Cheap flights from Raleigh to Chicago from $90

The month of October is, on average, the cheapest month to fly to Chicago Midway Airport from Raleigh, with most prices found around $237. If you are unable to visit Chicago Midway Airport during the month of October, then departing from Raleigh during the month January is also very affordable. Most momondo users find prices during this month for around $243.

According to our data, Thursday is the cheapest day to fly to Chicago Midway Airport from Raleigh. The lowest ticket price found for a Thursday departure recently was $331. Keep in mind that prices can always vary depending on your route and whether or not you are flying domestic or international. 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 $398.

Flying to Chicago Midway Airport from Raleigh in the afternoon is the least expensive time of day to depart. momondo users have found prices as low as $299 when looking at flights departing in the afternoon. Try not to purchase tickets in the morning because they tend to be around $368. Of course, these prices can vary depending on the time of year and what airport you fly to.

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

You are more likely to see cheaper flights to Chicago Midway Airport from Raleigh when booking weeks ahead of your departure date. In general, you can expect to find flights to Chicago Midway Airport for around $340 when searching weeks out. However, flight prices might be lower outside of this timeframe. For example, people recently found flights to Chicago Midway Airport from Raleigh for as low as $171 on momondo.

There is only 1 cabin class available to choose from on Raleigh-Durham to Chicago Midway 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 2% on your flight if you consider stops on a Raleigh to Chicago Midway Airport flight.

Southwest is the most popular carrier operating from Raleigh-Durham to Chicago Midway

Southwest, Delta and Frontier are the top three most popular airlines that fly to Chicago Midway Airport from Raleigh according to our data. Southwest is the first choice among our users, with 77% of people opting to fly with this airline when traveling to Chicago Midway Airport. Keep in mind that there are 3 different airlines that fly to Chicago Midway Airport on a routine basis, so you have a few additional options to choose from.

Detroit (DTW) was the most common stop: 50% of momondo users choosing 1-stop flights on this route connected there.

Flights via Atlanta (ATL) offer the lowest average round-trip price of $288.

Flights connecting via Detroit (DTW) have the shortest average one-way travel time: 3h 59m.

Detroit (DTW) has the shortest average layover time for this route: 0h 59m.

As of March 2026, 1 flights take off from Raleigh and land in Chicago Midway Airport each day. The most common flight departure time for this route is 7:00PM, with 50% of daily flights taking off at noon.

As of March 2026, 10 flights take off from Raleigh and land in Chicago Midway Airport each week. The most common flight departure day for this route is Mon, with 20% of weekly flights taking off on this day.