Cheap flights from Chicago to New York from $89

The cheapest month to fly to New York from Chicago is in January. Flight prices, which tend to average around $202, are often lower during this time because this is during the off-season. The month of November is another great option to travel to New York, with average flight prices from Chicago averaging around $207.

The cheapest day to depart from Chicago to New York is on a Friday when prices can be found for as low as $270. On the other hand, Sunday is the most expensive day to depart from Chicago because it is more convenient for both business and leisure travelers. As a result, prices tend to be around $390.

Our most recent data shows that the best time of day to fly to New York is in the evening. Flights from Chicago to New York during this time can be as low as $273. Flights to New York are more costly in the afternoon, with an average ticket price of $364. Departure times in the afternoon fall within the peak daily travel times, which is why tickets can be more expensive.

Fly from Chicago O'Hare Intl to New York John F Kennedy Intl for the best Chicago - New York flight prices

You are more likely to see cheaper flights to New York from Chicago when booking weeks ahead of your departure date. In general, you can expect to find flights to New York for around $205 when searching weeks out. However, flight prices might be lower outside of this timeframe. For example, people recently found flights to New York from Chicago for as low as $142 on momondo.

There are 4 cabin classes available to choose from on Chicago to New York flights. Cabin price and availability will vary by airline so perform a search above to find the right deals for you.

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

United Airlines, American Airlines and Delta are the top three most popular airlines that fly to New York from Chicago according to our data. United Airlines is the first choice among our users, with 54% of people opting to fly with this airline when traveling to New York. Keep in mind that there are 6 different airlines that fly to New York on a routine basis, so you have a few additional options to choose from.

Historically, on average around 24% of flights between Chicago and New York have experienced a delay on any given week. The average delay length over the past 12 months has been 144 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.

Saturday 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, Delta have had the least number of delays on this route over the last 12 months; with about 21% of their flights experiencing any sort of delay.

182 flights are operational daily from Chicago to New York as of June 2026. The most popular departure time for this route is 10:00AM, with 42% of flights per day taking off at noon.

As of June 2026, 1,276 flights take off from Chicago and land in New York each week. The most common flight departure day for this route is Mon, with 17% of weekly flights taking off on this day.