$209+ Cheap flights from O'Hare Intl (ORD) to Hilton Head Island (HHH)
This is the cheapest round-trip flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 11/10. Fares are subject to change and may not be available on all flights or dates of travel.
ORD — HHH
Nov 3 — Nov 101
Round-trip
1 adult, Economy
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Find cheap flights from O'Hare Intl 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.Cheapflights Tip: The best prices from Chicago O'Hare Intl to Hilton Head Island are usually found in August or January, booked 50 days in advance, depart on a Tuesday or Wednesday and return on a Wednesday
Cheap flight deals from O'Hare Intl to Hilton Head Island
Cheapest
Best
Last-minute
One-way
Cheapest flights from O'Hare Intl to Hilton Head IslandExplore the most affordable flight options available from O'Hare Intl to Hilton Head Island. Find the lowest fares from popular airlines and budget airlines, with prices last updated on October 4, 2026.
Explore the most affordable flight options available from O'Hare Intl to Hilton Head Island. Find the lowest fares from popular airlines and budget airlines, with prices last updated on October 4, 2026.
This American Airlines deal was found by Cheapflights users on 10/3. 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 10/249:55 am -
Nonstop2h 25m
Sat 10/311:55 pm -
Nonstop2h 44m
Deal found 10/3![American Airlines logo]()
$319
This American Airlines deal was found by Cheapflights users on 9/29. 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.
Sun 11/159:00 am -
1 stop7h 10m
Sat 11/215:47 pm -
1 stop6h 08m
Deal found 9/29![American Airlines logo]()
$339
This American Airlines deal was found by Cheapflights users on 10/3. 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.
Tue 11/175:19 am -
1 stop5h 34m
Tue 11/245:47 pm -
1 stop5h 47m
Deal found 10/3![American Airlines logo]()
$340
This Delta deal was found by Cheapflights users on 10/3. 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 10/248:05 am -
1 stop6h 25m
Sat 10/3112:23 pm -
2 stops9h 07m
Deal found 10/3![Delta logo]()
$344
This Delta deal was found by Cheapflights users on 9/30. 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 10/278:05 am -
1 stop6h 25m
Sat 10/3112:23 pm -
2 stops9h 07m
Deal found 9/30![Delta logo]()
$364
This American Airlines deal was found by Cheapflights users on 9/30. 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 10/179:55 am -
Nonstop2h 25m
Tue 10/205:11 pm -
1 stop6h 49m
Deal found 9/30![American Airlines logo]()
$369
This American Airlines deal was found by Cheapflights users on 10/1. 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.
Thu 11/128:05 am -
1 stop5h 16m
Sat 11/141:55 pm -
Nonstop2h 42m
Deal found 10/1![American Airlines logo]()
$406
This American Airlines deal was found by Cheapflights users on 10/1. 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 12/236:50 am -
1 stop6h 40m
Tue 12/2911:08 am -
1 stop6h 11m
Deal found 10/1![American Airlines logo]()
$409
This American Airlines deal was found by Cheapflights users on 9/30. 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
Wed 10/146:08 pm -
1 stop5h 52m
Deal found 9/30![American Airlines logo]()
$414
Best flights from O'Hare Intl to Hilton Head IslandDiscover carefully curated flight deals from O'Hare Intl to Hilton Head Island that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated October 4, 2026.
Discover carefully curated flight deals from O'Hare Intl to Hilton Head Island that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated October 4, 2026.
This American Airlines deal was found by Cheapflights users on 10/3. 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 10/179:55 am -
Nonstop2h 25m
Wed 10/2110:55 am -
1 stop7h 22m
Deal found 10/3![American Airlines logo]()
$369
This Delta deal was found by Cheapflights users on 9/30. 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 10/248:05 am -
1 stop6h 25m
Wed 10/284:13 pm -
1 stop7h 04m
Deal found 9/30![Delta logo]()
$419
This American Airlines deal was found by Cheapflights users on 10/1. 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.
