Cheap flights from New York to Chicago from C$ 158

In general, January is the cheapest month to fly from New York 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$ 280. The month of February is another great option to travel to Chicago O'Hare Intl Airport, with average flight prices from New York averaging around C$ 335.

The cheapest day to depart on your flight to Chicago O'Hare Intl Airport is on a Tuesday when prices can be found for as low as C$ 193. 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 New York to Chicago O'Hare Intl Airport for around C$ 1,145.

In the evening is the cheapest time of day to fly from New York to Chicago O'Hare Intl Airport when you can find flight prices for as low as C$ 276. 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 at noon when prices are C$ 1,167 on average. Flights to Chicago O'Hare Intl Airport from New York at noon are generally more expensive because this time of day is more convenient for travellers’ schedules.

Fly from New York John F Kennedy Intl to Chicago O'Hare Intl for the best New York - Chicago O'Hare Intl flight prices

You are more likely to see cheaper flights to Chicago O'Hare Intl Airport from New York 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$ 336 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 New York for as low as C$ 245 on momondo.

There are 3 cabin classes available to choose from on New York 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.

You could potentially save up to 45% on your flight if you consider stops on a New York to Chicago O'Hare Intl Airport flight.

As of September 2026, prices for New York to Chicago O'Hare Intl Airport flights are approximately 29% more expensive when compared to flights at the same time last year.

Historically, on average around 15% of flights between New York and Chicago have experienced a delay on any given week. The average delay length over the past 12 months has been 161 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.

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

According to our data, United Airlines has had the least delays on this route over the last 12 months, with about 13% of their flights experiencing any sort of delay.

As of September 2026, 115 flights take off from New York and land in Chicago O'Hare Intl Airport each day. The most common flight departure time for this route is 2:00p.m., with 43% of daily flights taking off at noon.

As of September 2026, 806 flights take off from New York and land in Chicago O'Hare Intl Airport each week. The most common flight departure day for this route is Thu, with 17% of weekly flights taking off on this day.