ORD - HHH

$144 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 6/24. 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
Travelers love KAYAK
41,299,237 searches in the past 7 days on KAYAK

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Everything you should know

Cheapest round-trip
$193
Overall average: $379
Delta
Tue 5/26Tue 6/2
ORD - HHH • 1 stop
Cheapest non-stop
$209
United Airlines
Thu 4/9Thu 4/16
ORD - HHH • Non-stop
Top airlines
Delta
Cheapest • from $193 (round-trip)
United Airlines
Best reviews • 7.4 score
Airline reviews
Airline reviews
+1
+1
Airline reviews
Airline reviews
+1
Nonstop flights
Every day
You can fly direct with United Airlines. Average duration is 2h 24m
Direct flights
Direct flights
+1
+1
Direct flights
Direct flights
+1
When to book
3 weeks
in advance
Our data shows that travelers who book at least 3 weeks in advance save around 32% compared to booking last minute.
Insights
Insights
Insights
Insights
When to travel
November
Cheapest • 20% price drop
May
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, May 26 - Tue, Jun 2
Delta Logo
7:05 am - 3:22 pm
ORD
-
HHH
7h 17m
1 stop
Delta Logo
4:05 pm - 10:36 pm
HHH
-
ORD
7h 31m
1 stop
$193Delta
Thu, Apr 9 - Thu, Apr 16
United Airlines Logo
10:50 am - 2:16 pm
ORD
-
HHH
2h 26mnonstop
United Airlines Logo
3:05 pm - 4:49 pm
HHH
-
ORD
2h 44mnonstop
$209United Airlines
Wed, Apr 22 - Thu, Apr 30
United Airlines Logo
10:50 am - 2:16 pm
ORD
-
HHH
2h 26mnonstop
United Airlines Logo
3:08 pm - 4:49 pm
HHH
-
ORD
2h 41mnonstop
$229United Airlines
Tue, May 26 - Tue, Jun 2
Delta Logo
7:00 am - 3:22 pm
ORD
-
HHH
7h 22m
2 stops
Delta Logo
4:05 pm - 10:36 pm
HHH
-
ORD
7h 31m
1 stop
$234Delta
Tue, Jun 9 - Tue, Jun 16
Delta Logo
9:35 am - 11:23 am
ORD
-
HHH
24h 48m
1 stop
Delta Logo
4:00 pm - 10:43 pm
HHH
-
ORD
7h 43m
1 stop
$240Delta
Sat, Apr 18 - Tue, Apr 28
Delta Logo
7:10 am - 3:20 pm
ORD
-
HHH
7h 10m
1 stop
Delta Logo
4:00 pm - 10:15 pm
HHH
-
ORD
7h 15m
1 stop
$243Delta
Sat, Apr 18 - Tue, Apr 28
Delta Logo
9:48 am - 3:20 pm
ORD
-
HHH
4h 32m
1 stop
Delta Logo
12:08 pm - 8:36 pm
HHH
-
ORD
9h 28m
2 stops
$248Delta
Sat, Jun 6 - Tue, Jun 16
Delta Logo
2:40 pm - 11:23 am
ORD
-
HHH
19h 43m
1 stop
Delta Logo
4:00 pm - 10:43 pm
HHH
-
ORD
7h 43m
1 stop
$275Delta
Wed, Jun 3 - Tue, Jun 16
United Airlines Logo
10:45 am - 2:21 pm
ORD
-
HHH
2h 36mnonstop
United Airlines Logo
3:05 pm - 4:51 pm
HHH
-
ORD
2h 46mnonstop
$279United Airlines
Thu, Jun 4 - Wed, Jun 10
Delta Logo
8:10 am - 3:22 pm
ORD
-
HHH
6h 12m
1 stop
Delta Logo
4:00 pm - 10:43 pm
HHH
-
ORD
7h 43m
1 stop
$284Delta
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.

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 $346 (return) on average. On the other hand, the most expensive months are August and June, where the average cost of round-trip tickets is $600 and $477 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 $459, 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 3 weeks before departure, which saves you about 32% compared to booking last minute. For the absolute cheapest price, our data suggests you should book 3 weeks before departure.

Good to know

Low seasonJanuary
Cheapest flight$144
Best time to beat the crowds with an average 11% drop in price.
Most popular time to fly and prices are also 13% 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

  • How many flights are there between Chicago O'Hare Intl Airport and Hilton Head Island per day?

    There is a maximum of 1 nonstop flight a day that takes off from Chicago O'Hare Intl Airport and lands in Hilton Head Island, with an average flight time of 2h 24m. The most common departure time is 10:00 am and most flights take off in the morning. Each week, there are 1 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 $144 for a one-way ticket and $193 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 $444 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 $454 and an overall rating of 7.2.

