On this page, you can find and purchase flights from Chicago to Hilton Head Island. The flight distance is 1,233 km, and the flight frequency on this route reaches approximately 8 flights per week.
Flights are operated by UA and AA. Before booking, you can find out how to get to Chicago airport and check transportation in Hilton Head Island for a convenient transfer after arrival.
The table shows direct flights Chicago → Hilton Head Island on the selected date. The flight takes approximately 2 h 33 min. Regular flights are operated by United Airlines and American Airlines. Departures from O'Hare International Airport, Chicago Midway International Airport and Midway International Airport airports, arrivals at Hilton Head Airport.
For each flight, the following details are shown: departure time (local), arrival city and airport, flight number and airline, terminal or gate, and status. Click on a flight to open its details and go to ticket search. To view flights on a different day, change the date above the table.
Below is a calendar of the lowest flight ticket prices for Chicago — Hilton Head Island by day. Pick a convenient date and instantly see the fare. The cheapest flights on this route start from $179 in ,, and the most expensive are around $276 in y. If your travel dates are flexible, the calendar will help you find the best price for your preferred period. To view round-trip fares, switch to the "Round trip" tab above the calendar, select your departure date — and the right-hand calendar will highlight the lowest prices for return flights on each day.
Chicago → Hilton Head Island, average one-way price
| Month | Average price | Level | Month | Average price | Level | Month | Average price | Level |
|---|---|---|---|---|---|---|---|---|
| Jan | $281 | low | May | $342 | medium | Sep | $318 | medium |
| Feb | $269 | low | Jun | $416 | high | Oct | $306 | medium |
| Mar | $318 | medium | Jul | $440 | high | Nov | $281 | low |
| Apr | $391 | high | Aug | $257 | low | Dec | $379 | high |
Some values are estimated based on seasonality.
The warmest period in Hilton Head Island is July, with average temperatures reaching up to 31.5°C, while January is the coolest month. The wet season occurs during the summer months, peaking in August with up to 23 rainy days.
The lowest airfare for this destination was recorded in July, starting $271. To track the best offers for other months, we recommend using the price dynamics chart on this page.
October is considered a good compromise between weather and travel conditions. During this time, the temperature remains comfortable at around 25.6°C, and the month sees the highest number of dry days in the year, which is convenient for trip planning.
Two airlines operate on this route, with United Airlines (UA) and American Airlines (AA) being the primary carriers. A total of about 8 flights per week are available, including both direct flights and connecting options. You can find detailed information about schedules, departure days, and available fares for each airline in the interactive list below.
Flights Chicago — Hilton Head Island depart from O'Hare International Airport, Chicago Midway International Airport, Midway International Airport and Chicago Rockford International Airport and arrive at Hilton Head Airport. Below are pages for the cities, countries, and airports on the route: airlines, schedules, and travel guides.
With a distance of 1,233 km, the estimated direct flight time is approximately 1 hour and 45 minutes, excluding time for connections and pre-flight procedures.
Regular air service between these cities is provided by American carriers UA (United Airlines) and AA (American Airlines).
Both non-stop flights and routes with one stop are available on this destination. You can check the current availability of direct flights for specific dates in the search results.
Flights from Chicago arrive at Hilton Head Airport (HHH), located in close proximity to the main resort areas.
To find the most affordable fares, it is recommended to start monitoring prices a month before departure, focusing on mid-week offers.
Where travelers fly most — pick a route and check prices
