Cheap flights from Chicago to New York from £51

The month of January is, on average, the cheapest month to fly to New York from Chicago, with most prices found around £148. The month of November is another great option to travel to New York, with average flight prices from Chicago averaging around £156.

According to our data, Wednesday is the cheapest day to fly to New York from Chicago. The lowest ticket price found for a Wednesday departure recently was £131. 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 New York is Sunday, with ticket prices averaging around £282.

According to our data, the cheapest time of day to fly to New York is at midday. momondo users have found flights departing from Chicago to New York at midday for as low as £149. Keep in mind that these prices may fluctuate based on what airline you choose and the time of year you plan to travel. If you have a flexible travel schedule, then try to avoid flying in the afternoon when prices are £265 on average. Flights to New York from Chicago in the afternoon are generally more expensive because this time of day is more convenient for travellers’ schedules.

Fly from Chicago Midway to Newark 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 £153 when searching weeks before you fly. 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 £103 on momondo.

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

As of May 2026, prices for Chicago to New York flights are approximately 37% more expensive when compared to flights at the same time last year.

Historically, on average around 23% 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 143 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, Delta have had the fewest delays on this route over the last 12 months, with about 21% of their flights experiencing any sort of delay.

155 flights are operational daily from Chicago to New York as of May 2026. The most popular departure time for this route is 11:00, with 48% of flights per day taking off at midday.

As of May 2026, 1,087 flights take off from Chicago and land in New York each week. The most common flight departure day for this route is Fri, with 17% of weekly flights taking off on this day.