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Cheap flights from Chicago O'Hare International to Hilton Head

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Flight deals from Chicago O'Hare International to Hilton Head

Looking for a cheap last-minute deal or the best round-trip flight from Chicago O'Hare International Airport to Hilton Head Airport? If you want to travel next month, round-trip fares start from $288. Find the lowest prices on one-way and round-trip tickets right here.
Hilton Head Island.$288 per passenger.Departing Tue, Jun 2, returning Tue, Jun 9.Round-trip flight with Delta.Outbound indirect flight with Delta, departing from Chicago O'Hare International on Tue, Jun 2, arriving in Hilton Head.Inbound indirect flight with Delta, departing from Hilton Head on Tue, Jun 9, arriving in Chicago O'Hare International.Price includes taxes and charges.From $288, select.
Hilton Head Island.$289 per passenger.Departing Wed, Jul 8, returning Tue, Jul 14.Round-trip flight with Delta.Outbound indirect flight with Delta, departing from Chicago O'Hare International on Wed, Jul 8, arriving in Hilton Head.Inbound indirect flight with Delta, departing from Hilton Head on Tue, Jul 14, arriving in Chicago O'Hare International.Price includes taxes and charges.From $289, select.
Hilton Head Island.$289 per passenger.Departing Fri, Aug 7, returning Tue, Aug 11.Round-trip flight with Delta.Outbound indirect flight with Delta, departing from Chicago O'Hare International on Fri, Aug 7, arriving in Hilton Head.Inbound indirect flight with Delta, departing from Hilton Head on Tue, Aug 11, arriving in Chicago O'Hare International.Price includes taxes and charges.From $289, select.
Hilton Head Island.$289 per passenger.Departing Wed, Sep 9, returning Wed, Sep 16.Round-trip flight with Delta.Outbound indirect flight with Delta, departing from Chicago O'Hare International on Wed, Sep 9, arriving in Hilton Head.Inbound indirect flight with Delta, departing from Hilton Head on Wed, Sep 16, arriving in Chicago O'Hare International.Price includes taxes and charges.From $289, select.
Hilton Head Island.$346 per passenger.Departing Sun, May 17, returning Wed, May 20.Round-trip flight with Delta.Outbound indirect flight with Delta, departing from Chicago O'Hare International on Sun, May 17, arriving in Hilton Head.Inbound indirect flight with Delta, departing from Hilton Head on Wed, May 20, arriving in Chicago O'Hare International.Price includes taxes and charges.From $346, select.
Hilton Head Island.$351 per passenger.Departing Wed, Jun 17, returning Wed, Jun 24.Round-trip flight with United.Outbound direct flight with United departing from Chicago O'Hare International on Wed, Jun 17, arriving in Hilton Head.Inbound direct flight with United departing from Hilton Head on Wed, Jun 24, arriving in Chicago O'Hare International.Price includes taxes and charges.From $351, select.
Hilton Head Island.$388 per passenger.Departing Sat, Jun 27, returning Sat, Jul 4.Round-trip flight with Delta.Outbound indirect flight with Delta, departing from Chicago O'Hare International on Sat, Jun 27, arriving in Hilton Head.Inbound indirect flight with Delta, departing from Hilton Head on Sat, Jul 4, arriving in Chicago O'Hare International.Price includes taxes and charges.From $388, select.
Hilton Head Island.$400 per passenger.Departing Mon, Oct 19, returning Sat, Oct 24.Round-trip flight with Delta.Outbound indirect flight with Delta, departing from Chicago O'Hare International on Mon, Oct 19, arriving in Hilton Head.Inbound indirect flight with Delta, departing from Hilton Head on Sat, Oct 24, arriving in Chicago O'Hare International.Price includes taxes and charges.From $400, select.
Hilton Head Island.$402 per passenger.Departing Thu, Jul 9, returning Tue, Jul 14.Round-trip flight with United.Outbound direct flight with United departing from Chicago O'Hare International on Thu, Jul 9, arriving in Hilton Head.Inbound direct flight with United departing from Hilton Head on Tue, Jul 14, arriving in Chicago O'Hare International.Price includes taxes and charges.From $402, select.
Hilton Head Island.$404 per passenger.Departing Fri, May 15, returning Mon, May 18.Round-trip flight with United.Outbound direct flight with United departing from Chicago O'Hare International on Fri, May 15, arriving in Hilton Head.Inbound direct flight with United departing from Hilton Head on Mon, May 18, arriving in Chicago O'Hare International.Price includes taxes and charges.From $404, select.
Hilton Head Island.$405 per passenger.Departing Fri, Jul 31, returning Sun, Aug 2.Round-trip flight with Delta.Outbound indirect flight with Delta, departing from Chicago O'Hare International on Fri, Jul 31, arriving in Hilton Head.Inbound indirect flight with Delta, departing from Hilton Head on Sun, Aug 2, arriving in Chicago O'Hare International.Price includes taxes and charges.From $405, select.
Hilton Head Island.$427 per passenger.Departing Fri, Aug 7, returning Tue, Aug 11.Round-trip flight with United.Outbound direct flight with United departing from Chicago O'Hare International on Fri, Aug 7, arriving in Hilton Head.Inbound direct flight with United departing from Hilton Head on Tue, Aug 11, arriving in Chicago O'Hare International.Price includes taxes and charges.From $427, select.
Hilton Head Island.$487 per passenger.Departing Sat, May 30, returning Sat, Jun 6.Round-trip flight with Delta.Outbound indirect flight with Delta, departing from Chicago O'Hare International on Sat, May 30, arriving in Hilton Head.Inbound indirect flight with Delta, departing from Hilton Head on Sat, Jun 6, arriving in Chicago O'Hare International.Price includes taxes and charges.From $487, select.
Hilton Head Island.$509 per passenger.Departing Sun, May 31, returning Wed, Jun 3.Round-trip flight with United.Outbound direct flight with United departing from Chicago O'Hare International on Sun, May 31, arriving in Hilton Head.Inbound direct flight with United departing from Hilton Head on Wed, Jun 3, arriving in Chicago O'Hare International.Price includes taxes and charges.From $509, select.
Hilton Head Island.$719 per passenger.Departing Tue, Jul 28, returning Sat, Aug 8.Round-trip flight with United.Outbound direct flight with United departing from Chicago O'Hare International on Tue, Jul 28, arriving in Hilton Head.Inbound direct flight with United departing from Hilton Head on Sat, Aug 8, arriving in Chicago O'Hare International.Price includes taxes and charges.From $719, select.

