Cheap flights from Chicago to New York from £98

In general, January 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 £100. The month of November is another great option to travel to New York John F Kennedy Intl Airport, with average flight prices from Chicago averaging around £112.

The cheapest day to depart from Chicago to New York John F Kennedy Intl Airport is on a Friday. Travellers who choose to depart for New York John F Kennedy Intl Airport on a Friday will often find tickets for as low as £509. 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 £1,461.

Flying to New York John F Kennedy Intl Airport from Chicago in the morning is the least expensive time of day to depart. momondo users have found prices as low as £370 when looking at flights departing in the morning. Try not to purchase tickets in the afternoon because they tend to be around £1,421. 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 £159 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 £127 on momondo.

There are 2 cabin classes available to choose from on Chicago to New York John F Kennedy Intl Airport 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 21% 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 150 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.

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 14% of their flights experiencing any sort of delay.

As of September 2026, 45 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 06:00, with 43% of daily flights taking off in the afternoon.

As of September 2026, 318 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 Fri, with 19% of weekly flights taking off on this day.