Cheap flights from New York to Chicago from €50

The cheapest month to fly to Chicago from New York is in January. Flight prices, which tend to average around €149, 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 February to fly from New York, when ticket prices are also cheap, with an average price of €173.

On average, the least expensive day to fly to Chicago from New York is on a Saturday. momondo users have found tickets for Saturday departures for as low as €134. However, this price may fluctuate depending on the airline, the season, and holidays. Be sure to avoid booking your departure on a Tuesday as prices are generally higher than usual. According to our data, the average ticket price to Chicago on Tuesday is €517.

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 €115. 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 €306 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 €198 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 €148 on momondo.

There are 2 cabin classes 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.

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

As of February 2026, prices for New York to Chicago flights are approximately 5% cheaper when compared to flights at the same time last year.

Historically, on average around 18% 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 at night 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.

115 flights are operational daily from New York to Chicago as of February 2026. The most popular departure time for this route is 15:00, with 43% of flights per day taking off in the afternoon.

805 flights are operational weekly from New York to Chicago as of February 2026. The most popular departure day for this route is Thu, with 21% of flights per week taking off on this day.