Find the cheapest month to fly from Chicago O'Hare International to Hilton Head

We’re always keeping an eye on fares, so you can find the best one in seconds. It looks like Chicago O'Hare International to Hilton Head flights are currently cheapest in June.
May
from $346
Jun
from $288
Jul
from $289
Aug
from $289
Sep
from $289
Oct
from $400
Nov
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Dec
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Jan
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Feb
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Mar
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Apr
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Direct flights from Chicago O'Hare International to Hilton Head

Chicago O'Hare International to Hilton Head: Alternative routes

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

Hilton Head

7km from central Hilton Head Island
Closest
from $288
Search flights

Savannah / Hilton Head

43km from central Hilton Head Island
Cheapest
from $237
Search flights

Chicago to Hilton Head Island: Flight information

The things to know before you go.
Cheapest flight found$288
Cheapest month to flyJune
Average flight time2 hrs, 29 mins
Most popular airlineAmerican Airlines
Average flights per week20

Finding cheap flights from Chicago O'Hare International to Hilton Head: Frequently asked questions

The best price we found for a round-trip flight from Chicago O'Hare International to Hilton Head is $288. 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 29 minutes is the average flight time from Chicago O'Hare International to Hilton Head.
American Airlines, Envoy Air and Republic Airways fly direct from Chicago O'Hare International to Hilton Head.
There are 20 flights per week flying from Chicago O'Hare International to Hilton Head, as of May 2026.
The cheapest month to fly from Chicago O'Hare International to Hilton Head is usually June.
After crunching the numbers on our flight calendar, we found that it's currently cheapest to fly from Chicago O'Hare International Airport to Hilton Head Airport on Tuesday, June 2, 2026.
Yes – the average flight time is 2 hours and 29 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.
Currently, Delta and United offer the cheapest flight tickets to Hilton Head.

Flying from O'Hare International Airport (ORD) to Hilton Head Airport (HHH): what you need to know

  • Arrive at the airport on time so you don't miss your ORD to HHH flight. Be there at least two hours ahead for international flights and an hour early for domestic departures to avoid sprinting to your gate.

  • During popular months like August, you'll want to get to the airport earlier than normal. Arrive two hours before domestic departures and four hours ahead for an international flight whenever you're flying during a peak period in general.

