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 |
|---|---|
| September 2026 | find now |
| October 2026 | find now |
| November 2026 | find now |
| December 2026 | find now |
| January 2027 | find now |
| February 2027 | find now |
| March 2027 | find now |
| April 2027 | find now |
| May 2027 | find now |
| June 2027 | find now |
| July 2027 | find now |
| August 2027 | 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 |
Popular flights from Toronto
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Frequently asked questions about flights from Toronto to Chicago
How long does the flight from Toronto to Chicago take?
Flight duration from Toronto to Chicago varies by route, airline, and number of stops. Direct flights are faster; connecting flights may take longer. Use our search to compare options and see exact durations for your dates.
Are there direct flights from Toronto to Chicago?
Availability of direct flights from Toronto to Chicago depends on the route and season. Use our search and filter by "Direct" or "Non-stop" to see only direct options. We compare offers from many airlines and agencies.
Which airlines fly from Toronto to Chicago?
Several airlines may operate flights from Toronto to Chicago. On this page you can see airlines that serve this route. Our search compares prices across airlines and agencies so you can choose the best offer. We do not sell tickets; you book directly with the airline or agency.
What is the cheapest month to fly from Toronto to Chicago?
Prices from Toronto to Chicago vary by month and demand. On this page you can see average round-trip prices by month. Use the low-fare calendar and monthly table to find the cheapest dates. Booking in advance and avoiding peak seasons often helps get the best price.