Cheap flights from Roanoke to Chicago from $136

The month of January is, on average, the cheapest month to fly to Chicago from Roanoke, with most prices found around $270. If you’re not able to fly to Chicago in January, then September is your next best option. Flight prices from Roanoke to Chicago during September average around $279.

The cheapest day to depart on your flight to Chicago is on a Friday when prices can be found for as low as $409. 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 Roanoke to Chicago for around $632.

Our most recent data shows that the best time of day to fly to Chicago is in the afternoon. Flights from Roanoke to Chicago during this time can be as low as $422. In contrast, the most expensive time of day to depart to Chicago is at noon when prices are around $456.

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

You are more likely to see cheaper flights to Chicago from Roanoke when booking weeks ahead of your departure date. In general, you can expect to find flights to Chicago for around $332 when searching weeks out. However, flight prices might be lower outside of this timeframe. For example, people recently found flights to Chicago from Roanoke for as low as $263 on momondo.

There are 4 cabin classes available to choose from on Roanoke to Chicago 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 36% on your flight if you consider stops on a Roanoke to Chicago flight.

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

American Airlines, United Airlines and Delta are the top three most popular airlines that fly to Chicago from Roanoke according to our data. American Airlines is the first choice among our users, with 48% of people opting to fly with this airline when traveling to Chicago. Keep in mind that there are 3 different airlines that fly to Chicago on a routine basis, so you have a few additional options to choose from.

As of April 2026, 11 flights take off from Roanoke and land in Chicago each day. The most common flight departure time for this route is 5:00PM, with 62% of daily flights taking off at noon.

As of April 2026, there are 82 flights per week flying from Roanoke to Chicago. The most common day of the week flights depart is Thu, with 16% of flights taking off on this day.