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Cheap flights from Toronto Pearson Intl Airport to Chicago from C$ 133

This is the cheapest one-way flight price, found on 5/12. Prices may vary by date and flight preferences.
YYZ — CHI
11 Dec — 18 Dec1
1 adult
Mon 11/12
Mon 18/12

Flights from Chicago to Pearson Intl

How to find the cheapest flight from Pearson Intl (YYZ) to Chicago (CHI)

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 6 December 2023.

Popular in

August

Cheapest in

February

Round-trip from

C$ 501

One-way from

C$ 189
High demand for flights, 21% potential price rise
Best time to find cheap flights, 24% potential price drop
From Toronto Pearson Intl to Chicago (CHI)
One-way flight from Toronto Pearson Intl to Chicago (CHI)

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

To save up to 78% on this flight, we recommend booking at least 27 days prior to travel. The price may fluctuate and will likely increase closer to your departure date. Users on Cheapflights have found tickets from Toronto Pearson Intl Airport to Chicago from C$ 487 1-2 weeks out and tickets from C$ 662 for flights departing within the next 72 hours.

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

Due to multiple factors, expect to potentially pay more when booking in July. For low rates, January can be a great choice for travel to Chicago. Flights to Chicago from Toronto Pearson Intl Airport in January are about C$ 396 on average during January, but can be found for as low as C$ 242.

When is the cheapest time to fly from Toronto Pearson Intl Airport to Chicago (YYZ - CHI)?

When flying from Toronto Pearson Intl Airport to Chicago, the time of day you decide to fly out makes little to no difference towards the overall price you’ll pay on tickets.

Cheap Air Canada flights from Pearson Intl to Chicago

Explore cheap flight options specifically provided by Air Canada for the route between Pearson Intl and Chicago. Find affordable fares and compare prices with other airlines to secure the best deal for your journey. Over the last 7 days, Cheapflights users made 500,832 searches. Data last updated 6 December 2023.
Find some of the cheapest Air Canada flights travelling from Toronto to Chicago. Come back soon if you're not finding the exact deal you're looking for.
  • If you’re travelling from Toronto Pearson Intl Airport to Chicago, one of the more common airlines travelling that route is Air Canada. Flights from Air Canada travelling this route typically cost C$ 321.64 RT. This price is typically 90% cheaper than other airlines that offer Toronto Pearson Intl Airport to Chicago flights. When booking this route, the cheapest RT price found was C$ 237. When travelling from Toronto Pearson Intl Airport to Chicago on Air Canada, the most popular airport to depart from is Toronto Pearson Intl Airport and the most popular airport to arrive at is Chicago O'Hare Intl Airport. When flying from Toronto Pearson Intl Airport to Chicago, Air Canada flights are 6% more popular than any other airline flying that same route.

Cheap Delta flights from Pearson Intl to Chicago

Explore cheap flight options specifically provided by Delta for the route between Pearson Intl and Chicago. Find affordable fares and compare prices with other airlines to secure the best deal for your journey. Over the last 7 days, Cheapflights users made 500,832 searches. Data last updated 6 December 2023.
Have a look at some of the cheapest available Delta flights departing from Toronto and landing in Chicago. Deals frequently update to provide users with more options.
  • One of the most popular airlines travelling from Toronto Pearson Intl Airport to Chicago is Delta. Flights on this route from Delta typically cost C$ 240.73 RT, a price that is 143% cheaper than the average Toronto Pearson Intl Airport to Chicago flight. The cheapest flight found was C$ 219 RT. The most popular departure airport in Toronto Pearson Intl Airport when flying to Chicago is Toronto Pearson Intl Airport. The most popular airport to fly into when visiting Chicago is Chicago O'Hare Intl Airport. When flying from Toronto Pearson Intl Airport to Chicago, Delta flights are 5% more popular than any other airline flying that same route.

Cheap Pearson Intl to Chicago flights in December & January 2023

Find cheap flight options from Pearson Intl to Chicago specifically for the months of December and January 2023. Explore affordable fares based on user searches. Over the last 7 days, Cheapflights users made 500,832 searches. Prices were last updated on 6 December 2023.
The lowest fares we've come across on flights travelling from Toronto to Chicago in December and January 2023. More deals are always being added, so be sure to check back regularly.

Pearson Intl to Chicago 2023 flight deals

Discover exclusive flight deals for travel between Pearson Intl and Chicago in 2023. Find excellent offers based on user searches. Over the last 7 days, Cheapflights users made 500,832 searches. Data last updated 6 December 2023.
The lowest fares we've come across on flights travelling from Toronto to Chicago in December and January 2023. More deals are always being added, so be sure to check back regularly.

Direct flights to Chicago from Pearson Intl

Discover non-stop flight options from Pearson Intl to Chicago. Find direct flights with no layovers, providing a convenient travel experience. Explore non-stop flight options based on user searches, and compare prices and availability for your desired travel dates. Over the last 7 days, Cheapflights users made 500,832 searches. Data last updated 6 December 2023.
If you're seeking options on non-stop flights from Toronto to Chicago, check out these fares. Users can also choose from other Toronto to Chicago flights by using the search form above.

