Cheap flights from New York to Chicago from R2 206

The month of January is, on average, the cheapest month to fly to Chicago from New York, with most prices found around R3 161. If you are unable to visit Chicago during the month of January, then departing from New York during the month February is also very affordable. Most momondo users find prices during this month for around R3 655.

On average, the least expensive day to fly to Chicago from New York is on a Sunday. momondo users have found tickets for Sunday departures for as low as R2 468. However, this price may fluctuate depending on the airline, the season, and holidays. Be sure to avoid booking your departure on a Saturday as prices are generally higher than usual. According to our data, the average ticket price to Chicago on Saturday is R5 632.

Our data shows that the cheapest New York to Chicago flights are usually those with departure times in the afternoon. Our users have found flights to Chicago in the afternoon for as low as R4 177. Try not to purchase tickets in the morning because they tend to be around R4 386. Of course, these prices can vary depending on the time of year and what airport you fly to.

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 R4 172 when searching weeks before you fly. 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 R2 914 on momondo.

There are 2 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 21% on your flight if you consider stops on a New York to Chicago flight.

As of October 2026, prices for New York to Chicago flights are approximately 15% cheaper when compared to flights at the same time last year.

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 150 minutes.

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

Tuesday 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, United Airlines have had the fewest delays on this route over the last 12 months, with about 13% of their flights experiencing any sort of delay.

The number of flights available between New York and Chicago is 109 per day as of October 2026. The most frequent departure time is 10:00, with 44% of daily flights leaving at midday.

As of October 2026, there are 768 flights per week flying from New York to Chicago. The most common day of the week flights depart is Thu, with 24% of flights taking off on this day.