Cheap flights from New York to Chicago from £103

The cheapest month to fly to Chicago O'Hare Intl Airport from New York is in January. Flight prices, which tend to average around £154, are often lower during this time because this is during the off-season. If you aren’t able to travel during the month of January, then book flights to Chicago O'Hare Intl Airport from New York during February instead. Flights to Chicago O'Hare Intl Airport in February, while not as cheap as those in January, still average around £183.

The cheapest day to depart from New York to Chicago O'Hare Intl Airport is on a Tuesday. Travellers who choose to depart for Chicago O'Hare Intl Airport on a Tuesday will often find tickets for as low as £159. 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 O'Hare Intl Airport on Sunday is £293.

The cheapest time of day to fly to Chicago O'Hare Intl Airport is in the morning when flights can be purchased for as low as £229. In contrast, the most expensive time of day to depart to Chicago O'Hare Intl Airport is at midday when prices are around £269.

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

You are more likely to see cheaper flights to Chicago O'Hare Intl Airport from New York when booking weeks ahead of your departure date. In general, you can expect to find flights to Chicago O'Hare Intl Airport for around £192 when searching weeks before you fly. However, flight prices might be lower outside of this timeframe. For example, people recently found flights to Chicago O'Hare Intl Airport from New York for as low as £133 on momondo.

There are 3 cabin classes available to choose from on New York to Chicago O'Hare Intl Airport flights. Cabin price and availability will vary by airline so perform a search above to find the right deals for you.

You could potentially save up to 23% on your flight if you consider stops on a New York to Chicago O'Hare Intl Airport flight.

As of October 2026, prices for New York to Chicago O'Hare Intl Airport flights are approximately 100% more expensive when compared to flights at the same time last year.

Historically, on average around 15% 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 159 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. Sunday has historically seen more delays on average compared to the rest of the week.

According to our data, United 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.

128 flights are operational daily from New York to Chicago O'Hare Intl Airport as of October 2026. The most popular departure time for this route is 10:00, with 45% of flights per day taking off at midday.

896 flights are operational weekly from New York to Chicago O'Hare Intl Airport as of October 2026. The most popular departure day for this route is Tue, with 21% of flights per week taking off on this day.