Cheap flights from Raleigh to Chicago from $101

The month of October is another great option to travel to Chicago O'Hare Intl Airport, with average flight prices from Raleigh averaging around $232.

The cheapest day to depart on your flight to Chicago O'Hare Intl Airport is on a Thursday when prices can be found for as low as $336. This is often the case because there is less demand to fly during this day of the week. On the other hand, Sunday is the most expensive day to depart from Raleigh because it is more convenient for both business and leisure travelers. As a result, prices tend to be around $521.

Flying to Chicago O'Hare Intl Airport from Raleigh in the evening is the least expensive time of day to depart. momondo users have found prices as low as $230 when looking at flights departing in the evening. Try not to purchase tickets at noon because they tend to be around $471. Of course, these prices can vary depending on the time of year and what airport you fly to.

Fly from Raleigh-Durham to Chicago O'Hare Intl for the best Raleigh-Durham - Chicago O'Hare Intl flight prices

You are more likely to see cheaper flights to Chicago O'Hare Intl Airport from Raleigh when booking weeks ahead of your departure date. In general, you can expect to find flights to Chicago O'Hare Intl Airport for around $280 when searching weeks out. However, flight prices might be lower outside of this timeframe. For example, people recently found flights to Chicago O'Hare Intl Airport from Raleigh for as low as $225 on momondo.

United Airlines, Southwest, and Sun Country Air are the most popular carriers operating from Raleigh-Durham to Chicago O'Hare Intl

American Airlines, United Airlines and Frontier are the top three most popular airlines that fly to Chicago O'Hare Intl Airport from Raleigh according to our data. American Airlines is the first choice among our users, with 43% of people opting to fly with this airline when traveling to Chicago O'Hare Intl Airport. Keep in mind that there are 5 different airlines that fly to Chicago O'Hare Intl Airport on a routine basis, so you have a few additional options to choose from.

Historically, on average around 11% of flights between Raleigh and Chicago have experienced a delay on any given week. The average delay length over the past 12 months has been 154 minutes.

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

Monday is statistically the day of the week which experiences the fewest number of 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 least number of delays on this route over the last 12 months; with about 9% of their flights experiencing any sort of delay.

As of May 2026, 33 flights take off from Raleigh and land in Chicago O'Hare Intl Airport each day. The most common flight departure time for this route is 10:00AM, with 49% of daily flights taking off in the afternoon.

As of May 2026, there are 235 flights per week flying from Raleigh to Chicago O'Hare Intl Airport. The most common day of the week flights depart is Mon, with 16% of flights taking off on this day.