$259+ 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 9/21. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — HHH
Sep 25 — Oct 21
Round-trip
1 adult, Economy
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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.Cheap flight deals from Chicago to Hilton Head Island
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Best
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One-way
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 August 26, 2026.
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 August 26, 2026.
This United Airlines deal was found by Cheapflights users on 8/23. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/1710:35 am -
Nonstop2h 35m
Sat 10/242:51 pm -
Nonstop3h 14m
Deal found 8/23![United Airlines logo]()
$279
This Delta deal was found by Cheapflights users on 8/24. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/38:05 am -
1 stop6h 22m
Tue 10/64:13 pm -
1 stop7h 04m
Deal found 8/24![Delta logo]()
$299
This Delta deal was found by Cheapflights users on 8/24. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/306:00 am -
2 stops8h 27m
Wed 10/74:13 pm -
1 stop7h 04m
Deal found 8/24![Delta logo]()
$304
This American Airlines deal was found by Cheapflights users on 8/23. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 9/79:53 am -
Nonstop2h 24m
Mon 9/212:15 pm -
1 stop6h 23m
Deal found 8/23![American Airlines logo]()
$309
This American Airlines deal was found by Cheapflights users on 8/25. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/255:20 am -
1 stop5h 55m
Mon 9/285:15 pm -
1 stop6h 16m
Deal found 8/25![American Airlines logo]()
$319
This Delta deal was found by Cheapflights users on 8/24. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/96:00 am -
2 stops8h 27m
Mon 9/144:17 pm -
1 stop7h 01m
Deal found 8/24![Delta logo]()
$324
This United Airlines deal was found by Cheapflights users on 8/25. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/1710:25 am -
Nonstop2h 38m
Tue 9/222:48 pm -
Nonstop3h 17m
Deal found 8/25![United Airlines logo]()
$334
This Delta deal was found by Cheapflights users on 8/25. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/108:05 am -
1 stop6h 25m
Wed 10/144:13 pm -
1 stop7h 04m
Deal found 8/25![Delta logo]()
$339
This Delta deal was found by Cheapflights users on 8/25. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/66:00 am -
2 stops8h 30m
Wed 10/1412:23 pm -
2 stops10h 54m
Deal found 8/25![Delta logo]()
$349
This American Airlines deal was found by Cheapflights users on 8/24. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/75:00 am -
1 stop5h 05m
Mon 10/126:08 pm -
1 stop5h 52m
Deal found 8/24![American Airlines logo]()
$354
This American Airlines deal was found by Cheapflights users on 8/21. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 10/56:29 am -
1 stop6h 57m
Mon 10/126:08 pm -
1 stop7h 00m
Deal found 8/21![American Airlines logo]()
$356
This United Airlines deal was found by Cheapflights users on 8/24. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/1910:25 am -
Nonstop2h 38m
Wed 9/232:48 pm -
Nonstop3h 17m
Deal found 8/24![United Airlines logo]()
$359
Best flights from Chicago to Hilton Head IslandDiscover 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 August 26, 2026.
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 August 26, 2026.
This United Airlines deal was found by Cheapflights users on 8/23. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/310:35 am -
Nonstop2h 35m
Sat 10/102:51 pm -
Nonstop3h 14m
Deal found 8/23![United Airlines logo]()
$279
This American Airlines deal was found by Cheapflights users on 8/25. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/306:29 am -
1 stop6h 57m
Tue 11/34:17 pm -
1 stop7h 13m
Deal found 8/25![American Airlines logo]()
$319
This Delta deal was found by Cheapflights users on 8/25. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/308:05 am -
1 stop6h 25m
Tue 11/312:23 pm -
1 stop6h 24m
Deal found 8/25![Delta logo]()
$319
This United Airlines deal was found by Cheapflights users on 8/23. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/1910:25 am -
Nonstop2h 38m
Wed 9/232:48 pm -
Nonstop3h 17m
Deal found 8/23![United Airlines logo]()
$359
This American Airlines deal was found by Cheapflights users on 8/25. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/75:00 am -
1 stop5h 05m
Mon 10/126:08 pm -
1 stop5h 52m
Deal found 8/25![American Airlines logo]()
$374
This United Airlines deal was found by Cheapflights users on 8/21. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/810:25 am -
Nonstop2h 38m
Tue 9/152:48 pm -
Nonstop3h 17m
Deal found 8/21![United Airlines logo]()
$379
This Delta deal was found by Cheapflights users on 8/21. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/37:05 am -
2 stops7h 22m
Tue 10/612:23 pm -
2 stops9h 07m
Deal found 8/21![Delta logo]()
$463
Last-minute flights from Chicago to Hilton Head IslandDiscover last-minute flight deals from Chicago to Hilton Head Island. Data last updated August 26, 2026 and is based on user searches.
