On this page, you can book flights from Toronto to Chicago. The direct distance between the cities is 703 km, and flight frequency reaches 265 flights per week, providing a wide selection of departure times.
Flights are operated by airlines such as United Airlines, Air Canada, and American Airlines. Prices are dynamic, so we recommend using the low-fare calendar and checking information in advance on how to get to Toronto airport and how to get from Chicago airport to your destination.
The table shows direct flights Toronto → Chicago on the selected date. The flight takes approximately 1 h 50 min. Regular flights are operated by Air Canada, United Airlines, Porter Airlines and American Airlines. Departures from Pearson International Airport, Billy Bishop Toronto City Airport and Hamilton Airport airports, arrivals at O'Hare International Airport, Chicago Midway International Airport and Midway International Airport.
For each flight, the following details are shown: departure time (local), arrival city and airport, flight number and airline, terminal or gate, and status. Click on a flight to open its details and go to ticket search. To view flights on a different day, change the date above the table.
Below is a calendar of the lowest flight ticket prices for Toronto — Chicago by day. Pick a convenient date and instantly see the fare. The cheapest flights on this route start from AED 519 in F, and the most expensive are around AED 706 in n. If your travel dates are flexible, the calendar will help you find the best price for your preferred period. To view round-trip fares, switch to the "Round trip" tab above the calendar, select your departure date — and the right-hand calendar will highlight the lowest prices for return flights on each day.
Toronto → Chicago, average one-way price
| Month | Average price | Level | Month | Average price | Level | Month | Average price | Level |
|---|---|---|---|---|---|---|---|---|
| Jan | AED 552 | low | May | AED 677 | medium | Sep | AED 702 | medium |
| Feb | AED 527 | low | Jun | AED 802 | high | Oct | AED 652 | medium |
| Mar | AED 577 | low | Jul | AED 852 | high | Nov | AED 602 | low |
| Apr | AED 627 | medium | Aug | AED 827 | high | Dec | AED 777 | high |
Some values are estimated based on seasonality.
Weather conditions in Chicago are most favorable in July and August, when the average high is 26.5°C. The coldest months are January and February with temperatures as low as -5°C, while peak precipitation occurs in May.
The most budget-friendly flights are available in September with prices starting AED 519. The most expensive period for travel is March, when the minimum ticket cost increases to AED 706.
The optimal time to book is September or October: during this period, the weather remains comfortable, and prices are among the lowest of the year. It is recommended to avoid the winter months due to the risk of flight delays caused by weather conditions.
Ten airlines operate on the Toronto—Chicago route, with United Airlines, Air Canada, and American Airlines leading in flight frequency. Flights are primarily direct, providing up to 265 flights per week. You can check the detailed schedule and choose a suitable option by day of the week in the interactive list below.
Flights Toronto — Chicago depart from Pearson International Airport, Billy Bishop Toronto City Airport, Hamilton Airport and Region of Waterloo International Airport and arrive at O'Hare International Airport, Chicago Midway International Airport, Midway International Airport and Chicago Rockford International Airport. Below are pages for the cities, countries, and airports on the route: airlines, schedules, and travel guides.
The average travel time for a direct flight is between 1 hour 20 minutes and 1 hour 40 minutes, given the route distance of 703 km.
Major carriers such as United Airlines, Air Canada, and American Airlines operate on this route, along with regional airlines including Porter Airlines.
Yes, there are approximately 265 direct flights per week on this route, making it easy to find a convenient departure time throughout the day.
The best deals are usually available when booking 1–2 months before the trip. The current minimum for this season starts from 10,346 ₽.
Most flights arrive at Chicago's major international airports — O'Hare (ORD) and Midway (MDW).
Where travelers fly most — pick a route and check prices