  • Getting to Hilton Head (and then seeing more of United States!) is a snap with American Airlines. This popular carrier offers direct flights from O'Hare International Airport to Hilton Head Airport.

  • Most travelers choose to travel with American Airlines on this route.

  • We make it a breeze to book a flight with a stopover. To see your options for tickets from O'Hare International Airport to Hilton Head Airport, deselect 'Direct flights only.' Then, pick a flight offering a stop long enough to tour the city of your choice. Popular stopovers between ORD and HHH include:

    • Charlotte Douglas International Airport

    • Hartsfield-Jackson Atlanta International Airport

    • Logan International Airport

How to find the cheapest flights from O'Hare International Airport (ORD) to Hilton Head Airport (HHH)

  • The lowest price we've found for a one-way O'Hare International Airport to Hilton Head Airport flight is $254. A round-trip fare right now is $288. Depending on the availability and when you book, these fares can change.

  • It's often best to book early if you're looking for cheap tickets from ORD to HHH. That's because flight prices are based on demand, which tends to increase closer to the date of departure.

  • The 'Whole month' search tool shows you the cheapest flights from O'Hare International Airport to Hilton Head Airport throughout the entire month. It's a great way to snap up a bargain if your travel plans are flexible.

  • Never miss a deal on cheap flights from ORD to HHH by setting up a Price Alert. We'll send you an email or notification through the app when a new discounted fare appears.

  • Discover the right flight for you with the help of the filters. To see the 'Best,' 'Fastest' or 'Cheapest' flights from O'Hare International Airport to Hilton Head Airport, use the 'Sort by' tool. You can also filter results by departure and arrival times, airline, and number of stops.

Handy information about O'Hare International Airport (ORD)

  • You'll find ORD at 10000 West O'Hare.

  • Of all flights departing from O'Hare International Airport, 74.85% land on schedule at their destination.

  • O'Hare International Airport is around 40 kilometers from central Chicago. If you're driving, ride-sharing or catching a cab from the center, it'll take you 35 minutes or so to arrive, depending on the traffic.

  • Planning to catch public transport? You can expect a journey time of around 55 minutes.

  • Get your travels off to a stress-free start by staying near ORD. Whether you have an early flight from O'Hare International Airport to Hilton Head Airport or want to avoid feeling rushed, these stays are ideal:

Arriving at Hilton Head Airport (HHH)

  • The last thing you want is a long trip to your hotel if you're arriving on a late O'Hare International Airport to Hilton Head Airport flight. Reserve one of these accommodation options near HHH instead:

  • Grab a Hilton Head Airport rental car and discover Hilton Head and beyond with your own set of wheels. Enterprise, Budget and Avis are leading providers to choose from here.

  • Reserve your ride from Hilton Head Airport at least a few weeks before your trip to get the best deal. If you're planning to travel during a busy period, it's a smart idea to book even earlier.

Getting from Hilton Head Airport (HHH) to central Hilton Head

  • The address for HHH is 120 Beach City Road.

  • Hilton Head Airport is approximately 6 kilometers from central Hilton Head. The drive time takes about 10 minutes.

When to fly to Hilton Head Airport (HHH)

  • It's time to choose your travel dates for your flight from O'Hare International Airport to Hilton Head Airport. July is the most popular month to head to Hilton Head. If you prefer a more low-key vibe, go in January.

  • Lock in your flight from O'Hare International Airport to Hilton Head Airport for July if you want to go to Hilton Head during its warmest month. Expect temperatures of between 24ºC (75ºF) and 32ºC (90ºF).

  • If you'd rather travel in cooler conditions, search for a cheap ticket from ORD to HHH in January. Average temperatures are between 4ºC (39ºF) and 18ºC (64ºF) then.

Explore more of United States

  • You've done Hilton Head, now it's time to discover other parts of United States. Journey about 225 kilometers south-west to Jacksonville to tick off its top attractions. From Jacksonville Zoo and Gardens to The Cummer Museum of Art & Gardens and Friendship Fountain, there's plenty to keep you on the go.

  • Around 338 kilometers north of Hilton Head, Charlotte is another essential stop in United States. Experience this destination's highlights firsthand at NASCAR Hall of Fame, Freedom Park and Carolinas Aviation Museum.

More travel options

Plan the rest of your trip from Chicago to Hilton Head Island

Prices shown on this page are estimated lowest prices only. Found in the last 45 days.