Cheap flights from Chicago to Raleigh from $99

The cheapest month to fly to Raleigh from Chicago is in December. Flight prices, which tend to average around $25, are often lower during this time because this is during the off-season. If you are unable to visit Raleigh during the month of December, then departing from Chicago during the month January is also very affordable. Most momondo users find prices during this month for around $27.

The cheapest day to depart from Chicago to Raleigh is on a Friday when prices can be found for as low as $239. If your travel schedule is flexible, try to avoid departing on a Monday because tickets tend to average around $325. These prices are subject to change though, so be sure to set up a Price Alert for flights to Raleigh.

At noon is the cheapest time of day to fly from Chicago to Raleigh when you can find flight prices for as low as $225. Flying to Raleigh at noon is an ideal time because this is during off-peak travel hours. In contrast, the most expensive time of day to depart to Raleigh is in the afternoon when prices are around $320.

Fly from Chicago Midway to Raleigh-Durham for the best Chicago - Raleigh-Durham flight prices

You are more likely to see cheaper flights to Raleigh from Chicago when booking weeks ahead of your departure date. In general, you can expect to find flights to Raleigh for around $274 when searching weeks out. However, flight prices might be lower outside of this timeframe. For example, people recently found flights to Raleigh from Chicago for as low as $210 on momondo.

There are 4 cabin classes available to choose from on Chicago to Raleigh 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 26% on your flight if you consider stops on a Chicago to Raleigh flight.

As of June 2026, prices for Chicago to Raleigh flights are approximately 307% more expensive when compared to flights at the same time last year.

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

American Airlines, United Airlines and Frontier are the top three most popular airlines that fly to Raleigh from Chicago according to our data. American Airlines is the first choice among our users, with 38% of people opting to fly with this airline when traveling to Raleigh. Keep in mind that there are 5 different airlines that fly to Raleigh on a routine basis, so you have a few additional options to choose from.

The number of flights available between Chicago and Raleigh is 32 per day as of June 2026. The most frequent departure time is 6:00PM, with 42% of daily flights leaving in the evening.

226 flights are operational weekly from Chicago to Raleigh as of June 2026. The most popular departure day for this route is Thu, with 16% of flights per week taking off on this day.