Thu 11/128:05 am -
1 stop5h 16m
Sat 11/141:55 pm -
Nonstop2h 42m
Deal found 10/1![American Airlines logo]()
$406
This Delta deal was found by Cheapflights users on 9/30. 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 10/248:05 am -
1 stop6h 25m
Tue 11/312:23 pm -
1 stop6h 24m
Deal found 9/30![Delta logo]()
$419
This Delta deal was found by Cheapflights users on 10/3. 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 10/247:00 am -
2 stops7h 30m
Sat 10/3112:23 pm -
2 stops9h 07m
Deal found 10/3![Delta logo]()
$429
This American Airlines deal was found by Cheapflights users on 10/3. 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 11/166:41 am -
1 stop4h 12m
Sat 11/212:49 pm -
2 stops7h 45m
Deal found 10/3![American Airlines logo]()
$431
This American Airlines deal was found by Cheapflights users on 9/29. 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 10/168:05 am -
1 stop5h 21m
Tue 10/2012:29 pm -
1 stop6h 22m
Deal found 9/29![American Airlines logo]()
$492
This Delta deal was found by Cheapflights users on 10/3. 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 10/177:00 am -
2 stops7h 30m
Wed 10/214:13 pm -
1 stop7h 04m
Deal found 10/3![Delta logo]()
$504
This Delta deal was found by Cheapflights users on 10/1. 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 10/177:00 am -
2 stops7h 30m
Tue 10/204:13 pm -
1 stop7h 04m
Deal found 10/1![Delta logo]()
$504
Last-minute flights from O'Hare Intl to Hilton Head IslandDiscover last-minute flight deals from O'Hare Intl to Hilton Head Island. Data last updated October 4, 2026 and is based on user searches.
Discover last-minute flight deals from O'Hare Intl to Hilton Head Island. Data last updated October 4, 2026 and is based on user searches.
This American Airlines deal was found by Cheapflights users on 9/30. 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
Wed 10/146:08 pm -
1 stop5h 52m
Deal found 9/30![American Airlines logo]()
$414
This American Airlines deal was found by Cheapflights users on 9/30. 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 10/179:55 am -
Nonstop2h 25m
Tue 10/205:11 pm -
1 stop6h 49m
Deal found 9/30![American Airlines logo]()
$369
This American Airlines deal was found by Cheapflights users on 10/3. 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 10/249:55 am -
Nonstop2h 25m
Sat 10/311:55 pm -
Nonstop2h 44m
Deal found 10/3![American Airlines logo]()
$319
This Delta deal was found by Cheapflights users on 10/3. 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 10/248:05 am -
1 stop6h 25m
Sat 10/3112:23 pm -
2 stops9h 07m
Deal found 10/3![Delta logo]()
$344
This Delta deal was found by Cheapflights users on 9/30. 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 10/278:05 am -
1 stop6h 25m
Sat 10/3112:23 pm -
2 stops9h 07m
Deal found 9/30![Delta logo]()
$364
This American Airlines deal was found by Cheapflights users on 10/1. 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.
Thu 11/128:05 am -
1 stop5h 16m
Sat 11/141:55 pm -
Nonstop2h 42m
Deal found 10/1![American Airlines logo]()
$406
This American Airlines deal was found by Cheapflights users on 9/30. 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.
Thu 11/1211:40 am -
1 stop4h 30m
Mon 11/164:17 pm -
1 stop7h 13m
Deal found 9/30![American Airlines logo]()
$416
This American Airlines deal was found by Cheapflights users on 9/29. 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.
Sun 11/159:00 am -
1 stop7h 10m
Sat 11/215:47 pm -
1 stop6h 08m
Deal found 9/29![American Airlines logo]()
$339
This American Airlines deal was found by Cheapflights users on 10/3. 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.
Tue 11/175:19 am -
1 stop5h 34m
Tue 11/245:47 pm -
1 stop5h 47m
Deal found 10/3![American Airlines logo]()
$340
One-way flights from O'Hare Intl to Hilton Head IslandSearch for one-way flight options from O'Hare Intl to Hilton Head Island. Find affordable one-way fares based on user searches. Data last updated October 4, 2026.
Search for one-way flight options from O'Hare Intl to Hilton Head Island. Find affordable one-way fares based on user searches. Data last updated October 4, 2026.
