Cheap flights from Charleston to Chicago from $92

The month of September is, on average, the cheapest month to fly to Chicago from Charleston, with most prices found around $104. If you’re not able to fly to Chicago in September, then October is your next best option. Flight prices from Charleston to Chicago during October average around $120.

The cheapest day to depart on your flight to Chicago is on a Friday when prices can be found for as low as $401. This is often the case because there is less demand to fly during this day of the week. When flying out on a Monday, the most expensive travel day of the week, you can expect to see flight prices from Charleston to Chicago for around $693.

Our most recent data shows that the best time of day to fly to Chicago is in the evening. Flights from Charleston to Chicago during this time can be as low as $390. In contrast, the most expensive time of day to depart to Chicago is at noon when prices are around $543.

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

You are more likely to see cheaper flights to Chicago from Charleston when booking weeks ahead of your departure date. In general, you can expect to find flights to Chicago for around $367 when searching weeks out. However, flight prices might be lower outside of this timeframe. For example, people recently found flights to Chicago from Charleston for as low as $268 on momondo.

You could potentially save up to 29% on your flight if you consider stops on a Charleston to Chicago flight.

As of May 2026, prices for Charleston to Chicago flights are approximately 118% more expensive when compared to flights at the same time last year.

Delta, Southwest, and United Airlines are the most popular carriers operating from Charleston to Chicago

United Airlines, American Airlines and Southwest are the top three most popular airlines that fly to Chicago from Charleston according to our data. United Airlines is the first choice among our users, with 49% of people opting to fly with this airline when traveling to Chicago. Keep in mind that there are 6 different airlines that fly to Chicago on a routine basis, so you have a few additional options to choose from.

As of May 2026, 22 flights take off from Charleston and land in Chicago each day. The most common flight departure time for this route is 6:00PM, with 47% of daily flights taking off in the evening.

As of May 2026, there are 156 flights per week flying from Charleston to Chicago. The most common day of the week flights depart is Mon, with 20% of flights taking off on this day.