Discover last-minute flight deals from Chicago to Hilton Head Island. Data last updated August 26, 2026 and is based on user searches.
This American Airlines deal was found by Cheapflights users on 8/25. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/58:51 am -
Nonstop2h 24m
Fri 9/115:15 pm -
1 stop6h 16m
Deal found 8/25![American Airlines logo]()
$369
This United Airlines deal was found by Cheapflights users on 8/22. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 9/610:25 am -
Nonstop2h 38m
Sun 9/202:48 pm -
Nonstop3h 17m
Deal found 8/22![United Airlines logo]()
$354
This United Airlines deal was found by Cheapflights users on 8/22. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 9/710:25 am -
Nonstop2h 38m
Mon 9/212:48 pm -
Nonstop3h 17m
Deal found 8/22![United Airlines logo]()
$299
This American Airlines deal was found by Cheapflights users on 8/23. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 9/79:53 am -
Nonstop2h 24m
Mon 9/212:15 pm -
1 stop6h 23m
Deal found 8/23![American Airlines logo]()
$309
This Delta deal was found by Cheapflights users on 8/24. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/96:00 am -
2 stops8h 27m
Mon 9/144:17 pm -
1 stop7h 01m
Deal found 8/24![Delta logo]()
$324
This Delta deal was found by Cheapflights users on 8/24. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/128:05 am -
1 stop6h 22m
Wed 9/164:17 pm -
1 stop7h 01m
Deal found 8/24![Delta logo]()
$339
This United Airlines deal was found by Cheapflights users on 8/25. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/1710:25 am -
Nonstop2h 38m
Tue 9/222:48 pm -
Nonstop3h 17m
Deal found 8/25![United Airlines logo]()
$334
This United Airlines deal was found by Cheapflights users on 8/24. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/1910:25 am -
Nonstop2h 38m
Wed 9/232:48 pm -
Nonstop3h 17m
Deal found 8/24![United Airlines logo]()
$359
This American Airlines deal was found by Cheapflights users on 8/21. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/258:59 am -
1 stop6h 46m
Mon 9/285:15 pm -
1 stop6h 16m
Deal found 8/21![American Airlines logo]()
$319
This United Airlines deal was found by Cheapflights users on 8/23. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/2610:35 am -
Nonstop2h 35m
Sat 10/32:51 pm -
Nonstop3h 14m
Deal found 8/23![United Airlines logo]()
$279
This Delta deal was found by Cheapflights users on 8/24. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/306:00 am -
2 stops8h 27m
Wed 10/74:13 pm -
1 stop7h 04m
Deal found 8/24![Delta logo]()
$304
One-way flights from Chicago to Hilton Head IslandSearch for one-way flight options from Chicago to Hilton Head Island. Find affordable one-way fares based on user searches. Data last updated August 26, 2026.
Search for one-way flight options from Chicago to Hilton Head Island. Find affordable one-way fares based on user searches. Data last updated August 26, 2026.
