Cheap flights from 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
Pearson Intl (YYZ) to Chicago (CHI)

All the information you need to plan the best YYZ to CHI flight in 2021: compare Pearson Intl to Chicago flight prices with the expected peak season, weather and rainfall in Chicago.
YYZ - CHI
Price
C$ 285 - C$ 394
CHI
Temperature
-5 - 23 °C
CHI
Precipitation
43 - 125 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$ 285

From Toronto Pearson Intl to Chicago All airports (CHI)

One-way from

C$ 193

One-way flight from Toronto Pearson Intl to Chicago All airports (CHI)

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 Toronto Pearson Intl Airport to Chicago?

To save up to 86% on this flight, we recommend booking at least 34 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$ 440 1-2 weeks out and tickets from C$ 596 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 January. For low rates, April can be a great choice for travel to Chicago. Flights to Chicago from Toronto Pearson Intl Airport in April are about C$ 320 on average during April, 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 flights from Pearson Intl to Chicago in September, October 2021

The best prices found for YYZ to CHI flights for September, October
31 Oct - 13 Nov
C$ 269pp
YYZ
Toronto Pearson Intl
Multiple Airlines
 
1 STOP
ORD
Chicago O'Hare Intl
ORD
Chicago O'Hare Intl
Multiple Airlines
 
1 STOP
YYZ
Toronto Pearson Intl
16 Oct - 23 Oct
C$ 275pp
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
14 Oct - 18 Oct
C$ 286pp
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

Toronto Pearson Intl to Chicago 2021 flight deals

Cheap flights to Chicago from Pearson Intl found for this year
6 Nov - 8 Nov
C$ 266pp
YYZ
Toronto Pearson Intl
Multiple Airlines
 
1 STOP
ORD
Chicago O'Hare Intl
ORD
Chicago O'Hare Intl
Multiple Airlines
 
1 STOP
YYZ
Toronto Pearson Intl
31 Oct - 13 Nov
C$ 269pp
YYZ
Toronto Pearson Intl
Multiple Airlines
 
1 STOP
ORD
Chicago O'Hare Intl
ORD
Chicago O'Hare Intl
Multiple Airlines
 
1 STOP
YYZ
Toronto Pearson Intl
11 Nov - 15 Nov
C$ 270pp
YYZ
Toronto Pearson Intl
Multiple Airlines
 
1 STOP
ORD
Chicago O'Hare Intl
ORD
Chicago O'Hare Intl
Multiple Airlines
 
1 STOP
YYZ
Toronto Pearson Intl

Direct flights to Chicago from Pearson Intl

Save time with Pearson Intl to Chicago direct flight deals
10 Nov - 14 Nov
C$ 291pp
YYZ
Toronto Pearson Intl
Air Canada
Direct
ORD
Chicago O'Hare Intl
ORD
Chicago O'Hare Intl
Air Canada
Direct
YYZ
Toronto Pearson Intl
30 Oct - 2 Nov
C$ 312pp
YYZ
Toronto Pearson Intl
Air Canada
Direct
ORD
Chicago O'Hare Intl
ORD
Chicago O'Hare Intl
Air Canada
Direct
YYZ
Toronto Pearson Intl
12 Nov - 15 Nov
C$ 313pp
YYZ
Toronto Pearson Intl
American Airlines
Direct
ORD
Chicago O'Hare Intl
ORD
Chicago O'Hare Intl
American Airlines
Direct
YYZ
Toronto Pearson Intl

Last minute flights from Pearson Intl to Chicago

Late deals on round-trip flights to Chicago from Pearson Intl, departing today and this week
4 Oct - 3 Nov
C$ 343pp
YYZ
Toronto Pearson Intl
Multiple Airlines
 
1 STOP
ORD
Chicago O'Hare Intl
ORD
Chicago O'Hare Intl
Multiple Airlines
 
1 STOP
YYZ
Toronto Pearson Intl
4 Oct - 11 Oct
C$ 366pp
YYZ
Toronto Pearson Intl
Multiple Airlines
 
1 STOP
ORD
Chicago O'Hare Intl
ORD
Chicago O'Hare Intl
Multiple Airlines
 
1 STOP
YYZ
Toronto Pearson Intl
4 Oct - 11 Oct
C$ 383pp
YYZ
Toronto Pearson Intl
Multiple Airlines
   
2 STOPS
ORD
Chicago O'Hare Intl
ORD
Chicago O'Hare Intl
Multiple Airlines
 
1 STOP
YYZ
Toronto Pearson Intl

One-way flights to Chicago from Toronto Pearson Intl

The cheapest one-way flights from Pearson Intl to Chicago
2:55 p.m. - 1:20 a.m.
Multiple Airlines
1 stop
11h 25m
YYZ - ORD
Multiple Airlines
C$ 193
FlyFar
4:00 a.m. - 3:43 p.m.
Air Canada
2 stops
12h 43m
YYZ - ORD
Air Canada
C$ 199
Gotogate
2:45 a.m. - 3:54 a.m.
American Airlines
Direct
2h 09m
YYZ - ORD
American Airlines
C$ 200

Related info for your journey

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

Flight FAQs

From Pearson Intl to Chicago

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.

