Cheap flights from New York to Chicago from ₹ 8,923

In general, January is the cheapest month to fly from New York to Chicago. Due to it being the ‘off-season’ during this time, you can expect flight prices to be around ₹ 18,890. The month of November is another great option to travel to Chicago, with average flight prices from New York averaging around ₹ 20,219.

According to our data, Tuesday is the cheapest day to fly to Chicago from New York. The lowest ticket price found for a Tuesday departure recently was ₹ 24,378. Keep in mind that prices can always vary depending on your route and whether or not you are flying domestic or international. The most expensive day to fly to Chicago is Wednesday, with ticket prices averaging around ₹ 44,877.

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 ₹ 24,378. Flying to Chicago in the evening is an ideal time because this is during off-peak travel hours. Flights to Chicago are more costly in the afternoon, with an average ticket price of ₹ 39,235. Departure times in the afternoon fall within the peak daily travel times, which is why tickets can be more expensive.

Fly from New York LaGuardia 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 ₹ 23,185 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 ₹ 15,378 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.

You could potentially save up to 11% on your flight if you consider stops on a New York to Chicago flight.

As of June 2026, prices for New York to Chicago flights are approximately 109% 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 14% of their flights experiencing any sort of delay.

128 flights are operational daily from New York to Chicago as of June 2026. The most popular departure time for this route is 07:00, with 44% of flights per day taking off at midday.

896 flights are operational weekly from New York to Chicago as of June 2026. The most popular departure day for this route is Fri, with 16% of flights per week taking off on this day.