Compare airlines, prices, and flight durations for your trip
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.
The cost of a one-way flight from Toronto to Chicago ranges from $122 (May 2026) to $207 (January 2026). On average, the ticket price is about $165–$207.
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.
A direct flight is the easiest way to get to your destination. The following airlines operate non-stop flights from Toronto to Chicago:
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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.
The cheapest one-way flight from Toronto to Chicago departs on 05/02/2026, is operated by Porter Airlines and costs $105
The cheapest roundtrip flight from Toronto to Chicago departs on 05/15/2026, is operated by Porter Airlines and costs $139
Fastest flight from Toronto to Chicago takes 1h 50m
There are direct flights on this route 5 days a week: Su, Mo, We, Th, and Sa
The distance between Toronto and Chicago is 701km (435 miles). There are 30 direct flights from Toronto to Chicago. The time difference between Toronto and Chicago is 1h. Flights from Toronto begin at 6:00 AM. The latest flight from Toronto departs at 9:00 PM
More than 5 airlines operate flights from Toronto to Chicago, including Air Canada, Porter Airlines, United Airlines, Air Transat, and Flair Airlines Ltd.. This is a popular route, so passengers can choose tickets based on budget and preferences. Ticket prices start from $105, 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.
starting at $122
starting at $105
starting at $131
starting at $192
starting at $207
Toronto — Chicago
01/31/2026
Departure
Direct flight
AC4408
starting at $426
Toronto — Chicago
04/30/2026
Departure
Direct flight
PD2387
starting at $109
Toronto — Chicago
05/02/2026
Departure
Direct flight
UA3576
starting at $187
Toronto — Chicago
05/14/2026
Departure
Direct flight
PD2387
starting at $245
Toronto — Chicago
05/17/2026
Departure
Direct flight
AC511
starting at $201
Toronto — Chicago
05/18/2026
Departure
Direct flight
TS7060
starting at $192
Toronto — Chicago
08/26/2026
Departure
Direct flight
PD2393
starting at $163
Unable to find information about the schedule of direct flights from
The cheapest flight ticket from Toronto to Chicago according to data for the last 48 hours costs $105
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: May, January.
The fastest flights from Toronto to Chicago start from 1 hour 50 minutes in the air.
The following airlines operate direct flights on the route Toronto — Chicago: Air Canada, Porter Airlines, United Airlines
We couldn't find any special offers for flights from Toronto to Chicago
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