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Cheap flights from Toronto Pearson Intl Airport to Chicago from C$ 148

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 10/9. Fares are subject to change and may not be available on all flights or dates of travel.
YYZ — CHI
17 Jun — 24 Jun1
1 adult

Cheapflights Tip: The best prices from Toronto Pearson Intl to Chicago are usually found in May or June, booked 88 days in advance, depart on a Friday or Saturday and return on a Saturday

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 12 June 2025.

Round-trip from

C$ 227

One-way from

C$ 152

Popular in

December

Cheapest in

May

Average price

C$ 358

Good round-trip deal

C$ 442 or less

Good one-way deal

C$ 257 or less
Air Canada
  • Air Canada
  • 25/8-11/9
  • Nonstop
  • 3h 37m total
  • Toronto to Chicago
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United Airlines
  • United Airlines
  • 11/9
  • Nonstop
  • 1h 55m total
  • Toronto to Chicago
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Highest demand for flights based on searches. 8% potential increase in price (C$ 47 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 June 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 12 June 2025.

Wed 10/98:15 a.m.YYZ - ORD
Nonstop1h 53mAir Canada
Fri 12/96:20 p.m.ORD - YYZ
Nonstop1h 42mAir Canada
Deal found 12/6C$ 226
Thu 4/92:30 p.m.YYZ - ORD
1 stop6h 18mUnited Airlines
Wed 10/97:15 a.m.ORD - YYZ
1 stop5h 32mUnited Airlines
Deal found 10/6C$ 235
Tue 30/93:45 p.m.YYZ - ORD
1 stop5h 42mAmerican Airlines
Thu 2/109:48 a.m.ORD - YYZ
1 stop6h 27mAmerican Airlines
Deal found 10/6C$ 261
Thu 3/77:00 a.m.YYZ - ORD
Nonstop1h 59mLufthansa
Mon 7/79:14 p.m.ORD - YYZ
Nonstop1h 44mLufthansa
Deal found 11/6C$ 286
Sun 12/1012:15 p.m.YYZ - ORD
1 stop7h 23mDelta
Sat 18/105:45 p.m.ORD - YYZ
1 stop4h 13mDelta
Deal found 11/6C$ 291
Sat 4/1012:15 p.m.YYZ - MDW
1 stop7h 21mDelta
Wed 15/109:30 a.m.MDW - YYZ
1 stop6h 53mDelta
Deal found 11/6C$ 291
Fri 25/74:00 p.m.YYZ - ORD
1 stop6h 30mMultiple Airlines
Fri 1/86:20 p.m.ORD - YYZ
Nonstop1h 44mMultiple Airlines
Deal found 10/6C$ 340
Mon 21/77:25 p.m.YYZ - ORD
1 stop12h 58mPorter Airlines
Sun 27/75:55 p.m.ORD - YYZ
Nonstop1h 49mPorter Airlines
Deal found 12/6C$ 358
Tue 22/76:30 p.m.YYZ - MDW
2 stops16h 15mWestJet
Tue 29/71:46 p.m.MDW - YYZ
2 stops15h 28mWestJet
Deal found 11/6C$ 494

Cheapflights Fare Finder

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 12 June 2025.
Use the filters below to find and compare flights from Toronto Pearson Intl Airport to Chicago that are best for you.

Fly from

Pearson Intl

Fly to

Chicago

Route

Depart

Return

Price

TorontoChicago

YYZ - ORD

YYZORD

Toronto Pearson Intl

Wed 10/9

8:15 a.m.-9:08 a.m.

Nonstop1h 53m

Chicago O'Hare Intl

Fri 12/9

6:20 p.m.-9:02 p.m.

Nonstop1h 42m

C$ 226

TorontoChicago

YYZ - ORD

YYZORD

Toronto Pearson Intl

Thu 4/9

2:30 p.m.-7:48 p.m.

1 stop6h 18m

Chicago O'Hare Intl

Wed 10/9

7:15 a.m.-1:47 p.m.

1 stop5h 32m

C$ 235

TorontoChicago

YYZ - ORD

YYZORD

Toronto Pearson Intl

Tue 30/9

3:45 p.m.-8:27 p.m.

1 stop5h 42m

Chicago O'Hare Intl

Thu 2/10

9:48 a.m.-5:15 p.m.

1 stop6h 27m

C$ 261

TorontoChicago

YYZ - ORD

YYZORD

Toronto Pearson Intl

Thu 3/7

7:00 a.m.-7:59 a.m.

Nonstop1h 59m

Chicago O'Hare Intl

Mon 7/7

9:14 p.m.-11:58 p.m.

Nonstop1h 44m

C$ 286

TorontoChicago

YYZ - ORD

YYZORD

Toronto Pearson Intl

Sun 12/10

12:15 p.m.-6:38 p.m.

1 stop7h 23m

Chicago O'Hare Intl

Sat 18/10

5:45 p.m.-10:58 p.m.

1 stop4h 13m

C$ 291

TorontoChicago

YYZ - MDW

YYZMDW

Toronto Pearson Intl

Sat 4/10

12:15 p.m.-6:36 p.m.

1 stop7h 21m

Chicago Midway

Wed 15/10

9:30 a.m.-5:23 p.m.

1 stop6h 53m

C$ 291

TorontoChicago

YYZ - ORD

YYZORD

Toronto Pearson Intl

Fri 25/7

4:00 p.m.-9:30 p.m.

