Cheap flights from Chicago to New York from R2 326

The month of January is, on average, the cheapest month to fly to New York from Chicago, with most prices found around R3 019. If you aren’t able to travel during the month of January, then book flights to New York from Chicago during February instead. Flights to New York in February, while not as cheap as those in January, still average around R3 828.

On average, the least expensive day to fly to New York from Chicago is on a Friday. momondo users have found tickets for Friday departures for as low as R5 326. However, this price may fluctuate depending on the airline, the season, and holidays. The most expensive day to fly to New York is Monday, with ticket prices averaging around R22 034.

According to our data, the cheapest time of day to fly to New York is in the afternoon. momondo users have found flights departing from Chicago to New York in the afternoon for as low as R3 160. Keep in mind that these prices may fluctuate based on what airline you choose and the time of year you plan to travel. In the morning is when there is more demand to fly to New York, so prices are often more expensive at around R17 689 per ticket.

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 R3 727 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 R2 953 on momondo.

There is only 1 cabin class 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.

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 145 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 22% of their flights experiencing any sort of delay.

173 flights are operational daily from Chicago to New York as of October 2026. The most popular departure time for this route is 10:00, with 40% of flights per day taking off at midday.

The number of flights available between Chicago and New York is 1 211 per week as of October 2026. The most frequent departure day is Tue, with 17% of weekly flights leaving on this day.