Cheap flights from Chicago to Asheville from $54

In general, August is the cheapest month to fly from Chicago to Asheville. Due to it being the ‘off-season’ during this time, you can expect flight prices to be around $207. The month of September is another great option to travel to Asheville, with average flight prices from Chicago averaging around $275.

The cheapest day to depart from Chicago to Asheville is on a Saturday. Travelers who choose to depart for Asheville on a Saturday will often find tickets for as low as $256. If your travel schedule is flexible, try to avoid departing on a Sunday because tickets tend to average around $363. These prices are subject to change though, so be sure to set up a Price Alert for flights to Asheville.

Our data shows that the cheapest Chicago to Asheville flights are usually those with departure times in the evening. Our users have found flights to Asheville in the evening for as low as $82. In contrast, the most expensive time of day to depart to Asheville is in the morning when prices are around $299.

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

You are more likely to see cheaper flights to Asheville from Chicago when booking weeks ahead of your departure date. In general, you can expect to find flights to Asheville for around $312 when searching weeks out. However, flight prices might be lower outside of this timeframe. For example, people recently found flights to Asheville from Chicago for as low as $254 on momondo.

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

Allegiant Air, United Airlines, and Delta are the most popular carriers operating from Chicago to Asheville Regional

American Airlines, United Airlines and Frontier are the top three most popular airlines that fly to Asheville from Chicago according to our data. American Airlines is the first choice among our users, with 56% of people opting to fly with this airline when traveling to Asheville. Keep in mind that there are 6 different airlines that fly to Asheville on a routine basis, so you have a few additional options to choose from.

As of March 2026, there are 6 flights per day flying from Chicago to Asheville. The most common time of day flights depart is 2:00PM, with 82% of flights taking off in the afternoon.

As of March 2026, 42 flights take off from Chicago and land in Asheville each week. The most common flight departure day for this route is Mon, with 14% of weekly flights taking off on this day.