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Cheap flights from Toronto Pearson Intl Airport to Chicago from C$ 178

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 22/4. Fares are subject to change and may not be available on all flights or dates of travel.
YYZ — CHI
30 mar. — 6 abr.1
1 adult

Cheapflights Tip: 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 25 marzo 2025.

Round-trip from

C$ 276

One-way from

C$ 178

Popular in

December

Cheapest in

April

Average price

C$ 424

Good round-trip deal

C$ 430 or less

Good one-way deal

C$ 306 or less
Air Canada
  • Air Canada
  • 16/4-23/4
  • Nonstop
  • 3h 41m total
  • Toronto to Chicago
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Air Canada
  • Air Canada
  • 22/4
  • Nonstop
  • 2h 05m total
  • Toronto to Chicago
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Highest demand for flights based on searches. 5% potential increase in price (C$ 32 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 March 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 25 marzo 2025.

mié. 16/49:00 p.m.YYZ - ORD
Nonstop2h 06mAir Canada
mié. 23/49:40 a.m.ORD - YYZ
Nonstop1h 35mAir Canada
Deal found 23/3C$ 276
mar. 6/512:54 p.m.YYZ - MDW
1 stop5h 25mDelta
mié. 7/56:25 p.m.MDW - YYZ
1 stop3h 33mDelta
Deal found 24/3C$ 319
mié. 16/49:45 a.m.YYZ - ORD
1 stop7h 26mDelta
mar. 22/44:15 p.m.ORD - YYZ
1 stop6h 00mDelta
Deal found 25/3C$ 321
vie. 13/68:15 a.m.YYZ - ORD
Nonstop1h 54mUnited Airlines
dom. 29/610:00 a.m.ORD - YYZ
Nonstop1h 44mUnited Airlines
Deal found 24/3C$ 325
mié. 30/41:00 p.m.YYZ - ORD
Nonstop2h 07mMultiple Airlines
mié. 7/59:35 a.m.ORD - YYZ
Nonstop1h 40mMultiple Airlines
Deal found 23/3C$ 344
vie. 18/46:20 p.m.YYZ - ORD
Nonstop1h 55mAmerican Airlines
mar. 22/46:04 a.m.ORD - YYZ
1 stop4h 51mAmerican Airlines
Deal found 24/3C$ 378
sáb. 26/412:54 p.m.YYZ - MDW
1 stop5h 25mWestJet
lun. 28/410:20 a.m.MDW - YYZ
1 stop11h 55mWestJet
Deal found 24/3C$ 407
mié. 16/46:08 p.m.YYZ - ORD
1 stop3h 37mWestJet
lun. 21/46:15 p.m.ORD - YYZ
1 stop13h 40mWestJet
Deal found 25/3C$ 427
dom. 6/46:30 a.m.YYZ - MDW
2 stops23h 50mMultiple Airlines
mié. 9/412:46 p.m.MDW - YYZ
1 stop29h 44mMultiple Airlines
Deal found 24/3C$ 467

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 25 marzo 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

mié. 16/4

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

Nonstop2h 06m

Chicago O'Hare Intl

mié. 23/4

9:40 a.m.-12:15 p.m.

Nonstop1h 35m

C$ 276

TorontoChicago

YYZ - MDW

YYZMDW

Toronto Pearson Intl

mar. 6/5

12:54 p.m.-5:19 p.m.

1 stop5h 25m

Chicago Midway

mié. 7/5

6:25 p.m.-10:58 p.m.

1 stop3h 33m

C$ 319

TorontoChicago

YYZ - ORD

YYZORD

Toronto Pearson Intl

mié. 16/4

9:45 a.m.-4:11 p.m.

1 stop7h 26m

Chicago O'Hare Intl

mar. 22/4

4:15 p.m.-11:15 p.m.

1 stop6h 00m

C$ 321

TorontoChicago

YYZ - ORD

YYZORD

Toronto Pearson Intl

vie. 13/6

8:15 a.m.-9:09 a.m.

Nonstop1h 54m

Chicago O'Hare Intl

dom. 29/6

10:00 a.m.-12:44 p.m.

Nonstop1h 44m

C$ 325

TorontoChicago

YYZ - ORD

YYZORD

Toronto Pearson Intl

mié. 30/4

1:00 p.m.-2:07 p.m.

Nonstop2h 07m

Chicago O'Hare Intl

mié. 7/5

9:35 a.m.-12:15 p.m.

