Cheap Flights from Chicago (CHIA) to Hilton Head Island (HHH)

Compare Chicago to Hilton Head flight deals

Find the cheapest month or even day of the year to fly to Hilton Head

Book the best Hilton Head fare with no extra fees

Flight deals from Chicago to Hilton Head

Looking for a cheap last-minute deal or the best return flight from Chicago to Hilton Head Airport? If you want to travel next month, return fares start from $388. Find the lowest prices on one-way and return tickets right here.

Find the cheapest month to fly from Chicago to Hilton Head

We’re always keeping an eye on fares, so you can find the best one in seconds. It looks like Chicago to Hilton Head flights are currently cheapest in September.

Direct flights from Chicago to Hilton Head

Chicago to Hilton Head: Alternative routes

Compare routes from Chicago to Hilton Head Island below. You may find an airport to fly into that's cheaper, faster, or easier than Hilton Head.

Chicago to Hilton Head Island: Flight information

The things to know before you go.
Cheapest flight found$387
Cheapest month to flySeptember
Average flight time2 hrs, 30 mins
Most popular airlineEnvoy Air
Average flights per week32

Finding cheap flights from Chicago to Hilton Head: Frequently asked questions

The best price we found for a return flight from Chicago to Hilton Head is $387. This is an estimate based on information collected from different airlines and travel providers over the last 4 days and is subject to change and availability.
2 hours and 30 minutes is the average flight time from Chicago to Hilton Head.
Envoy Air, American Airlines and United fly direct from Chicago to Hilton Head.
As of July 2026, there are 16 flights per week flying from Chicago to Hilton Head.
The cheapest month to fly from Chicago to Hilton Head is usually September.
After crunching the numbers on our flight calendar, we found that it is currently cheapest to fly from Chicago to Hilton Head Airport on Saturday, 5 September 2026.
Yes – the average flight time is 2 hours and 30 minutes.
We show every price from over 1,200 airlines and travel agents, comparing them all so you don’t have to. If you know you want to fly to Hilton Head but you’re not ready to book, set up a Price Alert. We’ll track prices for you, and let you know when they rise or fall.

We crunched all the numbers in our flight calendar and it looks like the cheapest time to book a flight to Hilton Head Island is around 40 days in advance, so don’t leave your flight to the last minute.

The cheapest airline that flies to Hilton Head is United .

Flying from Chicago to Hilton Head Airport (HHH): What you need to know

  • Your trip gets off the ground at Chicago's main airport, Chicago O'Hare International Airport (ORD). Explore the options for booking a flight from Chicago to Hilton Head Airport (HHH) departing from this terminal.

  • The average length of a direct Chicago to Hilton Head Airport flight is 2 hours 25 minutes.

  • The timezone in Hilton Head Island is UTC-5, which is one hour ahead of Chicago. Hilton Head Airport is located in Hilton Head Island.

  • Chicago O'Hare International Airport (ORD) to Hilton Head Airport (HHH) is the most popular route, with 3 direct services every week. Get from ORD to HHH on American Airlines's 10:08am departure.

  • Arriving two hours before an international flight and one hour ahead of a domestic departure are tried-and-true travel tips. Be at the airport with enough time to catch your flight from Chicago to HHH.

  • Going away during a peak month like July? Popular periods (like Christmas and New Year) can easily add another hour at security. Play things extra safe and arrive up to four hours before international flights and two hours before domestic departures.

Airports in Chicago

Chicago O'Hare International Airport (ORD)

  • You can hop on a direct flight from Chicago to Hilton Head Airport (HHH) leaving from Chicago O'Hare International Airport (ORD).

  • Book your direct flight from Chicago to Hilton Head Airport with United Airlines. This well-known airline operates departures from ORD.

  • The preferred choice for passengers flying between ORD and HHH is United.

  • With 66.67% of its services landing on schedule, American Airlines is the top performer for punctuality on this route.

  • Located around 27 kilometres from central Chicago, ORD can be reached in about 30 minutes by car (depending on traffic). The journey by public transport will take roughly 45 minutes.

