Cheap flight from Chicago to Hilton Head Island from AED 1,506
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Flights from Chicago to Hilton Head Island
Cheap flight deals from Chicago to Hilton Head Island
We've found these cheap flights for you. You can book one-way or round-trip flight tickets.
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Round-trip
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One way
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Cheapest nonstop
ORD 10:352h 26mNonstopHHH 14:01Chicago - Hilton Head Island | Sat, Jul 12 | United Airlines
HHH 17:002h 35mNonstopORD 18:35Hilton Head Island - Chicago | Sat, Jul 19 | United AirlinesAED 1,506 AED 2,76546% OFF46% OFFAED 2,765 AED 1,506 -
ORD 10:352h 26mNonstopHHH 14:01Chicago - Hilton Head Island | Sat, Jul 19 | United Airlines
HHH 17:002h 35mNonstopORD 18:35Hilton Head Island - Chicago | Sat, Jul 26 | United AirlinesAED 2,074 AED 2,76525% OFF25% OFFAED 2,765 AED 2,074
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ORD 09:504h 28m1 stopsHHH 15:18Chicago - Hilton Head Island | Tue, Jul 8 | Delta Air Lines
HHH 12:055h 15m1 stopsORD 16:20Hilton Head Island - Chicago | Tue, Jul 15 | Delta Air LinesAED 747 AED 2,76573% OFF73% OFFAED 2,765 AED 747 -
MDW 10:303h 48m1 stopsHHH 15:18Chicago - Hilton Head Island | Tue, Jul 15 | Delta Air Lines
HHH 15:585h 51m1 stopsORD 20:49Hilton Head Island - Chicago | Tue, Jul 22 | Delta Air LinesAED 79671% OFFAED 2,765 AED 796
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ORD 07:107h 8m1 stopsHHH 15:18Chicago - Hilton Head Island | Tue, Jun 10 | Delta Air Lines
HHH 15:585h 44m1 stopsORD 20:42Hilton Head Island - Chicago | Tue, Jun 17 | Delta Air LinesAED 80371% OFFAED 2,765 AED 803
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ORD 07:107h 12m1 stopsHHH 15:22Chicago - Hilton Head Island | Fri, Jun 20 | Delta Air Lines
HHH 17:306h 16m1 stopsORD 22:46Hilton Head Island - Chicago | Tue, Jun 24 | Delta Air LinesAED 80571% OFFAED 2,765 AED 805
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ORD 07:107h 8m1 stopsHHH 15:18Chicago - Hilton Head Island | Tue, Jun 17 | Delta Air Lines
HHH 12:005h 59m1 stopsORD 16:59Hilton Head Island - Chicago | Tue, Jun 24 | Delta Air LinesAED 81171% OFFAED 2,765 AED 811
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ORD 09:394h 41m1 stopsHHH 15:20Chicago - Hilton Head Island | Thu, Jun 5 | Delta Air Lines
HHH 12:005h 38m1 stopsORD 16:38Hilton Head Island - Chicago | Tue, Jun 10 | Delta Air LinesAED 81271% OFFAED 2,765 AED 812
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ORD 09:494h 29m1 stopsHHH 15:18Chicago - Hilton Head Island | Tue, Jul 1 | Delta Air Lines
HHH 15:585h 51m1 stopsORD 20:49Hilton Head Island - Chicago | Tue, Jul 8 | Delta Air LinesAED 81671% OFFAED 2,765 AED 816
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ORD 09:494h 29m1 stopsHHH 15:18Chicago - Hilton Head Island | Thu, Jun 12 | Delta Air Lines
HHH 12:007h 2m1 stopsMDW 18:02Hilton Head Island - Chicago | Mon, Jun 16 | Delta Air LinesAED 82070% OFFAED 2,765 AED 820
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ORD 07:107h 8m1 stopsHHH 15:18Chicago - Hilton Head Island | Mon, Jun 9 | Delta Air Lines
HHH 12:007h 2m1 stopsMDW 18:02Hilton Head Island - Chicago | Mon, Jun 16 | Delta Air LinesAED 82770% OFFAED 2,765 AED 827
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MDW 10:263h 52m1 stopsHHH 15:18Chicago - Hilton Head Island | Wed, Jun 18 | Delta Air Lines
HHH 15:585h 44m1 stopsORD 20:42Hilton Head Island - Chicago | Wed, Jun 25 | Delta Air LinesAED 83070% OFFAED 2,765 AED 830
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CHI 13:0017h 25m1 stopsHHH Invalid DateChicago - Hilton Head Island | Sat, Jun 7 | Normal Airline
HHH 15:006hNonstopCHI 16:00Hilton Head Island - Chicago | Mon, Jun 9 | Normal AirlineFind More FlightsFind More Flights
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Cheapest nonstop
ORD 10:352h 26mNonstopHHH 14:01Chicago - Hilton Head Island | Sat, Jun 21 | United AirlinesAED 981 AED 1,78745% OFF45% OFFAED 1,787 AED 981
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ORD 10:352h 26mNonstopHHH 14:01Chicago - Hilton Head Island | Sat, Jun 28 | United AirlinesAED 1,340 AED 1,78725% OFF25% OFFAED 1,787 AED 1,340
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ORD 21:2812h 49m1 stopsHHH 11:17Chicago - Hilton Head Island | Tue, Jul 8 | Spirit AirlinesAED 847 AED 1,78753% OFF53% OFFAED 1,787 AED 847 -
ORD 07:007h 15m1 stopsHHH 15:15Chicago - Hilton Head Island | Thu, Jul 31 | Delta Air LinesAED 86052% OFFAED 1,787 AED 860
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ORD 07:007h 15m1 stopsHHH 15:15Chicago - Hilton Head Island | Sat, Aug 2 | Delta Air LinesAED 86052% OFFAED 1,787 AED 860
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ORD 09:494h 29m1 stopsHHH 15:18Chicago - Hilton Head Island | Sun, Jun 15 | Delta Air LinesAED 86751% OFFAED 1,787 AED 867