Pearson Intl to Chicago flights leaving soon

Find last-minute flight options from Pearson Intl to Chicago for spontaneous travel. Discover available flights and compare prices based on user searches. Secure great deals and offers for spontaneous trips with quick booking options. Over the last 7 days, Cheapflights users made 500,832 searches. Data last updated 6 December 2023.
Have a look at some of the flights available from Toronto to Chicago departing last-minute. To prevent any unwanted surprises, users should verify their flight info before booking.

One-way flights to Chicago from Pearson Intl

Search for one-way flight options from Pearson Intl to Chicago. Find affordable one-way fares based on user searches. Compare prices and availability to plan your one-way journey according to your preferred dates and budget. Over the last 7 days, Cheapflights users made 500,832 searches. Data last updated 6 December 2023.
Some of the best available deals we've found on one-way flights from Toronto to Chicago. Users in need of a round-trip flight from Toronto to Chicago instead should update the search form at the top of page.

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 500,832 searches. Data last updated 6 December 2023.

Fly from

Any airport

Fly to

Any airport

Budget

C$ 236 - C$ 569

Route

Depart

Return

Price

Toronto Pearson IntlChicago O'Hare Intl

YYZ - ORD

YYZORD

Toronto Pearson Intl

Sat 13/1

1 stop13h 36m

Chicago O'Hare Intl

Wed 17/1

1 stop13h 48m

C$ 236

Toronto Pearson IntlChicago O'Hare Intl

YYZ - ORD

YYZORD

Toronto Pearson Intl

Sat 16/12

1 stop18h 54m

Chicago O'Hare Intl

Tue 19/12

1 stop16h 56m

C$ 239

Toronto Pearson IntlChicago O'Hare Intl

YYZ - ORD

YYZORD

Toronto Pearson Intl

Sat 16/12

1 stop16h 24m

Chicago O'Hare Intl

Tue 19/12

1 stop16h 56m

C$ 262

Toronto Pearson IntlChicago O'Hare Intl

YYZ - ORD

YYZORD

Toronto Pearson Intl

Thu 28/12

Nonstop2h 02m

Chicago O'Hare Intl

Sun 31/12

Nonstop1h 33m

C$ 290

Toronto Pearson IntlChicago O'Hare Intl

YYZ - ORD

YYZORD

Toronto Pearson Intl

Tue 19/12

1 stop5h 23m

Chicago O'Hare Intl

Thu 21/12

Nonstop1h 33m

C$ 292

Toronto Pearson IntlChicago O'Hare Intl

YYZ - ORD

YYZORD

Toronto Pearson Intl

Sun 24/12

Nonstop2h 02m

Chicago O'Hare Intl

Sun 31/12

Nonstop1h 33m

C$ 294

Toronto Pearson IntlChicago O'Hare Intl

YYZ - ORD

YYZORD

Toronto Pearson Intl

Sat 20/1

Nonstop2h 11m

Chicago O'Hare Intl

Wed 24/1

Nonstop1h 46m

C$ 316

Toronto Pearson IntlChicago O'Hare Intl

YYZ - ORD

YYZORD

Toronto Pearson Intl

Mon 25/12

1 stop5h 01m

Chicago O'Hare Intl

Sun 7/1

1 stop9h 14m

C$ 345

Toronto Pearson IntlChicago Midway

YYZ - MDW

YYZMDW

Toronto Pearson Intl

Fri 15/3

1 stop6h 51m

Chicago Midway

Mon 18/3

1 stop6h 02m

C$ 569

Flights are sorted by cheapest first

Deals found on 5/12

Average price of flights to Chicago by month

Plan your trip from Pearson Intl to Chicago by taking into account the cheapest months to travel. The average price of a one-way flight from Pearson Intl to Chicago is currently 157.70 CAD while a round-trip flight costs 315.84 CAD. Price data was last updated on 3 December 2023.

Currently, January is the cheapest month in which you can book a flight from Toronto Pearson Intl Airport to Chicago (average of C$ 290). Flying from Toronto Pearson Intl Airport to Chicago in August is currently the most expensive (average of C$ 432). 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.

January

C$ 393

February

C$ 474

March

C$ 479

April

C$ 522

May

C$ 486

June

C$ 558

July

C$ 585

August

C$ 586

September

C$ 464

October

C$ 499

November

C$ 459

December

C$ 441

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 6 December 2023.
To help decide which airline to fly from Toronto to Chicago, see what other customers have to say about Air Canada, Delta and United Airlines. You can also see how each airline stacks up in terms of entertainment options, comfort, food, crew/service, and boarding process.
WestJet Encore
10.0
Wonderful
2 reviews

