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Cheap flights from Chicago to Hilton Head Island (CHI - HHH)

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The best prices from Chicago to Hilton Head Island are usually found in January or August, booked 25 days in advance, depart on a Monday or Thursday and return on a Wednesday

How to find the cheapest flight from
Chicago (CHI) to Hilton Head Island (HHH)

CHI - HHH
Price
$304 - $472
HHH
Temperature
64.4 - 93.2 °F
HHH
Rainfall
2.3 - 6.7 inches

Popular in

December

High demand for flights, 23% potential price rise

Cheapest in

January

Best time to find cheap flights, 16% potential price drop

Round-trip from

$304

From Chicago to Hilton Head Island

One-way from

$148

One-way flight from Chicago to Hilton Head Island

Flight route prices based on searches on Cheapflights within the last 3 days, monthly prices based on aggregated historical data.
What is the cheapest day to fly round-trip from Chicago to Hilton Head Island?

Flying to your destination on a Saturday can be more expensive, but this shouldn’t discourage you from finding affordable options to get to Hilton Head Island. Check prices with Cheapflights to find a great deal for your trip.

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

Travelers have found it’s best to book a flight 47 days in advance to save up to 44% compared to booking the same week of travel. As your travel date approaches, the cost of this flight route may potentially increase. While opting to book 47 days out may not be an option for all, there are still additional ways to secure a deal in the near future. You might find a flight from Chicago to Hilton Head Island 1-2 weeks in advance for as low as $281, or $366 for flights within the next 24 hours.

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

The best pricing can be found in the month of August. Prices to Hilton Head Island from Chicago average $250. You can even find prices in August for less than $250, as users have found deals to Hilton Head Island from as low as $162. The month of April appears to be one of the more expensive times to travel to Hilton Head Island from Chicago. Flying in the targeted month can save you up to 27%.

When is the cheapest time to fly from Chicago to Hilton Head Island (CHI - HHH)?

Unlike in the evening, when flights are generally more expensive, you can save up to 8% on flights from Chicago to Hilton Head Island by exploring options for tickets in the afternoon.

Cheap flights from Chicago to Hilton Head Island in December, January 2021

The best prices found for CHI to HHH flights for December, January
13 Jan - 16 Jan
$203pp
ORD
Chicago O'Hare Intl
American Airlines
 
1 STOP
HHH
Hilton Head Island
HHH
Hilton Head Island
American Airlines
   
2 STOPS
ORD
Chicago O'Hare Intl
13 Jan - 16 Jan
$204pp
ORD
Chicago O'Hare Intl
American Airlines
   
2 STOPS
HHH
Hilton Head Island
HHH
Hilton Head Island
American Airlines
   
2 STOPS
ORD
Chicago O'Hare Intl
27 Dec - 7 Jan
$223pp
ORD
Chicago O'Hare Intl
American Airlines
 
1 STOP
HHH
Hilton Head Island
HHH
Hilton Head Island
American Airlines
   
2 STOPS
ORD
Chicago O'Hare Intl

Chicago to Hilton Head Island 2021 flight deals

Cheap flights to Hilton Head Island from Chicago found for this year
27 Dec - 7 Jan
$223pp
ORD
Chicago O'Hare Intl
American Airlines
 
1 STOP
HHH
Hilton Head Island
HHH
Hilton Head Island
American Airlines
   
2 STOPS
ORD
Chicago O'Hare Intl
28 Dec - 28 May
$249pp
ORD
Chicago O'Hare Intl
American Airlines
 
1 STOP
HHH
Hilton Head Island
HHH
Hilton Head Island
American Airlines
 
1 STOP
ORD
Chicago O'Hare Intl
29 Dec - 6 Jan
$255pp
ORD
Chicago O'Hare Intl
American Airlines
 
1 STOP
HHH
Hilton Head Island
HHH
Hilton Head Island
American Airlines
 
1 STOP
ORD
Chicago O'Hare Intl

Last minute flights from Chicago to Hilton Head Island

Late deals on round-trip flights to Hilton Head Island from Chicago, departing today and this week
7 Dec - 14 Dec
$319pp
ORD
Chicago O'Hare Intl
American Airlines
 
1 STOP
HHH
Hilton Head Island
HHH
Hilton Head Island
American Airlines
 
1 STOP
ORD
Chicago O'Hare Intl

One-way flights to Hilton Head Island from Chicago

The cheapest one-way flights from Chicago to Hilton Head Island
7:19 am - 12:47 pm
American Airlines
1 Stop
4h 28m
ORD - HHH
American Airlines
12:30 am - 5:30 am
American Airlines
1 Stop
4h 00m
ORD - HHH
American Airlines
1:05 am - 7:14 am
Delta
1 Stop
5h 09m
ORD - HHH
Delta
$347
Delta

Related info for your journey

Useful info, stats and facts about Chicago to Hilton Head Island flights.

