ORD - HHH

$177 Find Cheap Flights from Chicago to Hilton Head Island

This is the cheapest one-way flight price found by a KAYAK user in the last 72 hours by searching for a flight from Chicago to Hilton Head Island departing on 5/24. Fares are subject to change and may not be available on all flights or dates of travel. Click the price to replicate the search for this deal.
1 adult
1 adult, Economy, 0 bags

KAYAK searches hundreds of travel sites at once for deals on flights to Hilton Head Island

 
These are the airlines KAYAK users have selected most often from within our search results in flight searches from Chicago to Hilton Head Island, as well as popular online travel agencies
These are the airlines KAYAK users have selected most often from within our search results in flight searches from Chicago to Hilton Head Island, as well as popular online travel agencies
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41,299,237 searches in the past 7 days on KAYAK

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Everything you should know

Cheapest round-trip
$289
Typical prices: $534-$318
Delta
Tue 6/23Mon 6/29
ORD - HHH • 1 stop
Cheapest non-stop
$309
United Airlines
Sat 5/9Wed 5/13
ORD - HHH • Non-stop
Top airlines
Cheapest • from $289 (round-trip)
Best reviews • 7.4 score
Airline reviews
Airline reviews
+1
+1
Airline reviews
Airline reviews
+1
Nonstop flights
You can fly direct with American Airlines and United Airlines. Average duration is 2h 27m
Direct flights
Direct flights
+1
+1
Direct flights
Direct flights
+1
Top layover airports
Cheapest • Avg $275 (round-trip)
Shortest trip • 4h 48m (one-way)
Insights
Insights
Insights
Insights
When to book
in advance
Our data shows that travelers who book at least 5 weeks in advance save around 26% compared to booking last minute.
Insights
Insights
Insights
Insights
When to travel
Cheapest • 17% price drop
Most popular
Good to know
Good to know
+1
+1
Good to know
Good to know
+1
Start a new search
KAYAK searches 100s of sites at once to find you the best travel deals.
We hope you love your trip to Hilton Head Island!
Flight Deals
Booking Insights
Flight Deals

Cheap Flights from Chicago to Hilton Head Island (ORD-HHH)

 
Here are some of the best deals found on KAYAK recently from the most popular airlines for round-trip flights from Chicago to Hilton Head Island that are departing in the next months. While these flights were available on KAYAK in the last 72 hours, prices and availability are subject to change and deals may expire.
Discover the best prices for you by selecting your travel dates on KAYAK.

Recent round-trip flight deals from Chicago to Hilton Head Island

Tue, Jun 23 - Mon, Jun 29
Delta Logo
8:08 am - 3:32 pm
ORD
-
HHH
6h 24m
1 stop
Delta Logo
12:13 pm - 6:42 pm
HHH
-
ORD
7h 29m
1 stop
$289Delta
Wed, Jul 22 - Tue, Jul 28
Delta Logo
8:03 am - 3:29 pm
ORD
-
HHH
6h 26m
1 stop
Delta Logo
12:11 pm - 8:31 pm
HHH
-
ORD
9h 20m
2 stops
$294Delta
Tue, Jun 2 - Tue, Jun 9
Delta Logo
6:00 am - 3:33 pm
ORD
-
HHH
8h 33m
2 stops
Delta Logo
12:13 pm - 10:34 pm
HHH
-
ORD
11h 21m
2 stops
$300Delta
Fri, Jul 24 - Mon, Jul 27
Delta Logo
8:03 am - 3:29 pm
ORD
-
HHH
6h 26m
1 stop
Delta Logo
12:11 pm - 5:12 pm
HHH
-
ORD
6h 01m
1 stop
$309Delta
Wed, Jul 15 - Tue, Jul 21
Delta Logo
6:00 am - 3:29 pm
ORD
-
HHH
8h 29m
2 stops
Delta Logo
12:11 pm - 6:45 pm
HHH
-
ORD
7h 34m
1 stop
$314Delta
Wed, Aug 5 - Wed, Aug 12
Delta Logo
6:00 am - 3:29 pm
ORD
-
HHH
8h 29m
2 stops
Delta Logo
12:00 pm - 8:45 pm
HHH
-
ORD
9h 45m
2 stops
$319Delta
Sat, Sep 19 - Wed, Sep 23
Delta Logo
7:10 am - 3:20 pm
ORD
-
HHH
7h 10m
1 stop
Delta Logo
4:00 pm - 8:45 pm
HHH
-
ORD
5h 45m
1 stop
$329Delta
Tue, May 26 - Tue, Jun 2
Delta Logo
7:00 am - 3:33 pm
ORD
-
HHH
7h 33m
2 stops
Delta Logo
4:16 pm - 10:36 pm
HHH
-
ORD
7h 20m
1 stop
$334Delta
Tue, Aug 4 - Tue, Aug 11
Delta Logo
6:00 am - 3:29 pm
ORD
-
HHH
8h 29m
2 stops
Delta Logo
12:00 pm - 10:43 pm
HHH
-
ORD
11h 43m
2 stops
$339Delta
Wed, Sep 16 - Wed, Sep 23
Delta Logo
6:00 am - 3:20 pm
ORD
-
HHH
8h 20m
2 stops
Delta Logo
12:00 pm - 10:43 pm
HHH
-
ORD
11h 43m
2 stops
$340Delta
Booking Insights