Boarding

10.0

Comfort

10.0

Entertainment

10.0

Food

10.0

Overall

10.0

Crew

10.0

Reviews

1 / 1

Pros: Overall great flight

Cons: The people in front of us were over served and loud

WestJet Encore
10.0
Wonderful
2 reviews
WestJet Encore
10.0
Wonderful
2 reviews

Boarding

10.0

Comfort

10.0

Entertainment

10.0

Food

10.0

Overall

10.0

Crew

10.0

Reviews

1 / 1

Pros: Overall great flight

Cons: The people in front of us were over served and loud

7.9
Good
3,035 reviews
WestJet Encore
10.0
Wonderful
2 reviews

Boarding

10.0

Comfort

10.0

Entertainment

10.0

Food

10.0

Overall

10.0

Crew

10.0

Reviews

1 / 1

Pros: Overall great flight

Cons: The people in front of us were over served and loud

7.4
Good
1,901 reviews
WestJet Encore
10.0
Wonderful
2 reviews

Boarding

10.0

Comfort

10.0

Entertainment

10.0

Food

10.0

Overall

10.0

Crew

10.0

Reviews

1 / 1

Pros: Overall great flight

Cons: The people in front of us were over served and loud

7.2
Good
2,645 reviews
WestJet Encore
10.0
Wonderful
2 reviews

Boarding

10.0

Comfort

10.0

Entertainment

10.0

Food

10.0

Overall

10.0

Crew

10.0

Reviews

1 / 1

Pros: Overall great flight

Cons: The people in front of us were over served and loud

7.2
Good
918 reviews
WestJet Encore
10.0
Wonderful
2 reviews

Boarding

10.0

Comfort

10.0

Entertainment

10.0

Food

10.0

Overall

10.0

Crew

10.0

Reviews

1 / 1

Pros: Overall great flight

Cons: The people in front of us were over served and loud

Average temperature in Chicago by month

Plan your trip to Chicago by selecting the month that matches your preferred temperature. January sees the highest average temperature while July sees the lowest average temperature. Temperature data was last updated on 3 December 2023.

CHI

Temperature

-5 - 23 °C

Average rainfall in Chicago by month

Keep in mind the precipitation totals in Chicago by selecting the month that matches your preferred temperature. Chicago sees an average of 78.50 precipitation per year with the most occurring in August. Precipitation data was last updated on 3 December 2023.

CHI

Rainfall

43 - 125 mm

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.

Can I find flights from Toronto Pearson Intl Airport to Chicago for under C$ 300 on Cheapflights?

Yes, there are multiple flights from Toronto Pearson Intl Airport to Chicago for under C$ 300. The cheapest flight booked recently is on Multiple Airlines for just C$ 236, but on average you can expect to pay C$ 289.

Are there direct flights from Toronto Pearson Intl Airport to Chicago for under C$ 300 on Cheapflights?

Cheapflights has 20 direct flights from Toronto Pearson Intl Airport to Chicago under C$ 300. A good price for a direct flight from Toronto Pearson Intl Airport to Chicago is less than C$ 328.

Are there last-minute flights available from Toronto Pearson Intl Airport to Chicago for under C$ 300?

There are currently 20+ open flights from Toronto Pearson Intl Airport to Chicago within the next 7 days for less than C$ 300.

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

Currently priced at C$ 290, 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$ 294 and C$ 316, respectively. Users have found that Air Canada is 36% cheaper than the other options available to this destination.

What are the most popular airlines that fly from Toronto Pearson Intl Airport to Chicago?

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: Korean Air (100%), Royal Jordanian (92%), Egypt Air( 90%).

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

On average you can expect to pay C$ 1,582 for a flight from Toronto Pearson Intl Airport to Chicago. The cheapest flight overall is C$ 229 while the most popular route, (Toronto Pearson Intl - Chicago O'Hare Intl) is currently priced at C$ 262.

What does YYZ to ORD mean?

YYZ stands for Toronto Pearson Intl Airport, while ORD stands for Chicago O'Hare Intl Airport. These codes are often called IATA codes, a set of identifiers established by IATA (International Air Transport Association) that is widely used by airlines and the aviation industry. Chicago Midway Airport (MDW), Chicago Greater Rockford Airport (RFD) are other airports near this flight route and their unique identifiers/IATA codes.

Browse thousands of different options on Cheapflights for your next trip

Toggle through the tabs below to find thousands of options on Cheapflights for your next trip.

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 6 December 2023.

Top 10 airlines flying from Pearson Intl to Chicago

Discover the top 10 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 500,832 searches. Data last updated 6 December 2023.
AirlineCheapestAverageFlexibilityOn-time
Porter AirlinesCheapestC$ 235AverageC$ 413FlexibilityNo cancel feeOn-time52%
Search Porter Airlines flights
United AirlinesCheapestC$ 267AverageC$ 491FlexibilityNo cancel feeOn-time69%
Search United Airlines flights
Air CanadaCheapestC$ 284AverageC$ 487FlexibilityNo cancel feeOn-time67%
Search Air Canada flights
Air New ZealandCheapestC$ 297AverageC$ 327FlexibilityNo cancel feeOn-time78%
Search Air New Zealand flights
ANACheapestC$ 321AverageC$ 436FlexibilityNo cancel feeOn-time80%
Search ANA flights
American AirlinesCheapestC$ 327AverageC$ 555FlexibilityNo cancel feeOn-time71%
Search American Airlines flights
Alaska AirlinesCheapestC$ 328