What are the cheapest airlines flying from Chicago to Hilton Head Island round-trip?

American Airlines, at $249, was found to be the cheapest airline from Chicago to Hilton Head Island.Alternate airlines to your destination round-trip include United Airlines and Delta. American Airlines is currently priced 43% below the average price you’ll pay for this route.

What are the cheapest airlines to fly from Chicago to Hilton Head Island one-way?

The cheapest airline one-way is United Airlines, with whom users have recently found tickets for as low as $224. However, be on the lookout for offers from Delta and American Airlines, as they are both options that can get you from Chicago to Hilton Head Island for a low price.

What is the cheapest day to fly from Chicago to Hilton Head Island?

Travelers seeking maximum savings on their Chicago to Hilton Head Island flight should consider departing on Wednesday mornings when fares are most often at their lowest. Sunday mornings flights should be avoided if possible as fares are typically the most expensive at this time.

What are the cheapest flights from Chicago to Hilton Head Island?

Looking at all options, your cheapest flight can be booked for $309. While the most popular route (Chicago O'Hare Intl - Hilton Head Island) can be booked for $279 on average our data indicates $499 when flying from Chicago to Hilton Head Island.

What is the cheapest day to fly round-trip from Chicago to Hilton Head Island?

Leaving on a Monday is a viable option for saving on travel. Heavily demanded days of the week can typically drive up the prices you see. Booking your travel for a less competitive day can save up to 35% on the overall cost on flights from Chicago to Hilton Head Island.

How far in advance should I book a flight from Chicago to Hilton Head Island?

When searching for a good deal, it’s best to be prepared for potential fluctuations in price. We recommend booking at least 14 days in advance, which can save you up to 59% on flights from Chicago to Hilton Head Island compared to booking the week you need them. Waiting 14 days out may not be for everyone, so we have options available for flights within the next two weeks, with the lowest price starting at $225. For sooner than that we have options available in the next 3 days from $358.

What is the cheapest month to fly from Chicago to Hilton Head Island?

Flights from Chicago to Hilton Head Island lean towards being more expensive in March. Prices are generally better when you fly from Chicago to Hilton Head Island in January, with the cheapest ticket starting at $210.

Most accurate provider : When it comes to deals on Chicago-Hilton Head Island flights, users find the pricing of FlightHub to be most consistent on Cheapflights vs. FlightHub Users can find the same prices on Chicago-Hilton Head Island flight deals on Cheapflights vs. FlightHub >95% of the time. Price accuracy is based on data collected from Chicago-Hilton Head Island flight searches over the past month and is updated monthly.

Most trusted provider : When it comes to deals on Chicago-Hilton Head Island flights, Cheapflights users trust FlightHub the most. FlightHub has received a user feedback score of 3 out of 3 stars (3 being the best), meaning they have been trusted the most by Cheapflights users looking for Chicago-Hilton Head Island flight deals. Provider user feedback score is based on Cheapflights searches over the past month and is updated monthly.

What airport do you fly into for flights to Hilton Head Island from Chicago?

Hilton Head Island (HHH) is the airport you will fly into if you book a flight from Chicago to Hilton Head Island. You should not have trouble finding flights to Hilton Head from Chicago; the airport handles an average of 0 inbound flights from Chicago per day. You should also have plenty of airline options to choose from since 2 airlines have flights to the Hilton Head Island airport from Chicago. It is only a 3.3 mi journey from Hilton Head (HHH) to Hilton Head Island’s city center.

Can I find deals for flights from Chicago to Hilton Head Island that include hotel bookings?

Yes. In addition to deals on Chicago to Hilton Head Island flights, Cheapflights offers vacation packages that include both flights and hotel.

How can I find direct flights from Chicago to Hilton Head Island?

After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Chicago to Hilton Head Island.

Can I find deals for business class flights from Chicago to Hilton Head Island?

Yes. Cheapflights offers flight deals from Chicago to Hilton Head Island by cabin class. In addition to browsing deals, you can also filter by cabin class on the search results page after making a search.