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MDW 10:263h 52m1 stopsHHH 15:18Chicago - Hilton Head Island | Mon, Jun 9 | Delta Air LinesAED 86951% OFFAED 1,787 AED 869
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ORD 07:107h 8m1 stopsHHH 15:18Chicago - Hilton Head Island | Wed, Jun 11 | Delta Air LinesAED 87051% OFFAED 1,787 AED 870
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ORD 07:107h 8m1 stopsHHH 15:18Chicago - Hilton Head Island | Tue, Jun 17 | Delta Air LinesAED 87051% OFFAED 1,787 AED 870
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ORD 09:494h 29m1 stopsHHH 15:18Chicago - Hilton Head Island | Wed, Jun 18 | Delta Air LinesAED 87051% OFFAED 1,787 AED 870
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MDW 10:263h 52m1 stopsHHH 15:18Chicago - Hilton Head Island | Wed, Jul 2 | Delta Air LinesAED 87451% OFFAED 1,787 AED 874
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MDW 10:263h 52m1 stopsHHH 15:18Chicago - Hilton Head Island | Wed, Jun 25 | Delta Air LinesAED 87651% OFFAED 1,787 AED 876
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CHI 13:0017h 25m1 stopsHHH Invalid DateChicago - Hilton Head Island | Sat, Jun 7 | Normal AirlineFind More FlightsFind More Flights
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Crossed out prices are calculated based on the average price of the corresponding route on Trip.com.
Flight Info | Chicago to Hilton Head Island
| Cheapest one-way flight price | AED 846 |
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| Cheapest return ticket price | AED 1,394 |
| Off-season for travel | May |
| Peak season for travel | March |
| Flight distance | 1,236.42 km |
| Average flight time | 2 hours 22 minutes |
| Popular airline | Delta Air Lines |
When is the cheapest time to fly from Chicago to Hilton Head Island?
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Displayed prices are calculated based on the cheapest average weekly prices of the corresponding route on Trip.com.
Frequently Asked Questions
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When are flight tickets from Chicago (CHI) to Hilton Head Island (HHH) the cheapest?
Airlines adjust prices for flights from Chicago to Hilton Head Island based on the date and time of your booking. By analyzing data from all airlines, on Trip.com, you can find the lowest flight prices on Tuesdays, Wednesdays, and Saturdays. -
How much do flights from Chicago (CHI) to Hilton Head Island (HHH) cost?
According to Trip.com's data, the lowest price is around AED 1,907. -
How long does it take to fly from Chicago (CHI) to Hilton Head Island (HHH)?
It takes about 2 hours 22 minutes to fly from Chicago (CHI) to Hilton Head Island (HHH). -
What are the most popular airlines that fly from Chicago (CHI) to Hilton Head Island (HHH)?
Airlines with flights from Chicago (CHI) to Hilton Head Island (HHH): United Airlines and American Airlines. -
How many airports are there in Hilton Head Island (HHH)?
There are 1 airport(s) near Hilton Head Island (HHH): Hilton Head International Airport.
How to find a cheap flight from Chicago to Hilton Head Island
Wait until the last minute and flight costs are often sky-high. Plan ahead, book the right way, and your savings can soar. We have loads of saving tips to help you find a cheap flight from Chicago to Hilton Head Island. Book your flights at the right time and save more.
Being flexible with your dates to get the cheapest Chicago to Hilton Head Island ticket.
Tap "Date" on flight search bar to scan through the calender for Chicago to Hilton Head Island airfare over next 6 months in 2025. If you would like to fly in next 3 months, it seems the cheapest date is on Sat, Jun 21 at AED 981 for one-way flights.
Compare cheap Chicago to Hilton Head Island flight deals from over hundreds of airlines.
Our extensive search allows you to compare prices from over 500 airlines to choose the cheapest flight tickets from Chicago to Hilton Head Island. The cheapest airline operating is United Airlines.
Set up a Price Alert
By setting up a Price Alert for your Chicago to Hilton Head Island route, you can easily track the price of your airline tickets from without manually checking every day.
Don't miss cheap Chicago to Hilton Head Island flight deals and promo codes.
You can always get the latest deals through Trip.com Deals and Promo Codes for cheap flights. If registering a free membership, you can receive more deals for your flights.
Book early or wait unitl the last minute.
It's always better to book early. Flight tickets tend to be the cheapest when they are first released, normally about a year before the departure date. So, check online as soon as the flights you want become available. If you miss the cheapest time, you can still find lower-priced tickets as the flight date approaches.
Search for flights on the go.
To get the best flight booking experience on the go, download Trip.com and search for cheap flight tickets from Chicago to Hilton Head Island to get exclusive deals for you.
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