Cheap flights from New York John F Kennedy Intl Airport to Chicago from £111

The cheapest month to fly to Chicago from New York John F Kennedy Intl Airport is in January. Flight prices, which tend to average around £126, are often lower during this time because this is during the off-season. If you aren’t able to travel during the month of January, then book flights to Chicago from New York John F Kennedy Intl Airport during February instead. Flights to Chicago in February, while not as cheap as those in January, still average around £127.

The cheapest day to depart on your flight to Chicago is on a Tuesday when prices can be found for as low as £213. This is often the case because there is less demand to fly during this day of the week. The most expensive day to fly to Chicago is Sunday, with ticket prices averaging around £318.

Flying to Chicago from New York John F Kennedy Intl Airport in the morning is the least expensive time of day to depart. momondo users have found prices as low as £220 when looking at flights departing in the morning. Flights in the evening are often more expensive, with an average ticket price of £282.

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

You are more likely to see cheaper flights to Chicago from New York John F Kennedy Intl Airport when booking weeks ahead of your departure date. In general, you can expect to find flights to Chicago for around £198 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 New York John F Kennedy Intl Airport for as low as £133 on momondo.

There are 2 cabin classes available to choose from on New York John F Kennedy Intl Airport to Chicago 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 22% on your flight if you consider stops on a New York John F Kennedy Intl Airport to Chicago flight.

As of November 2026, prices for New York John F Kennedy Intl Airport to Chicago flights are approximately 42% cheaper when compared to flights at the same time last year.

Historically, on average around 24% 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 147 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.

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

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

28 flights are operational daily from New York John F Kennedy Intl Airport to Chicago as of November 2026. The most popular departure time for this route is 19:00, with 37% of flights per day taking off at midday.

As of November 2026, there are 200 flights per week flying from New York John F Kennedy Intl Airport to Chicago. The most common day of the week flights depart is Sun, with 22% of flights taking off on this day.