Cheap flights from Toronto to Chicago from R2 327

The month of January is, on average, the cheapest month to fly to Chicago from Toronto, with most prices found around R4 322. If you are unable to visit Chicago during the month of January, then departing from Toronto during the month February is also very affordable. Most momondo users find prices during this month for around R4 521.

Fly from Toronto Pearson Intl to Chicago O'Hare Intl for the best Toronto - Chicago flight prices

You are more likely to see cheaper flights to Chicago from Toronto when booking weeks ahead of your departure date. In general, you can expect to find flights to Chicago for around R5 228 when searching weeks before you fly. However, flight prices might be lower outside of this timeframe. For example, people recently found flights to Chicago from Toronto for as low as R3 757 on momondo.

There is only 1 cabin class available to choose from on Toronto to Chicago flights. Cabin price and availability will vary by airline so perform a search above to find the right deals for you.

Historically, on average around 14% of flights between Toronto and Chicago have experienced a delay on any given week. The average delay length over the past 12 months has been 134 minutes.

Generally, flights departing in the morning tend to experience fewer delays. Flights departing in the evening have, in the past, seen delays more frequently in comparison.

Thursday is statistically the day of the week that experiences the fewest delays on this flight route. Saturday has historically seen more delays on average compared to the rest of the week.

According to our data, United Airlines have had the fewest delays on this route over the last 12 months, with about 9% of their flights experiencing any sort of delay.

The number of flights available between Toronto and Chicago is 52 per day as of October 2026. The most frequent departure time is 13:00, with 47% of daily flights leaving in the afternoon.

The number of flights available between Toronto and Chicago is 368 per week as of October 2026. The most frequent departure day is Sun, with 17% of weekly flights leaving on this day.