This United Airlines deal was found by Cheapflights users on 8/25. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/1810:25 am -
Nonstop2h 38m
Deal found 8/25![United Airlines logo]()
$259
This Delta deal was found by Cheapflights users on 8/23. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/226:00 pm -
2 stops20h 27m
Deal found 8/23![Delta logo]()
$263
This American Airlines deal was found by Cheapflights users on 8/22. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/29:53 am -
Nonstop2h 24m
Deal found 8/22![American Airlines logo]()
$273
This Delta deal was found by Cheapflights users on 8/23. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/236:00 am -
2 stops8h 27m
Deal found 8/23![Delta logo]()
$274
This American Airlines deal was found by Cheapflights users on 8/25. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 9/219:16 pm -
2 stops12h 21m
Deal found 8/25![American Airlines logo]()
$282
This American Airlines deal was found by Cheapflights users on 8/21. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/199:45 am -
Nonstop2h 25m
Deal found 8/21![American Airlines logo]()
$289
This American Airlines deal was found by Cheapflights users on 8/21. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/48:30 pm -
1 stop15h 30m
Deal found 8/21![American Airlines logo]()
$292
This Delta deal was found by Cheapflights users on 8/21. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 9/215:30 am -
1 stop8h 57m
Deal found 8/21![Delta logo]()
$298
Find flight deals from Chicago to Hilton Head Island
Discover tips and strategies to find the most affordable flight options for your journey from Chicago (CHI) to Hilton Head Island (HHH). Learn about various techniques such as flexible date searches, comparing prices across and setting up price alerts. Use these methods to find the cheapest flights available for your travel needs. Data last updated August 26, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $279 (United Airlines) |
One-way from | $259 (United Airlines) |
Popular in | September |
Cheapest in | July |
Average price | $382 |
Good round-trip deal | $309 or less |
Good one-way deal | $288 or less |
Cheapflights Fare Finder
Customize your flight search to find flights from Chicago to Hilton Head Island that fit within your specific budget. Explore options based on user searches and filter the results based on your desired price range. Find flights that match your budget for a cost-effective journey. Over the last 7 days, Cheapflights users made 7,457,451 searches. Data last updated August 26, 2026.
Use the filters below to find and compare flights from Chicago to Hilton Head Island that are best for you.
Fly from
Fly to
Route
Depart
Return
Cheapest round-trip
Quickest round-trip
ChicagoHilton Head Island
ORD Chicago O'Hare Intl - HHH Hilton Head Island
ORDHHH
Chicago O'Hare Intl
Sat 10/3
10:35 am-2:10 pm
Nonstop2h 35m
Hilton Head Island
Sat 10/10
2:51 pm-5:05 pm
Nonstop3h 14m
$279
ChicagoHilton Head Island
ORD Chicago O'Hare Intl - HHH Hilton Head Island
ORDHHH
Chicago O'Hare Intl
Fri 10/30
6:29 am-2:26 pm
1 stop6h 57m
Hilton Head Island
Tue 11/3
4:17 pm-10:30 pm
1 stop7h 13m
$319
ChicagoHilton Head Island
ORD Chicago O'Hare Intl - HHH Hilton Head Island
ORDHHH
Chicago O'Hare Intl
Fri 10/30
8:05 am-3:30 pm
1 stop6h 25m
Hilton Head Island
Tue 11/3
12:23 pm-5:47 pm
1 stop6h 24m
$319
ChicagoHilton Head Island
ORD Chicago O'Hare Intl - HHH Hilton Head Island
ORDHHH
Chicago O'Hare Intl
Sat 9/19
10:25 am-2:03 pm
Nonstop2h 38m
Hilton Head Island
Wed 9/23
2:48 pm-5:05 pm
Nonstop3h 17m
$359
ChicagoHilton Head Island
ORD Chicago O'Hare Intl - HHH Hilton Head Island
ORDHHH
Chicago O'Hare Intl
Wed 10/7
5:00 am-11:05 am
1 stop5h 05m
Hilton Head Island
Mon 10/12
6:08 pm-11:00 pm
1 stop5h 52m
$374
ChicagoHilton Head Island
ORD Chicago O'Hare Intl - HHH Hilton Head Island
ORDHHH
Chicago O'Hare Intl
Tue 9/8
10:25 am-2:03 pm
Nonstop2h 38m
Hilton Head Island
Tue 9/15
2:48 pm-5:05 pm
Nonstop3h 17m
$379
ChicagoHilton Head Island
ORD Chicago O'Hare Intl - HHH Hilton Head Island
ORDHHH
Chicago O'Hare Intl
Sat 10/3
7:05 am-3:27 pm
2 stops7h 22m
Hilton Head Island
Tue 10/6
12:23 pm-8:30 pm
2 stops9h 07m
$463
Cheapest one-way
ChicagoHilton Head Island
ORD Chicago O'Hare Intl - HHH Hilton Head Island
ORDHHH
Chicago O'Hare Intl
Mon 9/21
10:25 am-2:03 pm
Nonstop2h 38m
$259
Quickest one-way
ChicagoHilton Head Island
ORD Chicago O'Hare Intl - HHH Hilton Head Island
ORDHHH
Chicago O'Hare Intl
Sat 10/24
10:35 am-2:10 pm
Nonstop2h 35m
$259
ChicagoHilton Head Island
ORD Chicago O'Hare Intl - HHH Hilton Head Island
ORDHHH
Chicago O'Hare Intl
Wed 9/23
8:05 am-3:27 pm
1 stop6h 22m
$269
Showing 1-10 of 15 resultsSorted by cheapest first
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 August.
| Provider | Price Accuracy | Trust Score* |
|---|---|---|
| Price Accuracy1 star | Trust Score*3 stars | |
| Price Accuracy3 stars | Trust Score*3 stars |
- 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.