$224+ Flights from Chicago to Hilton Head Island

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Find cheap flights from Chicago to Hilton Head Island with Cheapflights

1. Tell us where you want to go

Enter your travel information like dates, passengers, trip type (one-way or round trip), and preferred cabin class then click “Find deals”

2. Select your favorite providers

We find the providers serving your travel needs. Choose up to four travel providers to compare side-by-side for flights, hotels, or car rentals.

3. Compare prices and book

Review each provider’s pricing and select the best option for you! Book through your favorite provider’s website for a seamless experience.

The best prices from Chicago to Hilton Head Island are usually found in January or April, booked 71 days in advance, depart on a Tuesday or Wednesday and return on a Friday

Cheap flight deals from Chicago to Hilton Head Island

Most accurate provider	FlightHub 3 stars
Most trusted provider	FlightHub 3 stars
Round-trip from	$249 (American Airlines)
One-way from	$224 (United Airlines)
Popular in	March
Cheapest in	January
Average price	$274
Good round-trip deal	$457 or less

Provider with most accurate pricing for Chicago (CHI)-Hilton Head Island flight deals.

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Provider most trusted by Cheapflights users for Chicago (CHI)-Hilton Head Island flights.

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From Chicago (CHI) to Hilton Head Island

Search Deals

One-way flight from Chicago (CHI) to Hilton Head Island

Search Deals

Highest demand for flights based on searches. 9% potential increase in price ($46 potential increase over avg. RT price).

Search Deals

Cheapest flight prices on average. 3% potential price decrease ($15 potential savings vs. average RT price).

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Average for round-trip flights in January 2025

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Price to beat on a round-trip flight from Chicago (CHI) to Hilton Head Island.

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Find flight deals from Chicago to Hilton Head Island

Cheapest flights from Chicago to Hilton Head Island
Explore the most affordable flight options available from Chicago to Hilton Head Island. Find the lowest fares from popular airlines and budget airlines, with prices last updated on January 21, 2025.

Tue 2/48:12 amORD - HHH

1 stop5h 06mAmerican Airlines

Sat 2/86:05 pmHHH - ORD

1 stop7h 04mAmerican Airlines

Deal found 1/21

$249

Sat 5/310:35 amORD - HHH

Nonstop2h 24mUnited Airlines

Sat 5/105:00 pmHHH - ORD

Nonstop2h 44mUnited Airlines

Deal found 1/21

$280

Sun 9/147:00 amORD - HHH

2 stops8h 42mDelta

Wed 9/241:15 pmHHH - ORD

2 stops10h 31mDelta

Deal found 1/21

$459

Best flights from Chicago to Hilton Head Island
Discover carefully curated flight deals from Chicago to Hilton Head Island that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated January 21, 2025.

Tue 2/48:12 amORD - HHH

1 stop5h 06mAmerican Airlines

Sat 2/86:05 pmHHH - ORD

1 stop7h 04mAmerican Airlines

Deal found 1/21

$249

Sat 5/310:35 amORD - HHH

Nonstop2h 24mUnited Airlines

Sat 5/105:00 pmHHH - ORD

Nonstop2h 44mUnited Airlines

Deal found 1/21

$280

Thu 6/197:00 amORD - HHH

2 stops8h 42mDelta

Wed 6/255:30 pmHHH - ORD

1 stop6h 16mDelta

Deal found 1/21

$484

Last-minute flights from Chicago to Hilton Head Island
Discover last-minute flight deals from Chicago to Hilton Head Island. Data last updated January 21, 2025 and is based on user searches.

Sun 1/2612:25 pmORD - HHH

1 stop4h 10mAmerican Airlines

Sun 2/26:05 pmHHH - ORD

1 stop7h 04mAmerican Airlines

Deal found 1/21

$469

Tue 2/48:12 amORD - HHH

1 stop5h 06mAmerican Airlines

Sat 2/86:05 pmHHH - ORD

1 stop7h 04mAmerican Airlines

Deal found 1/21

$249

One-way flights from Chicago to Hilton Head Island
Search for one-way flight options from Chicago to Hilton Head Island. Find affordable one-way fares based on user searches. Data last updated January 21, 2025.

