$239 Cheap Flights from Chicago (MDW) to Hilton Head Island (HHH)

View $239 flight on Mon, Aug 31, 2026Opens in a new window

Popular airlines from Chicago Midway Airport (MDW) to Hilton Head Island Airport (HHH)

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Cheap Flights from Chicago to Hilton Head Island (MDW-HHH)

Prices were available within the past 7 days and start at $239 for one-way flights and $492 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

Delta
Mon, Apr 20 - Wed, Apr 29
MDW
Chicago
HHH
Hilton Head Island
$492 Roundtrip, found 7 hours ago
$492
Roundtrip
found 7 hours ago
Select Delta flight, departing Mon, Apr 20 from Chicago to Hilton Head Island, returning Wed, Apr 29, priced at $492 found 7 hours ago
Delta
Sat, Apr 18 - Tue, Apr 21
MDW
Chicago
HHH
Hilton Head Island
$508 Roundtrip, found 7 hours ago
$508
Roundtrip
found 7 hours ago
Select Delta flight, departing Sat, Apr 18 from Chicago to Hilton Head Island, returning Tue, Apr 21, priced at $508 found 7 hours ago
Delta
Tue, May 26 - Tue, Jun 9
MDW
Chicago
HHH
Hilton Head Island
$518 Roundtrip, found 16 hours ago
$518
Roundtrip
found 16 hours ago
Select Delta flight, departing Tue, May 26 from Chicago to Hilton Head Island, returning Tue, Jun 9, priced at $518 found 16 hours ago
Delta
Wed, Apr 22 - Wed, Apr 29
MDW
Chicago
HHH
Hilton Head Island
$522 Roundtrip, found 7 hours ago
$522
Roundtrip
found 7 hours ago
Select Delta flight, departing Wed, Apr 22 from Chicago to Hilton Head Island, returning Wed, Apr 29, priced at $522 found 7 hours ago
Delta
Mon, May 4 - Wed, May 20
MDW
Chicago
HHH
Hilton Head Island
$528 Roundtrip, found 16 hours ago
$528
Roundtrip
found 16 hours ago
Select Delta flight, departing Mon, May 4 from Chicago to Hilton Head Island, returning Wed, May 20, priced at $528 found 16 hours ago
Delta
Sun, May 3 - Wed, May 20
MDW
Chicago
HHH
Hilton Head Island
$530 Roundtrip, found 16 hours ago
$530
Roundtrip
found 16 hours ago
Select Delta flight, departing Sun, May 3 from Chicago to Hilton Head Island, returning Wed, May 20, priced at $530 found 16 hours ago
Delta
Tue, Apr 28 - Wed, May 13
MDW
Chicago
HHH
Hilton Head Island
$536 Roundtrip, found 16 hours ago
$536
Roundtrip
found 16 hours ago
Select Delta flight, departing Tue, Apr 28 from Chicago to Hilton Head Island, returning Wed, May 13, priced at $536 found 16 hours ago
Delta
Mon, Apr 27 - Tue, May 12
MDW
Chicago
HHH
Hilton Head Island
$538 Roundtrip, found 16 hours ago
$538
Roundtrip
found 16 hours ago
Select Delta flight, departing Mon, Apr 27 from Chicago to Hilton Head Island, returning Tue, May 12, priced at $538 found 16 hours ago
Delta
Sun, Apr 19 - Wed, Apr 29
MDW
Chicago
HHH
Hilton Head Island
$539 Roundtrip, found 7 hours ago
$539
Roundtrip
found 7 hours ago
Select Delta flight, departing Sun, Apr 19 from Chicago to Hilton Head Island, returning Wed, Apr 29, priced at $539 found 7 hours ago
Delta
Tue, May 5 - Tue, May 19
MDW
Chicago
HHH
Hilton Head Island
$546 Roundtrip, found 16 hours ago
$546
Roundtrip
found 16 hours ago
Select Delta flight, departing Tue, May 5 from Chicago to Hilton Head Island, returning Tue, May 19, priced at $546 found 16 hours ago

Alternative airports near Hilton Head Island

Prices were available within the past 7 days. Prices and availability are subject to change.

Select flight to Savannah - Hilton Head Intl. SAV. Cheapest option available. Average driving time to city center is 59 minutes. Flights from $420
SAV
Savannah - Hilton Head Intl.
Cheapest
Average driving time to city center59 min
Flights from $420

