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  1. Flights
  2. United States
  3. Chicago
  4. Toronto - Chicago

Book cheap flights from Toronto to Chicago from $181

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Discover the cheapest flights from Toronto to Chicago
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Wed, 1 July - Fri, 3 July
Porter Airlines
Porter AirlinesDirect
YTO - CHI
Porter Airlines
Porter AirlinesDirect
CHI - YTO
336$
328$
Prime price per passenger
Sun, 9 Aug
Porter Airlines
Porter AirlinesDirect
YTO - CHI
196$
181$
Prime price per passenger
Tue, 30 June
Porter Airlines
Porter AirlinesDirect
YTO - CHI
187$
182$
Prime price per passenger
Wed, 12 Aug
Porter Airlines
Porter AirlinesDirect
YTO - CHI
199$
183$
Prime price per passenger
Wed, 22 July
Porter Airlines
Porter AirlinesDirect
YTO - CHI
189$
185$
Prime price per passenger
Tue, 7 July
Air Canada
Air CanadaDirect
YTO - CHI
207$
204$
Prime price per passenger
The prices shown on this page were available within the last 20 days for the specified periods and should not be considered the final price offered. Please note that availability and prices are subject to change.

Cheapest time to fly from Toronto to Chicago

If you’re planning to fly this route soon, keep in mind that the lowest fares are usually available in the middle of July. Take advantage of this per
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week: 13 July - 19 July
Flights from just $176
$198
$235
$261
$176
$201
$255
$228
$238
$237
$215
$268
$192
JuneJulyAugustSeptember
Distance: 711 kms
Toronto airports
Pearson International Airport (YYZ)How far from city centre: 20 kms
Chicago airports

Get the Best Deals on Flights from Toronto to Chicago

Discover the best last-minute airfares and cheap prices from Toronto to Chicago with Opodo Australia. Avoid overspending on flight tickets and start planning your perfect getaway. Opodo offers a hassle-free booking experience, providing access to top airline carriers and the most competitive prices.


Find the best flights that fit your needs

When do you want to depart from Toronto? Adjust your travel dates and explore a wide range of options to Chicago. With Opodo, you can find the perfect flight from our extensive selection, ensuring a seamless and enjoyable trip. Compare prices, flight durations, and amenities to choose the best option that suits your needs.


Book all in one place

But wait, there's more! Enhance your travel experience by booking a hotel and renting a car along with your flight. It's easier and often cheaper to book everything together. Choose the best offer from Toronto to Chicago and get ready for an incredible journey. Enjoy your holiday, and remember to fasten your seatbelt. We’re ready for takeoff!

Frequently asked questions about flights from Toronto to Chicago

How long does the flight take to go from Toronto to Chicago?
The total flight time between Toronto and Chicago is of around 1 h and 55 m on average, considering an average distance of 710.98 km, for both direct and indirect flights for the route (which may have 1 or more stops in other cities in between).
On average, how much is the price of a flight from Toronto to Chicago?
When you fly from Toronto to Chicago the average price is $285. However, this price depends on many other factors such as seasonality or how far in advance the route has been booked.
How can I find cheap flights from Toronto to Chicago at Opodo?
The cheapest price for a flight from Toronto to Chicago is $181. At Opodo we use different machine learned based methodologies to find our costumers the best option available, considering airline combinations, stopovers and direct flights as well as different criteria for inbound and outbound journeys.
When is the best time to book a flight from Toronto to Chicago?
The most popular months to book a trip from Toronto to Chicago are July, September and October, based on the searches of our customers.
When is the best time to travel from Toronto to Chicago?
The best time of the year to go to Chicago when flying from Toronto depends on several preference factors like climate, seasonality and, of course, price. When it comes to popularity, October is the top 1º month to fly to Chicago from Toronto in terms of searches from our customer, followed by July and June. If you prefer to avoid high peaks of turism, however, and escape a crowded period, February, April and March are the months with less volume of searchs for the route Toronto - Chicago.
How is the weather in Chicago compared to Toronto?
While in Toronto temperatures can reach an average of 21º ºC in summer, Chicago's temperatures can rise to 22º ºC during the hot season. In winter, however, weather data show around -3º ºC in Chicago, compared to the -3º ºC average in Toronto.

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