  • 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 $178 or less one-way and $358 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

United Airlines

United Airlines

Tuesday

United Airlines

United Airlines

Wednesday

United Airlines

United Airlines

Thursday

United Airlines

United Airlines

Friday

United Airlines

United Airlines

Saturday

United Airlines

United Airlines

Sunday

United Airlines

United Airlines

See more direct flights

Direct returns

Hilton Head Island to Chicago O'Hare Intl

Monday

United Airlines

United Airlines

Tuesday

United Airlines

United Airlines

Wednesday

United Airlines

United Airlines

Thursday

United Airlines

United Airlines

Friday

United Airlines

United Airlines

Saturday

United Airlines

United Airlines

Sunday

United 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 9341 reviews
7.7Boarding
8.1Crew
7.1Entertainment
7.3Comfort
6.6Food
Airline reviews

We were delayed for about an hour from taking off due to traffic control procedures at the destination airport. But once in the air, the flight went well. The crew members were great and provided cabin service despite moderate turbulence during much of the flight.

8.0 ExcellentDr. Joseph, Feb 2026
ORD - DCA
Read more United Airlines reviews

We were delayed for about an hour from taking off due to traffic control procedures at the destination airport. But once in the air, the flight went well. The crew members were great and provided cabin service despite moderate turbulence during much of the flight.

Short flight, but no drink/snack service. The flights both going and coming were delayed.

Not being stranded in Chicago for her airport to 11:30 tomorrow morning the 3rd

I was fully checked in the prior night and i was unchecked and then didn’t have a seat when I boarded. Instead of an aisle seat, I was out in the middle seat of the very last row of the plane.

In overall it was a good experience, the only down point was that the entertainment screen was working properly.

They lost my luggage, so, not happy. The crew was nice but my suitcases never made it, still trying to find out what happened!

I understand weather is an issue, but making us chase our plane down at five scheduled gates across three terminals in an airport the size of O'Hare was unfair. They'd have probably been better off to leave gates as TBD until the inbound plane is in final approach instead of running us all over the place. Also, props to the consistently-unprepared ground crew in Richmond for once again leaving my lane parked short of the gate because they couldn't have a crew in place on time with 2 hours notice...

cabin crew was OK, food was OK, the trip from the US to Munich was actually pretty bad comfort wise. Noisy aircraft, lights never dimmed even in Business class (night flight) barely sufficient amenities for the price. I have millions of miles with United but TBH American is gaining ground and Delta has always been marginally better then United although on paper United has more longes and cheaper upgrades.

Essy to get on. The hostess gave very little pop, the plane was late getting in, and we are still waiting for our bags. This sucks. :/

Great flight. On time boarding. Smooth flight and on time arrival at EWR. The flight crew was marvelous and there was a great selection of movies on the entertainment system. Our bags were at the carousel before we got there. Another excellent flight from United.

As previously stated the delay I experienced flying from Wichita to Chicago caused a host of issues. When I finally was able to be booked on the last remaining American flight from Chicago to Cincinnati, the gate changed four times with the last change occurring very near the scheduled boarding time. While I didn't have a problem moving from gate to gate, I did notice and make note of others that had mobility issues and had to move each time for the gate change.

Maintenance took a very long time and then we were in a holding pattern. While a one-off maintenance issue is standard, there were delays on both of my flights for this trip based on maintenance issues with the planes, which delayed both flights over 45 minutes. Thankfully, I didn't have any connections but it wasn't an experience that would make me pick AA if I have other options.

No Snacks or Entertainment. The flight was short, snacks should still be given.

See prior comment about how Kayak mishandled my reservation and delayed my arrival by 6 hours.

Boarding delayed 20 minutes for no reason, no wifi, in flight entertainment, or snacks / waters?

Delayed an hour due to operational issues. Minimal apologies or care for the significant inconvenience caused. Landed at nearly 1am and they still couldn’t find ground staff to get us off the plane promptly.

The aircraft had several problems - from excess fuel to non operational ac. Two hours of delay in Chicago could have been avoided with proper planning and aircraft maintenance.

Crew in Columbia was not prepared for landing. It was a bit of a disaster and getting bags took forever.

We were upgraded to First Class and it was a great flight

We experienced gate changes and a long delay. My seat was dirty when I boarded and I had to use wipes to clean it myself. There was an unpleasant and overpowering cleaning product scent on the plane as well that lingered through the flight.

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

Information on your arrival and departure airports