starting at $125
starting at $125
starting at $131
starting at $135
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.
The airlines on the Toronto — Chicago route each fly on specific days: Porter Airlines and Air Canada fly on Monday, Wednesday, Thursday, and Friday.
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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.
More than 4 airlines operate flights from Toronto to Chicago, including Porter Airlines, Air Transat, Air Canada, and Passaredo Linhas Aereas. This is a popular route, so passengers can choose tickets based on budget and preferences. Ticket prices start from $125, 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 $125
starting at $125
starting at $131
starting at $135
Toronto — Chicago
07/15/2026
Departure
Direct flight
PD2387
starting at $125
Toronto — Chicago
08/08/2026
Departure
Direct flight
TS7060
starting at $125
Toronto — Chicago
06/21/2026
Departure
Direct flight
AC8901
starting at $131
Toronto — Chicago
06/22/2026
Departure
Direct flight
P32393
starting at $135
Toronto — Chicago
07/26/2026
Departure
Direct flight
AC8547
starting at $137
Toronto — Chicago
07/22/2026
Departure
Direct flight
P32387
starting at $142
Toronto — Chicago
07/25/2026
Departure
Direct flight
AC8547
starting at $159
Toronto — Chicago
06/12/2026
Departure
Direct flight
P32393
starting at $159
Toronto — Chicago
06/20/2026
Departure
Direct flight
PD2387
starting at $160
Toronto — Chicago
05/01/2027
Departure
Direct flight
PD2387
starting at $210
Porter Airlines
Mo, We, Th, and Fr
starting at $160
Air Canada
Mo, We, Th, and Fr
starting at $160
We couldn't find any special offers for flights from Toronto to Chicago
The cheapest one-way flight from Toronto to Chicago departs on 07/15/2026, is operated by Porter Airlines and costs $125
The cheapest roundtrip flight from Toronto to Chicago departs on 07/10/2026, is operated by Porter Airlines and costs $213
Fastest flight from Toronto to Chicago takes 1h 50m
There are direct flights on this route 5 days a week: Su, Mo, We, Fr, and Sa
The distance between Toronto and Chicago is 701km (435 miles). The average flight duration is 2h 5m. There are 44 direct flights from Toronto to Chicago. The time difference between Toronto and Chicago is 1h. Flights from Toronto begin at 7:00 AM. The latest flight from Toronto departs at 9:00 PM
The cheapest flight ticket from Toronto to Chicago according to data for the last 48 hours costs $125
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: July, August, June.
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: Porter Airlines, Air Transat, Air Canada
The cost of a one-way flight from Toronto to Chicago ranges from $125 (July 2026) to $210 (May 2027). On average, the ticket price is about $131–$148.
Ticket prices for Toronto — Chicago follow a predictable curve: rise, peak, and decline. This typical seasonal pattern lets you plan your purchase to avoid overpaying.
Prices rise from August 2026 to May 2027 (+68%), then decline from June 2026 to August 2026 (5%). The cheapest tickets are in July 2026–August 2026 (averaging $125), while the priciest are in August 2026–May 2027 ($167).
For savings, plan your flight for July 2026–August 2026 — you could save up to 25%. Try to avoid August 2026–May 2027 when possible: prices are at their highest then.
Price spread on this route is 24.3%. Costs depend heavily on the season, so flexibility in choosing your departure month is especially valuable here.