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Toronto To Chicago Flights

  • One-Way
  • Round-Trip
  • Multi-City

From

Indira Gandhi International Airport

To

Chhatrapati Shivaji International Airport

DEPARTURE DATE

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Friday

Return Date

Book a round trip
to save more

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TRAVELLER & CLASS

1 Traveller

Economy

December
January
February
March
April
August
September
October
November

December is by far the best month, wherein you can get cheapest flights for Toronto to Chicago. Meanwhile, December is perceived as the expensive month due to the varying factors. That’s why it’s highly advised to make advanced online flight booking to save huge amounts of money.

Things to know
arrow One Way Fare
December

December- During this month the footfall is less so, the flight is gradually inexpensive.

round Round Trip Fare
December

December - is the cheapest month to book round trip flights.

Cheaper Fare
$ 164

Cheapest Fare- Currently, this is the fare price based on the current demand.

disclDisclaimer - All the mentioned fares were found within last 48 hrs. The displayed fares are based on historical data and are subject to change. The fares cannot be guaranteed at the time of booking.

Best Flight From Toronto To Chicago

Cheapest
Porter Airlines
Porter Airlines

YTZ

09:15

Toronto Billy Bishop Toronto City Centre Airport

Mon , 01 Dec 2025

01h 50m
ellipse
Non Stop

MDW

10:05

Chicago Chicago Midway International Airport

Mon, 01 Dec 2025

$173
Air Transat
Air Transat

YTZ

09:15

Toronto Billy Bishop Toronto City Centre Airport

Mon , 01 Dec 2025

01h 50m
ellipse
Non Stop

MDW

10:05

Chicago Chicago Midway International Airport

Mon, 01 Dec 2025

$188
Porter Airlines
Porter Airlines

YTZ

09:15

Toronto Billy Bishop Toronto City Centre Airport

Tue , 02 Dec 2025

01h 50m
ellipse
Non Stop

MDW

10:05

Chicago Chicago Midway International Airport

Tue, 02 Dec 2025

$259
Air Transat
Air Transat

YTZ

09:15

Toronto Billy Bishop Toronto City Centre Airport

Tue , 02 Dec 2025

01h 50m
ellipse
Non Stop

MDW

10:05

Chicago Chicago Midway International Airport

Tue, 02 Dec 2025

$275
Porter Airlines
Porter Airlines

YTZ

14:30

Toronto Billy Bishop Toronto City Centre Airport

Mon , 01 Dec 2025

01h 50m
ellipse
Non Stop

MDW

15:20

Chicago Chicago Midway International Airport

Mon, 01 Dec 2025

$378
Air Transat
Air Transat

YTZ

14:30

Toronto Billy Bishop Toronto City Centre Airport

Mon , 01 Dec 2025

01h 50m
ellipse
Non Stop

MDW

15:20

Chicago Chicago Midway International Airport

Mon, 01 Dec 2025

$394
ellipse

Find the Lowest Airfare Toronto to Chicago

Cheapest Fares
Fare
Date
Airline
Departure
Lowest Airfare
$164
21 December 2025
Porter Airlines
09:15 AM
Cheapest Airfare Within 30 Days
$164
21 December 2025
Porter Airlines
09:15 AM
Cheapest Airfare Within 90 Days
$164
21 December 2025
Porter Airlines
09:15 AM
ellipse

Early Morning Flight Toronto to Chicago

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Cheapest Flight
Found
$173
group
Average Flight
Time
01h 50m
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Date/Time
01 Dec 2025
09:15 AM
plane
Airlines
Porter Airlines
Ellipse

Late Night Flight Toronto to Chicago

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Cheapest Flight
Found
$378
group
Average Flight
Time
01h 50m
calendar
Date/Time
01 Dec 2025
14:30 PM
plane
Airlines
Porter Airlines