Cheap flights from New York to Chicago from $58

The month of February is another great option to travel to Chicago O'Hare Intl Airport, with average flight prices from New York averaging around $208.

The cheapest day to depart on your flight to Chicago O'Hare Intl Airport is on a Wednesday when prices can be found for as low as $289. This is often the case because there is less demand to fly during this day of the week. On the other hand, Sunday is the most expensive day to depart from New York because it is more convenient for both business and leisure travelers. As a result, prices tend to be around $365.

Flying to Chicago O'Hare Intl Airport from New York in the evening is the least expensive time of day to depart. momondo users have found prices as low as $272 when looking at flights departing in the evening. Try not to purchase tickets at noon because they tend to be around $361. Of course, these prices can vary depending on the time of year and what airport you fly to.

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 $235 when searching weeks out. 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 $184 on momondo.

There are 4 cabin classes available to choose from on New York to Chicago O'Hare Intl flights. Cabin price and availability will vary by airline so perform a search above to find the right deals for you.

No. A direct flight is the cheapest option for a flight between New York to Chicago O'Hare Intl Airport.

As of March 2026, prices for New York to Chicago O'Hare Intl Airport flights are approximately 13% cheaper when compared to flights at the same time last year.

Spirit Airlines, United Airlines, and Delta are the most popular carriers operating from New York to Chicago O'Hare Intl

United Airlines, American Airlines and Spirit Airlines are the top three most popular airlines that fly to Chicago O'Hare Intl Airport from New York according to our data. United Airlines is the first choice among our users, with 45% of people opting to fly with this airline when traveling to Chicago O'Hare Intl Airport. Keep in mind that there are 6 different airlines that fly to Chicago O'Hare Intl Airport on a routine basis, so you have a few additional options to choose from.

Historically, on average around 16% 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 165 minutes.

Generally, flights departing in the morning tend to experience fewer delays. Flights in the evening have, in the past, seen delays more frequently in comparison.

Saturday is statistically the day of the week which experiences the fewest number of 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 least number of delays on this route over the last 12 months; with about 14% of their flights experiencing any sort of delay.

As of March 2026, there are 156 flights per day flying from New York to Chicago O'Hare Intl Airport. The most common time of day flights depart is 3:00PM, with 42% of flights taking off at noon.

The number of flights available between New York and Chicago O'Hare Intl Airport is 1,095 per week as of March 2026. The most frequent departure day is Mon, with 17% of weekly flights leaving on this day.