Cheap flights from New York to Chicago from $103

The month of January is, on average, the cheapest month to fly to Chicago from New York, with most prices found around $189. If you’re not able to fly to Chicago in January, then February is your next best option. Flight prices from New York to Chicago during February average around $220.

The cheapest day to depart on your flight to Chicago is on a Saturday when prices can be found for as low as $323. This is often the case because there is less demand to fly during this day of the week. When flying out on a Monday, the most expensive travel day of the week, you can expect to see flight prices from New York to Chicago for around $405.

Our most recent data shows that the best time of day to fly to Chicago is in the evening. Flights from New York to Chicago during this time can be as low as $311. In contrast, the most expensive time of day to depart to Chicago is at noon when prices are around $373.

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 $243 when searching weeks out. 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 $174 on momondo.

There are 4 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 22% on your flight if you consider stops on a New York to Chicago flight.

As of August 2026, prices for New York to Chicago flights are approximately 4% cheaper when compared to flights at the same time last year.

Delta, Southwest, and United Airlines are the most popular carriers operating from New York to Chicago

United Airlines, American Airlines and Delta are the top three most popular airlines that fly to Chicago from New York according to our data. United Airlines is the first choice among our users, with 55% of people opting to fly with this airline when traveling to Chicago. Keep in mind that there are 6 different airlines that fly to Chicago on a routine basis, so you have a few additional options to choose from.

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 155 minutes.

Generally, flights departing in the morning tend to experience fewer delays. Flights in the evening have, in the past, seen delays more frequently in comparison.

Tuesday is statistically the day of the week which experiences the fewest number of 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 least number of delays on this route over the last 12 months; with about 14% of their flights experiencing any sort of delay.

As of August 2026, 125 flights take off from New York and land in Chicago each day. The most common flight departure time for this route is 10:00AM, with 44% of daily flights taking off at noon.

880 flights are operational weekly from New York to Chicago as of August 2026. The most popular departure day for this route is Sat, with 20% of flights per week taking off on this day.