KAYAK's insights & trends for Chicago to Hilton Head Island flights

Get data-powered insights and trends into flights from Chicago to Hilton Head Island to help you find the cheapest flights, the best time to fly and much more.

How much is a round-trip flight from Chicago O'Hare Intl Airport to Hilton Head Island?

This analysis is based on the cheapest round-trip price found on KAYAK in the last 12 months by searching for a flight from Chicago O'Hare Intl Airport to Hilton Head Island departing in June.

What’s the cheapest day of the week to fly from Chicago to Hilton Head Island?

The average price of all round-trip flights from Chicago O'Hare Intl Airport to Hilton Head Island clicked on KAYAK for each day over the last 12 months.

If your flying dates are flexible, you should consider flying to Hilton Head Island on a Wednesday, as we generally find the cheapest rates on that day for this route. On the other hand, Sunday is the most expensive day to fly from Chicago to Hilton Head Island. For your return ticket, we recommend flying on a Thursday and avoiding Sundays for the best deals.

What is the cheapest month to fly from Chicago O'Hare Intl Airport to Hilton Head Island?

To calculate monthly average prices, KAYAK takes all prices for each month over the last year for round-trip flights from Chicago O'Hare Intl Airport to Hilton Head Island, removes the top 0.1% to account for outliers, and then takes the median of all values for each month.

The cheapest month for flights from Chicago O'Hare Intl Airport to Hilton Head Island is November, where tickets cost $365 (return) on average. On the other hand, the most expensive months are March and August, where the average cost of round-trip tickets is $610 and $600 respectively.

Can I save money by flying with a layover from Chicago O'Hare Intl Airport to Hilton Head Island?

The average round-trip price for all non-stop flights, flights with one layover, and flights with two layovers for the route found by users searching on KAYAK in the last 2 weeks.

No, with an average price for the route of $453, prices are generally cheapest when you fly direct.

How far in advance should I book a flight from Chicago O'Hare Intl Airport to Hilton Head Island?

To calculate weekly average prices, KAYAK takes all prices for each week before departure over the last year for round-trip flights from Chicago O'Hare Intl Airport to Hilton Head Island, removes the top 0.1% to account for outliers, and then takes the average of all the values for each week.

To get a below average price on the flight from Chicago O'Hare Intl Airport to Hilton Head Island, you should book around 5 weeks before departure, which saves you about 26% compared to booking last minute. For the absolute cheapest price, our data suggests you should book 15 weeks before departure.

Good to know

Low seasonJanuary
Cheapest flight$177
Best time to beat the crowds with an average 12% drop in price.
Most popular time to fly and prices are also 11% lower on average.
Flight from Chicago to Hilton Head Island

When to book flights from Chicago to Hilton Head Island

Are your dates flexible? Find out the best times to travel from Chicago to Hilton Head Island based on our flight data from the last year. Discover the cheapest month and even day to fly.
Estimated round-trip price
KAYAK looks at all historical flight data for each date to provide a predicted price for one-way trips or round-trips with a duration up to 40 days. While we try to provide actual minimum prices for each date, some prices are predictions and actual prices may differ.

