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Cheap flights from Toronto Pearson Intl Airport to Chicago from C$ 200

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 29/1. Fares are subject to change and may not be available on all flights or dates of travel.
YYZ — CHI
23 Dec — 30 Dec1
1 adult

The best prices from Toronto Pearson Intl to Chicago are usually found in January or April, booked 84 days in advance, depart on a Tuesday or Wednesday 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 18 December 2024.

Round-trip from

C$ 328

One-way from

C$ 206

Popular in

December

Cheapest in

January

Average price

C$ 461
Air Canada
  • Air Canada
  • 9/1-12/1
  • 2 total stops
  • 10h 50m total
  • Toronto to Chicago
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7/1
  • 7/1
  • 1 total stop
  • 12h 52m total
  • Toronto to Chicago
Search Deals
High demand for flights, 2% potential price rise
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Best time to find cheap flights, 1% potential price drop
Search Deals
Average for round-trip flights in December 2024
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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 18 December 2024.

Tue 31/1212:20 p.m.YYZ - ORD
Nonstop1h 51mUnited Airlines
Wed 8/110:53 a.m.ORD - YYZ
Nonstop1h 49mUnited Airlines
Deal found 17/12C$ 390
Tue 31/128:00 a.m.YYZ - ORD
Nonstop1h 57mAir Canada
Tue 7/112:51 p.m.ORD - YYZ
Nonstop1h 54mAir Canada
Deal found 17/12C$ 391
Sat 28/127:35 a.m.YYZ - ORD
1 stop5h 40mAmerican Airlines
Wed 8/13:00 p.m.ORD - YYZ
Nonstop1h 35mAmerican Airlines
Deal found 18/12C$ 478
Mon 30/129:00 p.m.YYZ - ORD
1 stop15h 58mMultiple Airlines
Thu 9/17:20 a.m.ORD - YYZ
1 stop5h 21mMultiple Airlines
Deal found 17/12C$ 480
Wed 25/121:00 p.m.YYZ - ORD
1 stop4h 40mWestJet
Mon 3/24:15 p.m.ORD - YYZ
2 stops13h 02mWestJet
Deal found 17/12C$ 547
Tue 31/127:10 a.m.YYZ - MDW
1 stop11h 44mMultiple Airlines
Wed 8/110:57 a.m.MDW - YYZ
1 stop5h 03mMultiple Airlines
Deal found 17/12C$ 594
Wed 25/126:30 a.m.YYZ - MDW
1 stop5h 38mWestJet
Mon 3/21:26 p.m.MDW - YYZ
1 stop8h 41mWestJet
Deal found 17/12C$ 647
Thu 19/1210:05 a.m.YYZ - MDW
1 stop7h 19mDelta
Thu 26/129:30 a.m.MDW - YYZ
1 stop5h 44mDelta
Deal found 17/12C$ 823

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 18 December 2024.

Fly from

Any airport

Fly to

Any airport

Route

Depart

Return

Price

TorontoChicago

YYZ - ORD

YYZORD

Toronto Pearson Intl

Thu 9/1

6:25 a.m.-10:54 a.m.

1 stop5h 29m

Chicago O'Hare Intl

Sun 12/1

7:20 a.m.-1:41 p.m.

1 stop5h 21m

C$ 328

TorontoChicago

YYZ - ORD

YYZORD

Toronto Pearson Intl

Fri 31/1

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

Nonstop2h 00m

Chicago O'Hare Intl

Fri 7/2

3:00 p.m.-5:35 p.m.

Nonstop1h 35m

C$ 330

TorontoChicago

YYZ - ORD

YYZORD

Toronto Pearson Intl

Thu 9/1

11:00 a.m.-12:13 p.m.

Nonstop2h 13m

Chicago O'Hare Intl

Sun 12/1

8:30 p.m.-11:11 p.m.

Nonstop1h 41m

C$ 340

TorontoChicago

YYZ - ORD

YYZORD

Toronto Pearson Intl

Mon 17/2

4:44 p.m.-5:44 p.m.

Nonstop2h 00m

Chicago O'Hare Intl

Fri 21/2

9:50 a.m.-12:30 p.m.

Nonstop1h 40m

C$ 343

TorontoChicago

YYZ - ORD

YYZORD

Toronto Pearson Intl

Tue 14/1

7:05 a.m.-8:13 p.m.

1 stop14h 08m

Chicago O'Hare Intl

Tue 21/1

5:11 a.m.-11:55 p.m.

1 stop17h 44m

C$ 344

TorontoChicago

YYZ - ORD

YYZORD

Toronto Pearson Intl

Thu 16/1

11:00 a.m.-12:13 p.m.

Nonstop2h 13m

Chicago O'Hare Intl

Sun 19/1

6:00 a.m.-11:46 a.m.

1 stop4h 46m

C$ 350

TorontoChicago

YYZ - ORD

YYZORD

Toronto Pearson Intl

Tue 7/1

7:45 a.m.-12:55 p.m.