This American Airlines deal was found by Cheapflights users on 9/30. 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.
Tue 11/106:41 am -
1 stop4h 12m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/30![American Airlines logo]()
$209
This American Airlines deal was found by Cheapflights users on 10/1. 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.
Thu 11/128:05 am -
1 stop5h 16m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/1![American Airlines logo]()
$249
This American Airlines deal was found by Cheapflights users on 9/30. 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 10/3110:00 am -
Nonstop2h 25m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/30![American Airlines logo]()
$279
This Delta deal was found by Cheapflights users on 9/30. 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 10/318:05 am -
1 stop6h 25m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/30![Delta logo]()
$289
This Delta deal was found by Cheapflights users on 9/30. 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 10/276:00 am -
2 stops8h 30m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/30![Delta logo]()
$294
This American Airlines deal was found by Cheapflights users on 9/30. 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 11/29:20 pm -
2 stops13h 33m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/30![American Airlines logo]()
$302
This Delta deal was found by Cheapflights users on 9/29. 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 10/305:27 am -
1 stop9h 03m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/29![Delta logo]()
$305
This American Airlines deal was found by Cheapflights users on 10/3. 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 12/26:59 am -
2 stops7h 54m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/3![American Airlines logo]()
$308
This American Airlines deal was found by Cheapflights users on 10/1. 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 12/285:21 am -
1 stop4h 17m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/1![American Airlines logo]()
$319
This Delta deal was found by Cheapflights users on 9/29. 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.
Sun 10/259:51 am -
1 stop4h 39m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/29![Delta logo]()
$320
Find flight deals from O'Hare Intl to Hilton Head Island
Discover tips and strategies to find the most affordable flight options for your journey from O'Hare Intl (ORD) 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 October 4, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $319 (American Airlines) |
One-way from | $209 (American Airlines) |
Popular in | March |
Cheapest in | August |
Average price | $441 |
Good round-trip deal | $369 or less |
Good one-way deal | $278 or less |
Cheapflights Fare Finder
Customize your flight search to find flights from O'Hare Intl 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 October 4, 2026.
Use the filters below to find and compare flights from Chicago O'Hare Intl Airport to Hilton Head Island that are best for you.
Fly from
Fly to
Route
Depart
Return
Cheapest round-trip
ChicagoHilton Head Island
ORD Chicago O'Hare Intl - HHH Hilton Head Island
ORDHHH
Chicago O'Hare Intl
Sat 12/5
10:00 am-1:29 pm
Nonstop2h 29m
Hilton Head Island
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$279
Quickest round-trip
ChicagoHilton Head Island
ORD Chicago O'Hare Intl - HHH Hilton Head Island
ORDHHH
Chicago O'Hare Intl
Sat 10/31
10:00 am-1:25 pm
Nonstop2h 25m
Hilton Head Island
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$279
ChicagoHilton Head Island
ORD Chicago O'Hare Intl - HHH Hilton Head Island
ORDHHH
Chicago O'Hare Intl
Mon 11/2
10:35 am-3:30 pm
1 stop3h 55m
Hilton Head Island
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$289
ChicagoHilton Head Island
ORD Chicago O'Hare Intl - HHH Hilton Head Island
ORDHHH
Chicago O'Hare Intl
Mon 10/26
9:51 am-3:30 pm
1 stop4h 39m
Hilton Head Island
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$289
ChicagoHilton Head Island
ORD Chicago O'Hare Intl - HHH Hilton Head Island
ORDHHH
Chicago O'Hare Intl
Thu 12/3
8:10 am-2:22 pm
1 stop5h 12m
Hilton Head Island
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$289
ChicagoHilton Head Island
ORD Chicago O'Hare Intl - HHH Hilton Head Island
ORDHHH
Chicago O'Hare Intl
Tue 11/3
10:35 am-3:30 pm
1 stop3h 55m
Hilton Head Island
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$289
ChicagoHilton Head Island
ORD Chicago O'Hare Intl - HHH Hilton Head Island
ORDHHH
Chicago O'Hare Intl
Wed 10/28
8:05 am-3:30 pm
1 stop6h 25m
Hilton Head Island
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$289
ChicagoHilton Head Island
ORD Chicago O'Hare Intl - HHH Hilton Head Island
ORDHHH
Chicago O'Hare Intl
Thu 11/12
8:05 am-2:21 pm
1 stop5h 16m
Hilton Head Island
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$289
ChicagoHilton Head Island
ORD Chicago O'Hare Intl - HHH Hilton Head Island
ORDHHH
Chicago O'Hare Intl
Wed 11/4
10:35 am-3:30 pm
1 stop3h 55m
Hilton Head Island
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$289
ChicagoHilton Head Island
ORD Chicago O'Hare Intl - HHH Hilton Head Island
ORDHHH
Chicago O'Hare Intl
Sat 10/17
9:55 am-1:20 pm
Nonstop2h 25m
Hilton Head Island
Wed 10/21
10:55 am-5:17 pm
1 stop7h 22m
$369
Showing 1-10 of 18 resultsSorted by cheapest first
Compare providers for flights from O'Hare Intl 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 O'Hare Intl to Hilton Head Island in October.
