Cheap flights from New York to Chicago from $186

The month of January is, on average, the cheapest month to fly to Chicago O'Hare Intl Airport from New York, with most prices found around $280. If you are unable to visit Chicago O'Hare Intl Airport 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 $335.

The cheapest day to depart from New York to Chicago O'Hare Intl Airport is on a Thursday. Travellers who choose to depart for Chicago O'Hare Intl Airport on a Thursday will often find tickets for as low as $491. The most expensive day to fly to Chicago O'Hare Intl Airport is Monday, with ticket prices averaging around $1,930.

Our data shows that the cheapest New York to Chicago O'Hare Intl Airport flights are usually those with departure times in the morning. Our users have found flights to Chicago O'Hare Intl Airport in the morning for as low as $702. In contrast, the most expensive time of day to depart to Chicago O'Hare Intl Airport is in the afternoon when prices are around $1,822.

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

You are more likely to see cheaper flights to Chicago O'Hare Intl Airport from New York when booking weeks ahead of your departure date. In general, you can expect to find flights to Chicago O'Hare Intl Airport for around $336 when searching weeks before you fly. However, flight prices might be lower outside of this timeframe. For example, people recently found flights to Chicago O'Hare Intl Airport from New York for as low as $245 on momondo.

There is only 1 cabin class available to choose from on New York to Chicago O'Hare Intl Airport 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 15% 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 161 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.

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 O'Hare Intl Airport is 45 per day as of September 2026. The most frequent departure time is 14:00, with 43% of daily flights leaving at midday.

The number of flights available between New York and Chicago O'Hare Intl Airport is 318 per week as of September 2026. The most frequent departure day is Wed, with 18% of weekly flights leaving on this day.