Flying from Lester B. Pearson International 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 Lester B. Pearson International - Chicago (YYZ - 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 Lester B. Pearson International.
Average round-trip airfares from Lester B. Pearson International to Chicago by months
| Month | Round-Trip |
|---|---|
| February 2026 | 28.02 - 01.03from C$273 |
| March 2026 | 06.03 - 09.03from C$273 |
| April 2026 | 15.04 - 15.04from C$283 |
| May 2026 | find now |
| 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 |
| January 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 Lester B. Pearson International to Chicago
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Frequently asked questions about flights from Lester B. Pearson International to Chicago
How long does the flight from Lester B. Pearson International to Chicago take?
Flight duration from Lester B. Pearson International 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 Lester B. Pearson International to Chicago?
Availability of direct flights from Lester B. Pearson International 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 Lester B. Pearson International to Chicago?
Several airlines may operate flights from Lester B. Pearson International 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 Lester B. Pearson International to Chicago?
Prices from Lester B. Pearson International 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.