Cheap flights from New York to Chicago from $158

If you don’t want to visit Chicago in January, then you should wait until November to fly from New York, when ticket prices are also cheap, with an average price of $307.

Our data shows that Thursday is the least expensive day to fly to Chicago. Tickets to fly out on this day can be as low as $477. Flights from New York to Chicago on a Monday will generally be more expensive and average around $2,022. Keep in mind that these prices on both days could fluctuate depending on the season and the demand.

Our data shows that the cheapest New York to Chicago flights are usually those with departure times in the morning. Our users have found flights to Chicago in the morning for as low as $539. Flights in the afternoon are often more expensive, with an average ticket price of $1,908.

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

You are more likely to see cheaper flights to Chicago from New York when booking weeks ahead of your departure date. In general, you can expect to find flights to Chicago for around $352 when searching weeks before you fly. However, flight prices might be lower outside of this timeframe. For example, people recently found flights to Chicago from New York for as low as $252 on momondo.

There is only 1 cabin class available to choose from on New York to Chicago 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 36% on your flight if you consider stops on a New York to Chicago flight.

As of July 2026, prices for New York to Chicago flights are approximately 26% more expensive when compared to flights at the same time last year.

Historically, on average around 19% 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 158 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, United Airlines have had the fewest delays on this route over the last 12 months, with about 14% of their flights experiencing any sort of delay.

The number of flights available between New York and Chicago is 43 per day as of July 2026. The most frequent departure time is 10:00, with 40% of daily flights leaving at midday.

The number of flights available between New York and Chicago is 303 per week as of July 2026. The most frequent departure day is Wed, with 21% of weekly flights leaving on this day.