Cheap flights from Lester B. Pearson Intl to Chicago

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The best prices from Lester B. Pearson Intl to Chicago are usually found in April or July, booked 45 days in advance, depart on a Thursday or Wednesday and return on a Sunday

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

YYZ - CHI
Price
C$ 298 - C$ 412
CHI
Temperature
1 - 29 °C
CHI
Rainfall
17 - 109 mm

Popular in

October

High demand for flights, 15% potential price rise

Cheapest in

April

Best time to find cheap flights, 15% potential price drop

Round-trip from

C$ 298

From Lester B. Pearson Intl to Chicago

One-way from

C$ 221

One-way flight from Lester B. Pearson Intl to Chicago

Flight route prices based on searches on Cheapflights within the last 3 days, monthly prices based on aggregated historical data.
What is the cheapest day to fly round-trip from Lester B. Pearson Intl to Chicago?

Sunday flights are generally found to be more expensive for flights from Lester B. Pearson Intl to Chicago. This shouldn’t discourage you from searching, as you can still find great deals by being flexible with your options. Use our search form to find deals on tickets to Chicago.

How far in advance should I book a flight from Lester B. Pearson Intl to Chicago?

To save on the cost of your flight from Lester B. Pearson Intl to Chicago, book at least 34 days before your planned departure. Booking around this time can save you about 86% on the cost of this flight compared to booking a flight leaving this week. We have found prices from C$ 460 if you need a flight within two weeks. For flights within the next 72 hours, you can find tickets from as low as C$ 623.

What is the cheapest month to fly from Lester B. Pearson Intl to Chicago?

April is one of the best times of the year to fly to Chicago from Lester B. Pearson Intl. Prices for April average C$ 335 per person but you can even find prices for as low as C$ 253. The most expensive prices can be found in the month of January. Opting for a April flight can save you 10% on your journey compared to booking in April

When is the cheapest time to fly from Lester B. Pearson Intl to Chicago (YYZ - CHI)?

One of the essential ways to save on airfare from Lester B. Pearson Intl to Chicago is to remain as flexible as possible. Flights that are in the afternoon tend to be the most expensive. A flight at noon could potentially save you up to 7% on airfare.

Cheap flights from Lester B. Pearson Intl to Chicago in October, November 2020

The best prices found for YYZ to CHI flights for October, November
30 Oct - 6 Nov
C$ 285pp
YYZ
Toronto Pearson Intl
Qantas Airways
Direct
ORD
Chicago O'Hare Intl
ORD
Chicago O'Hare Intl
Qantas Airways
Direct
YYZ
Toronto Pearson Intl
21 Nov - 7 Dec
C$ 298pp
YYZ
Toronto Pearson Intl
American Airlines
Direct
ORD
Chicago O'Hare Intl
ORD
Chicago O'Hare Intl
American Airlines
 
1 STOP
YYZ
Toronto Pearson Intl
10 Nov - 15 Nov
C$ 300pp
YYZ
Toronto Pearson Intl
United Airlines
Direct
ORD
Chicago O'Hare Intl
ORD
Chicago O'Hare Intl
United Airlines
Direct
YYZ
Toronto Pearson Intl

Lester B. Pearson Intl to Chicago 2020 flight deals

Cheap flights to Chicago from Lester B. Pearson Intl found for this year
5 Dec - 8 Dec
C$ 257pp
YYZ
Toronto Pearson Intl
Air Canada
 
1 STOP
ORD
Chicago O'Hare Intl
ORD
Chicago O'Hare Intl
Air Canada
 
1 STOP
YYZ
Toronto Pearson Intl
5 Dec - 8 Dec
C$ 260pp
YYZ
Toronto Pearson Intl
Air Canada
Direct
ORD
Chicago O'Hare Intl
ORD
Chicago O'Hare Intl
Air Canada
 
1 STOP
YYZ
Toronto Pearson Intl
5 Dec - 8 Dec
C$ 262pp
YYZ
Toronto Pearson Intl
Air Canada
   
2 STOPS
ORD
Chicago O'Hare Intl
ORD
Chicago O'Hare Intl
Air Canada
 
1 STOP
YYZ
Toronto Pearson Intl

Direct flights to Chicago from Lester B. Pearson Intl

Save time with Lester B. Pearson Intl to Chicago direct flight deals
5 Dec - 8 Dec
C$ 264pp
YYZ
Toronto Pearson Intl
Air Canada
Direct
ORD
Chicago O'Hare Intl
ORD
Chicago O'Hare Intl
Air Canada
Direct
YYZ
Toronto Pearson Intl
24 Dec - 3 Jan
C$ 298pp
YYZ
Toronto Pearson Intl
American Airlines
Direct
ORD
Chicago O'Hare Intl
ORD
Chicago O'Hare Intl
American Airlines
Direct
YYZ
Toronto Pearson Intl
20 Nov - 29 Nov
C$ 300pp
YYZ
Toronto Pearson Intl
United Airlines
Direct
ORD
Chicago O'Hare Intl
ORD
Chicago O'Hare Intl
United Airlines
Direct
YYZ
Toronto Pearson Intl

Last minute flights from Lester B. Pearson Intl to Chicago

Late deals on round-trip flights to Chicago from Lester B. Pearson Intl, departing today and this week
8 Nov - 9 Nov
C$ 334pp
YYZ
Toronto Pearson Intl
American Airlines
Direct
ORD
Chicago O'Hare Intl
ORD
Chicago O'Hare Intl
American Airlines
 
1 STOP
YYZ
Toronto Pearson Intl
6 Nov - 14 Nov
C$ 335pp
YYZ
Toronto Pearson Intl
American Airlines
Direct
ORD
Chicago O'Hare Intl
ORD
Chicago O'Hare Intl
American Airlines
 
