$264 Find Cheap Flights from Hilton Head Island to Florida - Compare and Save

1 adult
1 adult, Economy, 0 bags

Save 26% or more on flights. Compare deals from all over the web.

Never overpay with our price tracking tools.

Filter searches by price, airline and more to find your best flights.

Flight Deals
Booking Insights
Flight Deals

Cheap Flights from Hilton Head Island to Florida

Cheapest round-trip prices found by our users on KAYAK in the last 5 days
Sort by: Cheapest
Orlando
3h 41m2 stops
from $427per person
Tampa
4h 46m2 stops
from $427per person
Fort Myers
Fort Myers
4h 03m2 stops
from $447per person
Miami
4h 13m2 stops
from $457per person
Jacksonville
Jacksonville
19h 59m2 stops
from $1,132per person
Explore the map
Booking Insights

Price, demand and travel trends for Hilton Head Island to Florida flights

Use KAYAK data on prices, travel dates, airlines and seasonal trends to compare options and book flights with more confidence.

What are the cheapest fares from Hilton Head Island to Florida recently?

Here are the cheapest round-trip fares from Hilton Head Island to Florida on KAYAK in the last week:

• Tampa (TPA) from $427
• Orlando (MCO) from $427
• Fort Myers SW Florida Intl (RSW) from $447
• Miami (MIA) from $457
• Jacksonville (JAX) from $1,132

How do fares into airports in Florida compare?

According to KAYAK data from the last 12 months, the cheapest airports to fly into Florida from Hilton Head Island are:

• Fort Myers SW Florida Intl (RSW) (avg. price $396)
• Tampa (TPA) (avg. price $456)
• Miami (MIA) (avg. price $476)

What's the cheapest month to fly from Hilton Head Island to Florida?

September is typically the cheapest month to fly from Hilton Head Island to Florida, with round-trip fares averaging $322. June and October are usually the most expensive, averaging $784 and $722, respectively.

How do fares from Hilton Head Island to Florida vary by day of the week?

On average, Wednesday is the cheapest day to fly from Hilton Head Island to Florida and Sunday is the most expensive. Looking at the past 12 months of KAYAK data, it's 123% more expensive to fly on a Sunday compared to Wednesday.

What's the best time of day to fly from Hilton Head Island to Florida?

It's cheapest to fly to Florida in the evening with average prices of $366. The morning is the most expensive time to fly, with average prices of $556.

Key details for Hilton Head Island to Florida flights

Low season

August

Cheapest flight

$264
Beat the crowds with an average 56% drop in travelers.
The most popular month to fly with an average 67% increase in travelers.
One-way flight from Hilton Head Island to Orlando Airport

Your Hilton Head Island to Florida flight questions, answered

Find helpful answers about this route, including flight times, airports, airlines and booking tips.

  • Is now a good time to book a flight from Hilton Head Island to Florida?

    Fares from Hilton Head Island to Florida are around their usual level right now. A round-trip under $350 is considered a good deal, so it's worth keeping an eye out, or setting a Price Alert to catch fare changes.

  • How much should I budget for a flight from Hilton Head Island to Florida?

    Over the past 12 months, round-trip fares from Hilton Head Island to Florida have typically cost between $350 and $579.

  • What are the main airports serving Florida?

    There are 30 airports in Florida. 30% of KAYAK users choose Fort Myers SW Florida Intl (RSW) as their arrival airport, while 20% choose Orlando (MCO).

  • Which cabin classes are available from Hilton Head Island to Florida?

    On flights from Hilton Head Island to Florida you can only book Economy Class.

  • What are some popular landmarks around Florida?

    Florida is home to many popular sights. KAYAK travelers' favorites include:

    • Universal Orlando Resort
    • Duval Street
    • Raymond James Stadium
    • Las Olas Beach

Your guide to booking Hilton Head Island to Florida flights

Get tips on when to book, when to fly and what to know before your trip.
  • Flexible with your dates? Fly in September to save some money. It's typically the cheapest month on this route, while flights in June will cost you the most.
  • Fly out on a Wednesday to get the cheapest fares. Avoid Sunday flights, which are about 123% more expensive.
  • If you're watching your budget, fly into Fort Myers SW Florida Intl (RSW) which has the lowest average airfare in the region. Just remember to budget for any onward travel by bus, car or domestic flight.
  • Start your trip in Orlando, the most popular destination in Florida. From there, it's easy to continue on to other popular spots such as Miami, Key West and Fort Lauderdale.

