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Cheap flights from Pensacola to Hilton Head Island from $299

This is the cheapest round-trip flight price found by a momondo user in the last 72 hours by searching for a flight from Pensacola to Hilton Head Island departing on 10/28. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.
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0 bags

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Find the cheapest flights from Pensacola to Hilton Head Island

Cheap round-trip flights

Enter your travel dates to find the best prices.
Delta Logo
9:25 am - 3:19 pm
PNS
-
HHH
4h 54m
1 stop
Delta Logo
12:00 pm - 4:32 pm
HHH
-
PNS
5h 32m
1 stop
$299Delta
Wed, Oct 28 - Wed, Nov 4
American Airlines Logo
6:40 am - 5:32 pm
PNS
-
HHH
9h 52m
2 stops
American Airlines Logo
2:51 pm - 8:55 pm
HHH
-
PNS
7h 04m
1 stop
$496American Airlines
Wed, Oct 28 - Wed, Nov 4
American Airlines Logo
6:40 am - 5:32 pm
PNS
-
HHH
9h 52m
2 stops
American Airlines Logo
2:51 pm - 10:55 pm
HHH
-
PNS
9h 04m
2 stops
$502American Airlines
Wed, Oct 28 - Wed, Nov 4
American Airlines Logo
7:10 am - 2:13 pm
PNS
-
HHH
6h 03m
1 stop
American Airlines Logo
2:43 pm - 7:12 pm
HHH
-
PNS
5h 29m
1 stop
$519American Airlines
Sun, May 24 - Thu, May 28
American Airlines Logo
5:22 am - 11:10 am
PNS
-
HHH
4h 48m
1 stop
American Airlines Logo
2:43 pm - 11:58 pm
HHH
-
PNS
10h 15m
2 stops
$524American Airlines
Sun, May 24 - Thu, May 28
American Airlines Logo
5:22 am - 11:10 am
PNS
-
HHH
4h 48m
1 stop
American Airlines Logo
12:56 pm - 4:09 pm
HHH
-
PNS
4h 13m
1 stop
$603American Airlines
Mon, Jun 8 - Sun, Jun 14
American Airlines Logo
5:22 am - 11:10 am
PNS
-
HHH
4h 48m
1 stop
American Airlines Logo
2:43 pm - 11:58 pm
HHH
-
PNS
10h 15m
2 stops
$726American Airlines
Mon, Jun 8 - Sun, Jun 14
American Airlines Logo
6:15 am - 4:32 pm
PNS
-
HHH
9h 17m
2 stops
American Airlines Logo
2:43 pm - 11:58 pm
HHH
-
PNS
10h 15m
2 stops
$841American Airlines
Sun, May 24 - Thu, May 28
United Airlines Logo
7:05 am - 2:21 pm
PNS
-
HHH
30h 16m
3 stops
United Airlines Logo
1:45 pm - 10:01 pm
HHH
-
PNS
33h 16m
2 stops
$884United Airlines
Sun, May 24 - Thu, May 28
American Airlines Logo
6:05 am - 4:32 pm
PNS
-
HHH
9h 27m
2 stops
American Airlines Logo
12:56 pm - 11:58 pm
HHH
-
PNS
12h 02m
2 stops
$945American Airlines
Mon, Jun 8 - Sun, Jun 14

Delta flights from Pensacola to Hilton Head Island

Our best Delta deals on Pensacola to Hilton Head Island flight tickets
Delta
Oct 28
PNS9:25 amPensacola
4h 54m
1 stop
HHH3:19 pmHilton Head Island
Nov 4
HHH12:00 pmHilton Head Island
5h 32m
1 stop
PNS4:32 pmPensacola
$299
Delta
May 17
PNS9:20 amPensacola
5h 13m
1 stop
HHH3:33 pmHilton Head Island
May 22
HHH12:18 pmHilton Head Island
25h 15m
1 stop
PNS12:33 pmPensacola
$727
Delta
May 17
PNS9:20 amPensacola
5h 13m
1 stop
HHH3:33 pmHilton Head Island
May 23
HHH4:16 pmHilton Head Island
19h 23m
2 stops
PNS10:39 amPensacola
$771

