18m
Air Canada
Sun 29/38:20 p.m.
ORD
-
YYZ
Nonstop1h 43m
Air Canada
Deal found 23/2C$ 264
Thu 9/42:15 p.m.
YYZ
-
ORD
Nonstop2h 00m
Air Canada
Mon 13/43:45 p.m.
ORD
-
YYZ
1 stop7h 09m
Air Canada
Deal found 24/2C$ 265
Tue 17/38:45 a.m.
YYZ
-
ORD
Nonstop2h 05m
United Airlines
Sat 28/39:15 p.m.
ORD
-
YYZ
Nonstop1h 43m
United Airlines
Deal found 26/2C$ 266
Sat 6/66:15 a.m.
YYZ
-
ORD
1 stop5h 03m
Air Canada
Tue 9/68:20 p.m.
ORD
-
YYZ
Nonstop1h 43m
Air Canada
Deal found 26/2C$ 270
Fri 10/412:05 p.m.
YYZ
-
ORD
Nonstop2h 00m
Air Canada
Sun 12/44:15 p.m.
ORD
-
YYZ
Nonstop1h 42m
Air Canada
Deal found 24/2C$ 273
Sat 11/48:15 a.m.
YYZ
-
ORD
Nonstop1h 55m
Air Canada
Sat 18/48:40 a.m.
ORD
-
YYZ
1 stop6h 59m
Air Canada
Deal found 25/2C$ 277
Sat 6/67:00 a.m.
YYZ
-
ORD
Nonstop2h 00m
United Airlines
Wed 10/69:15 p.m.
ORD
-
YYZ
Nonstop1h 44m
United Airlines
Deal found 23/2C$ 279

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 27 February 2026.

Round-trip from

C$ 258

One-way from

C$ 168

Popular in

December

Cheapest in

May

Average price

C$ 427

Good round-trip deal

C$ 500 or less

Good one-way deal

C$ 331 or less
Air Canada
  • Air Canada
  • 6/6-10/6
  • Nonstop
  • 3h 43m total
  • Toronto to Chicago
Search Deals
Air Canada
  • Air Canada
  • 14/4
  • Nonstop
  • 1h 55m total
  • Toronto to Chicago
Search Deals
Highest demand for flights based on searches. 2% potential increase in price (C$ 14 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 February 2026
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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.
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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 27 February 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

TorontoChicago

YYZ - ORD

YYZORD

Toronto Pearson Intl

Fri 10/4

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

Nonstop2h 00m

Chicago O'Hare Intl

Sun 12/4

9:20 p.m.-11:59 p.m.

Nonstop1h 39m

C$ 272

TorontoChicago

YYZ - ORD

YYZORD

Toronto Pearson Intl

Tue 10/3

12:45 p.m.-5:01 p.m.

1 stop5h 16m

Chicago O'Hare Intl

Sun 15/3

7:10 a.m.-9:58 a.m.

Nonstop1h 48m

C$ 294

TorontoChicago

YYZ - ORD

YYZORD

Toronto Pearson Intl

Sat 4/4

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

Nonstop2h 00m

Chicago O'Hare Intl

Tue 7/4

3:35 p.m.-10:23 p.m.

1 stop5h 48m

C$ 299

TorontoChicago

YYZ - ORD

YYZORD

Toronto Pearson Intl

Mon 30/3

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

Nonstop2h 03m

Chicago O'Hare Intl

Mon 6/4

9:20 p.m.-11:59 p.m.

Nonstop1h 39m

C$ 299

TorontoChicago

YYZ - ORD

YYZORD

Toronto Pearson Intl

Sat 4/4

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

Nonstop2h 00m

Chicago O'Hare Intl

Sun 5/4

8:00 a.m.-7:02 p.m.

1 stop10h 02m

C$ 299

TorontoChicago

YYZ - ORD

YYZORD

Toronto Pearson Intl

Fri 27/3

6:45 a.m.-8:00 a.m.

Nonstop2h 15m

Chicago O'Hare Intl

Fri 3/4

6:00 a.m.-1:47 p.m.

1 stop6h 47m

C$ 299

TorontoChicago

YYZ - ORD

YYZORD

Toronto Pearson Intl

Thu 23/4

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

Nonstop2h 03m

Chicago O'Hare Intl

Sun 26/4

4:43 p.m.-7:37 p.m.

Nonstop1h 54m

C$ 299

TorontoChicago

YYZ - ORD

YYZORD

Toronto Pearson Intl

Fri 27/3

3:59 p.m.-8:17 p.m.

1 stop5h 18m

Chicago O'Hare Intl

Fri 3/4

5:40 p.m.-10:39 p.m.

1 stop3h 59m

C$ 307

TorontoChicago

YYZ - ORD

YYZORD

Toronto Pearson Intl

Fri 29/5

2:20 p.m.-8:14 p.m.

1 stop6h 54m

Chicago O'Hare Intl

Sun 31/5

7:00 a.m.-11:19 a.m.