Sat 5/1710:35 amORD - HHH

Nonstop2h 24mUnited Airlines

Deal found 1/21

$224

Sat 4/191:16 pmORD - HHH

1 stop26h 25mDelta

Deal found 1/20

$227

Wed 4/1612:07 pmORD - HHH

1 stop4h 29mAmerican Airlines

Deal found 1/20

$232

Find flights from Chicago to Hilton Head Island within your budget

Fly from

Fly to

Route

Depart

Return

Price

ChicagoHilton Head Island

ORD - HHH

ORDHHH

Chicago O'Hare Intl

Tue 2/4

8:12 am-2:18 pm

1 stop5h 06m

Hilton Head Island

Sat 2/8

6:05 pm-12:09 am

1 stop7h 04m

$249

ChicagoHilton Head Island

ORD - HHH

ORDHHH

Chicago O'Hare Intl

Sat 5/3

10:35 am-1:59 pm

Nonstop2h 24m

Hilton Head Island

Sat 5/10

5:00 pm-6:44 pm

Nonstop2h 44m

$280

ChicagoHilton Head Island

ORD - HHH

ORDHHH

Chicago O'Hare Intl

Thu 6/19

7:00 am-4:42 pm

2 stops8h 42m

Hilton Head Island

Wed 6/25

5:30 pm-10:46 pm

1 stop6h 16m

$484

ChicagoHilton Head Island

ORD - HHH

ORDHHH

Chicago O'Hare Intl

Sat 5/17

10:35 am-1:59 pm

Nonstop2h 24m

$224

ChicagoHilton Head Island

ORD - HHH

ORDHHH

Chicago O'Hare Intl

Sat 4/19

1:16 pm-4:41 pm

1 stop26h 25m

$227

ChicagoHilton Head Island

ORD - HHH

ORDHHH

Chicago O'Hare Intl

Wed 4/16

12:07 pm-5:36 pm

1 stop4h 29m

$232

Flights are sorted by cheapest round-trip flights first.

Deals found on 1/21

Compare providers for flights from Chicago to Hilton Head Island

Use the table below to compare price accuracy, trust ratings, and cancellation policies for each provider offering flight deals from Chicago to Hilton Head Island in January.

Provider	Price Accuracy	Trust Score*
Expedia	Price Accuracy1 star	Trust Score*3 stars
FlightHub	Price Accuracy3 stars	Trust Score*3 stars
eDreams	Price Accuracy3 stars	Trust Score*3 stars

*The Trust Score is based on feedback from users after their booking experience. It measures overall satisfaction, helping us identify issues like hidden fees, problems during the ticketing process, and the quality of customer service. This score is our best indicator of the provider's quality and reliability.

Most accurate provider: When it comes to deals on Chicago-Hilton Head Island flights, users find the pricing of FlightHub to be most consistent on Cheapflights vs. FlightHub Users can find the same prices on Chicago-Hilton Head Island flight deals on Cheapflights vs. FlightHub >95% of the time. Price accuracy is based on data collected from Chicago-Hilton Head Island flight searches over the past month and is updated monthly.
Most trusted provider: When it comes to deals on Chicago-Hilton Head Island flights, Cheapflights users trust FlightHub the most. FlightHub has received a user feedback score of 3 out of 3 stars (3 being the best), meaning they have been trusted the most by Cheapflights users looking for Chicago-Hilton Head Island flight deals. Provider user feedback score is based on Cheapflights searches over the past month and is updated monthly.

Best time to book a flight from Chicago to Hilton Head Island

Have a flexible travel schedule? Discover the best time to fly to Hilton Head Island from Chicago with our price prediction graph.

Estimated round-trip price

Rates are based on past data. Find the cheapest month and day to book your flight based on your travel requirements, then search for cheap deals.

Travel insights for flights from Chicago to Hilton Head Island

Get recent, data-driven insights about flights from Chicago to Hilton Head Island including ideal travel times, pricing trends, and more.

How far ahead should I book a flight from Chicago to Hilton Head Island?