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$ 266, but on average you can expect to pay C$ 286.

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$ 332.

Are there last-minute flights available from Toronto Pearson Intl Airport to Chicago for under C$ 400?

There are currently 20+ open flights from Toronto Pearson Intl Airport to Chicago within the next 7 days for less than C$ 400.

What days are direct flights available from Toronto Pearson Intl Airport to Chicago?

You can find direct flights on the following days: Monday, Tuesday.

How many flights depart from Toronto Pearson Intl Airport to Chicago on average per day?

1 flight departure from Toronto Pearson Intl Airport to Chicago per day on average.
Afternoon (Noon - 6pm) - 100% of flight departures

How long is the flight from Toronto Pearson Intl Airport to Chicago?

Airlines like Air Canada and American Airlines fly from Toronto Pearson Intl Airport to Chicago in about 2h 13m. The time it takes to get you to your destination can typically vary by up to 2h 30m. The distance between Toronto Pearson Intl Airport and Chicago is about 703 km. This flight may include one or multiple stops.

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

Currently priced at C$ 275, 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. Check Cheapflights for deals on American Airlines for as low as C$ 313. Users have found that Air Canada is 18% 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$ 148 on Air Canada. Other airlines that offer cheap prices include American Airlines from C$ 184 and Delta from C$ 200 one-way.

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

Before booking your flight from Toronto Pearson Intl Airport to Chicago check out the most popular airlines for this route: Major Airline, American Airlines or Air Canada.

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

On average you can expect to pay C$ 338 for a flight from Toronto Pearson Intl Airport to Chicago. The cheapest flight overall is C$ 178 while the most popular route, (Toronto Pearson Intl - Chicago O'Hare Intl) is currently priced at C$ 266.

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: ANA (100%), Finnair (93%), Republic Airways( 92%).

COVID Restrictions

View COVID Travel Restrictions for Chicago, IL

Do I need a COVID test to fly to Chicago from Pearson Intl?

Information is based on travel restrictions from Toronto Pearson Intl to Chicago

Most visitors from Toronto Pearson Intl need to provide a negative COVID-19 test result and/or quarantine to enter Chicago.

COVID-19 testing requirements
Visitors from Toronto Pearson Intl must present a negative RT-PCR (NAAT) or Antigen (quick-test) test taken 72 hours before departing to Chicago.

Quarantine requirements
Visitors from Toronto Pearson Intl are not required to quarantine after entering Chicago.

Do I need a test to fly back to Pearson Intl from Chicago?

Returning to Toronto Pearson Intl from Chicago

COVID-19 testing requirements
Visitors from Chicago must present a negative RT-PCR (NAAT) test taken 72 hours before departing to Toronto Pearson Intl.

Quarantine requirements
Visitors from Chicago are not required to quarantine after entering Toronto Pearson Intl.

Hide COVID Travel Restrictions for Chicago, IL

Alternative routes for 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 Pearson Intl to Chicago.
Today's exchange rate
C$ 1 = $0.79
Flight duration from Toronto Pearson Intl to Chicago
1h 56m
Average temperature for September in Chicago
25.0 °C
Avg rainfall for September in Chicago
60.0 mm

Airports servicing Toronto

Airports servicing Chicago

Midway (MDW)
Rockford (RFD)

Top 6 airlines flying from Toronto Pearson Intl to Chicago

The chart below displays the airlines Cheapflights users travelling from 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
American Airlines
C$ 165 C$ 438 No cancel fee 71%
Search American Airlines flights
Air Canada
C$ 178 C$ 379 No cancel fee 67%
Search Air Canada flights
United Airlines
C$ 223 C$ 395 No cancel fee 69%
Search United Airlines flights
WestJet
C$ 224 C$ 469 No cancel fee 60%
Search WestJet flights
Porter Airlines
C$ 256 C$ 394 No cancel fee 52%
Search Porter Airlines flights
Delta
C$ 261 C$ 488 No cancel fee N/A
Search Delta flights

Hourly flight availability from Pearson Intl to Chicago

See what time of day planes typically take off from Pearson Intl towards Chicago.
Afternoon Noon to 6 PM 57% of flight departures
Morning 6 AM to noon 42% 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 Pearson Intl to Chicago
See how many times per day planes take to the skies headed from Pearson Intl to Chicago.
Sunday
21 daily flights
Monday
23 daily flights
Tuesday
21 daily flights
Wednesday
22 daily flights
Thursday
22 daily flights
Friday
26 daily flights
Saturday
24 daily flights
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