| 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 O'Hare Intl Airport-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 O'Hare Intl Airport-Hilton Head Island flight deals on Cheapflights vs. FlightHub >95% of the time. Price accuracy is based on data collected from Chicago O'Hare Intl Airport-Hilton Head Island flight searches over the past month and is updated monthly.
- Most trusted provider: When it comes to deals on Chicago O'Hare Intl Airport-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 O'Hare Intl Airport-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 O'Hare Intl to Hilton Head Island
Have a flexible travel schedule? Discover the best time to fly to Hilton Head Island from O'Hare Intl with our price prediction graph.
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 O'Hare Intl Airport to Hilton Head Island
How far ahead should I book a flight from Chicago O'Hare Intl Airport to Hilton Head Island?
To ensure you get the cheapest price possible for a flight from Chicago O'Hare Intl Airport to Hilton Head Island, you should look to book at least 49 days in advance of your intended travel date. The price of your flight may increase if you delay and leave booking until a week or so before departure.
What is the cheapest month to book a flight from Chicago O'Hare Intl Airport to Hilton Head Island?
Currently, August is the cheapest month in which you can book a flight from Chicago O'Hare Intl Airport to Hilton Head Island (average of $349). Flying from Chicago O'Hare Intl Airport to Hilton Head Island in March is currently the most expensive (average of $587). 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 ORD to HHH?
Find hourly flight availability from O'Hare Intl 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 October 4, 2026.
Regardless of the time of day you decide to fly, the ticket price will remain around the same. Book flights from Chicago O'Hare Intl Airport to Hilton Head Island as you normally would.
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 October 4, 2026.
See what other customers who have flown with United Airlines and American Airlines from Chicago O'Hare Intl Airport to Hilton Head Island have to say. You can also see how each airline compares in terms of entertainment options, comfort, food, crew/service, and boarding process.
Overall
7.4
Boarding
7.7
Food
6.7
Comfort
7.3
Crew
8.1
Entertainment
7.1
Reviews
1 / 20
2.0
MediocreDawn,Aug 2026
ORD - DEN
Overall
7.4
Boarding
7.7
Food
6.7
Comfort
7.3
Crew
8.1
Entertainment
7.1
Reviews
1 / 20
2.0
MediocreDawn,Aug 2026
ORD - DEN
Overall
7.4
Boarding
7.7
Food
6.7
Comfort
7.3
Crew
8.1
Entertainment
7.1
Reviews
1 / 20
2.0
MediocreDawn,Aug 2026
ORD - DEN
Related info for your journey
Find useful and relevant information for your journey from O'Hare Intl 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.
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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 October 4, 2026.
O'Hare Intl and Hilton Head Island flights
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Top 2 airlines flying from O'Hare Intl to Hilton Head Island
Discover the top 2 airlines that operate flights from O'Hare Intl 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 October 4, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$220 | Average$442 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$279 | Average$454 | FlexibilityNo cancel fee | On-time71% |