$229 Cheap United flights Chicago (ORD) to Hilton Head Island (HHH)

Finding cheap one-way United Airlines flights from ORD to HHH from $229 on Expedia is easy — just filter by "Price (lowest to highest)." Alternatively, check out our affordable return fares from $279 for your next exciting getaway.**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.

Begin your search one to three months ahead of your travel date to find cheaper fares on United Airlines flights from O'Hare Intl. Airport (ORD) to Hilton Head Island Airport (HHH). You can save 25% by booking your domestic flight 34 to 86 days in advance versus last-minute reservations made 6 to 12 days out. You could also reduce costs by buying your fare on a Sunday, as it's 6% cheaper on average than a Monday, the most expensive day to book.* Nail your timing, and you can enjoy significant savings on domestic journeys.*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 find the earliest departure from ORD to HHH with United Airlines, sort your results by "Early Morning" and "Morning." Booking an early flight generally means you'll experience fewer cancellations.**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.

A rewarding loyalty program and the ability to rack up points through United Mileage Plus are the start of the reasons to travel from ORD to HHH with United Airlines. Plus, when you sign up to our One Key™ program, you can earn OneKeyCash™* in addition to United Airlines's loyalty program earnings. It's yours to use wherever your next trip takes you.*OneKeyCash™ disclaimer - OneKeyCash™ is not redeemable for cash and can only be used on Expedia, Hotels.com and Vrbo.