$179 Find Cheap Flights from Chicago to Hilton Head Island - Compare and Save

If your flying dates are flexible, you should consider flying to Hilton Head Island on a Tuesday, as we generally find the cheapest rates on that day for this route. On the other hand, Sunday is the most expensive day to fly from Chicago to Hilton Head Island. For your return ticket, we recommend flying on a Wednesday and avoiding Sundays for the best deals.

The cheapest month for flights from Chicago O'Hare Intl Airport to Hilton Head Island is October, where tickets cost $350 (return) on average. On the other hand, the most expensive months are March and August, where the average cost of round-trip tickets is $633 and $600 respectively.

No, with an average price for the route of $389, prices are generally cheapest when you fly direct.

To get a below average price on the flight from Chicago O'Hare Intl Airport to Hilton Head Island, you should book around 4 weeks before departure, which saves you about 7% compared to booking last minute. For the absolute cheapest price, our data suggests you should book 25 weeks before departure.

In the past 5 days, the cheapest round-trip tickets from Chicago to Hilton Head Island were found on American Airlines ($279) and Delta ($304).

There are 2 airlines that fly nonstop from Chicago O'Hare Intl Airport to Hilton Head Island. They are American Airlines and United Airlines. The cheapest airline for this route is United Airlines, with the best round-trip deal found costing $220. On average, the best prices for this route can be found at United Airlines.

Charlotte (CLT) is the top choice – 90% of KAYAK users who clicked on 1-stop flights from Chicago to Hilton Head Island picked an itinerary connecting there.

Flights via Atlanta (ATL) offer the most affordable fares, with an average round-trip price of $334.

Consider flying via Charlotte (CLT) for the shortest journey. The average one-way travel time for flights connecting there is 4h 52m.

If you prefer a quick connection, Charlotte (CLT) often has the shortest layovers from Chicago to Hilton Head Island, with an average of 1h 33m.

There are 2 cabin class options for the route. These are First and Economy. Perform a search on KAYAK to find the latest prices and availability for all cabin fares, which differ across airlines.

Each day, there are 2 nonstop flights that take off from Chicago O'Hare Intl Airport and land in Hilton Head Island, with an average flight time of 2h 29m. The most common departure time is 8:00 am and most flights take off in the morning. Each week, there are 14 flights and there are the same amount of flights each day (2).