Reviews of the top airline flying from Hilton Head Island to Florida

 
Need help choosing which airline to fly with from Hilton Head Island to Florida? KAYAK airline reviews give an overall score for each airline based on loads of factors, including comfort, boarding, in-flight entertainment and more, to make your decision easier. See airline scores according to verified KAYAK customer reviews.
7.0
American AirlinesOverall score based on 12231 reviews
6.4Food
7.9Crew
7.4Boarding
7.1Comfort
6.8Entertainment
Airline reviews

Three aircraft in succession experienced maintenance issues, resulting in a six-hour delay. The original aircraft required replacement, and the substitute aircraft arrived more than two hours late. Passengers boarded that aircraft, only to be told later to deplane due to maintenance concerns. We then boarded a different aircraft that had arrived at the gate, only to be instructed to deplane once again because it, too, experienced maintenance issues. After hours of delays and two separate boarding and deplaning events, passengers were directed to a third aircraft departing from a different terminal and had to rush across the airport to make that flight. That was the only aircraft that ultimately departed without incident. Of course, passenger safety must come first, and I am grateful these issues were identified before takeoff. However, when three aircraft in succession require maintenance attention and passengers are repeatedly boarded before those issues are discovered, it raises legitimate concerns about American Airlines' preventive maintenance procedures and aircraft readiness checks. One aircraft with an unexpected issue can happen. Three aircraft in a row, combined with multiple boarding and deplaning events, suggests a pattern that warrants review. American Airlines needs to take a hard look at both its maintenance practices and its decision-making process for boarding passengers before determining that an aircraft is ready for service.

2.0 MediocreJoseph, Nov 2026
Read more American Airlines reviews

Three aircraft in succession experienced maintenance issues, resulting in a six-hour delay. The original aircraft required replacement, and the substitute aircraft arrived more than two hours late. Passengers boarded that aircraft, only to be told later to deplane due to maintenance concerns. We then boarded a different aircraft that had arrived at the gate, only to be instructed to deplane once again because it, too, experienced maintenance issues. After hours of delays and two separate boarding and deplaning events, passengers were directed to a third aircraft departing from a different terminal and had to rush across the airport to make that flight. That was the only aircraft that ultimately departed without incident. Of course, passenger safety must come first, and I am grateful these issues were identified before takeoff. However, when three aircraft in succession require maintenance attention and passengers are repeatedly boarded before those issues are discovered, it raises legitimate concerns about American Airlines' preventive maintenance procedures and aircraft readiness checks. One aircraft with an unexpected issue can happen. Three aircraft in a row, combined with multiple boarding and deplaning events, suggests a pattern that warrants review. American Airlines needs to take a hard look at both its maintenance practices and its decision-making process for boarding passengers before determining that an aircraft is ready for service.

Delay for 1 hour due to maintenance issue and late boarding

Flight attendant super rude demanding I remove my carry on baggage from overhead and place under seat. I stated I am an ADA passenger and need the leg room as the seats are very tight. That’s why I boarded early for the extra time to get situated. She said, we need the space. I replied “How can that be as only a few passengers have boarded so far? I am executive platinum status so I understand the rules and you are discriminating against ADA federal law. Please stop”. Her answer… then you should find another flight! Not ok. Addressed with senior flight attendant. So unprofessional and discriminatory.

Good flight, excellent personnel; poor comfort, small seats, big cost.

What an amazing plane! We flew a 787 to Miami. Although the Internet was not functioning, it was a wonderful flight.

It was freezing in the cabin. That's on me to be better prepared in the future.

I paid extra for a seat up front and at last minute was moved to the 2nd to last row - which I could have had for free. No reason and no refund. Really great customer service American

One of our group members was struggling to walk. In Charlotte we asked for a wheelchair and she was accompanied by Desmond. I was impressed by his patience and attention. In Boston she received the same service. I didn’t get the name of the helper but she went above and beyond in assisting us. A great AA service

Would have thought that they would gas up plane before everyone got on board

The flights were terribly delayed and then cancelled which forced us booking another night at the hotel. Very poor management from American Airlines

More options for your flight from Hilton Head Island to Florida

Complete your trip to Florida with a hotel stay or car rental