Cheap flights from Asheville to Chicago from $81

The month of March is, on average, the cheapest month to fly to Chicago from Asheville, with most prices found around $279. If you’re not able to fly to Chicago in March, then May is your next best option. Flight prices from Asheville to Chicago during May average around $301.

The cheapest day to depart on your flight to Chicago is on a Friday when prices can be found for as low as $379. 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 Asheville to Chicago for around $699.

Our most recent data shows that the best time of day to fly to Chicago is at noon. Flights from Asheville to Chicago during this time can be as low as $369. In contrast, the most expensive time of day to depart to Chicago is in the morning when prices are around $481.

Fly from Asheville Regional to Chicago Midway for the best Asheville Regional - Chicago flight prices

You are more likely to see cheaper flights to Chicago from Asheville when booking weeks ahead of your departure date. In general, you can expect to find flights to Chicago for around $346 when searching weeks out. However, flight prices might be lower outside of this timeframe. For example, people recently found flights to Chicago from Asheville for as low as $209 on momondo.

There are 4 cabin classes available to choose from on Asheville 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 Asheville to Chicago.

As of November 2026, prices for Asheville to Chicago flights are approximately 127% more expensive when compared to flights at the same time last year.

United Airlines and American Airlines are the most popular carriers operating from Asheville Regional to Chicago

American Airlines, United Airlines and Frontier are the top three most popular airlines that fly to Chicago from Asheville according to our data. American Airlines is the first choice among our users, with 58% of people opting to fly with this airline when traveling to Chicago. Keep in mind that there are 7 different airlines that fly to Chicago on a routine basis, so you have a few additional options to choose from.

11 flights are operational daily from Asheville to Chicago as of November 2026. The most popular departure time for this route is 11:00AM, with 52% of flights per day taking off at noon.

As of November 2026, there are 79 flights per week flying from Asheville to Chicago. The most common day of the week flights depart is Sat, with 18% of flights taking off on this day.