1 stop6h 10m

Chicago O'Hare Intl

Fri 7/2

1:40 p.m.-7:06 p.m.

1 stop4h 26m

C$ 351

TorontoChicago

YYZ - MDW

YYZMDW

Toronto Pearson Intl

Tue 7/1

6:00 a.m.-8:54 a.m.

1 stop3h 54m

Chicago Midway

Mon 3/2

6:28 p.m.-10:49 p.m.

1 stop3h 21m

C$ 351

TorontoChicago

YYZ - MDW

YYZMDW

Toronto Pearson Intl

Thu 9/1

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

1 stop22h 52m

Chicago Midway

Sun 12/1

10:19 a.m.-11:11 p.m.

1 stop11h 52m

C$ 391

TorontoChicago

YYZ - ORD

YYZORD

Toronto Pearson Intl

Tue 14/1

2:45 p.m.-9:58 p.m.

1 stop8h 13m

Chicago O'Hare Intl

Fri 17/1

10:30 a.m.-4:12 p.m.

1 stop4h 42m

C$ 406

Flights are sorted by cheapest round-trip flights first.

Deals found on 18/12

Showing 1-10 of 21 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 13 December 2024.

Booking 84 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 May is currently the most expensive (average of C$ 342). 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 18 December 2024.

It’s optimal to fly from Toronto Pearson Intl Airport to Chicago in the evening. By choosing this option you can save up to 4% on the cost of your flight, compared to a flight at noon.

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 Thursday at noon when fares are most often at their lowest. Sunday at noon 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 18 December 2024.

The most flights from YYZ to CHI are scheduled on a Monday (51 on average). You will have fewer flight options on Friday, which is when the least amount of flights are scheduled (9 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 18 December 2024.
To help decide which airline to fly from Toronto to Chicago, see what other customers have to say about Air Canada, American Airlines and Delta. 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
8,604 reviews
Check prices

Boarding

8.2

Crew

8.6

Entertainment

7.9

Comfort

7.9

Overall

8.0

Food

7.3

Reviews

1 / 10

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

Delta
8.0
Very good
8,604 reviews
Delta
8.0
Very good
8,604 reviews
Check prices

Boarding

8.2

Crew

8.6

Entertainment

7.9

Comfort

7.9

Overall

8.0

Food

7.3

Reviews

1 / 10

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

Finnair
7.7
Good
1,285 reviews
Delta
8.0
Very good
8,604 reviews
Check prices

Boarding

8.2

Crew

8.6

Entertainment

7.9

Comfort

7.9

Overall

8.0

Food

7.3

Reviews

1 / 10

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

United Airlines
7.4
Good
9,059 reviews
Delta
8.0
Very good
8,604 reviews
Check prices

Boarding

8.2

Crew

8.6

Entertainment

7.9

Comfort

7.9

Overall

8.0

Food

7.3

Reviews

1 / 10

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

WestJet
7.3
Good
2,818 reviews
Delta
8.0
Very good
8,604 reviews
Check prices

Boarding

8.2

Crew

8.6

Entertainment

7.9

Comfort

7.9

Overall

8.0

Food

7.3

Reviews

1 / 10

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
8,604 reviews
Check prices

Boarding

8.2

Crew

8.6

Entertainment

7.9

Comfort

7.9

Overall

8.0

Food

7.3

Reviews

1 / 10

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$ 328, 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 Finnair and Lufthansa - these airlines can fly you to your destination from C$ 330 and C$ 340, respectively. Users have found that Air Canada is 20% 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$ 209 on Air Canada. Other airlines that offer cheap prices include United Airlines from C$ 210 and Delta from C$ 214 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: Lufthansa (100%), Royal Jordanian (97%), SkyWest Airlines( 97%).

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

    On average you can expect to pay C$ 1,454 for a flight from Toronto Pearson Intl Airport to Chicago. The cheapest flight overall is C$ 221 while the most popular route, (Toronto Pearson Intl - Chicago O'Hare Intl) is currently priced at C$ 314.

  • 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 May is currently the most expensive (average of C$ 342). 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 18 December 2024.
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 18 December 2024.
AirlineCheapestAverageFlexibilityOn-time
Porter AirlinesCheapestC$ 277AverageC$ 367FlexibilityNo cancel feeOn-time52%
Search Porter Airlines flights
Air CanadaCheapestC$ 312AverageC$ 416FlexibilityNo cancel feeOn-time67%
Search Air Canada flights
United AirlinesCheapestC$ 356AverageC$ 458FlexibilityNo cancel feeOn-time69%
Search United Airlines flights
American AirlinesCheapestC$ 357AverageC$ 546FlexibilityNo cancel feeOn-time71%
Search American Airlines flights
WestJetCheapestC$ 453AverageC$ 592FlexibilityNo cancel feeOn-time60%
Search WestJet flights

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

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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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