Cheap flights from Chicago to New York from $65

The month of January is, on average, the cheapest month to fly to New York from Chicago, with most prices found around $226. The month of April is another great option to travel to New York, with average flight prices from Chicago averaging around $266.

According to our data, Thursday is the cheapest day to fly to New York from Chicago. The lowest ticket price found for a Thursday departure recently was $208. Keep in mind that prices can always vary depending on your route and whether or not you are flying domestic or international. On the other hand, Sunday is the most expensive day to depart from Chicago because it is more convenient for both business and leisure travellers. As a result, prices tend to be around $669.

Our data shows that the cheapest Chicago to New York flights are usually those with departure times in the evening. Our users have found flights to New York in the evening for as low as $169. In contrast, the most expensive time of day to depart to New York is in the afternoon when prices are around $631.

Fly from Chicago O'Hare Intl to New York LaGuardia 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 $299 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 $206 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.

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

As of February 2026, prices for Chicago to New York flights are approximately 13% cheaper when compared to flights at the same time last year.

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

The number of flights available between Chicago and New York is 139 per day as of February 2026. The most frequent departure time is 10:00, with 46% of daily flights leaving at midday.

The number of flights available between Chicago and New York is 977 per week as of February 2026. The most frequent departure day is Sun, with 18% of weekly flights leaving on this day.