Cheap flights from Lester B. Pearson Intl to Chicago

Round-trip
Economy
Toronto (YYZ)
Chicago (CHI)
Depart
Return
Any month
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How to find the cheapest flight from
Lester B. Pearson Intl (YYZ) to Chicago (CHI)

All the information you need to plan the best YYZ to CHI flight in 2021: compare Lester B. Pearson Intl to Chicago flight prices with the expected peak season, weather and rainfall in Chicago.
YYZ - CHI
Price
C$ 273 - C$ 377
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$ 273

From Lester B. Pearson Intl to Chicago

One-way from

C$ 215

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.
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$ 421 if you need a flight within two weeks. For flights within the next 72 hours, you can find tickets from as low as C$ 570.

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$ 306 per person but you can even find prices for as low as C$ 232. 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

Cheap flights from Lester B. Pearson Intl to Chicago in May, June 2021

The best prices found for YYZ to CHI flights for May, June
25 May - 27 May
C$ 377pp
YYZ
Toronto Pearson Intl
Air Canada
Direct
ORD
Chicago O'Hare Intl
ORD
Chicago O'Hare Intl
Air Canada
Direct
YYZ
Toronto Pearson Intl
6 Jun - 13 Jun
C$ 378pp
YYZ
Toronto Pearson Intl
Air Canada
Direct
ORD
Chicago O'Hare Intl
ORD
Chicago O'Hare Intl
Air Canada
Direct
YYZ
Toronto Pearson Intl
1 Jun - 15 Jun
C$ 380pp
YYZ
Toronto Pearson Intl
Air Canada
Direct
ORD
Chicago O'Hare Intl
ORD
Chicago O'Hare Intl
Air Canada
Direct
YYZ
Toronto Pearson Intl

Lester B. Pearson Intl to Chicago 2021 flight deals

Cheap flights to Chicago from Lester B. Pearson Intl found for this year
16 Aug - 19 Aug
C$ 354pp
YYZ
Toronto Pearson Intl
Air Canada
 
1 STOP
ORD
Chicago O'Hare Intl
ORD
Chicago O'Hare Intl
Air Canada
Direct
YYZ
Toronto Pearson Intl
16 Aug - 19 Aug
C$ 360pp
YYZ
Toronto Pearson Intl
Air Canada
Direct
ORD
Chicago O'Hare Intl
ORD
Chicago O'Hare Intl
Air Canada
Direct
YYZ
Toronto Pearson Intl
25 May - 27 May
C$ 377pp
YYZ
Toronto Pearson Intl
Air Canada
Direct
ORD
Chicago O'Hare Intl
ORD
Chicago O'Hare Intl
Air Canada
Direct
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
16 Aug - 19 Aug
C$ 360pp
YYZ
Toronto Pearson Intl
Air Canada
Direct
ORD
Chicago O'Hare Intl
ORD
Chicago O'Hare Intl
Air Canada
Direct
YYZ
Toronto Pearson Intl
25 May - 27 May
C$ 377pp
YYZ
Toronto Pearson Intl
Air Canada
Direct
ORD
Chicago O'Hare Intl
ORD
Chicago O'Hare Intl
Air Canada
Direct
YYZ
Toronto Pearson Intl
6 Jun - 13 Jun
C$ 378pp
YYZ
Toronto Pearson Intl
Air Canada
Direct
ORD
Chicago O'Hare Intl
ORD
Chicago O'Hare Intl
Air Canada
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
14 May - 9 Nov
C$ 424pp
YYZ
Toronto Pearson Intl
Air Canada
Direct
ORD
Chicago O'Hare Intl
ORD
Chicago O'Hare Intl
Air Canada
Direct
YYZ
Toronto Pearson Intl
14 May - 9 Nov
C$ 429pp
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
19 May - 10 Jun
C$ 432pp
YYZ
Toronto Pearson Intl
Air Canada
Direct
ORD
Chicago O'Hare Intl
ORD
Chicago O'Hare Intl
Air Canada
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
12:55 p.m. - 1:57 p.m.
Major Airline
Direct
2h 02m
YYZ - ORD
Major Airline
C$ 215
StudentUniverse
12:40 p.m. - 4:38 a.m.
American Airlines
1 stop
16h 58m
YYZ - ORD
American Airlines
C$ 233
10:45 a.m. - 11:35 a.m.
Air Canada
Direct
1h 50m
YYZ - ORD
Air Canada
C$ 266

