Cheap flights from New York to Chicago from £99

The cheapest month to fly to Chicago from New York is in January. Flight prices, which tend to average around £143, are often lower during this time because this is during the off-season. If you aren’t able to travel during the month of January, then book flights to Chicago from New York during February instead. Flights to Chicago in February, while not as cheap as those in January, still average around £166.

The cheapest day to depart on your flight to Chicago is on a Tuesday when prices can be found for as low as £213. This is often the case because there is less demand to fly during this day of the week. The most expensive day to fly to Chicago is Sunday, with ticket prices averaging around £292.

Flying to Chicago from New York in the morning is the least expensive time of day to depart. momondo users have found prices as low as £219 when looking at flights departing in the morning. Flights at midday are often more expensive, with an average ticket price of £267.

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 £189 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 £132 on momondo.

There are 3 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 October 2026, prices for New York to Chicago flights are approximately 17% cheaper 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 150 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.

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

The number of flights available between New York and Chicago is 145 per day as of October 2026. The most frequent departure time is 10:00, with 44% of daily flights leaving at midday.

As of October 2026, there are 1,020 flights per week flying from New York to Chicago. The most common day of the week flights depart is Mon, with 19% of flights taking off on this day.