Cheap flights from Chicago to New York from $127

The cheapest month to fly to New York John F Kennedy Intl Airport from Chicago is in January. Flight prices, which tend to average around $192, are often lower during this time because this is during the off-season. If you aren’t able to travel to New York John F Kennedy Intl Airport during the month of January, then flying in November is also cheap. Prices for this month can be found on momondo for an average of $213.

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

You are more likely to see cheaper flights to New York John F Kennedy Intl Airport from Chicago when booking weeks ahead of your departure date. In general, you can expect to find flights to New York John F Kennedy Intl Airport for around $299 when searching weeks before you fly. However, flight prices might be lower outside of this timeframe. For example, people recently found flights to New York John F Kennedy Intl Airport from Chicago for as low as $199 on momondo.

There are 3 cabin classes available to choose from on Chicago to New York John F Kennedy Intl 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 22% of flights between Chicago and New York have experienced a delay on any given week. The average delay length over the past 12 months has been 145 minutes.

Generally, flights departing in the morning tend to experience fewer delays. Flights departing at night 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. Sunday has historically seen more delays on average compared to the rest of the week.

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

The number of flights available between Chicago and New York John F Kennedy Intl Airport is 48 per day as of March 2026. The most frequent departure time is 07:00, with 57% of daily flights leaving at midday.

339 flights are operational weekly from Chicago to New York John F Kennedy Intl Airport as of March 2026. The most popular departure day for this route is Fri, with 17% of flights per week taking off on this day.