Flight FAQs

From Chicago to Hilton Head Island

Are flight prices decreasing from Chicago to Hilton Head Island due to COVID-19 (coronavirus)?

At this time, Cheapflights has noticed price decreases for many domestic flights due to COVID-19. Travel is not necessarily recommended at this time, and flights may be prone to cancellation: please check with local authorities in both Chicago and Hilton Head Island for travel alerts, and be sure to review the airline's cancellation policy and travel advisories before booking. For more information, please view our post on what to know about COVID-19 (coronavirus) and travel.

What safety measures are being taken by airlines flying from Chicago to Hilton Head Island to control the spread of COVID-19?

Airlines globally have implemented additional safety measures to accommodate you. Delta is one of them. Airline carriers are regularly disinfecting and sanitizing their aircraft. Masks are provided and are mandatory while on board. Pre-flight testing for symptoms and antibodies, alongside socially distanced seating (for a limited time) will work towards keeping travelers safer while flying from Chicago to Hilton Head Island. Policies will vary by airline.

Which airlines flying from Chicago to Hilton Head Island have flexible cancellations due to COVID-19?

Some of the carriers operating flights from Chicago to Hilton Head Island that may be offering flexible cancellation policies are United Airlines, American Airlines, and Delta. Our site will let you filter for all airlines offering greater flexibility due to COVID-19.

Can I find flights from Chicago to Hilton Head Island for under $300 on Cheapflights?

Yes, there are multiple flights from Chicago to Hilton Head Island for under $300. The cheapest flight booked recently is on American Airlines for just $203, but on average you can expect to pay $265.

Are there nonstop flights from Chicago to Hilton Head Island for under $200 on Cheapflights?

There are no nonstop flights from Chicago to Hilton Head Island, but Cheapflights can provide you with all the information you need to find the fastest route with the fewest stops.

Are there last-minute flights available from Chicago to Hilton Head Island for under $400?

There are currently 1+ open flights from Chicago to Hilton Head Island within the next 7 days for less than $400.

Is Chicago weather warmer or cooler than Hilton Head Island?

Expect the weather to be around 93 °F on average in July. As the temperature peaks, try to get your plans done early, as flight price and availability will have an impact on your travels. The climate in Hilton Head Island is generally hotter than in Chicago.

How long is the flight from Chicago to Hilton Head Island?

For as low as $203, American Airlines can have you in Hilton Head Island from Chicago in 3h 36m. When browsing for deals, the options you’ll see will be for both nonstop flights and flights with stops.

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

Our cheapest airline available from Chicago to Hilton Head Island is American Airlines. Our recent data shows that you can find tickets from as low as $203 on this airline. An additional option worth looking into is Delta, starting at $206. These flights start at 43% lower than the current average price 3 months from now.

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

To fly one-way, consider booking your trip with American Airlines, which is currently one of the cheapest options available, starting at $148. American Airlines is not the only option available. At the moment, Delta is another option, for $347.

Alternative routes for Chicago to Hilton Head Island

Destination information for Hilton Head Island

Things to know before you go. Useful info for your trip from Chicago to Hilton Head Island
Average temperature for December in Hilton Head Island
64.4 °F
Avg rainfall for December in Hilton Head Island
2.8 ″

Airports servicing Chicago

Chicago Midway (MDW)
Rockford (RFD)

Airports servicing Hilton Head Island

Top 3 airlines from Chicago to Hilton Head Island

The chart below displays the airlines Cheapflights users traveling from Chicago to Hilton Head Island choose most often. Cheapest and average prices are based on aggregated data from the past 12 months.

Airline Cheapest Average Flexibility On-time COVID-19 safety
American Airlines
$194 $372 No cancel fee 71%
Delta
$192 $377 No cancel fee N/A
United Airlines
$227 $396 No cancel fee 69%
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