Cheap flights from New York to Chicago from €50

In general, January is the cheapest month to fly from New York to Chicago O'Hare Intl Airport. Due to it being the ‘off-season’ during this time, you can expect flight prices to be around €166. 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 €186.

On average, the least expensive day to fly to Chicago O'Hare Intl Airport from New York is on a Saturday. momondo users have found tickets for Saturday departures for as low as €135. However, this price may fluctuate depending on the airline, the season, and holidays. The most expensive day to fly to Chicago O'Hare Intl Airport is Tuesday, with ticket prices averaging around €519.

Our data shows that the cheapest New York to Chicago O'Hare Intl Airport flights are usually those with departure times in the evening. Our users have found flights to Chicago O'Hare Intl Airport in the evening for as low as €115. Flights to Chicago O'Hare Intl Airport are more costly at midday, with an average ticket price of €306. Departure times at midday fall within the peak daily travel times, which is why tickets can be more expensive.

Fly from New York LaGuardia 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 €198 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 €148 on momondo.

There are 2 cabin classes available to choose from on New York to Chicago O'Hare Intl 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 New York to Chicago O'Hare Intl Airport.

As of February 2026, prices for New York to Chicago O'Hare Intl Airport flights are approximately 5% more expensive when compared to flights at the same time last year.

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 164 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, United Airlines have had the fewest delays on this route over the last 12 months, with about 14% of their flights experiencing any sort of delay.

As of February 2026, 157 flights take off from New York and land in Chicago O'Hare Intl Airport each day. The most common flight departure time for this route is 15:00, with 43% of daily flights taking off in the afternoon.

As of February 2026, 1,103 flights take off from New York and land in Chicago O'Hare Intl Airport each week. The most common flight departure day for this route is Fri, with 17% of weekly flights taking off on this day.