Booking 71 days in advance of your planned departure date is, on average, the best time to get cheap flights from Chicago to Hilton Head Island. The general trend is that the closer you book to the departure date, the more expensive your flight will be.

What is the cheapest month to book a flight from Chicago to Hilton Head Island?

Currently, January is the cheapest month in which you can book a flight from Chicago to Hilton Head Island (average of $275). Flying from Chicago to Hilton Head Island in March is currently the most expensive (average of $526). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

What is the cheapest time of day to fly from CHI to HHH?

When flying from Chicago to Hilton Head Island, the time of day you decide to fly out makes little to no difference towards the overall price you’ll pay on tickets.

Rainfall in Hilton Head Island by month

In terms of precipitation, rainfall in Hilton Head Island ranges from 2.4 - 7.8 inches per month. August is typically the wettest month, when rainfall can reach 7.8 in. November is typically the driest time to visit Hilton Head Island when rainfall is around 2.4 in.

Temperature in Hilton Head Island by month

If weather is an important factor for your trip to Hilton Head Island, use this chart to help with planning. For those seeking warmer temperatures, July is the ideal time of year to visit, when temperatures reach an average of 80.6 F. Travelers looking to avoid the cold should look outside of January, when temperatures are typically at their lowest (around 50.0 F).

Reviews of airlines servicing Hilton Head Island

Delta

8.0

Very good

8,521 reviews

Reviews

1 / 10

Delta has consistently been the best U.S. airline for my travels and this flight was no exception

Delta

8.0

Very good

8,521 reviews

Delta

8.0

Very good

8,521 reviews

Reviews

1 / 10

Delta has consistently been the best U.S. airline for my travels and this flight was no exception

United Airlines

7.4

Good

8,985 reviews

Delta

8.0

Very good

8,521 reviews

Reviews

1 / 10

Delta has consistently been the best U.S. airline for my travels and this flight was no exception

American Airlines

7.2

Good

10,000 reviews

Delta

8.0

Very good

8,521 reviews

Reviews

1 / 10

Delta has consistently been the best U.S. airline for my travels and this flight was no exception

Related info for your journey

What airport do you fly into for flights to Hilton Head Island from Chicago?
Hilton Head Island (HHH) is the airport you will fly into if you book a flight from Chicago to Hilton Head Island. You should not have trouble finding flights to Hilton Head from Chicago; the airport handles an average of 0 inbound flights from Chicago per day. You should also have plenty of airline options to choose from since 2 airlines have flights to the Hilton Head Island airport from Chicago. It is only a 3.3 mi journey from Hilton Head (HHH) to Hilton Head Island’s city center.
What are the cheapest airlines flying from Chicago to Hilton Head Island round-trip?
American Airlines, at $249, was found to be the cheapest airline from Chicago to Hilton Head Island.Alternate airlines to your destination round-trip include United Airlines and Delta. American Airlines is currently priced 43% below the average price you’ll pay for this route.
What are the cheapest airlines to fly from Chicago to Hilton Head Island one-way?
The cheapest airline one-way is United Airlines, with whom users have recently found tickets for as low as $224. However, be on the lookout for offers from Delta and American Airlines, as they are both options that can get you from Chicago to Hilton Head Island for a low price.
What are the cheapest flights from Chicago to Hilton Head Island?
Looking at all options, your cheapest flight can be booked for $309. While the most popular route (Chicago O'Hare Intl - Hilton Head Island) can be booked for $279 on average our data indicates $499 when flying from Chicago to Hilton Head Island.
Can I find deals for flights from Chicago to Hilton Head Island that include hotel bookings?
Yes. In addition to deals on Chicago to Hilton Head Island flights, Cheapflights offers vacation packages that include both flights and hotel.
How can I find direct flights from Chicago to Hilton Head Island?
After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Chicago to Hilton Head Island.
Can I find deals for business class flights from Chicago to Hilton Head Island?
Yes. Cheapflights offers flight deals from Chicago to Hilton Head Island by cabin class. In addition to browsing deals, you can also filter by cabin class on the search results page after making a search.
What is the cheapest month to book a flight from Chicago to Hilton Head Island?
Currently, January is the cheapest month in which you can book a flight from Chicago to Hilton Head Island (average of $275). Flying from Chicago to Hilton Head Island in March is currently the most expensive (average of $526). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