American Airlines flights from Pensacola to Hilton Head Island

Our best American Airlines deals on Pensacola to Hilton Head Island flight tickets
American Airlines
Oct 28
PNS6:40 amPensacola
9h 52m
2 stops
HHH5:32 pmHilton Head Island
Nov 4
HHH2:51 pmHilton Head Island
7h 04m
1 stop
PNS8:55 pmPensacola
$496
American Airlines
Oct 28
PNS6:40 amPensacola
9h 52m
2 stops
HHH5:32 pmHilton Head Island
Nov 4
HHH2:51 pmHilton Head Island
9h 04m
2 stops
PNS10:55 pmPensacola
$502
American Airlines
May 24
PNS7:10 amPensacola
6h 03m
1 stop
HHH2:13 pmHilton Head Island
May 28
HHH2:43 pmHilton Head Island
5h 29m
1 stop
PNS7:12 pmPensacola
$519

momondo Fare Finder

 
Customize your flight search to find flights from Pensacola to Hilton Head Island that fit within your specific budget. Explore options based on user searches and filter the results based on your desired price range. Find flights that match your budget for a cost-effective journey. Over the last 7 days, momondo users made 832,500 searches. Data last updated May 14, 2026.
Use the filters below to find and compare flights from Pensacola to Hilton Head Island that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip

PensacolaHilton Head Island

PNS - HHH

PNSHHH

Pensacola

Wed 10/28

9:25 am-3:19 pm

1 stop4h 54m

Hilton Head Island

Wed 11/4

12:00 pm-4:32 pm

1 stop5h 32m

$299

PensacolaHilton Head Island

PNS - HHH

PNSHHH

Pensacola

Wed 10/28

6:40 am-5:32 pm

2 stops9h 52m

Hilton Head Island

Wed 11/4

2:51 pm-8:55 pm

1 stop7h 04m

$496

PensacolaHilton Head Island

PNS - HHH

PNSHHH

Pensacola

Wed 10/28

6:40 am-5:32 pm

2 stops9h 52m

Hilton Head Island

Wed 11/4

2:51 pm-10:55 pm

2 stops9h 04m

$502

PensacolaHilton Head Island

PNS - HHH

PNSHHH

Pensacola

Sun 5/24

7:10 am-2:13 pm

1 stop6h 03m

Hilton Head Island

Thu 5/28

2:43 pm-7:12 pm

1 stop5h 29m

$519

PensacolaHilton Head Island

PNS - HHH

PNSHHH

Pensacola

Sun 5/24

5:22 am-11:10 am

1 stop4h 48m

Hilton Head Island

Thu 5/28

2:43 pm-11:58 pm

2 stops10h 15m

$524
Quickest round-trip

PensacolaHilton Head Island

PNS - HHH

PNSHHH

Pensacola

Mon 6/8

5:22 am-11:10 am

1 stop4h 48m

Hilton Head Island

Sun 6/14

12:56 pm-4:09 pm

1 stop4h 13m

$603

PensacolaHilton Head Island

PNS - HHH

PNSHHH

Pensacola

Mon 6/8

5:22 am-11:10 am

1 stop4h 48m

Hilton Head Island

Sun 6/14

2:43 pm-11:58 pm

2 stops10h 15m

$726

PensacolaHilton Head Island

PNS - HHH

PNSHHH

Pensacola

Sun 5/24

6:15 am-4:32 pm

2 stops9h 17m

Hilton Head Island

Thu 5/28

2:43 pm-11:58 pm

2 stops10h 15m

$841

PensacolaHilton Head Island

PNS - HHH

PNSHHH

Pensacola

Sun 5/24

7:05 am-2:21 pm

3 stops30h 16m

Hilton Head Island

Thu 5/28

1:45 pm-10:01 pm

2 stops33h 16m

$884

PensacolaHilton Head Island

PNS - HHH

PNSHHH

Pensacola

Mon 6/8

6:05 am-4:32 pm

2 stops9h 27m

Hilton Head Island

Sun 6/14

12:56 pm-11:58 pm

2 stops12h 02m

$945

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 11 resultsSorted by cheapest first
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See travel insights to Hilton Head Island from

