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Cheap flights from Toronto Pearson Intl Airport to Chicago from C$ 185

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 21/4. Fares are subject to change and may not be available on all flights or dates of travel.
YYZ — CHI
25 Feb — 4 Mar1
1 adult

The best prices from Toronto Pearson Intl to Chicago are usually found in April or July, booked 88 days in advance, depart on a Friday or Saturday and return on a Tuesday

Cheap flight deals from Pearson Intl to Chicago

Discover tips and strategies to find the most affordable flight options for your journey from Pearson Intl (YYZ) to Chicago (CHI). 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 20 February 2025.

Round-trip from

C$ 314

One-way from

C$ 186

Popular in

December

Cheapest in

April

Average price

C$ 439

Good round-trip deal

C$ 471 or less

Good one-way deal

C$ 245 or less
Air Canada
  • Air Canada
  • 26/3-29/3
  • Nonstop
  • 3h 45m total
  • Toronto to Chicago
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17/3
  • 17/3
  • 1 total stop
  • 24h 13m total
  • Toronto to Chicago
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Highest demand for flights based on searches. 4% potential increase in price (C$ 29 potential increase over avg. RT price).
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Cheapest flight prices on average. 1% potential price decrease (C$ 10 potential savings vs. average RT price).
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Average for round-trip flights in February 2025
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Price to beat on a round-trip flight from Toronto Pearson Intl to Chicago (CHI).
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Price to beat on a one-way flight from Toronto Pearson Intl to Chicago (CHI).
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Find flight deals from Pearson Intl to Chicago

Cheapest flights from Pearson Intl to Chicago
Explore the most affordable flight options available from Pearson Intl to Chicago. Find the lowest fares from popular airlines and budget airlines, with prices last updated on 20 February 2025.

Sat 24/54:00 p.m.YYZ - ORD
1 stop5h 12mAir Canada
Sat 7/610:40 a.m.ORD - YYZ
1 stop6h 18mAir Canada
Deal found 20/2C$ 290
Thu 13/39:00 p.m.YYZ - ORD
Nonstop2h 06mMultiple Airlines
Thu 10/47:10 a.m.ORD - YYZ
Nonstop1h 48mMultiple Airlines
Deal found 19/2C$ 315
Sat 12/46:30 a.m.YYZ - MDW
1 stop13h 03mWestJet
Mon 21/41:16 p.m.MDW - YYZ
1 stop21h 18mWestJet
Deal found 20/2C$ 347
Sat 26/412:45 p.m.YYZ - ORD
1 stop4h 59mUnited Airlines
Wed 30/411:15 a.m.ORD - YYZ
1 stop4h 54mUnited Airlines
Deal found 20/2C$ 349
Thu 20/310:20 a.m.YYZ - MDW
1 stop3h 16mDelta
Mon 24/32:55 p.m.MDW - YYZ
1 stop6h 43mDelta
Deal found 19/2C$ 351
Fri 18/49:45 a.m.YYZ - ORD
1 stop7h 23mDelta
Sat 19/45:00 p.m.ORD - YYZ
1 stop4h 55mDelta
Deal found 20/2C$ 359
Fri 28/26:15 a.m.YYZ - ORD
1 stop10h 54mWestJet
Sun 2/32:35 p.m.ORD - YYZ
1 stop7h 17mWestJet
Deal found 20/2C$ 395
Thu 20/34:10 p.m.YYZ - ORD
1 stop4h 56mAmerican Airlines
Mon 24/36:30 p.m.ORD - YYZ
Nonstop1h 45mAmerican Airlines
Deal found 19/2C$ 439
Sat 1/37:10 a.m.YYZ - MDW
1 stop13h 19mMultiple Airlines
Tue 4/38:30 a.m.MDW - YYZ
1 stop10h 00mMultiple Airlines
Deal found 18/2C$ 443

Find flights from Pearson Intl to Chicago within your budget

Customize your flight search to find flights from Pearson Intl to Chicago 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 20 February 2025.

Fly from

Pearson Intl

Fly to

Chicago

Route

Depart

Return

Price

TorontoChicago

YYZ - ORD

YYZORD

Toronto Pearson Intl

Sat 24/5

4:00 p.m.-8:12 p.m.

