Cheap flights from Toronto Pearson Intl Airport to Chicago O'Hare Intl Airport from C$ 194

YYZ — ORD
29 Nov — 6 Dec1
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 February 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

Fri 20/118:00 a.m. -
1 stop8h 00m
Tue 24/1110:15 a.m. -
Nonstop1h 37m
Deal found 26/10C$ 310
Fri 11/122:35 p.m. -
Nonstop2h 03m
Mon 14/1210:05 a.m. -
Nonstop1h 37m
Deal found 26/10C$ 312
Mon 16/114:30 p.m. -
Nonstop2h 13m
Mon 16/118:40 p.m. -
Nonstop1h 43m
Deal found 26/10C$ 319
Thu 17/128:05 a.m. -
Nonstop2h 13m
Thu 31/124:30 p.m. -
Nonstop1h 40m
Deal found 27/10C$ 320
Sat 14/117:44 p.m. -
1 stop5h 17m
Sun 15/117:03 a.m. -
Nonstop1h 44m
Deal found 30/10C$ 327
Sat 12/122:45 p.m. -
1 stop9h 44m
Sun 13/1211:05 a.m. -
Nonstop1h 58m
Deal found 29/10C$ 329
Tue 1/1210:00 a.m. -
1 stop6h 02m
Fri 4/1210:05 a.m. -
Nonstop1h 37m
Deal found 26/10C$ 331
Thu 17/129:00 a.m. -
1 stop7h 02m
Fri 1/14:30 p.m. -
Nonstop1h 40m
Deal found 27/10C$ 333
Thu 3/121:22 p.m. -
Nonstop2h 20m
Wed 9/123:42 p.m. -
1 stop5h 02m
Deal found 27/10C$ 334
Mon 28/122:35 p.m. -
Nonstop2h 03m
Fri 1/18:50 p.m. -
Nonstop1h 42m
Deal found 27/10C$ 341
Fri 13/117:44 p.m. -
1 stop5h 17m
Sat 14/117:03 a.m. -
Nonstop1h 44m
Deal found 28/10C$ 345

Find flight deals from Pearson Intl to O'Hare Intl

Round-trip from

C$ 310

One-way from

C$ 194

Popular in

November

Cheapest in

February

Average price

C$ 464

Good round-trip deal

C$ 659 or less

Good one-way deal

C$ 382 or less
Air Canada
  • Air Canada
  • 20/11-24/11
  • 1 total stop
  • 9h 37m total
  • Toronto to Chicago
Air Canada
  • Air Canada
  • 26/11-31/12
  • 2 total stops
  • 7h 57m total
  • Toronto to Chicago
Highest demand for flights based on searches. 7% potential increase in price (C$ 49 potential increase over avg. RT price).
Cheapest flight prices on average. 0% potential price decrease (C$ 7 potential savings vs. average RT price).
Average for round-trip flights in October 2026
Price to beat on a round-trip flight from Toronto Pearson Intl to Chicago O'Hare Intl.
Price to beat on a one-way flight from Toronto Pearson Intl to Chicago O'Hare Intl.

Cheapflights Fare Finder

 
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 Toronto Pearson Intl - ORD Chicago O'Hare Intl

YYZORD

Toronto Pearson Intl

Fri 4/12

12:15 p.m.-6:26 p.m.

1 stop7h 11m

Chicago O'Hare Intl

Wed 31/12

12:00 a.m.-1:00 a.m.

Nonstop0h 00m

C$ 224
Quickest round-trip

TorontoChicago

YYZ Toronto Pearson Intl - ORD Chicago O'Hare Intl

YYZORD

Toronto Pearson Intl

Tue 17/11

10:53 a.m.-11:57 a.m.

Nonstop2h 04m

Chicago O'Hare Intl

Wed 31/12

12:00 a.m.-1:00 a.m.

