$155 Cheap American Airlines flights Chicago (ORD) to Hilton Head Island (HHH)

Landing cheap one-way American Airlines flights from ORD to HHH from $155 on Expedia couldn’t be simpler — just filter by “Price (lowest to highest).” Or check out our budget-friendly return fares from $303 for your next exciting vacation.**These prices were available on Expedia within the past 7 days, for flights departing within the next year. Prices and availability are subject to change. Additional terms apply.

American Airlines flights to Hilton Head Island are often more affordable in the quieter months of January and December. Whether you need a round-trip or one-way ticket, you could score a better deal then.

Search for affordable American Airlines flights from O’Hare Intl. Airport (ORD) to Hilton Head Island Airport (HHH) one to three months before your departure. Travelers who book domestic flights 34 to 86 days in advance can save 25% compared to those who book just 6 to 12 days ahead. No matter the fare class and itinerary, the best day to book a domestic flight is generally Sunday and the most expensive day is typically Monday. Passengers who book on a Sunday can save 6% on average compared to those who book their travel on a Monday.**Ideal booking window recommendation is based on average round-trip ticket prices for January through November for 2024. Best day of the week to book recommendation is based on average round-trip ticket prices for January through October 2024. All data sourced from ARC’s global airline sales database.

To see if there’s a direct journey from ORD to HHH with American Airlines or any other carriers, select the “Nonstop” filter when looking for tickets.

To find the earliest departures from ORD to HHH with American Airlines, sort your results by “Morning” and “Early Morning.” Booking an early flight generally means cancellations are less likely.**Most reliable time of the day recommendation is based on January through August 2024 flight status data sourced from OAG’s global flight data platform.

American Airlines flights from O’Hare Intl. Airport (ORD) to Hilton Head Island touch down at Hilton Head Island Airport (HHH). This is the main gateway to this city.

In most cases, you can cancel or reschedule your flight, although there may be additional charges if you made your booking more than 24 hours ago. Need to keep your options open? Use our “Changes included” or “No cancel fee” filter to find flights that won’t charge you extra if you have to adjust your plans. To update your booking, head to “Trips,” select your flight and click on “Manage Booking” for further information.