1 stop5h 12m

Chicago O'Hare Intl

Sat 7/6

10:40 a.m.-5:58 p.m.

1 stop6h 18m

C$ 290

TorontoChicago

YYZ - ORD

YYZORD

Toronto Pearson Intl

Thu 13/3

9:00 p.m.-10:06 p.m.

Nonstop2h 06m

Chicago O'Hare Intl

Thu 10/4

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

Nonstop1h 48m

C$ 315

TorontoChicago

YYZ - MDW

YYZMDW

Toronto Pearson Intl

Sat 12/4

6:30 a.m.-6:33 p.m.

1 stop13h 03m

Chicago Midway

Sun 20/4

10:20 a.m.-11:34 a.m.

1 stop24h 14m

C$ 347

TorontoChicago

YYZ - ORD

YYZORD

Toronto Pearson Intl

Sat 26/4

12:45 p.m.-4:44 p.m.

1 stop4h 59m

Chicago O'Hare Intl

Wed 30/4

11:15 a.m.-5:09 p.m.

1 stop4h 54m

C$ 349

TorontoChicago

YYZ - MDW

YYZMDW

Toronto Pearson Intl

Thu 20/3

10:20 a.m.-12:36 p.m.

1 stop3h 16m

Chicago Midway

Mon 24/3

2:55 p.m.-10:38 p.m.

1 stop6h 43m

C$ 351

TorontoChicago

YYZ - ORD

YYZORD

Toronto Pearson Intl

Fri 18/4

9:45 a.m.-4:08 p.m.

1 stop7h 23m

Chicago O'Hare Intl

Sat 19/4

5:00 p.m.-10:55 p.m.

1 stop4h 55m

C$ 359

TorontoChicago

YYZ - ORD

YYZORD

Toronto Pearson Intl

Fri 28/3

5:15 p.m.-8:44 p.m.

1 stop4h 29m

Chicago O'Hare Intl

Mon 31/3

6:15 p.m.-10:38 p.m.

1 stop3h 23m

C$ 408

TorontoChicago

YYZ - ORD

YYZORD

Toronto Pearson Intl

Thu 20/3

4:10 p.m.-8:06 p.m.

1 stop4h 56m

Chicago O'Hare Intl

Mon 24/3

6:30 p.m.-9:15 p.m.

Nonstop1h 45m

C$ 439

TorontoChicago

YYZ - MDW

YYZMDW

Toronto Pearson Intl

Sat 1/3

7:10 a.m.-7:29 p.m.

1 stop13h 19m

Chicago Midway

Tue 4/3

8:30 a.m.-7:30 p.m.

1 stop10h 00m

C$ 443

TorontoChicago

YYZ - ORD

YYZORD

Toronto Pearson Intl

Mon 21/4

10:15 a.m.-12:23 a.m.

1 stop15h 08m

C$ 185

Flights are sorted by cheapest round-trip flights first.

Deals found on 20/2

Showing 1-10 of 20 results
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Best time to book a flight from Pearson Intl to Chicago

Have a flexible travel schedule? Discover the best time to fly to Chicago 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.

Travel insights for flights from Pearson Intl to Chicago

Get recent, data-driven insights about flights from Pearson Intl to Chicago including ideal travel times, pricing trends, and more.

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

Use this chart to determine the optimal time to book a round-trip flight from Pearson Intl to Chicago. Price data was last updated on 14 February 2025.

Booking 88 days in advance of your planned departure date is, on average, the best time to get cheap flights from Toronto Pearson Intl Airport to Chicago. The general trend is that the closer you book to the departure date, the more expensive your flight will be.

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

Currently, January is the cheapest month in which you can book a flight from Toronto Pearson Intl Airport to Chicago (average of C$ 261). Flying from Toronto Pearson Intl Airport to Chicago in March is currently the most expensive (average of C$ 355). 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 CHI?

Find hourly flight availability from Pearson Intl to Chicago. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated 20 February 2025.

It’s optimal to fly from Toronto Pearson Intl Airport to Chicago in the evening. By choosing this option you can save up to 64% on the cost of your flight, compared to a flight in the afternoon.