Related info for your journey

Useful info, stats and facts about <span class="emphasized">Lester B. Pearson Intl</span> to <span class="emphasized">Chicago</span> flights.

Flight FAQs

From Lester B. Pearson Intl to Chicago

Can I find flights from Lester B. Pearson Intl to Chicago for under C$ 364 on Cheapflights?

Yes, there are multiple flights from Lester B. Pearson Intl to Chicago for under C$ 364. The cheapest flight booked recently is on Air Canada for just C$ 354, but on average you can expect to pay C$ 386.

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$ 364 on Cheapflights?

Cheapflights has 18 direct flights from Lester B. Pearson Intl to Chicago under C$ 364. A good price for a direct flight from Lester B. Pearson Intl to Chicago is less than C$ 466.

Are there last-minute flights available from Lester B. Pearson Intl to Chicago for under C$ 485?

There are currently 17+ open flights from Lester B. Pearson Intl to Chicago within the next 7 days for less than C$ 485.

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 Air Canada, Air New Zealand, and United Airlines fly from Lester B. Pearson Intl to Chicago in about 1h 48m. The time it takes to get you to your destination is usually consistent. Generally, flights for this route are direct.

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 Air Canada. Our recent data shows that you can find tickets from as low as C$ 355 on this airline. Additional options worth looking into are American Airlines and Air New Zealand, starting at C$ 381 and C$ 391 round-trip.

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$ 215 on Major Airline. Other airlines that offer cheap prices include Air Canada from C$ 216 and American Airlines from C$ 218 one-way.

Alternative routes for Lester B. Pearson Intl to Chicago

See prices for flight routes from nearby airports that may be better suited for you.

Destination information for Chicago

Things to know before you go - useful duration and weather info for your trip from Lester B. Pearson Intl to Chicago.
Today's exchange rate
C$ 1 = $0.83
Flight duration
1h 45m
Average temperature for May in Chicago
22.0 °C
Avg rainfall for May in Chicago
109.0 mm

Airports servicing Toronto

Airports servicing Chicago

Chicago Midway (MDW)
Rockford (RFD)

Top 6 airlines flying from Lester B. Pearson Intl to Chicago

The chart below displays the airlines Cheapflights users travelling from Lester B. Pearson Intl to Chicago choose most often. Cheapest and average prices are based on aggregated data from the past 12 months.
Airline Cheapest Average Flexibility On-time COVID-19 safety
Air Canada
C$ 140 C$ 299 No cancel fee 67%
Search Air Canada flights
Porter Airlines
C$ 202 C$ 311 No cancel fee 52%
Search Porter Airlines flights
United Airlines
C$ 176 C$ 312 No cancel fee 69%
Search United Airlines flights
American Airlines
C$ 130 C$ 346 No cancel fee 71%
Search American Airlines flights
WestJet
C$ 177 C$ 370 No cancel fee 60%
Search WestJet flights
Delta
C$ 206 C$ 385 No cancel fee N/A
Search Delta flights

Hourly flight availability from Lester B. Pearson Intl to Chicago

See what time of day planes typically take off from Lester B. Pearson Intl towards Chicago.
Morning 6 AM to noon 75% of flight departures
Afternoon Noon to 6 PM 24% 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
See how many times per day planes take to the skies headed from Lester B. Pearson Intl to Chicago.
Sunday
12 daily flights
Monday
13 daily flights
Tuesday
11 daily flights
Wednesday
12 daily flights
Thursday
10 daily flights
Friday
12 daily flights
Saturday
9 daily flights
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