1 stop6h 30m

Chicago O'Hare Intl

Fri 1/8

6:20 p.m.-9:04 p.m.

Nonstop1h 44m

C$ 340

TorontoChicago

YYZ - ORD

YYZORD

Toronto Pearson Intl

Mon 21/7

7:25 p.m.-7:23 a.m.

1 stop12h 58m

Chicago O'Hare Intl

Sun 27/7

5:55 p.m.-8:44 p.m.

Nonstop1h 49m

C$ 358

TorontoChicago

YYZ - MDW

YYZMDW

Toronto Pearson Intl

Thu 17/7

1:04 p.m.-5:39 p.m.

1 stop5h 35m

Chicago Midway

Thu 24/7

6:20 p.m.-10:58 p.m.

1 stop3h 38m

C$ 483

TorontoChicago

YYZ - MDW

YYZMDW

Toronto Pearson Intl

Tue 22/7

6:30 p.m.-9:45 a.m.

2 stops16h 15m

Chicago Midway

Tue 29/7

1:46 p.m.-6:14 a.m.

2 stops15h 28m

C$ 494

Flights are sorted by cheapest round-trip flights first.

Deals found on 12/6

Showing 1-10 of 22 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.

Cheapflights Insights

Everything you need to know about your flight from Toronto Pearson Intl Airport to Chicago

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 9 June 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$ 352). 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 12 June 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 62% 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 12 June 2025.

The most flights from YYZ to CHI are scheduled on a Thursday (60 on average). You will have fewer flight options on Saturday, which is when the least amount of flights are scheduled (33 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 12 June 2025.
To help decide which airline to fly from Toronto to Chicago, see what other customers have to say about Delta, KLM and United 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
7,950 reviews
Check prices

Entertainment

7.9

Boarding

8.2

Comfort

7.9

Food

7.3

Overall

8.0

Crew

8.5

Reviews

1 / 20
10.0
Excellent

Kim,May 2025

PIH - SLC

This trip was fine even with delay I had plenty of time to get connection flight!
Delta
8.0
Very good
7,950 reviews
Delta
8.0
Very good
7,950 reviews
Check prices

Entertainment

7.9

Boarding

8.2

Comfort

7.9

Food

7.3

Overall

8.0

Crew

8.5

Reviews

1 / 20
10.0
Excellent

Kim,May 2025

PIH - SLC

This trip was fine even with delay I had plenty of time to get connection flight!
KLM
7.8
Good
1,358 reviews
Delta
8.0
Very good
7,950 reviews
Check prices

Entertainment

7.9

Boarding

8.2

Comfort

7.9

Food

7.3

Overall

8.0

Crew

8.5

Reviews

1 / 20
10.0
Excellent

Kim,May 2025

PIH - SLC

This trip was fine even with delay I had plenty of time to get connection flight!
United Airlines
7.4
Good
8,790 reviews
Delta
8.0
Very good
7,950 reviews
Check prices

Entertainment

7.9

Boarding

8.2

Comfort

7.9

Food

7.3

Overall

8.0

Crew

8.5

Reviews

1 / 20
10.0
Excellent

Kim,May 2025

PIH - SLC

This trip was fine even with delay I had plenty of time to get connection flight!
American Airlines
7.2
Good
10,000 reviews
Delta
8.0
Very good
7,950 reviews
Check prices

Entertainment

7.9

Boarding

8.2

Comfort

7.9

Food

7.3

Overall

8.0

Crew

8.5

Reviews

1 / 20
10.0
Excellent

Kim,May 2025

PIH - SLC

This trip was fine even with delay I had plenty of time to get connection flight!
WestJet
7.2
Good
2,868 reviews
Delta
8.0
Very good
7,950 reviews
Check prices

Entertainment

7.9

Boarding

8.2

Comfort

7.9

Food

7.3

Overall

8.0

Crew

8.5

Reviews

1 / 20
10.0
Excellent

Kim,May 2025

PIH - SLC

This trip was fine even with delay I had plenty of time to get connection flight!

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$ 227, 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 United Airlines and American Airlines - these airlines can fly you to your destination from C$ 235 and C$ 261, respectively. Users have found that Air Canada is 42% 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$ 152 on United Airlines. Other airlines that offer cheap prices include Air Canada from C$ 154 and American Airlines from C$ 176 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: SkyWest Airlines (98%), Republic Airways (92%), Copa Airlines( 91%).

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

    On average you can expect to pay C$ 2,717 for a flight from Toronto Pearson Intl Airport to Chicago. The cheapest flight overall is C$ 180 while the most popular route, (Toronto Pearson Intl - Chicago O'Hare Intl) is currently priced at C$ 201.

  • 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$ 352). 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 12 June 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 12 June 2025.
AirlineCheapestAverageFlexibilityOn-time
Porter AirlinesCheapestC$ 232AverageC$ 360FlexibilityNo cancel feeOn-time52%
Search Porter Airlines flights
American AirlinesCheapestC$ 278AverageC$ 512FlexibilityNo cancel feeOn-time71%
Search American Airlines flights
Air CanadaCheapestC$ 283AverageC$ 393FlexibilityNo cancel feeOn-time67%
Search Air Canada flights
United AirlinesCheapestC$ 302AverageC$ 441FlexibilityNo cancel feeOn-time69%
Search United Airlines flights
WestJetCheapestC$ 423AverageC$ 631FlexibilityNo 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?

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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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