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

Use this chart to determine the cheapest time to fly round-trip from Pearson Intl to Chicago. Price data was last updated on 16 December 2024.

Travelers seeking maximum savings on their Toronto Pearson Intl Airport to Chicago flight should consider departing on Friday evenings when fares are most often at their lowest. Wednesday afternoons flights should be avoided if possible as fares are typically the most expensive at this time.

Weekly flight availability from Toronto Pearson Intl Airport to Chicago

Explore weekly flight availability from Pearson Intl to Chicago. Discover flights operating on different days of the week, giving you the flexibility to choose a travel day that best fits your plans. Compare info to find the most convenient option for your journey. Data last updated 20 February 2025.

The most flights from YYZ to CHI are scheduled on a Thursday (53 on average). You will have fewer flight options on Saturday, which is when the least amount of flights are scheduled (38 on average).

Rainfall in Chicago by month

Plan your trip to Chicago by taking into account the average rainfall totals by month.

In terms of precipitation, rainfall in Chicago ranges from 43.0 - 125.0 mm per month. August is typically the wettest month, when rainfall can reach 125.0 mm. January is typically the driest time to visit Chicago when rainfall is around 43.0 mm.

Temperature in Chicago by month

Plan your trip to Chicago by taking into account the average temperature totals by month.

If weather is an important factor for your trip to Chicago, use this chart to help with planning. For those seeking warmer temperatures, July is the ideal time of year to visit, when temperatures reach an average of 23.0 C. Travellers hoping to avoid the cold should look outside of January, when temperatures are typically at their lowest (around -5.0 C).

Reviews of airlines servicing Chicago

Get insights into the airlines that provide service to Chicago. 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 Chicago. Reviews last updated 20 February 2025.
To help decide which airline to fly from Toronto to Chicago, see what other customers have to say about Delta, KLM and Austrian Airlines. You can also see how each airline stacks up in terms of entertainment options, comfort, food, crew/service, and boarding process.
Delta
8.0
Very good
8,219 reviews
Check prices

Crew

8.5

Overall

8.0

Boarding

8.2

Entertainment

7.9

Food

7.3

Comfort

8.0

Reviews

1 / 20

10.0
Excellent

Aaron,Oct 2024

TUS - LAX

Delta has consistently been the best U.S. airline for my travels and this flight was no exception

Delta
8.0
Very good
8,219 reviews
Delta
8.0
Very good
8,219 reviews
Check prices

Crew

8.5

Overall

8.0

Boarding

8.2

Entertainment

7.9

Food

7.3

Comfort

8.0

Reviews

1 / 20

10.0
Excellent

Aaron,Oct 2024

TUS - LAX

Delta has consistently been the best U.S. airline for my travels and this flight was no exception

KLM
7.8
Good
1,333 reviews
Delta
8.0
Very good
8,219 reviews
Check prices

Crew

8.5

Overall

8.0

Boarding

8.2

Entertainment

7.9

Food

7.3

Comfort

8.0

Reviews

1 / 20

10.0
Excellent

Aaron,Oct 2024

TUS - LAX

Delta has consistently been the best U.S. airline for my travels and this flight was no exception

Austrian Airlines
7.6
Good
773 reviews
Delta
8.0
Very good
8,219 reviews
Check prices

Crew

8.5

Overall

8.0

Boarding

8.2

Entertainment

7.9

Food

7.3

Comfort

8.0

Reviews

1 / 20

10.0
Excellent

Aaron,Oct 2024

TUS - LAX

Delta has consistently been the best U.S. airline for my travels and this flight was no exception

United Airlines
7.4
Good
8,765 reviews
Delta
8.0
Very good
8,219 reviews
Check prices

Crew

8.5

Overall

8.0

Boarding

8.2

Entertainment

7.9

Food

7.3

Comfort

8.0

Reviews

1 / 20

10.0
Excellent

Aaron,Oct 2024

TUS - LAX

Delta has consistently been the best U.S. airline for my travels and this flight was no exception

American Airlines
7.2
Good
10,000 reviews
Delta
8.0
Very good
8,219 reviews
Check prices

Crew

8.5

Overall

8.0

Boarding

8.2

Entertainment

7.9

Food

7.3

Comfort

8.0

Reviews

1 / 20

10.0
Excellent

Aaron,Oct 2024

TUS - LAX

Delta has consistently been the best U.S. airline for my travels and this flight was no exception

Related info for your journey

Find useful and relevant information for your journey from Pearson Intl to Chicago. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.