Nonstop0h 00m

C$ 248

TorontoChicago

YYZ Toronto Pearson Intl - ORD Chicago O'Hare Intl

YYZORD

Toronto Pearson Intl

Fri 27/11

7:26 p.m.-8:48 p.m.

Nonstop2h 22m

Chicago O'Hare Intl

Wed 31/12

12:00 a.m.-1:00 a.m.

Nonstop0h 00m

C$ 259

TorontoChicago

YYZ Toronto Pearson Intl - ORD Chicago O'Hare Intl

YYZORD

Toronto Pearson Intl

Wed 25/11

5:55 p.m.-7:05 p.m.

Nonstop2h 10m

Chicago O'Hare Intl

Wed 31/12

12:00 a.m.-1:00 a.m.

Nonstop0h 00m

C$ 259

TorontoChicago

YYZ Toronto Pearson Intl - ORD Chicago O'Hare Intl

YYZORD

Toronto Pearson Intl

Thu 10/12

7:26 p.m.-8:48 p.m.

Nonstop2h 22m

Chicago O'Hare Intl

Wed 31/12

12:00 a.m.-1:00 a.m.

Nonstop0h 00m

C$ 263

TorontoChicago

YYZ Toronto Pearson Intl - ORD Chicago O'Hare Intl

YYZORD

Toronto Pearson Intl

Mon 23/11

8:35 a.m.-9:44 a.m.

Nonstop2h 09m

Chicago O'Hare Intl

Wed 31/12

12:00 a.m.-1:00 a.m.

Nonstop0h 00m

C$ 263

TorontoChicago

YYZ Toronto Pearson Intl - ORD Chicago O'Hare Intl

YYZORD

Toronto Pearson Intl

Thu 10/12

9:45 a.m.-1:56 p.m.

1 stop5h 11m

Chicago O'Hare Intl

Wed 31/12

12:00 a.m.-1:00 a.m.

Nonstop0h 00m

C$ 271

TorontoChicago

YYZ Toronto Pearson Intl - ORD Chicago O'Hare Intl

YYZORD

Toronto Pearson Intl

Mon 9/11

12:15 p.m.-6:30 p.m.

1 stop7h 15m

Chicago O'Hare Intl

Wed 31/12

12:00 a.m.-1:00 a.m.

Nonstop0h 00m

C$ 271

TorontoChicago

YYZ Toronto Pearson Intl - ORD Chicago O'Hare Intl

YYZORD

Toronto Pearson Intl

Sat 20/3

7:40 p.m.-11:24 p.m.

1 stop4h 44m

Chicago O'Hare Intl

Wed 31/12

12:00 a.m.-1:00 a.m.

Nonstop0h 00m

C$ 271

TorontoChicago

YYZ Toronto Pearson Intl - ORD Chicago O'Hare Intl

YYZORD

Toronto Pearson Intl

Tue 5/1

12:55 p.m.-6:38 p.m.

1 stop6h 43m

Chicago O'Hare Intl

Wed 31/12

12:00 a.m.-1:00 a.m.

Nonstop0h 00m

C$ 273

Flights are sorted by cheapest round-trip flights first.

Deals found on 26/10

Showing 1-10 of 23 resultsSorted by cheapest first
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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

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?

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 83 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, February 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$ 393). Flying from Toronto Pearson Intl Airport to Chicago O'Hare Intl Airport in November is currently the most expensive (average of C$ 484). 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?

Unlike in the afternoon, 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?

Travelers seeking maximum savings on their Toronto Pearson Intl Airport to Chicago O'Hare Intl Airport flight should consider departing on Saturday 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?

Airfare is below average for this route at the moment.

Toronto Pearson Intl Airport to Chicago O'Hare Intl Airport flights typically cost between C$ 341 and C$ 863 in November.
The cheapest round-trip price found within the last 5 days was C$ 310 on Air Canada (20 Nov-24 Nov).

Reviews of airlines servicing O'Hare Intl

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.

