Flying from Toronto to Chicago can be expensive. Our search helps you compare cheap flights, airfare deals, and flight tickets across airlines and agencies so you can book at the best price.
We scan trusted travel agencies and airline booking systems for the route Toronto - Chicago (YTO - CHI). We do not sell tickets or add fees - you choose where to buy.
Airfares vary by date, time, and airport. Use filters to find the best option by departure/arrival time, number of stops, airline or alliance, and booking channel.
If your dates are flexible, check the low-fare calendar to find the cheapest days. Booking round-trip in one order often reduces fees, and prices usually rise as departure approaches.
We also recommend you to look through the prices for return tickets from Chicago to Toronto.
Airfares found by our users in the past 24 hours
The price for these dates could change. Use search to get the best price.
Average round-trip airfares from Toronto to Chicago by months
| Month | Round-Trip |
|---|---|
| January 2026 | 31.01 - 21.02from 20 193र |
| February 2026 | find now |
| March 2026 | 04.03 - 05.03from 11 281र |
| April 2026 | 15.04 - 16.04from 11 641र |
| May 2026 | 26.05 - 30.05from 11 946र |
| June 2026 | find now |
| July 2026 | find now |
| August 2026 | find now |
| September 2026 | find now |
| October 2026 | find now |
| November 2026 | find now |
| December 2026 | find now |
Prices shown are based on searches from the last few days. Ticket prices can change and depend on availability at the time of booking.
Airlines are flying from Toronto to Chicago
| Air Transat | Porter Airlines |