Frequently asked questions

How much does a flight from Midway Intl. Airport (MDW) to Hilton Head Island Airport (HHH) cost?
Lock in a cheap one-way flight from $239 or cheap return flight from $492 from Midway Intl. Airport (MDW) to Hilton Head Island Airport (HHH) with Expedia. Enter your travel dates and sort by "Price (lowest to highest)" to find our cheapest flight deals on this route.
What is the cheapest month to fly from Midway Intl. Airport (MDW) to Hilton Head Island Airport (HHH)?
Planning your getaway for April is a great way to save, as it's the cheapest month for flights between MDW and HHH. You'll usually find the lowest fares during the off-season.
What is the cheapest airline that flies from Midway Intl. Airport (MDW) to Hilton Head Island Airport (HHH)?
Expedia's filter tool lets you easily compare airlines, flight times and fares all in one place. Choose your preferences, then sort by "Price (lowest to highest)" to find the carrier with the cheapest MDW to HHH flight.
How many flights per day from Midway Intl. Airport (MDW) to Hilton Head Island Airport (HHH)?
Nonstop flights from Midway Intl. Airport (MDW) to Hilton Head Island Airport (HHH) aren't available daily, so you'll need to take a flight with a layover. Explore your options with Expedia's filters. Enter your travel dates and click on either "1 Stop" or "2+ Stops."
What day of the week has the most flights from MDW to HHH?
Typically you'll find the largest variety of flight choices on a Friday. Tuesdays are often the quietest.* However, this can vary depending on the season, airline and other factors.*Busiest/quietest day to travel is based on Expedia flight demand through January to December 2024.
What is the best time to fly from Midway Intl. Airport (MDW) to Hilton Head Island Airport (HHH)?
To avoid possible delays on the Midway Intl. Airport (MDW) to Hilton Head Island Airport (HHH) route, aim to fly before 3 PM. Later departures are 22% more likely to be canceled.**Most reliable time of the day and month to travel recommendation is based on January through August 2024 flight status data sourced from OAG's global flight data platform.
What airports do you fly into for Hilton Head Island from Midway Intl. Airport (MDW)?
Savannah - Hilton Head Intl. Airport (SAV) is the only airport in Hilton Head Island with direct flights from Midway Intl. Airport (MDW). Check out the options and find cheap fares on Expedia.
Is it cheaper to buy a plane ticket from Midway Intl. Airport (MDW) to Hilton Head Island Airport (HHH) last-minute?
Booking your ticket from MDW to HHH shortly before your journey is typically more expensive. However, if there's some wiggle room with your travel times and dates, you could bag a cheap last-minute fare.
Is it cheaper to book a MDW to HHH flight and hotel package?
Opting for a MDW to HHH flight and hotel package is typically cheaper than booking separately. With Expedia, you can enjoy the ease of organizing your trip in one place. Choose from our extensive range of accommodations and then add flights, activities and car rentals to your booking. Bundle everything together, and you could save hundreds of dollars.
Can I cancel or change the date of my flight from Midway Intl. Airport (MDW) to Hilton Head Island Airport (HHH)?
Typically, you can modify or cancel your MDW to HHH flight. However, additional fees may apply, especially if you made your booking more than 24 hours ago. Double-check your itinerary for the airline's rules and fees on flight changes, or if you need more details, head to our Customer Service portal.

Travel information

Origin airport
Midway Intl.
Destination airport
Hilton Head Island
Airlines serving
Delta
Roundtrip price
$492
Distance
765 mi

Book with confidence

Chicago to Hilton Head Island Flights

The cheapest times to fly from Chicago to Hilton Head Island

On average, Thursday can be the cheapest time to fly, according to data from the Airlines Reporting Corporation (ARC), one of the world's biggest databases for global airline sales. The data reveals that you could save up to 16% by flying on a Thursday—the cheapest day to travel on average—instead of a Sunday—the most expensive. Some of the most affordable flights from Chicago to Hilton Head Island are during the month of April. You can find some of the cheapest flights from Chicago to Hilton Head Island with Expedia's search tool and vast selection of airlines.

 

The best time to book a flight from Chicago to Hilton Head Island

Sunday is one of the best days to book for cheap flights from Chicago to Hilton Head Island: Tickets reserved on a Sunday cost between 6% and 13% less than those reserved on a Friday, according to ARC data. The data also suggests booking early can also lead to cheaper airfares. You could save 24% by buying your tickets for domestic flights at least a month in advance and 10% by booking international flights 2 months in advance.

 

How to find cheap round-trip tickets from Chicago to Hilton Head Island

Being flexible with your dates and using Expedia's Price Drop Protection and Price Tracking features are some of the best ways of finding a cheap ticket from Chicago to Hilton Head Island in 2025. You can also book with separate airlines for your outbound and return journeys, from $239 one-way. Expedia also offers Price Drop Protection, so if the cost of your airfare goes down after booking, you'll receive a credit for the difference*. This is available for a small fee, and is free to One Key Gold and Platinum tier members.

 

Expedia's Price Tracking feature means you can stay on top of airfares without manually checking every day. It sends you automated price alerts for cheap Chicago to Hilton Head Island flights and uses historical data to indicate when the best time to book is. Download Expedia's free app to activate this handy tool in a few easy taps.

 

You could also save big by booking one of Expedia's vacation packages. Bundling together your Chicago to Hilton Head Island airfare with your accommodations and car rental is often cheaper than booking everything separately. There’s also One Key, Expedia's generous rewards program. Join for free and you could earn One Key cash on most bookings to save on future adventures.

 

*Terms apply.

 

Disclaimer: ARC The statistics are based on average round-trip ticket prices between January and August 2023. The percentages you see are averages.

 

Chicago to Hilton Head Island Flights

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*Available to One Key members.