By air
Flights from Chicago to Hilton Head Island
Fly from Chicago to Hilton Head Island (HHH) — then arrive and explore.
Searched and booked on Aviasales. Head Your Way may earn a commission at no extra cost to you.
Flight details and fares
Chicago to Hilton Head Island at a glance
- Arrival airport
- HHH
- Routing
- 1 stop
- Recent fare from
- £211
- Fare found
- 2026-09-14
£211 is the cheapest recent one-way fare our flight-data partner found for Chicago to Hilton Head Island; live prices move daily by date and demand. Check current Chicago to Hilton Head Island fares and pick your dates:
Are there direct flights from Chicago to Hilton Head Island?
Our latest harvest found the best Chicago to Hilton Head Island fare with 1 stop; a non-stop fare was not returned at that check. Direct routes can appear seasonally, so check the live search above for your dates.
Keep planning Hilton Head Island
The fare is the cheapest our flight-data partner (Travelpayouts) found for Chicago to Hilton Head Island, found around 2026-09-14: a recent SIGNAL, NOT a live or guaranteed quote, always check current fares before booking. The direct/indirect status reflects the routing found at that check and can vary by season and date. Airport codes from OurAirports. How Head Your Way compiles its data.