$117 Find Cheap Flights from Chicago to Kiawah Island - Compare and Save

When flying out of Chicago you’ll be using one of these airports: Chicago Midway or Chicago O'Hare Intl. Kiawah Island does not have its own airport so you’ll be flying into nearby Charleston airport, which is 19.9 mi away.

Direct flights cover the 746 miles separating Chicago and Kiawah Island in about 2h 05m.

32 direct flights run between Chicago and Kiawah Island on a daily basis. On average, there are about 225 departures each week.

Consider leaving on a Tuesday and avoid Saturdays if you are looking for the best rates. For your return to Chicago, you’ll find the best rates on Fridays and the most expensive ones on Saturdays.

KAYAK is a travel search engine. That means we look across the web to find the best prices we can find for our users. With over 2 billion flight queries processed yearly, we are able to display a variety of prices and options on flights from Chicago to Kiawah Island.

KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight to Kiawah Island from Chicago is likely to change within 7 days, so travelers know whether to wait or book now.

Hacker Fares allow you to combine one-way tickets in order to save you money over a traditional round-trip ticket. You could then fly to Kiawah Island with an airline and back to Chicago with another airline.

Sometimes travel dates aren't set in stone. If your preferred travel dates have some wiggle room, flexible dates will show you all the options when flying to Kiawah Island from Chicago up to 3 days before/after your preferred dates. You can then pick the flights that suit you best.

In the last 5 days, the cheapest one-way ticket between Chicago and Kiawah Island found on KAYAK was with American Airlines for $124. American Airlines offered a round-trip connection from $237 and United Airlines from $238.