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

    Currently priced at C$ 322, Air Canada will fly you from Toronto Pearson Intl Airport to Chicago and back. In addition to Air Canada, many other airlines offer competitively priced options for your trip. Search Cheapflights for deals from WestJet and United Airlines - these airlines can fly you to your destination from C$ 347 and C$ 349, respectively. Users have found that Air Canada is 23% cheaper than the other options available to this destination.

  • What are the cheapest airlines to fly from Toronto Pearson Intl Airport to Chicago one-way?

    One-way options have recently been found by users for as low as C$ 192 on Air Canada. Other airlines that offer cheap prices include United Airlines from C$ 193 and American Airlines from C$ 212 one-way.

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

    Before booking your flight to Chicago from Toronto Pearson Intl Airport, check out the most reliable airlines to get you to your destination on time: Emirates (90%), Republic Airways (89%), ANA( 84%).

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

    On average you can expect to pay C$ 1,415 for a flight from Toronto Pearson Intl Airport to Chicago. The cheapest flight overall is C$ 189 while the most popular route, (Toronto Pearson Intl - Chicago O'Hare Intl) is currently priced at C$ 304.

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

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

  • How can I find direct flights from Pearson Intl to Chicago?

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

  • Can I find deals for business class flights from Pearson Intl to Chicago?

    Yes. Cheapflights offers flight deals from Pearson Intl to Chicago 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?

    Currently, January is the cheapest month in which you can book a flight from Toronto Pearson Intl Airport to Chicago (average of C$ 261). Flying from Toronto Pearson Intl Airport to Chicago in March is currently the most expensive (average of C$ 355). 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

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Fly from Pearson Intl to Chicago on these airlines

Choose from the following airlines for your flight from Pearson Intl to Chicago. Flights are based on user searches made on Cheapflights and were last updated on 20 February 2025.
Air Canada flights from Toronto Pearson Intl to Chicago
United Airlines flights from Toronto Pearson Intl to Chicago

Top 5 airlines flying from Pearson Intl to Chicago

Discover the top 5 airlines that operate flights from Pearson Intl to Chicago. 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 20 February 2025.
AirlineCheapestAverageFlexibilityOn-time
Porter AirlinesCheapestC$ 267AverageC$ 359FlexibilityNo cancel feeOn-time52%
Search Porter Airlines flights
Air CanadaCheapestC$ 322AverageC$ 416FlexibilityNo cancel feeOn-time67%
Search Air Canada flights
United AirlinesCheapestC$ 350AverageC$ 463FlexibilityNo cancel feeOn-time69%
Search United Airlines flights
American AirlinesCheapestC$ 354AverageC$ 541FlexibilityNo cancel feeOn-time71%
Search American Airlines flights
WestJetCheapestC$ 450AverageC$ 611FlexibilityNo cancel feeOn-time60%
Search WestJet flights

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How does Cheapflights help users find flights from Pearson Intl to Chicago?

Cheapflights makes it easy to find Pearson Intl to Chicago flights by helping our users search from 900+ travel sites for deals. We also provide you with filters for cabin, price, airline, airports, number of stops, and many more to narrow down that perfect flight.

Why should you use Cheapflights to find cheap flight tickets from Pearson Intl to Chicago?

Cheapflights simply makes it quick and affordable to book flights from Pearson Intl to Chicago by bringing together all flight options from hundreds of airlines and agencies online — and put it in one place for you to choose from. Plus, Cheapflights is 100% free to use for all.

Can Cheapflights find flights from Pearson Intl to Chicago with no change fees?

Certainly. Search results for flights to Chicago from Pearson Intl shown to you on Cheapflights can be narrowed down with different useful search filters, which includes flexible booking options.

Can Cheapflights notify me if prices for flights from Pearson Intl to Chicago become cheaper?

Yes, and it’s super simple to set up. Click the bell icon next to the flight deals above and provide a valid email address to enable Price Alerts. That’s it!

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