$383 Cheap Flights from Hilton Head Island (HHH) to Chicago (MDW)

View $383 flight on Mon, Apr 13, 2026Opens in a new window

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

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

Prices were available within the past 7 days and start at $383 for one-way flights and $435 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

Delta
Wed, Apr 15 - Mon, Apr 20
HHH
Hilton Head Island
MDW
Chicago
$435 Roundtrip, found 2 days ago
$435
Roundtrip
found 2 days ago
Select Delta flight, departing Wed, Apr 15 from Hilton Head Island to Chicago, returning Mon, Apr 20, priced at $435 found 2 days ago
Delta
Tue, Apr 14 - Mon, Apr 20
HHH
Hilton Head Island
MDW
Chicago
$460 Roundtrip, found 2 days ago
$460
Roundtrip
found 2 days ago
Select Delta flight, departing Tue, Apr 14 from Hilton Head Island to Chicago, returning Mon, Apr 20, priced at $460 found 2 days ago
Delta
Wed, Apr 15 - Sun, Apr 19
HHH
Hilton Head Island
MDW
Chicago
$482 Roundtrip, found 2 days ago
$482
Roundtrip
found 2 days ago
Select Delta flight, departing Wed, Apr 15 from Hilton Head Island to Chicago, returning Sun, Apr 19, priced at $482 found 2 days ago
Delta
Wed, Apr 15 - Wed, Apr 22
HHH
Hilton Head Island
MDW
Chicago
$487 Roundtrip, found 2 days ago
$487
Roundtrip
found 2 days ago
Select Delta flight, departing Wed, Apr 15 from Hilton Head Island to Chicago, returning Wed, Apr 22, priced at $487 found 2 days ago
Delta
Thu, Apr 16 - Mon, Apr 20
HHH
Hilton Head Island
MDW
Chicago
$492 Roundtrip, found 2 days ago
$492
Roundtrip
found 2 days ago
Select Delta flight, departing Thu, Apr 16 from Hilton Head Island to Chicago, returning Mon, Apr 20, priced at $492 found 2 days ago
Delta
Tue, Apr 14 - Sun, Apr 19
HHH
Hilton Head Island
MDW
Chicago
$507 Roundtrip, found 2 days ago
$507
Roundtrip
found 2 days ago
Select Delta flight, departing Tue, Apr 14 from Hilton Head Island to Chicago, returning Sun, Apr 19, priced at $507 found 2 days ago
Delta
Tue, Apr 14 - Wed, Apr 22
HHH
Hilton Head Island
MDW
Chicago
$512 Roundtrip, found 2 days ago
$512
Roundtrip
found 2 days ago
Select Delta flight, departing Tue, Apr 14 from Hilton Head Island to Chicago, returning Wed, Apr 22, priced at $512 found 2 days ago
Delta
Wed, Apr 15 - Sat, Apr 18
HHH
Hilton Head Island
MDW
Chicago
$535 Roundtrip, found 2 days ago
$535
Roundtrip
found 2 days ago
Select Delta flight, departing Wed, Apr 15 from Hilton Head Island to Chicago, returning Sat, Apr 18, priced at $535 found 2 days ago
Delta
Thu, Apr 16 - Sun, Apr 19
HHH
Hilton Head Island
MDW
Chicago
$539 Roundtrip, found 2 days ago
$539
Roundtrip
found 2 days ago
Select Delta flight, departing Thu, Apr 16 from Hilton Head Island to Chicago, returning Sun, Apr 19, priced at $539 found 2 days ago
Delta
Thu, Apr 16 - Wed, Apr 22
HHH
Hilton Head Island
MDW
Chicago
$544 Roundtrip, found 2 days ago
$544
Roundtrip
found 2 days ago
Select Delta flight, departing Thu, Apr 16 from Hilton Head Island to Chicago, returning Wed, Apr 22, priced at $544 found 2 days ago
Delta
Tue, Apr 14 - Sat, Apr 18
HHH
Hilton Head Island
MDW
Chicago
$560 Roundtrip, found 2 days ago
$560
Roundtrip
found 2 days ago
Select Delta flight, departing Tue, Apr 14 from Hilton Head Island to Chicago, returning Sat, Apr 18, priced at $560 found 2 days ago
Delta
Thu, Apr 16 - Sun, Apr 19
HHH
Hilton Head Island
MDW
Chicago
$592 Roundtrip, found 15 hours ago
$592
Roundtrip
found 15 hours ago
Select Delta flight, departing Thu, Apr 16 from Hilton Head Island to Chicago, returning Sun, Apr 19, priced at $592 found 15 hours ago
Delta
Wed, Apr 15 - Fri, Apr 17
HHH
Hilton Head Island
MDW
Chicago
$604 Roundtrip, found 2 days ago
$604
Roundtrip
found 2 days ago
Select Delta flight, departing Wed, Apr 15 from Hilton Head Island to Chicago, returning Fri, Apr 17, priced at $604 found 2 days ago
Delta
Thu, Apr 16 - Sun, Apr 19
HHH
Hilton Head Island
MDW
Chicago
$622 Roundtrip, found 2 days ago
$622
Roundtrip
found 2 days ago
Select Delta flight, departing Thu, Apr 16 from Hilton Head Island to Chicago, returning Sun, Apr 19, priced at $622 found 2 days ago
Delta
Tue, Apr 14 - Fri, Apr 17
HHH
Hilton Head Island
MDW
Chicago
$629 Roundtrip, found 2 days ago
$629
Roundtrip
found 2 days ago
Select Delta flight, departing Tue, Apr 14 from Hilton Head Island to Chicago, returning Fri, Apr 17, priced at $629 found 2 days ago
Delta
Mon, Apr 13 - Mon, Apr 20
HHH
Hilton Head Island
MDW
Chicago
$651 Roundtrip, found 2 days ago
$651
Roundtrip
found 2 days ago
Select Delta flight, departing Mon, Apr 13 from Hilton Head Island to Chicago, returning Mon, Apr 20, priced at $651 found 2 days ago
Delta
Thu, Apr 16 - Fri, Apr 17
HHH
Hilton Head Island
MDW
Chicago
$662 Roundtrip, found 2 days ago
$662
Roundtrip
found 2 days ago
Select Delta flight, departing Thu, Apr 16 from Hilton Head Island to Chicago, returning Fri, Apr 17, priced at $662 found 2 days ago

