Cheap flights from Chicago to Charleston from $105

The cheapest month to fly to Charleston from Chicago is in February. Flight prices, which tend to average around $101, are often lower during this time because this is during the off-season. The month of January is another great option to travel to Charleston, with average flight prices from Chicago averaging around $104.

The cheapest day to depart from Chicago to Charleston is on a Tuesday. Travelers who choose to depart for Charleston on a Tuesday will often find tickets for as low as $342. The most expensive day to fly to Charleston is Sunday, with ticket prices averaging around $403.

The cheapest time of day to fly to Charleston is in the evening when flights can be purchased for as low as $365. In the morning is when there is more demand to fly to Charleston, so prices are often more expensive at around $381 per ticket.

Fly from Chicago Midway to Charleston for the best Chicago - Charleston flight prices

You are more likely to see cheaper flights to Charleston from Chicago when booking weeks ahead of your departure date. In general, you can expect to find flights to Charleston for around $377 when searching weeks out. However, flight prices might be lower outside of this timeframe. For example, people recently found flights to Charleston from Chicago for as low as $293 on momondo.

No. A direct flight is the cheapest option for a flight between Chicago to Charleston.

As of May 2026, prices for Chicago to Charleston flights are approximately 19% more expensive when compared to flights at the same time last year.

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

United Airlines, American Airlines and Southwest are the top three most popular airlines that fly to Charleston from Chicago according to our data. United Airlines is the first choice among our users, with 48% of people opting to fly with this airline when traveling to Charleston. Keep in mind that there are 6 different airlines that fly to Charleston on a routine basis, so you have a few additional options to choose from.

Atlanta (ATL) 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 $284.

Flights connecting via Charlotte (CLT) have the shortest average one-way travel time: 4h 30m.

Charlotte (CLT) has the shortest average layover time for this route: 0h 57m.

As of May 2026, 21 flights take off from Chicago and land in Charleston each day. The most common flight departure time for this route is 2:00PM, with 47% of daily flights taking off in the afternoon.

As of May 2026, there are 153 flights per week flying from Chicago to Charleston. The most common day of the week flights depart is Wed, with 16% of flights taking off on this day.