Cheap flights from Chicago to New York from £65

In general, November is the cheapest month to fly from Chicago to New York John F Kennedy Intl Airport. Due to it being the ‘off-season’ during this time, you can expect flight prices to be around £18. The month of January is another great option to travel to New York John F Kennedy Intl Airport, with average flight prices from Chicago averaging around £20.

The cheapest day to depart from Chicago to New York John F Kennedy Intl Airport is on a Wednesday. Travellers who choose to depart for New York John F Kennedy Intl Airport on a Wednesday will often find tickets for as low as £504. On the other hand, Saturday is the most expensive day to depart from Chicago because it is more convenient for both business and leisure travellers. As a result, prices tend to be around £971.

Flying to New York John F Kennedy Intl Airport from Chicago at midday is the least expensive time of day to depart. momondo users have found prices as low as £504 when looking at flights departing at midday. Try not to purchase tickets in the afternoon because they tend to be around £971. Of course, these prices can vary depending on the time of year and what airport you fly to.

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 £153 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 £103 on momondo.

You could potentially save up to 16% on your flight if you consider stops on a Chicago to New York John F Kennedy Intl Airport flight.

As of May 2026, prices for Chicago to New York John F Kennedy Intl Airport flights are approximately 52% more expensive when compared to flights at the same time last year.

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.

Saturday 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 12% of their flights experiencing any sort of delay.

As of May 2026, 38 flights take off from Chicago and land in New York John F Kennedy Intl Airport each day. The most common flight departure time for this route is 11:00, with 55% of daily flights taking off at midday.

As of May 2026, 267 flights take off from Chicago and land in New York John F Kennedy Intl Airport each week. The most common flight departure day for this route is Sat, with 19% of weekly flights taking off on this day.