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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 nonstopORD 10:352h 24mNonstopHHH 13:59Chicago - Hilton Head Island | Sat, May 3 | United AirlinesHHH 17:002h 44mNonstopORD 18:44Hilton Head Island - Chicago | Sat, May 10 | United AirlinesAED 1,812 AED 2,70433% OFF33% OFFAED 2,704 AED 1,812
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ORD 10:352h 24mNonstopHHH 13:59Chicago - Hilton Head Island | Sat, May 10 | United AirlinesHHH 17:002h 44mNonstopORD 18:44Hilton Head Island - Chicago | Sat, May 17 | United AirlinesAED 2,163 AED 2,70420% OFF20% OFFAED 2,704 AED 2,163
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ORD 07:107h 12m1 stopsHHH 15:22Chicago - Hilton Head Island | Fri, Jun 20 | Delta Air LinesHHH 17:306h 16m1 stopsORD 22:46Hilton Head Island - Chicago | Tue, Jun 24 | Delta Air LinesAED 794 AED 2,70471% OFF71% OFFAED 2,704 AED 794
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ORD 09:394h 41m1 stopsHHH 15:20Chicago - Hilton Head Island | Thu, Jun 5 | Delta Air LinesHHH 12:005h 38m1 stopsORD 16:38Hilton Head Island - Chicago | Tue, Jun 10 | Delta Air LinesAED 80170% OFFAED 2,704 AED 801
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ORD 09:394h 41m1 stopsHHH 15:20Chicago - Hilton Head Island | Tue, May 13 | Delta Air LinesHHH 12:054h 15m1 stopsORD 15:20Hilton Head Island - Chicago | Tue, May 20 | Delta Air LinesAED 80170% OFFAED 2,704 AED 801
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ORD 07:107h 8m1 stopsHHH 15:18Chicago - Hilton Head Island | Fri, Jun 13 | Delta Air LinesHHH 12:007h 2m1 stopsMDW 18:02Hilton Head Island - Chicago | Mon, Jun 16 | Delta Air LinesAED 80870% OFFAED 2,704 AED 808
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ORD 09:494h 29m1 stopsHHH 15:18Chicago - Hilton Head Island | Thu, Jun 12 | Delta Air LinesHHH 12:007h 2m1 stopsMDW 18:02Hilton Head Island - Chicago | Mon, Jun 16 | Delta Air LinesAED 80870% OFFAED 2,704 AED 808
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ORD 07:107h 8m1 stopsHHH 15:18Chicago - Hilton Head Island | Tue, Jun 10 | Delta Air LinesHHH 12:005h 59m1 stopsORD 16:59Hilton Head Island - Chicago | Tue, Jun 17 | Delta Air LinesAED 81270% OFFAED 2,704 AED 812
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ORD 09:394h 41m1 stopsHHH 15:20Chicago - Hilton Head Island | Wed, May 28 | Delta Air LinesHHH 16:005h 46m1 stopsORD 20:46Hilton Head Island - Chicago | Wed, Jun 4 | Delta Air LinesAED 81370% OFFAED 2,704 AED 813
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ORD 09:394h 41m1 stopsHHH 15:20Chicago - Hilton Head Island | Tue, Jun 3 | Delta Air LinesHHH 15:587h 23m1 stopsORD 22:21Hilton Head Island - Chicago | Tue, Jun 10 | Delta Air LinesAED 81470% OFFAED 2,704 AED 814
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ORD 07:107h 8m1 stopsHHH 15:18Chicago - Hilton Head Island | Mon, Jun 9 | Delta Air LinesHHH 12:007h 2m1 stopsMDW 18:02Hilton Head Island - Chicago | Mon, Jun 16 | Delta Air LinesAED 81570% OFFAED 2,704 AED 815
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ORD 09:394h 41m1 stopsHHH 15:20Chicago - Hilton Head Island | Wed, May 21 | Delta Air LinesHHH 12:055h 42m1 stopsORD 16:47Hilton Head Island - Chicago | Wed, May 28 | Delta Air LinesAED 94565% OFFAED 2,704 AED 945
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CHI 13:0017h 25m1 stopsHHH Invalid DateChicago - Hilton Head Island | Sun, May 4 | Normal AirlineHHH 15:006hNonstopCHI 16:00Hilton Head Island - Chicago | Tue, May 6 | Normal AirlineFind More FlightsFind More Flights
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Cheapest nonstopORD 10:352h 24mNonstopHHH 13:59Chicago - Hilton Head Island | Sat, May 10 | United AirlinesAED 950 AED 1,20521% OFF21% OFFAED 1,205 AED 950
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ORD 10:352h 24mNonstopHHH 13:59Chicago - Hilton Head Island | Sat, May 3 | United AirlinesAED 964 AED 1,20520% OFF20% OFFAED 1,205 AED 964
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ORD 20:1514h 6m1 stopsHHH 11:21Chicago - Hilton Head Island | Fri, May 30 | Delta Air LinesAED 674 AED 1,20544% OFF44% OFFAED 1,205 AED 674
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ORD 18:3715h 44m1 stopsHHH 11:21Chicago - Hilton Head Island | Fri, May 9 | American AirlinesAED 70541% OFFAED 1,205 AED 705
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ORD 06:0028h 21m1 stopsHHH 11:21Chicago - Hilton Head Island | Mon, May 19 | Delta Air LinesAED 73639% OFFAED 1,205 AED 736
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ORD 17:4516h 36m1 stopsHHH 11:21Chicago - Hilton Head Island | Sat, May 24 | Delta Air LinesAED 81233% OFFAED 1,205 AED 812
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ORD 21:0817h 21m1 stopsHHH 15:29Chicago - Hilton Head Island | Mon, May 19 | Spirit AirlinesAED 82232% OFFAED 1,205 AED 822
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ORD 07:0027h 21m1 stopsHHH 11:21Chicago - Hilton Head Island | Fri, May 9 | United AirlinesAED 82931% OFFAED 1,205 AED 829
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MDW 06:008h 20m1 stopsHHH 15:20Chicago - Hilton Head Island | Fri, May 9 | Delta Air LinesAED 84330% OFFAED 1,205 AED 843
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ORD 07:057h 13m1 stopsHHH 15:18Chicago - Hilton Head Island | Mon, Jun 16 | Delta Air LinesAED 85128% OFFAED 1,205 AED 851
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ORD 07:0027h 21m1 stopsHHH 11:21Chicago - Hilton Head Island | Sat, May 31 | Delta Air LinesAED 85428% OFFAED 1,205 AED 854
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MDW 06:008h 20m1 stopsHHH 15:20Chicago - Hilton Head Island | Sun, May 11 | Delta Air LinesAED 85728% OFFAED 1,205 AED 857
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CHI 13:0017h 25m1 stopsHHH Invalid DateChicago - Hilton Head Island | Sun, May 4 | 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 673 |
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Cheapest return ticket price | AED 1,373 |
Off-season for travel | May |
Peak season for travel | February |
Flight distance | 1,236.42 km |
Average flight time | 2 hours 24 minutes |
Popular airline | United Airlines |
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 1,881. -
How long does it take to fly from Chicago (CHI) to Hilton Head Island (HHH)?
It takes about 2 hours 24 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. -
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, May 10 at AED 950 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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