CHI-HHH
ORD-HHH
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.
Cheapflights Insights
Everything you need to know about your flight from Chicago to Hilton Head Island
CHI-HHH
ORD-HHH
What is the cheapest month to book a flight from Chicago to Hilton Head Island?
Currently, August is the cheapest month in which you can book a flight from Chicago to Hilton Head Island (average of $359). Flying from Chicago to Hilton Head Island in November is currently the most expensive (average of $605). 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?
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 August 26, 2026.
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.
Weekly flight availability from Chicago to Hilton Head Island
Explore weekly flight availability from Chicago to Hilton Head Island. Discover flights operating on different days of the week, giving you the flexibility to choose a travel day that best fits your plans. Compare info to find the most convenient option for your journey. Data last updated August 26, 2026.
The most flights from CHI to HHH are scheduled on a Monday (2 on average). You will have fewer flight options on Thursday, which is when the least amount of flights are scheduled (1 on average).
How much does it cost to fly round-trip from Chicago to Hilton Head Island?
Airfare is typical for this route at the moment.
Chicago to Hilton Head Island flights typically cost between $274 and $655 in October.The cheapest round-trip price found within the last 5 days was $279 on United Airlines (Oct 17-Oct 24).
How far ahead should I book a flight from Chicago to Hilton Head Island?
Booking 70 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.
Reviews of airlines servicing Hilton Head Island
Get insights into the airlines that provide service to Hilton Head Island. Read reviews, discover amenities, and learn about the overall travel experience offered by airlines. Use this information to make informed decisions when choosing an airline for your flight to Hilton Head Island. Reviews last updated August 26, 2026.
Read through reviews of airlines operating flights from Chicago to Hilton Head Island, such as United Airlines and American Airlines. Reviews also offer insight into each airline's entertainment options, comfort, food, crew/service, and boarding process.
Comfort
7.3
Entertainment
7.1
Boarding
7.7
Crew
8.1
Overall
7.4
Food
6.7
Reviews
1 / 20
2.0
MediocreDawn,Aug 2026
ORD - DEN
Comfort
7.3
Entertainment
7.1
Boarding
7.7
Crew
8.1
Overall
7.4
Food
6.7
Reviews
1 / 20
2.0
MediocreDawn,Aug 2026
ORD - DEN
Comfort
7.3
Entertainment
7.1
Boarding
7.7
Crew
8.1
Overall
7.4
Food
6.7
Reviews
1 / 20
2.0
MediocreDawn,Aug 2026
ORD - DEN
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.
Traveling to a place near Hilton Head Island?
Book flights to Hilton Head Island if you plan to visit one of these locationsBeaufort
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Complete your trip to Hilton Head Island by adding a car rental and/or hotel reservation to your travel itinerary.
Search flights from Chicago to Hilton Head Island by cabin class
Find flights from Chicago to Hilton Head Island, based on your preferred cabin class, be it economy, premium economy, business, or first class.
Other flights to Hilton Head Island
Explore flights to Hilton Head Island departing from other origins. Flights are based on user searches made on Cheapflights and were last updated on August 26, 2026.
Chicago and Hilton Head Island flights
Browse other Chicago and Hilton Head Island flight options. Last updated on August 26, 2026.
Other flights from Chicago
Browse through other flights departing from Chicago. Flights are based on user searches made on Cheapflights and were last updated on August 26, 2026.
Popular flight searches
Check out other popular destinations found by fellow travelers in 2026
Top 2 airlines flying from Chicago to Hilton Head Island
Discover the top 2 airlines that operate flights from Chicago to Hilton Head Island. Compare their services, reliability, and customer satisfaction ratings to choose the airline that best suits your travel preferences and needs. Over the last 7 days, Cheapflights users made 7,457,451 searches. Data last updated August 26, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$220 | Average$443 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$269 | Average$452 | FlexibilityNo cancel fee | On-time71% |