Cheap flights from New York John F Kennedy Intl Airport to Chicago from €133

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 €151, are often lower during this time because this is during the off-season. If you don’t want to visit Chicago in January, then you should wait until February to fly from New York John F Kennedy Intl Airport, when ticket prices are also cheap, with an average price of €152.

On average, the least expensive day to fly to Chicago from New York John F Kennedy Intl Airport is on a Friday. momondo users have found tickets for Friday departures for as low as €137. However, this price may fluctuate depending on the airline, the season, and holidays. Be sure to avoid booking your departure on a Sunday as prices are generally higher than usual. According to our data, the average ticket price to Chicago on Sunday is €503.

In the evening is the cheapest time of day to fly from New York John F Kennedy Intl Airport to Chicago when you can find flight prices for as low as €250. Flying to Chicago 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 €449 on average. Flights to Chicago from New York John F Kennedy Intl Airport in the afternoon 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 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 €238 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 €159 on momondo.

There is only 1 cabin class 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.

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 Fri, with 23% of flights taking off on this day.