Nonstop1h 40m

C$ 344

TorontoChicago

YYZ - ORD

YYZORD

Toronto Pearson Intl

vie. 18/4

6:20 p.m.-7:15 p.m.

Nonstop1h 55m

Chicago O'Hare Intl

mar. 22/4

6:04 a.m.-11:55 a.m.

1 stop4h 51m

C$ 378

TorontoChicago

YYZ - MDW

YYZMDW

Toronto Pearson Intl

sáb. 26/4

12:54 p.m.-5:19 p.m.

1 stop5h 25m

Chicago Midway

lun. 28/4

10:20 a.m.-11:15 p.m.

1 stop11h 55m

C$ 407

TorontoChicago

YYZ - ORD

YYZORD

Toronto Pearson Intl

mié. 16/4

6:08 p.m.-8:45 p.m.

1 stop3h 37m

Chicago O'Hare Intl

lun. 21/4

6:15 p.m.-8:55 a.m.

1 stop13h 40m

C$ 427

TorontoChicago

YYZ - MDW

YYZMDW

Toronto Pearson Intl

dom. 6/4

6:30 a.m.-5:20 a.m.

2 stops23h 50m

Chicago Midway

mié. 9/4

12:46 p.m.-7:30 p.m.

1 stop29h 44m

C$ 467

TorontoChicago

YYZ - ORD

YYZORD

Toronto Pearson Intl

dom. 13/7

12:00 p.m.-12:54 p.m.

Nonstop1h 54m

C$ 181

Flights are sorted by cheapest round-trip flights first.

Deals found on 24/3

Showing 1-10 of 18 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 21 March 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 25 marzo 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 25 marzo 2025.

The most flights from YYZ to CHI are scheduled on a Monday (54 on average). You will have fewer flight options on Tuesday, which is when the least amount of flights are scheduled (42 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 25 marzo 2025.
To help decide which airline to fly from Toronto to Chicago, see what other customers have to say about Delta, United Airlines and American 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
7,890 reviews
Check prices

Entertainment

7.9

Crew

8.5

Comfort

8.0

Boarding

8.2

Food

7.3

Overall

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
7,890 reviews
Delta
8.0
Very good
7,890 reviews
Check prices

Entertainment

7.9

Crew

8.5

Comfort

8.0

Boarding

8.2

Food

7.3

Overall

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
8,605 reviews
Delta
8.0
Very good
7,890 reviews
Check prices

Entertainment

7.9

Crew

8.5

Comfort

8.0

Boarding

8.2

Food

7.3

Overall

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
7,890 reviews
Check prices

Entertainment

7.9

Crew

8.5

Comfort

8.0

Boarding

8.2

Food

7.3

Overall

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
WestJet
7.2
Good
2,785 reviews
Delta
8.0
Very good
7,890 reviews
Check prices

Entertainment

7.9

Crew

8.5

Comfort

8.0

Boarding

8.2

Food

7.3

Overall

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
Air Canada
7.0
Good
8,952 reviews
Delta
8.0
Very good
7,890 reviews
Check prices

Entertainment

7.9

Crew

8.5

Comfort

8.0

Boarding

8.2

Food

7.3

Overall

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$ 276, 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 British Airways and Delta - these airlines can fly you to your destination from C$ 288 and C$ 319, respectively. Users have found that Air Canada is 35% 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$ 178 on Air Canada. Other airlines that offer cheap prices include Delta from C$ 199 and United Airlines from C$ 211 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: Copa Airlines (88%), Emirates (87%), ANA( 86%).

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

    On average you can expect to pay C$ 2,916 for a flight from Toronto Pearson Intl Airport to Chicago. The cheapest flight overall is C$ 209 while the most popular route, (Toronto Pearson Intl - Chicago O'Hare Intl) is currently priced at C$ 294.

  • 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 25 marzo 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 25 marzo 2025.
AirlineCheapestAverageFlexibilityOn-time
Porter AirlinesCheapestC$ 269AverageC$ 374FlexibilityNo cancel feeOn-time52%
Search Porter Airlines flights
Air CanadaCheapestC$ 313AverageC$ 419FlexibilityNo cancel feeOn-time67%
Search Air Canada flights
American AirlinesCheapestC$ 330AverageC$ 540FlexibilityNo cancel feeOn-time71%
Search American Airlines flights
United AirlinesCheapestC$ 343AverageC$ 471FlexibilityNo cancel feeOn-time69%
Search United Airlines flights
WestJetCheapestC$ 461AverageC$ 654FlexibilityNo cancel feeOn-time60%
Search WestJet flights

Fly with Cheapflights

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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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