Alternative airports near Chicago

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

Select flight to O'Hare Intl. ORD. Cheapest option available. Average driving time to city center is 23 minutes. Flights from $321
ORD
O'Hare Intl.
Cheapest
Average driving time to city center23 min
Flights from $321

Frequently asked questions

How much does a flight from Hilton Head Island Airport (HHH) to Midway Intl. Airport (MDW) cost?
Get a cheap one-way flight from $383 or cheap return flight from $435 from Hilton Head Island Airport (HHH) to Midway Intl. Airport (MDW) 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 Hilton Head Island Airport (HHH) to Midway Intl. Airport (MDW)?
Traveling in April may help you find better deals, as it's the cheapest month for flights between HHH and MDW. You'll often find the lowest prices during off-peak months.
Which airlines fly direct from Hilton Head Island Airport (HHH) to Midway Intl. Airport (MDW)?
You can't take a direct flight to Midway Intl. Airport (MDW) from Hilton Head Island, SC (HHH). However, you can seamlessly travel to Chicago without any layovers by departing from Charleston Intl. Airport (CHS).
What is the cheapest airline that flies from Hilton Head Island Airport (HHH) to Midway Intl. Airport (MDW)?
To find the cheapest airline that'll fly you from HHH to MDW, use Expedia's filter tool. Tailor your search based on what matters most to you, such as preferred carriers and cabin class. You can then sort your results by "Price (lowest to highest)" to list the most affordable options first.
How many flights per day from Hilton Head Island Airport (HHH) to Midway Intl. Airport (MDW)?
You'll need to hop on a flight with a layover if you're traveling from Hilton Head Island Airport (HHH) to Midway Intl. Airport (MDW). There are no daily direct flights on this route. However, just filter your search to include one or more stops to find an option that works for you.
What day of the week has the most flights from HHH to MDW?
Friday is typically the busiest day for flights, while Tuesday is often the quietest.* Just remember that flight schedules can vary depending on a range of factors, including the carrier and season.*Busiest/quietest day to travel is based on Expedia flight demand through January to December 2024.
What is the best time to fly from Hilton Head Island Airport (HHH) to Midway Intl. Airport (MDW)?
Choose a flight from Hilton Head Island Airport (HHH) to Midway Intl. Airport (MDW) that leaves before 3 PM to reduce the risk of cancellations and delays. Departures after this hour are on average 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.
Is it cheaper to buy a plane ticket from Hilton Head Island Airport (HHH) to Midway Intl. Airport (MDW) last-minute?
Last-minute bookings from HHH to MDW are typically more expensive. For the cheapest rates, start looking for flights ahead of time. That said, if your travel plans are flexible, you may land a cheap fare right before your journey.
Is it cheaper to book a HHH to MDW flight and hotel package?
You'll typically save money by securing a HHH to MDW flight and hotel package compared to booking separately. In fact, travelers could save hundreds of dollars by bundling with Expedia. And it's simple to manage it all in one convenient place. After choosing your preferred accommodations and flights, you can add extras such as activities, tours and car rentals.
Can I cancel or change the date of my flight from Hilton Head Island Airport (HHH) to Midway Intl. Airport (MDW)?
Usually, it's possible to reschedule or cancel your HHH to MDW flight. However, if the booking was made more than 24 hours ago, additional fees may apply. Check your airline's policies in your itinerary to see what changes are allowed and whether any costs are involved. You'll also find more information on our Customer Service portal.

Travel information

Origin airport
Hilton Head Island
Destination airport
Midway Intl.
Airlines serving
Delta
Roundtrip price
$435
Distance
765 mi

Book with confidence

Hilton Head Island to Chicago Flights

The cheapest times to fly from Hilton Head Island to Chicago

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 Hilton Head Island to Chicago are during the month of April. You can find some of the cheapest flights from Hilton Head Island to Chicago with Expedia's search tool and vast selection of airlines.

 

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

Sunday is one of the best days to book for cheap flights from Hilton Head Island to Chicago: 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 Hilton Head Island to Chicago

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 Hilton Head Island to Chicago in 2025. You can also book with separate airlines for your outbound and return journeys, from $383 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 Hilton Head Island to Chicago 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 Hilton Head Island to Chicago 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.

 

Hilton Head Island to Chicago Flights

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*Available to One Key members.