FAQs for booking Chicago to Hilton Head Island flights

  • What is the cheapest flight from Chicago O'Hare Intl Airport to Hilton Head Island?

    In the last 3 days, the lowest price for a flight from Chicago O'Hare Intl Airport to Hilton Head Island was $177 for a one-way ticket and $289 for a round-trip.

  • Do I need a passport to fly between Chicago and Hilton Head Island?

    No

  • Which airports will I be using when flying from Chicago to Hilton Head Island?

    When flying out of Chicago you will be using Chicago O'Hare Intl. You will be landing at Hilton Head Island, also known as Hilton Head Island.

  • Which airlines offer Wi-Fi service onboard planes from Chicago to Hilton Head Island?

    Only American Airlines offers inflight Wi-Fi service on the Chicago to Hilton Head Island flight route.

  • Which aircraft models fly most regularly from Chicago to Hilton Head Island?

    The Embraer 175 (Enhanced Winglets) is the aircraft model that flies most regularly on the Chicago to Hilton Head Island flight route.

  • Which airline alliances offer flights from Chicago to Hilton Head Island?

    Star Alliance, and oneworld are the airline alliances operating flights between Chicago and Hilton Head Island, with Star Alliance being the most commonly used for this route.

  • On which days can I fly direct from Chicago to Hilton Head Island?

    There are nonstop flights from Chicago to Hilton Head Island on a daily basis.

  • Which is the best airline for flights from Chicago to Hilton Head Island, United Airlines or American Airlines?

    The two airlines most popular with KAYAK users for flights from Chicago to Hilton Head Island are United Airlines and American Airlines. With an average price for the route of $416 and an overall rating of 7.4, United Airlines is the most popular choice. American Airlines is also a great choice for the route, with an average price of $469 and an overall rating of 7.1.

  • How does KAYAK find such low prices on flights from Chicago to Hilton Head Island?

    KAYAK is a travel search engine. That means we look across the web to find the best prices we can find for our users. With over 2 billion flight queries processed yearly, we are able to display a variety of prices and options on flights from Chicago to Hilton Head Island.

  • How does KAYAK's flight Price Forecast tool help me choose the right time to buy my flight ticket from Chicago to Hilton Head Island?

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight to Hilton Head Island from Chicago is likely to change within 7 days, so travelers know whether to wait or book now.

  • What is the Hacker Fare option on flights from Chicago to Hilton Head Island?

    Hacker Fares allow you to combine one-way tickets in order to save you money over a traditional round-trip ticket. You could then fly to Hilton Head Island with an airline and back to Chicago with another airline. Booking your flights between Chicago and HHH can sometimes prove cheaper using this method.

  • What is KAYAK's "flexible dates" feature and why should I care when looking for a flight from Chicago to Hilton Head Island?

    Sometimes travel dates aren't set in stone. If your preferred travel dates have some wiggle room, flexible dates will show you all the options when flying to Hilton Head Island from Chicago up to 3 days before/after your preferred dates. You can then pick the flights that suit you best.

KAYAK’s top tips for finding a cheap flight from Chicago O'Hare Intl Airport to Hilton Head Island

  • Looking for a cheap flight? 25% of our users found flights on this route for $349 or less round-trip.

Prefer to fly direct from Chicago to Hilton Head Island?

 
Direct data is based off flight results for the next 60 days. Find direct flights from all airlines flying direct from Chicago O'Hare Intl to Hilton Head Island.
Find which airlines fly direct from Chicago O'Hare Intl Airport to Hilton Head Island Airport, which days they fly and book direct flights.