Overall

8.0

Crew

8.6

Food

7.6

Boarding

8.2

Entertainment

6.9

Comfort

8.0

Reviews

1 / 20
8.0
Excellent

D,Sep 2026

YHM - YVR

The flight including check-in, checked baggage, boarding, flight and timing were great. My checked bag was delayed two days which was concerning. They did deliver it to my door though which was great.

Overall

8.0

Crew

8.6

Food

7.6

Boarding

8.2

Entertainment

6.9

Comfort

8.0

Reviews

1 / 20
8.0
Excellent

D,Sep 2026

YHM - YVR

The flight including check-in, checked baggage, boarding, flight and timing were great. My checked bag was delayed two days which was concerning. They did deliver it to my door though which was great.

Overall

8.0

Crew

8.6

Food

7.6

Boarding

8.2

Entertainment

6.9

Comfort

8.0

Reviews

1 / 20
8.0
Excellent

D,Sep 2026

YHM - YVR

The flight including check-in, checked baggage, boarding, flight and timing were great. My checked bag was delayed two days which was concerning. They did deliver it to my door though which was great.

Overall

8.0

Crew

8.6

Food

7.6

Boarding

8.2

Entertainment

6.9

Comfort

8.0

Reviews

1 / 20
8.0
Excellent

D,Sep 2026

YHM - YVR

The flight including check-in, checked baggage, boarding, flight and timing were great. My checked bag was delayed two days which was concerning. They did deliver it to my door though which was great.

Overall

8.0

Crew

8.6

Food

7.6

Boarding

8.2

Entertainment

6.9

Comfort

8.0

Reviews

1 / 20
8.0
Excellent

D,Sep 2026

YHM - YVR

The flight including check-in, checked baggage, boarding, flight and timing were great. My checked bag was delayed two days which was concerning. They did deliver it to my door though which was great.

Overall

8.0

Crew

8.6

Food

7.6

Boarding

8.2

Entertainment

6.9

Comfort

8.0

Reviews

1 / 20
8.0
Excellent

D,Sep 2026

YHM - YVR

The flight including check-in, checked baggage, boarding, flight and timing were great. My checked bag was delayed two days which was concerning. They did deliver it to my door though which was great.

Related info for your journey

  • 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 5h 14m. The time it takes to get you to your destination can typically vary by up to 03m. 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, American Airlines (C$ 263), United Airlines (C$ 300), and Air Canada (C$ 303) offers the cheapest pricing from Toronto Pearson Intl Airport to Chicago O'Hare Intl Airport. These flights start at 40% 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 United Airlines, with whom users have recently found tickets for as low as C$ 158. However, be on the lookout for offers from Air Canada 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 Sun Country Air (100%), Copa Airlines (86%) or Republic Airways (82%) 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$ 272. While the most popular route (Toronto Pearson Intl - Chicago O'Hare Intl) can be booked for C$ 340 on average, our data indicates C$ 1,322 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, February 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$ 393). Flying from Toronto Pearson Intl Airport to Chicago O'Hare Intl Airport in November is currently the most expensive (average of C$ 484). 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
Schaumburg
Northbrook
Des Plaines
Racine
Rockford
Naperville
Elk Grove Village
Skokie

Browse thousands of different options on Cheapflights for your next trip

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

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

AirlineCheapestAverageFlexibilityOn-time
American AirlinesCheapestC$ 263AverageC$ 473FlexibilityNo cancel feeOn-time71%
Search American Airlines flights
United AirlinesCheapestC$ 300AverageC$ 420FlexibilityNo cancel feeOn-time69%
Search United Airlines flights
Air CanadaCheapestC$ 303AverageC$ 456FlexibilityNo cancel feeOn-time67%
Search Air Canada flights
Porter AirlinesCheapestC$ 305AverageC$ 519FlexibilityNo cancel feeOn-time52%
Search Porter Airlines flights
WestJetCheapestC$ 387AverageC$ 496FlexibilityNo cancel feeOn-time60%
Search WestJet flights

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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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