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Cheapest flights from Toronto to Chicago
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.
Remember that on average the ideal time to book flights is 2 months before departure!
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.
Schedule of direct flights from Toronto to Chicago
Toronto airports overview
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Chicago airports overview
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Frequently asked questions (FAQ)
Answers to questions about the route that travelers are most interested in.
Special offers and sales on air tickets from Toronto to Chicago
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 5 airlines operate flights from Toronto to Chicago, including United Airlines, Air Canada, American Airlines, Porter Airlines, and Westjet. This is a popular route, so passengers can choose tickets based on budget and preferences. Ticket prices start from $128, 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.
Cheapest one way flight
$128
Porter Airlines
Direct flight
2h 5m
11/15/2026
The cheapest one-way flight from Toronto to Chicago departs on 11/15/2026, is operated by Porter Airlines and costs $128
Cheapest round trip flight
$184
Porter Airlines
Direct flight
3h 30m
10/07/2026
The cheapest roundtrip flight from Toronto to Chicago departs on 10/07/2026, is operated by Porter Airlines and costs $184
The fastest flight
1h 55m
Fastest flight from Toronto to Chicago takes 1h 55m
Direct flights
Several times a week
There are direct flights on this route 4 days a week: Su, Tu, We, and Th
Earliest flight
7:00 AM
Latest flight
9:00 PM
Average flight duration
2h 4m
Direct flights count
84
Distance
701km
Timezone difference
1h
The distance between Toronto and Chicago is 701km (435 miles). The average flight duration is 2h 4m. There are 84 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
Air Canada
Every day
starting at $837
American Airlines
Every day
starting at $412
All airlines serving Toronto — Chicago operate daily direct flights: Air Canada and American Airlines fly every day.
Toronto is served primarily by Toronto Pearson International (YYZ) and Billy Bishop Toronto City (YTZ), with Pearson acting as the main international hub and Billy Bishop catering to regional and budget-conscious business travelers. Pearson typically hosts legacy carriers like Air Canada and many global airlines, as well as low-cost options, and can be perceived as mid-to-high priced for transfers and services. The airport is about 22 km (roughly 30–45 minutes by car depending on traffic) from downtown; options include the UP Express train (about 25 minutes, fares normally in the moderate range), taxis/ride-shares (30–60 minutes, fares vary), and shuttle services. Pros: extensive international connections and full-service facilities; Cons: can be busy with unpredictable checks and longer transfers. Billy Bishop sits on the Toronto Islands just 2 km from downtown (a short ferry or pedestrian tunnel access of 5–15 minutes) and is typically used by regional carriers and budget airlines for quick hops; it’s often seen as convenient and time-saving for central arrivals, though it offers fewer lounges and long-haul services.
September 2026
Lowest price
on average:
$120
October 2026
Highest price
on average:
$121
Avg Price
What is the cheapest price for flights from Toronto to Chicago?
The cheapest flight ticket from Toronto to Chicago according to data for the last 48 hours costs $128
When is the best time to buy air tickets on the route Toronto — Chicago?
Often the best time to buy tickets from Toronto to Chicago is 2 months before departure.
When is the cheapest time of year to fly from Toronto to Chicago?
Based on statistics over the past years, the lowest prices for flights from Toronto to Chicago can be found flying in these months: September, October.
How long does it take to fly from Toronto to Chicago?
The fastest flights from Toronto to Chicago start from 1 hour 55 minutes in the air.
Which airline can fly direct from Toronto to Chicago?
The following airlines operate direct flights on the route Toronto — Chicago: United Airlines, Air Canada, American Airlines
The cost of a one-way flight from Toronto to Chicago ranges from $120 (September 2026) to $121 (October 2026). On average, the ticket price is about $121–$121.
Chicago is served by two main airports with distinct roles. O'Hare International (ORD) is the city's primary international and connecting hub, typically hosting legacy carriers like United and American alongside many global airlines; fares from O'Hare can be competitive for long-haul and connecting itineraries. It's about 17–20 miles northwest of downtown; the CTA Blue Line offers direct service in roughly 45–50 minutes for a modest fare, while taxis or rideshares often take 30–60 minutes depending on traffic and can be pricier. Pros: extensive flight options and amenities; cons: busy terminals and potential for delays.
Midway Airport (MDW) functions more as a domestic and leisure-focused airport, usually favored by low-cost and point-to-point carriers, notably Southwest, which can make it a budget-friendly choice for short-haul travel. Located roughly 10–12 miles southwest of the Loop, it’s connected by the CTA Orange Line in about 25–35 minutes with a similar low fare, and rideshares/taxis typically take 20–40 minutes. Pros: smaller terminals and quicker walk times; cons: fewer international routes and less frequent late-night service compared with O'Hare.
