Cheap flights from Raleigh to Chicago from $52

The month of October is, on average, the cheapest month to fly to Chicago from Raleigh, with most prices found around $217. If you’re not able to fly to Chicago in October, then December is your next best option. Flight prices from Raleigh to Chicago during December average around $217.

The cheapest day to depart on your flight to Chicago is on a Thursday when prices can be found for as low as $341. This is often the case because there is less demand to fly during this day of the week. When flying out on a Sunday, the most expensive travel day of the week, you can expect to see flight prices from Raleigh to Chicago for around $502.

Our most recent data shows that the best time of day to fly to Chicago is in the evening. Flights from Raleigh to Chicago during this time can be as low as $309. In contrast, the most expensive time of day to depart to Chicago is at noon when prices are around $488.

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

You are more likely to see cheaper flights to Chicago from Raleigh when booking weeks ahead of your departure date. In general, you can expect to find flights to Chicago for around $279 when searching weeks out. However, flight prices might be lower outside of this timeframe. For example, people recently found flights to Chicago from Raleigh for as low as $214 on momondo.

There are 4 cabin classes available to choose from on Raleigh-Durham to Chicago 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 Raleigh to Chicago.

As of February 2026, prices for Raleigh to Chicago flights are approximately 20% cheaper when compared to flights at the same time last year.

Frontier and Southwest are the most popular carriers operating from Raleigh-Durham to Chicago

American Airlines, United Airlines and Frontier are the top three most popular airlines that fly to Chicago from Raleigh according to our data. American Airlines is the first choice among our users, with 42% of people opting to fly with this airline when traveling to Chicago. Keep in mind that there are 6 different airlines that fly to Chicago 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 151 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 10% of their flights experiencing any sort of delay.

The number of flights available between Raleigh and Chicago is 24 per day as of February 2026. The most frequent departure time is 6:00AM, with 55% of daily flights leaving in the afternoon.

As of February 2026, 171 flights take off from Raleigh and land in Chicago each week. The most common flight departure day for this route is Fri, with 18% of weekly flights taking off on this day.