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  4. Toronto - Chicago

Flights Toronto - Chicago - eDreams Canada

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Explore the best deals

Discover the cheapest flights from Toronto to Chicago
Filter by
Tue, Nov 3 - Wed, Nov 11
AC
ACDirect
YTO - CHI
AC
ACDirect
CHI - YTO
432$
406$
Prime price per passenger
Fri, Nov 27 - Thu, Dec 3
AC
ACDirect
YTO - CHI
AC
ACDirect
CHI - YTO
431$
410$
Prime price per passenger
Wed, Dec 9 - Tue, Dec 15
AC
ACDirect
YTO - CHI
AC
ACDirect
CHI - YTO
431$
410$
Prime price per passenger
Fri, Nov 20 - Thu, Nov 26
AC
ACDirect
YTO - CHI
AC
ACDirect
CHI - YTO
431$
410$
Prime price per passenger
Tue, Dec 22 - Fri, Dec 25
AA
AADirect
YTO - CHI
AA
AADirect
CHI - YTO
438$
424$
Prime price per passenger
Tue, Jan 5 - Fri, Jan 8
AA
AADirect
YTO - CHI
AA
AADirect
CHI - YTO
438$
424$
Prime price per passenger
Wed, Jan 6
AA
AADirect
YTO - CHI
206$
194$
Prime price per passenger
Wed, Nov 11
PD
PDDirect
YTO - CHI
248$
227$
Prime price per passenger
Thu, Dec 3
AC
ACDirect
YTO - CHI
253$
237$
Prime price per passenger
Tue, Nov 24
AC
ACDirect
YTO - CHI
253$
238$
Prime price per passenger
Sat, Dec 12
AC
ACDirect
YTO - CHI
253$
238$
Prime price per passenger
Wed, Dec 23
PD
PDDirect
YTO - CHI
326$
310$
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 October. Take advantage of this period to save on your flight tickets and make the most of your trip. Please note that prices may change after your search.
Filter by
week: Oct 12 - Oct 18
Flights from just $197
$197
$214
$214
$215
$220
$219
$212
$217
$210
$239
$259
$269
OctoberNovemberDecember
Airlines that fly from Toronto to Chicago
Air Canada
Air Canada
293$
United Airlines
United Airlines
930$
Distance: 711 km
Toronto airports
Toronto Pearson International Airport (YYZ)How far from city centre: 20 km
Billy Bishop City Airport (YTZ)How far from city centre: 4 km
John C. Munro Hamilton International Airport (YHM)How far from city centre: 71 km
Chicago airports
O'hare International Airport (ORD)How far from city centre: 22 km

FAQs about flights between Toronto and Chicago

What is the usual price for a ticket from Toronto to Chicago?
The average ticket price for a flight from Toronto to Chicago is about $386. This can change depending on travel dates, demand, and how far in advance the flight is booked.
What’s the best way to find cheap flights from Toronto to Chicago on eDreams?
The lowest current fare from Toronto to Chicago is $ 194. Thanks to our system, we identify the best options across different airlines and itineraries to combine value and flexibility for your journey.
When is the right time to book flights from Toronto to Chicago?
The top months when travelers usually book a ticket from Toronto to Chicago are November, July and October, based on search trends from our platform.
When is the best season to travel from Toronto to Chicago?
The best moment to travel to Chicago from Toronto depends on whether you prioritize price, climate, or avoiding crowds. The busiest travel month is June, followed by July and August. To avoid peak travel, consider going in January, February or November, when demand is lower for the Toronto - Chicago route.
How many hours is the flight from Toronto to Chicago?
Flying between Toronto and Chicago generally takes about 2 hours, for a distance of approximately 710.98 km. Times may vary depending on whether you choose a direct flight or one with layovers.
What’s the weather like in Chicago vs. Toronto?
In summer, Toronto experiences average highs of 21º ºC. At the same time, Chicago can reach 22º ºC. In winter, the climate is cooler, averaging -3º ºC in Toronto compared to -3º ºC in Chicago.

Plan your trip

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