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Top 2 airlines flying from Chicago to Hilton Head Island

Airline	Cheapest	Average	Flexibility	On-time
United Airlines	Cheapest$149	Average$500	FlexibilityNo cancel fee	On-time69%
American Airlines	Cheapest$223	Average$405	FlexibilityNo cancel fee	On-time71%

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$224+ Cheap flights from Chicago (CHI) to Hilton Head Island (HHH)

This is the cheapest one-way flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 5/17. Fares are subject to change and may not be available on all flights or dates of travel.

Find cheap flights from Chicago to Hilton Head Island with Cheapflights

1. Tell us where you want to go

2. Select your favorite providers

3. Compare prices and book

The best prices from Chicago to Hilton Head Island are usually found in January or April, booked 71 days in advance, depart on a Tuesday or Wednesday and return on a Friday

Cheap flight deals from Chicago to Hilton Head Island

Most accurate provider

Most trusted provider

Round-trip from

One-way from

Popular in

Cheapest in

Average price

Good round-trip deal

Find flight deals from Chicago to Hilton Head Island

Cheapest flights from Chicago to Hilton Head IslandExplore the most affordable flight options available from Chicago to Hilton Head Island. Find the lowest fares from popular airlines and budget airlines, with prices last updated on January 21, 2025.

Explore the most affordable flight options available from Chicago to Hilton Head Island. Find the lowest fares from popular airlines and budget airlines, with prices last updated on January 21, 2025.

Find flights from Chicago to Hilton Head Island within your budget

Compare providers for flights from Chicago to Hilton Head Island

Provider information is updated monthly. Please note that these providers often have deals for this flight, but the availability may vary on a day-by-day basis on Cheapflights.

Use the table below to compare price accuracy, trust ratings, and cancellation policies for each provider offering flight deals from Chicago to Hilton Head Island in January.

Best time to book a flight from Chicago to Hilton Head Island

Have a flexible travel schedule? Discover the best time to fly to Hilton Head Island from Chicago with our price prediction graph.

Travel insights for flights from Chicago to Hilton Head Island

Get recent, data-driven insights about flights from Chicago to Hilton Head Island including ideal travel times, pricing trends, and more.

How far ahead should I book a flight from Chicago to Hilton Head Island?

Use this chart to determine the optimal time to book a round-trip flight from Chicago to Hilton Head Island. Price data was last updated on January 17, 2025.

What is the cheapest month to book a flight from Chicago to Hilton Head Island?

What is the cheapest time of day to fly from CHI to HHH?

Find hourly flight availability from Chicago to Hilton Head Island. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated January 21, 2025.

Rainfall in Hilton Head Island by month

Plan your trip to Hilton Head Island by taking into account the average rainfall totals by month.

Temperature in Hilton Head Island by month

Plan your trip to Hilton Head Island by taking into account the average temperature totals by month.

Reviews of airlines servicing Hilton Head Island

Related info for your journey

Find useful and relevant information for your journey from Chicago to Hilton Head Island. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.

What airport do you fly into for flights to Hilton Head Island from Chicago?

What are the cheapest airlines flying from Chicago to Hilton Head Island round-trip?

What are the cheapest airlines to fly from Chicago to Hilton Head Island one-way?

What are the cheapest flights from Chicago to Hilton Head Island?

Can I find deals for flights from Chicago to Hilton Head Island that include hotel bookings?

How can I find direct flights from Chicago to Hilton Head Island?

Can I find deals for business class flights from Chicago to Hilton Head Island?

What is the cheapest month to book a flight from Chicago to Hilton Head Island?

Traveling to a place near Chicago?

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Alternative routes for Chicago to Hilton Head Island

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Top 2 airlines flying from Chicago to Hilton Head Island

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Cheapest flights from Chicago to Hilton Head Island
Explore the most affordable flight options available from Chicago to Hilton Head Island. Find the lowest fares from popular airlines and budget airlines, with prices last updated on January 21, 2025.