Cheap flights from Ontario to Chicago from C$ 189

In general, February is the cheapest month to fly from Region of Ontario to Chicago O'Hare Intl Airport. Due to it being the ‘off-season’ during this time, you can expect flight prices to be around C$ 398. The month of May is another great option to travel to Chicago O'Hare Intl Airport, with average flight prices from Region of Ontario averaging around C$ 416.

The cheapest day to depart on your flight to Chicago O'Hare Intl Airport is on a Friday when prices can be found for as low as C$ 685. This is often the case because there is less demand to fly during this day of the week. When flying out on a Sunday, the most expensive travel day of the week, you can expect to see flight prices from Region of Ontario to Chicago O'Hare Intl Airport for around C$ 950.

In the evening is the cheapest time of day to fly from Region of Ontario to Chicago O'Hare Intl Airport when you can find flight prices for as low as C$ 703. Flying to Chicago O'Hare Intl Airport in the evening is an ideal time because this is during off-peak travel hours. If you have a flexible travel schedule, then try to avoid flying in the afternoon when prices are C$ 1,126 on average. Flights to Chicago O'Hare Intl Airport from Region of Ontario in the afternoon are generally more expensive because this time of day is more convenient for travellers’ schedules.

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

You are more likely to see cheaper flights to Chicago O'Hare Intl Airport from Region of Ontario when booking weeks ahead of your departure date. In general, you can expect to find flights to Chicago O'Hare Intl Airport for around C$ 439 when searching weeks out. However, flight prices might be lower outside of this timeframe. For example, people recently found flights to Chicago O'Hare Intl Airport from Region of Ontario for as low as C$ 316 on momondo.

There are 4 cabin classes available to choose from on Region of Ontario to Chicago O'Hare Intl Airport flights. Cabin price and availability will vary by airline so perform a search above to find the right deals for you.

Delta, Porter Airlines, and Air Canada are the most popular carriers operating from Ontario to Chicago O'Hare Intl

Air Canada, United Airlines and American Airlines are the top three most popular airlines that fly to Chicago O'Hare Intl Airport from Region of Ontario according to our data. Air Canada is the first choice among our users, with 64% of people opting to fly with this airline when travelling to Chicago O'Hare Intl Airport. Keep in mind that there are 5 different airlines that fly to Chicago O'Hare Intl Airport on a routine basis, so you have a few additional options to choose from.

As of October 2026, there are 19 flights per day flying from Region of Ontario to Chicago O'Hare Intl Airport. The most common time of day flights depart is 3:00p.m., with 45% of flights taking off in the afternoon.

As of October 2026, 138 flights take off from Region of Ontario and land in Chicago O'Hare Intl Airport each week. The most common flight departure day for this route is Fri, with 57% of weekly flights taking off on this day.