Cheap flights from New York to Chicago from €76

The cheapest month to fly to Chicago from New York is in January. Flight prices, which tend to average around €169, are often lower during this time because this is during the off-season. 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 €185.

On average, the least expensive day to fly to Chicago from New York is on a Friday. momondo users have found tickets for Friday departures for as low as €130. However, this price may fluctuate depending on the airline, the season, and holidays. Be sure to avoid booking your departure on a Wednesday as prices are generally higher than usual. According to our data, the average ticket price to Chicago on Wednesday is €387.

In the evening is the cheapest time of day to fly from New York to Chicago when you can find flight prices for as low as €117. Flying to Chicago in the evening is an ideal time because this is during off-peak travel hours. If you have a flexible travel schedule, then try to avoid flying at midday when prices are €274 on average. Flights to Chicago from New York at midday are generally more expensive because this time of day is more convenient for travellers’ schedules.

Fly from Newark to Chicago Midway 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 €204 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 €138 on momondo.

No. A direct flight is the cheapest option for a flight between New York to Chicago.

As of May 2026, prices for New York to Chicago flights are approximately 64% 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 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.

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 15% of their flights experiencing any sort of delay.

147 flights are operational daily from New York to Chicago as of May 2026. The most popular departure time for this route is 14:00, with 44% of flights per day taking off at midday.

1,032 flights are operational weekly from New York to Chicago as of May 2026. The most popular departure day for this route is Mon, with 17% of flights per week taking off on this day.