1 stop3h 19m

C$ 307

TorontoChicago

YYZ - ORD

YYZORD

Toronto Pearson Intl

Sun 5/4

12:15 p.m.-4:43 p.m.

1 stop5h 28m

Chicago O'Hare Intl

Wed 8/4

5:40 p.m.-10:39 p.m.

1 stop3h 59m

C$ 307

Flights are sorted by cheapest round-trip flights first.

Deals found on 23/2

Showing 1-10 of 24 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 20 February 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 84 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$ 175). Flying from Toronto Pearson Intl Airport to Chicago O'Hare Intl Airport in April is currently the most expensive (average of C$ 290). 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 27 February 2026.

Unlike at noon, when flights are generally more expensive, you can save up to 41% 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 21 February 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.

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 27 February 2026.
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
420 reviews
Check prices

Boarding

8.2

Comfort

8.0

Crew

8.6

Food

7.6

Entertainment

7.0

Overall

8.0

Reviews

1 / 20
10.0
Excellent

Anonymous,Feb 2026

YYJ - YYZ

Always great! The Flight Attendants are always polite and attentive! The Polite was great and reminded us all that it was Valentine's Day!
Porter Airlines
8.0
Very good
420 reviews
Porter Airlines
8.0
Very good
420 reviews
Check prices

Boarding

8.2

Comfort

8.0

Crew

8.6

Food

7.6

Entertainment

7.0

Overall

8.0

Reviews

1 / 20
10.0
Excellent

Anonymous,Feb 2026

YYJ - YYZ

Always great! The Flight Attendants are always polite and attentive! The Polite was great and reminded us all that it was Valentine's Day!
United Airlines
7.4
Good
9,362 reviews
Porter Airlines
8.0
Very good
420 reviews
Check prices

Boarding

8.2

Comfort

8.0

Crew

8.6

Food

7.6

Entertainment

7.0

Overall

8.0

Reviews

1 / 20
10.0
Excellent

Anonymous,Feb 2026

YYJ - YYZ

Always great! The Flight Attendants are always polite and attentive! The Polite was great and reminded us all that it was Valentine's Day!
American Airlines
7.2
Good
11,367 reviews
Porter Airlines
8.0
Very good
420 reviews
Check prices

Boarding

8.2

Comfort

8.0

Crew

8.6

Food

7.6

Entertainment

7.0

Overall

8.0

Reviews

1 / 20
10.0
Excellent

Anonymous,Feb 2026

YYJ - YYZ

Always great! The Flight Attendants are always polite and attentive! The Polite was great and reminded us all that it was Valentine's Day!
WestJet
7.2
Good
3,276 reviews
Porter Airlines
8.0
Very good
420 reviews
Check prices

Boarding

8.2

Comfort

8.0

Crew

8.6

Food

7.6

Entertainment

7.0

Overall

8.0

Reviews

1 / 20
10.0
Excellent

Anonymous,Feb 2026

YYJ - YYZ

Always great! The Flight Attendants are always polite and attentive! The Polite was great and reminded us all that it was Valentine's Day!
Air Canada
7.1
Good
10,757 reviews
Porter Airlines
8.0
Very good
420 reviews
Check prices

Boarding

8.2

Comfort

8.0

Crew

8.6

Food

7.6

Entertainment

7.0

Overall

8.0

Reviews

1 / 20
10.0
Excellent

Anonymous,Feb 2026

YYJ - YYZ

Always great! The Flight Attendants are always polite and attentive! The Polite was great and reminded us all that it was Valentine's Day!

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 fly from Toronto Pearson Intl Airport to Chicago O'Hare Intl Airport in about 2h. The time it takes to get you to your destination is usually consistent. Toronto Pearson Intl Airport and Chicago O'Hare Intl Airport are separated by a distance of 702 km. Generally, flights for this route are direct.

  • 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$ 220), American Airlines (C$ 222), and Air Canada (C$ 244) 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$ 152. 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 Emirates (100%), Copa Airlines (87%) or Qatar Airways (80%) 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$ 217. While the most popular route (Toronto Pearson Intl - Chicago O'Hare Intl) can be booked for C$ 258 on average, our data indicates C$ 1,831 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$ 175). Flying from Toronto Pearson Intl Airport to Chicago O'Hare Intl Airport in April is currently the most expensive (average of C$ 290). 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 27 February 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 27 February 2026.
AirlineCheapestAverageFlexibilityOn-time
Porter AirlinesCheapestC$ 220AverageC$ 288FlexibilityNo cancel feeOn-time52%
Search Porter Airlines flights
American AirlinesCheapestC$ 222AverageC$ 412FlexibilityNo cancel feeOn-time71%
Search American Airlines flights
Air CanadaCheapestC$ 244AverageC$ 388FlexibilityNo cancel feeOn-time67%
Search Air Canada flights
United AirlinesCheapestC$ 259AverageC$ 395FlexibilityNo cancel feeOn-time69%
Search United Airlines flights
WestJetCheapestC$ 364AverageC$ 469FlexibilityNo 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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