Cheap flights from New York to Chicago from $124

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 $244.

The cheapest day to depart on your flight to Chicago O'Hare Intl Airport is on a Saturday when prices can be found for as low as $336. This is often the case because there is less demand to fly during this day of the week. On the other hand, Monday 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 $417.

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 $340 when looking at flights departing in the evening. Try not to purchase tickets at noon because they tend to be around $375. 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 $249 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 $177 on momondo.

There are 4 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 25% 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 12% more expensive when compared to flights at the same time last year.

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

United Airlines, American Airlines and Delta 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 57% of people opting to fly with this airline when traveling to Chicago O'Hare Intl Airport. Keep in mind that there are 5 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 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 in the evening have, in the past, seen delays more frequently in comparison.

Tuesday 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 13% of their flights experiencing any sort of delay.

Washington, D.C. (DCA) was the most common stop: 50% of momondo users choosing 1-stop flights on this route connected there.

Flights via Washington, D.C. (DCA) offer the lowest average round-trip price of $301.

Flights connecting via Washington, D.C. (DCA) have the shortest average one-way travel time: 4h 40m.

Washington, D.C. (DCA) has the shortest average layover time for this route: 1h 10m.

As of October 2026, there are 154 flights per day flying from New York to Chicago O'Hare Intl Airport. The most common time of day flights depart is 2:00PM, with 42% of flights taking off at noon.

The number of flights available between New York and Chicago O'Hare Intl Airport is 1,079 per week as of October 2026. The most frequent departure day is Thu, with 17% of weekly flights leaving on this day.