How to get the cheapest flight ticket from Pensacola to Hilton Head Island

Look no further. We've gone through all the searches for this route on momondo so you have the important information and insights to find the cheapest flight ticket for your trip

What is the cheapest airline that flies from Pensacola to Hilton Head Island?

United Airlines is the most popular carrier operating from Pensacola to Hilton Head Island

When to book flights from Pensacola to Hilton Head Island

Are you open to changing your travel dates? Check out the ideal times to fly from Pensacola to Hilton Head Island according to our flight data. Find out which month and days have the cheapest flights.
Estimated round-trip price

Cheap Pensacola to Hilton Head Island (PNS to HHH) flight deals and tips

Find info about flight duration, direct flights, and airports for your flight from Pensacola to Hilton Head Island

Fastest flight time

6h 27m

Direct flights

None
The fastest flight from Pensacola to Hilton Head Island takes 6h 27m
There are no direct flights from Pensacola to Hilton Head Island. There are no popular flight routes from Pensacola to Hilton Head Island.
Search flight deals

Frequently asked questions about flying from Pensacola to Hilton Head Island

  • How far is Pensacola to Hilton Head Island by plane?

    A flight from Pensacola to Hilton Head Island will travel around 400.8 mi. 6h 27m is a normal flight duration for this route.

  • When did momondo last update prices for flights from Pensacola Airport to Hilton Head Island Airport?

    Prices for flights from Pensacola Airport to Hilton Head Island Airport were last updated today.

  • How old do you have to be to fly from Pensacola Airport to Hilton Head Island Airport?

    The minimum age for a child to fly alone is five, but airlines offering an unaccompanied minor (UNMR) service may have their age restrictions, such as regulations concerning flight duration, timing, and layovers. It is recommended that you verify with the airline you are booking with for travel from Pensacola Airport to Hilton Head Island Airport.

  • What documentation or ID do you need to fly to Hilton Head Island Airport?

    The travel and health documents you'll need for your trip to Hilton Head Island Airport may differ based on your itinerary and personal situation. Typically, you should have several documents on hand, such as a national ID card or driver's license and a passport that is valid for six months after your intended arrival at Hilton Head Island Airport. It is always advisable to seek advice from your airline or a trusted third party, such as IATA.

Traveling to a place near Hilton Head Island?

Book flights to Hilton Head Island if you plan to visit one of these locations
Beaufort
Bluffton
Daufuskie Island

Why use momondo?

Why should I use momondo to find a flight deal from Pensacola to Hilton Head Island?

To find the flight that best suits your needs, momondo gathers a range of flights from a large pool of different airlines and agents; you can then use our insights and filters to find and book the right flight to Hilton Head Island from Pensacola.

Can I find flights from Pensacola to Hilton Head Island with flexible booking policies on momondo?

Yes. All flights to Hilton Head Island from Pensacola on momondo can be compared and filtered by various policies on offer, including flexible booking.

How can momondo help me find flights from Pensacola to Hilton Head Island?

momondo offers useful filters to help you find the right flight. Choose specific flight times, airports or even what payment method you prefer. We have numerous options to help you book your ideal flight from Pensacola to Hilton Head Island.

I’m not ready to book a flight from Pensacola to Hilton Head Island right now. Can momondo alert me if prices change?

If you are not ready to book a flight from Pensacola to Hilton Head Island now, use our insights above to find helpful tips or alternatively set up a price alert, where momondo will track prices on flights to Hilton Head Island and let you know when they change.

An easier way to manage your Hilton Head Island trip

We make it super easy to schedule, organize and travel with friends or family. Trips is free — and available to use no matter where you book.
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