Direct departures

Chicago O'Hare Intl to Hilton Head Island

Monday

American Airlines,United Airlines

American Airlines,United Airlines

Tuesday

American Airlines,United Airlines

American Airlines,United Airlines

Wednesday

American Airlines,United Airlines

American Airlines,United Airlines

Thursday

American Airlines,United Airlines

American Airlines,United Airlines

Friday

American Airlines,United Airlines

American Airlines,United Airlines

Saturday

American Airlines,United Airlines

American Airlines,United Airlines

Sunday

American Airlines,United Airlines

American Airlines,United Airlines

See more direct flights

Direct returns

Hilton Head Island to Chicago O'Hare Intl

Monday

American Airlines,United Airlines

American Airlines,United Airlines

Tuesday

American Airlines,United Airlines

American Airlines,United Airlines

Wednesday

American Airlines,United Airlines

American Airlines,United Airlines

Thursday

American Airlines,United Airlines

American Airlines,United Airlines

Friday

American Airlines,United Airlines

American Airlines,United Airlines

Saturday

American Airlines,United Airlines

American Airlines,United Airlines

Sunday

American Airlines,United Airlines

American Airlines,United Airlines

See more direct flights

Reviews of the top airlines flying from Chicago to Hilton Head Island

 
See real verified KAYAK customer reviews for airlines flying from Chicago to Hilton Head Island. Airline scores are aggregated from all reviews left by passengers on KAYAK after flying with an airline. KAYAK doesn’t show reviews that are older than 5 years. Learn how KAYAK collects reviews.
Need help choosing which airline to fly with from Chicago to Hilton Head Island? KAYAK airline reviews give an overall score for each airline based on loads of factors, including comfort, boarding, in-flight entertainment and more, to make your decision easier. See airline scores according to verified KAYAK customer reviews.
7.4
United AirlinesOverall score based on 9680 reviews
7.7Boarding
8.1Crew
7.1Entertainment
6.6Food
7.3Comfort
Airline reviews

A long delay. Don't travel late in the day.

8.0 ExcellentTimothy, Apr 2026
ORD - CID
Read more United Airlines reviews

A long delay. Don't travel late in the day.

Super friendly with lots of drink options an entertainment. Friendly crew.

The crew was great. Very friendly and responsive. The plane was old, small and tight. We ran out of overhead space and I had to check. Middle seat was particularly tight.

Several missed and almost missed connections. It felt like everything was being patched together last minute without enough resources and it ended up being an extremely stressful experience that basically ruined our weekend on the west coast. What a waste.

Crew was friendly. Seats are too narrow, particularly when a big person is in the adjacent seat, but I understand this is due to smaller planes usually flight into Lincoln. I have experienced several flight delays going out and coming into Lincoln airport, I say maybe 50% or higher of the flights I've taken out of this airport have been delayed.

Great flight. Boarded efficiently. Arrived early at CLT. There was no in flight entertainment on this aircraft. Great crew.

The seat was comfortable. There was a lot of turbulence. If it weren't for that,it would have been okay.

Poor communication, flight was delayed for preventable reasons. I missed my connection.

No meal service to the back of the plane as it started late or was too slow to get it out before it was time to land.

Terrible, if possible won't be flying again anytime soon!

The airplane was an old model, the overhead didn’t have enough room for people’s items and made boarding and boarding disappointing and stressful. Crew allowed passengers to bring more than the permitted baggage sizes.

Original flight was on time, then late, then changed gates...4 times. Once our newest plane came in, it was fine.

I almost missed my flight and they helped me out enormously

Delays experienced in boarding/take off due to incoming plane delayed. However, the boarding time/depart time in the app was significantly delayed in providing these updates. Usually not updated until an hour after we should have already boarded. Poorly managed.

Moved to earlier flight which unexpectedly had maintenance issues initially indicated as quick fix to ultimately plane changes. Moved back to original flight, also delayed. In all cases customer updates and communication very unclear, no updates on drivers for delays.

Typical AA - late by 90+ mn. Gate changed twice... Changed the departure time 6 times No explanation, no communication on reasons for delay I travel with AA twice a year... and it is consistently very poor.. I will continue to use AA only when i have to.

The gate got changed several times and the flight was delayed over an hour. Awful experience

American continues to decline in their customer service and its beyond disappointing.

It was an older plane. First Class was not especially roomy or comfortable. It was a short flight so there were no meal but they did offer mixed nuts which used to be normal but now is rare. Crew member was very polite and professional.

Flight to Tampa was delayed taking off due to plane arriving late but no other issues

Everything you need to know for your flight from Chicago to Hilton Head Island

Information on your arrival and departure airports