Flaut.Travel was designed and developed by a team dedicated to making the process of searching, comparing and booking airline tickets as easy and convenient as possible. Our service helps travelers to find and buy the cheapest flights from Toronto to Chicago. We have connected more than 40 airlines and airline ticketing agencies to help you find the most suitable and affordable flight option.
A non-stop flight is the most convenient and comfortable way to fly from Toronto to Chicago, despite the fact that sometimes flights with transfers can cost significantly less.
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Answers to questions about the route that travelers are most interested in.
We keep tight track on airlines' pre-holidays sales and other special offers occurences all the time to let you save maximum amount of funds while traveling to your family or just going out on vacation.
All airports
We carefully collect statistics on the search and pricing of airlines and, based on these data, we make an assumption about future prices. Thus, you can better understand which season is the cheapest to fly from Toronto to Chicago
Toronto — Chicago
11/22/2026
Departure
Direct flight
PD2703
starting at $227
Toronto — Chicago
11/15/2026
Departure
Direct flight
PD2705
starting at $295
Toronto — Chicago
11/11/2026
Departure
Direct flight
AA3610
starting at $172
Toronto — Chicago
11/10/2026
Departure
Direct flight
AA3608
starting at $173
Toronto — Chicago
11/18/2026
Departure
Direct flight
AC501
starting at $218
Toronto — Chicago
11/17/2026
Departure
Direct flight
PD2705
starting at $222
Toronto — Chicago
11/19/2026
Departure
Direct flight
PD2705
starting at $233
Toronto — Chicago
11/16/2026
Departure
Direct flight
PD2703
starting at $236
Toronto — Chicago
11/14/2026
Departure
Direct flight
AA3610
starting at $251
Toronto — Chicago
02/19/2027
Departure
Direct flight
PD2705
starting at $204
starting at $204
starting at $172
starting at $212
starting at $190
More than 4 airlines operate flights from Toronto to Chicago, including Porter Airlines, American Airlines, Air Canada, and Flair Airlines Ltd.. This is a popular route, so passengers can choose tickets based on budget and preferences. Ticket prices start from $172, and our service lets you instantly compare all options. The variety of offers simplifies planning: you can choose budget fares or more comfortable options with baggage included or extra services. We help you find the best deals so your trip is cost-efficient.
The cheapest flight ticket from Toronto to Chicago according to data for the last 48 hours costs $172
Often the best time to buy tickets from Toronto to Chicago is 2 months before departure.
Based on statistics over the past years, the lowest prices for flights from Toronto to Chicago can be found flying in these months: November.
The fastest flights from Toronto to Chicago start from 1 hour 55 minutes in the air.
The following airlines operate direct flights on the route Toronto — Chicago: Porter Airlines, American Airlines, Air Canada
American Airlines
Every day
starting at $264
The only airline operating direct flights from Toronto to Chicago is American Airlines. Flights operate every day.
The cheapest one-way flight from Toronto to Chicago departs on 11/11/2026, is operated by American Airlines and costs $172
The cheapest roundtrip flight from Toronto to Chicago departs on 11/26/2026, is operated by Porter Airlines and costs $268
Fastest flight from Toronto to Chicago takes 1h 55m
There are direct flights on this route 7 days a week: Su, Mo, Tu, We, Th, Fr, and Sa
The distance between Toronto and Chicago is 701km (435 miles). There are 212 direct flights from Toronto to Chicago. The time difference between Toronto and Chicago is 1h. Flights from Toronto begin at 6:45 AM. The latest flight from Toronto departs at 7:26 PM
We couldn't find any special offers for flights from Toronto to Chicago