ORD - HHH

$209 Find Cheap Flights from Chicago to Hilton Head Island

This is the cheapest round-trip 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 6/11. 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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Everything you should know

Cheapest round-trip
$209
Overall average: $488
United Airlines
Thu 6/11Mon 6/15
ORD - HHH • Non-stop
Cheapest one-way
$215
American Airlines
Sat 1/17
ORD - HHH • 2 stops
When to travel
November
Cheapest • 21% price drop
March
Most popular
Good to know
Good to know
+1
+1
Good to know
Good to know
+1
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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

Thu, Jun 11 - Mon, Jun 15
United Airlines Logo
10:35 am - 2:01 pm
ORD
-
HHH
2h 26mnonstop
United Airlines Logo
3:00 pm - 4:45 pm
HHH
-
ORD
2h 45mnonstop
$209United Airlines
Wed, Jun 10 - Mon, Jun 15
United Airlines Logo
10:35 am - 2:01 pm
ORD
-
HHH
2h 26mnonstop
United Airlines Logo
3:00 pm - 4:45 pm
HHH
-
ORD
2h 45mnonstop
$279United Airlines
Sun, May 24 - Sat, May 30
United Airlines Logo
10:35 am - 2:01 pm
ORD
-
HHH
2h 26mnonstop
United Airlines Logo
3:00 pm - 4:45 pm
HHH
-
ORD
2h 45mnonstop
$282United Airlines
Sat, Jan 17 - Tue, Jan 20
American Airlines Logo
8:50 pm - 12:20 pm
ORD
-
HHH
14h 30m2 stops
American Airlines Logo
3:29 pm - 7:50 pm
HHH
-
ORD
5h 21m1 stop
$293American Airlines
Sat, Jan 17 - Tue, Jan 20
American Airlines Logo
8:50 pm - 12:20 pm
ORD
-
HHH
14h 30m2 stops
American Airlines Logo
3:29 pm - 10:34 pm
HHH
-
ORD
8h 05m2 stops
$298American Airlines
Sat, Jan 17 - Tue, Jan 20
American Airlines Logo
6:05 am - 12:20 pm
ORD
-
HHH
5h 15m1 stop
American Airlines Logo
3:29 pm - 7:50 pm
HHH
-
ORD
5h 21m1 stop
$309American Airlines
Tue, Mar 3 - Sat, Mar 7
American Airlines Logo
5:35 am - 3:05 pm
ORD
-
HHH
8h 30m2 stops
American Airlines Logo
4:18 pm - 9:15 pm
HHH
-
ORD
5h 57m1 stop
$314American Airlines
Mon, Jan 19 - Sat, Jan 31
American Airlines Logo
8:12 am - 2:59 pm
ORD
-
HHH
5h 47m1 stop
American Airlines Logo
3:29 pm - 7:50 pm
HHH
-
ORD
5h 21m1 stop
$336American Airlines
Mon, Jan 19 - Sat, Jan 31
American Airlines Logo
10:10 am - 2:59 pm
ORD
-
HHH
3h 49m1 stop
American Airlines Logo
12:54 pm - 10:18 pm
HHH
-
ORD
10h 24m2 stops
$341American Airlines
Sat, Apr 25 - Sat, May 2
American Airlines Logo
6:07 am - 2:20 pm
ORD
-
HHH
7h 13m2 stops
American Airlines Logo
6:07 pm - 11:50 pm
HHH
-
ORD
6h 43m1 stop
$344American Airlines
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’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 Tuesday, as we generally find the cheapest rates on that day for this route. On the other hand, Saturday 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 Wednesdays 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 $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 $488 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 $367, 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 1 week before departure. For the absolute cheapest price, our data suggests you should book 6 weeks before departure.

Good to know

Low seasonSeptember
Cheapest flight$209
Best time to beat the crowds with an average 14% drop in price.
Most popular time to fly with an average 7% increase in price.
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 $215 for a one-way ticket and $209 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.

  • 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 $498 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 $455 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 $279 or less round-trip.

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 9091 reviews
7.3Comfort
6.6Food
7.7Boarding
7.1Entertainment
8.1Crew
Airline reviews

After a delay at the gate, C3, at Ohare on Sunday, I left my Blk ski coat on the bench at the gate, lost! Please review my lob claim, thx.

8.0 Excellentt, Dec 2025
ORD - RSW
Read more United Airlines reviews

After a delay at the gate, C3, at Ohare on Sunday, I left my Blk ski coat on the bench at the gate, lost! Please review my lob claim, thx.

Very thoughtful flight attendant offered me water immediately since I had run to make my connection.

Always wish for more healthy, gluten free options. We have to bring our own.

Having a long layover, I was very appreciative of the ability to stand by for an earlier flight. Other airlines like Delta have refused this to me in the past, just to be mean (because my ticket class wasn't high enough). United went out of their way to help me get to my destination early, which I really appreciated given that it was the third leg of a 24+ hour journey for me.

Other than a way way too cold cabinets for the entire flight, all was great

One bag is incorrect and not acceptable for an international flight. The food was not just good. I won't fly with them again.

Excellent flight. Smooth, efficient boarding. Quick flight. Arrived early at STL.

I will never book a flight through Cheap fare. They booked me from Portland Main . And would not give me a refund, so I bought 2 tickets one for 299. From Portland Main to ORD. Then I had to buy a ticket from Oregon PDX to ORD that was another 440. So Just so you know they even told me it was there fault but no refund. Bad bussniess. I did inform United but they said they couldn't help me due to the fact I booked through Cheap Tickets. Never again. And I'm spreding the word. I let everyone know at my 50th class reunion

Crew and customer service were excellent. This flight also had plenty of leg room and seat mounted screens for entertainment. A very pleasant flight all around!

It would have been better if the crew has supported my husband's reasons for needing to keep the space clear around his feet, rather than insisting that he put his knapsack in that space.

We loved the steward on the plane. He made the night enjoyable

The plane was late, when we did board the plane was as cold as a freezer. I was freezing the entire flight, no blankets. Lost miserable flight I’ve ever had.

3 hour weather delay followed by 1 hour (and counting) maintenance delay. UGH!

After we'd boarded , they canceled the flight. The crew didn't even know , we just all received text messages. Then after they deplaned us , AA was just like "too bad, go F your self, we sure ain't gonna help you"

After a two hour delay, my flight was CANCELLED! No pilot available. Such BS.

Amazing food, great staff, with one noticable detail missing ...but no seat entertainment in any of aircraft ...I am not a fan

I wish American Airlines would change the airline industry by loading the plane back to front instead of front to back. Planes would board so much more smoothly and quickly.

I have long legs, my foot was out in the aisle and when a flight attendant came walking by and I didn't notice, instead of saying "excuse me" or anything like that, she kicked my foot. Extremely rude

Excellent! The gate agents were kind enough to rebook me on an earlier flight saving me from a 6 hour layover. Even my luggage made it despite the fact that the connection was technically too narrow. The flight itself was very comfortable, roomy, and clean. Plenty of space for my carryon items with plugs to charge my phone. After a long international flight of 14 hours, this was an excellent way to end my travels!

Great experience. Flight boarded easily. Departed early. Smooth flight. Great arrival in DC--almost no taxing! Almost direct to gate from runway. Crew was terrific. Same cookies and beverages in main cabin. I did not use the entertainment system on this flight.

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

Information on your arrival and departure airports