  • Want an easy start to your journey? Stay near Chicago O'Hare International Airport. Whether you're catching an early flight from Chicago to Hilton Head Airport or aren't a fan of being rushed, these hotels offer the perfect solution:

  • 70% of flights that leave from Chicago O'Hare International Airport touch down at their destination on time.

  • ORD's address is 10000 West O'Hare.

Chicago Midway International Airport (MDW)

  • You can get to MDW from the centre of Chicago in about 25 minutes by car (depending on traffic). The journey on public transport will take roughly 30 minutes to cover the 16 kilometres or so.

  • Catching an early morning flight? You might like to check in to one of these accommodation options near Chicago Midway International Airport the day before your Chicago to HHH flight:

  • 76% of all departures from Chicago Midway International Airport make it to their destination as expected.

  • MDW is located at 5700 South Cicero.

Chicago Rockford International Airport (RFD)

  • From the centre of Chicago, RFD is around 145 kilometres away. It'll take you roughly 1 hour 40 minutes to reach the airport by car and 2 hours or so on public transport.

  • Make catching an early Chicago to Hilton Head Airport flight one of the easiest parts of your trip. Book a room at one of these hotels near Chicago Rockford International Airport and get to your departure gate with plenty of time to spare:

  • Airports have an on-time performance rating that measures how often flights get to their destinations without delays. At RFD, that rate is 71%.

  • Chicago Rockford International Airport is located at 2 Airport Cir.

About Hilton Head Airport (HHH)

How to find the cheapest flights from Chicago to Hilton Head Airport (HHH)

  • Right now, $365 is the best price we've found for a one-way ticket from Chicago to Hilton Head Airport. The cheapest price for a return flight is $387. Keep in mind fares can change due to demand at the time of booking.

  • Booking ahead of time is often the key to scoring a cheap flight from Chicago to HHH. Prices tend to rise as demand increases, so the closer your departure date, the more you'll likely pay.

  • If you're flexible with your travel plans, try using the 'Whole month' search tool. It'll show you the lowest price across the month when searching for your Chicago to Hilton Head Airport ticket.

  • There's no need to check back in every day to find out if fares have dropped when you create a Price Alert. We'll notify you when there's a better deal on plane tickets from Chicago to HHH.

  • Discover the best deal on a flight from Chicago to Hilton Head Airport with the help of the filters. Pick your ideal arrival and departure times, airlines and number of stops. You can also sort your results by 'Best,' 'Cheapest' or 'Fastest.'

The best time to fly from Chicago to Hilton Head Airport (HHH)

  • It's time to figure out your travel dates for your flight from Chicago to Hilton Head Airport (HHH). May is the busiest month to travel to Hilton Head Island. If a slower pace sounds more appealing, go in January.

  • Book a Chicago to HHH plane ticket departing in July if you want to visit the city during its warmest month. Expect temperatures in Hilton Head Island to range from 24ºC (75ºF) to 32ºC (90ºF).

  • January sees temperatures of between 4ºC (39ºF) and 18ºC (64ºF). Search for cheap tickets from Chicago to Hilton Head Airport around that time if you want to travel in cooler conditions.

More about Hilton Head Island

  • After booking your flight from Chicago to Hilton Head Airport, find a hotel that keeps you close to what you want to see. Make one of these options your base for exploring Hilton Head Island:

  • Your Hilton Head Island trip won't be complete without checking out the sights. Highlights that should be on your list include Coligny Beach, Hilton Head Island Beach and Pine Island Beach and Dolphin Head Recreation Area.

Explore more of the United States

  • Hilton Head Island will leave a lasting impression, but there are so many other corners of the United States you should also see. About 225 kilometres southwest of Hilton Head Island, a visit to Jacksonville will keep you busy. Check out popular attractions like St. John's Cathedral, Museum of Contemporary Art Jacksonville and The Cummer Museum of Art & Gardens.

  • If you're looking to explore another corner of the United States, head for Columbia, about 193 kilometres north of Hilton Head Island. South Carolina African American History Monument, 701 Centre for Contmporary Art and South Carolina State Museum are highlights.

Prices shown on this page are estimated lowest prices only. Found in the last 12 days.