Cheap flights from New York John F Kennedy Intl Airport to Chicago from $89

The month of May is, on average, the cheapest month to fly to Chicago from New York John F Kennedy Intl Airport, with most prices found around $28. If you’re not able to fly to Chicago in May, then March is your next best option. Flight prices from New York John F Kennedy Intl Airport to Chicago during March average around $28.

The cheapest day to depart on your flight to Chicago is on a Saturday when prices can be found for as low as $291. 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 John F Kennedy Intl Airport to Chicago for around $367.

Our most recent data shows that the best time of day to fly to Chicago is in the evening. Flights from New York John F Kennedy Intl Airport to Chicago during this time can be as low as $273. In contrast, the most expensive time of day to depart to Chicago is at noon when prices are around $361.

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 $239 when searching weeks out. 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 $162 on momondo.

You could potentially save up to 2% on your flight if you consider stops on a New York John F Kennedy Intl Airport to Chicago flight.

As of May 2026, prices for New York John F Kennedy Intl Airport to Chicago flights are approximately 16% more expensive when compared to flights at the same time last year.

JetBlue and Delta are the most popular carriers operating from New York John F Kennedy Intl to Chicago

American Airlines, Delta and JetBlue are the top three most popular airlines that fly to Chicago from New York John F Kennedy Intl Airport according to our data. American Airlines is the first choice among our users, with 38% of people opting to fly with this airline when traveling to Chicago. Keep in mind that there are 4 different airlines that fly to Chicago on a routine basis, so you have a few additional options to choose from.

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 154 minutes.

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

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

According to our data, Delta have had the least number of delays on this route over the last 12 months; with about 14% of their flights experiencing any sort of delay.

The number of flights available between New York John F Kennedy Intl Airport and Chicago is 38 per day as of May 2026. The most frequent departure time is 3:00PM, with 45% of daily flights leaving in the afternoon.

As of May 2026, there are 269 flights per week flying from New York John F Kennedy Intl Airport to Chicago. The most common day of the week flights depart is Fri, with 16% of flights taking off on this day.