1 STOP
YYZ
Toronto Pearson Intl
8 Nov - 10 Nov
C$ 337pp
YYZ
Toronto Pearson Intl
United Airlines
Direct
ORD
Chicago O'Hare Intl
ORD
Chicago O'Hare Intl
United Airlines
Direct
YYZ
Toronto Pearson Intl

One-way flights to Chicago from Lester B. Pearson Intl

The cheapest one-way flights from Lester B. Pearson Intl to Chicago
4:45 p.m. - 5:07 p.m.
WestJet
2 stops
25h 22m
YYZ - ORD
WestJet
C$ 222
10:51 a.m. - 7:24 a.m.
American Airlines
1 stop
21h 33m
YYZ - ORD
American Airlines
C$ 232
1:30 a.m. - 11:50 a.m.
Delta
2 stops
11h 20m
YYZ - MDW
Delta
C$ 274
Delta

Related info for your journey

Useful info, stats and facts about Lester B. Pearson Intl to Chicago flights.

Flight FAQs

From Lester B. Pearson Intl to Chicago

Can I find flights from Lester B. Pearson Intl to Chicago for under C$ 398 on Cheapflights?

Yes, there are multiple flights from Lester B. Pearson Intl to Chicago for under C$ 398. The cheapest flight booked recently is on American Airlines for just C$ 297, but on average you can expect to pay C$ 312.

What safety measures are being taken by airlines flying from Toronto Pearson Intl to Chicago to control the spread of COVID-19?

New policies can now be found on Delta to help keep travellers safe while flying. New policies for travellers booking flights from Toronto Pearson Intl to Chicago include masks being provided and required on board, daily cleaning and sanitization, use of HEPA filters, pre-flight testing for antibodies and symptoms, and socially-distanced seating (for a limited time). Keep in mind that policies will vary by airline.

Which airlines flying from Toronto Pearson Intl to Chicago have flexible cancellations due to COVID-19?

Some of the carriers operating flights from Toronto Pearson Intl to Chicago that may be offering flexible cancellation policies are Air Canada, American Airlines, and United Airlines. Our site will let you filter for all airlines offering greater flexibility due to COVID-19.

Are there direct flights from Lester B. Pearson Intl to Chicago for under C$ 265 on Cheapflights?

Cheapflights has 16 direct flights from Lester B. Pearson Intl to Chicago under C$ 265. A good price for a direct flight from Lester B. Pearson Intl to Chicago is less than C$ 400.

Are there last-minute flights available from Lester B. Pearson Intl to Chicago for under C$ 398?

There are currently 20+ open flights from Lester B. Pearson Intl to Chicago within the next 7 days for less than C$ 398.

What days are direct flights available from Lester B. Pearson Intl to Chicago?

You can find direct flights on the following days: Sunday, Thursday, Saturday.

How many flights depart from Lester B. Pearson Intl to Chicago on average per day?

10 flight departures from Toronto Pearson Intl to Chicago per day on average.
Morning (6am - Noon) - 90% of flight departures
Afternoon (Noon - 6pm) - 10% of flight departures

Is Lester B. Pearson Intl weather warmer or cooler than Chicago?

We forecast the temperature to be around the 29 °C's in July, on average. The temperature in Chicago is generally hotter than in Lester B. Pearson Intl. Book flights in a timely manner in correlation to your departure date.

How long is the flight from Lester B. Pearson Intl to Chicago?

Airlines like United Airlines, American Airlines, and Delta fly from Lester B. Pearson Intl to Chicago in about 1h 50m. The time it takes to get you to your destination can typically vary by up to 2h 09m. Lester B. Pearson Intl and Chicago are separated by a distance of 703 km. Both multi-stop and direct flights can be found to your destination and back.

What are the cheapest airlines to flying from Lester B. Pearson Intl to Chicago round-trip?

Our cheapest airline available from Lester B. Pearson Intl to Chicago is American Airlines. Our recent data shows that you can find tickets from as low as C$ 297 on this airline. Additional options worth looking into are United Airlines and Delta, starting at C$ 320 and C$ 339 round-trip. American Airlines is 15% cheaper than the average price of flights available within the next 90 days to this destination.

What are the cheapest airlines to fly from Lester B. Pearson Intl to Chicago one-way?

One-way options have recently been found by users for as low as C$ 175 on American Airlines. Other airlines that offer cheap prices include United Airlines from C$ 183 and Air Canada from C$ 185 one-way.

Alternative routes for Lester B. Pearson Intl to Chicago

Destination information for Chicago

Things to know before you go. Useful info for your trip from Lester B. Pearson Intl to Chicago
Today's exchange rate
C$ 1 = $0.76
Flight duration
1h 47m
Average temperature for October in Chicago
18.0 °C
Avg rainfall for October in Chicago
66.0 mm

Airports servicing Toronto

Airports servicing Chicago

Chicago Midway (MDW)
Rockford (RFD)

Hourly flight availability from Lester B. Pearson Intl to Chicago

Morning 6 AM to noon 67% of flight departures
Afternoon Noon to 6 PM 32% of flight departures
Early morning Midnight to 6 AM 1% of flight departures
Evening 6 PM to midnight 0% of flight departures
Midnight
6 AM
Noon
6 PM
Weekly flight availability
from Lester B. Pearson Intl to Chicago
Sunday
2 daily flights
Monday
2 daily flights
Tuesday
2 daily flights
Wednesday
8 daily flights
Thursday
15 daily flights
Friday
9 daily flights
Saturday
4 daily flights
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