ORD - HHH

$190 Find Cheap Flights from Chicago to Hilton Head Island - Compare and Save

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 9/9. 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

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Everything you should know

Cheapest round-trip
$279
Typical prices: $427-$785
United Airlines
Fri 8/21Mon 8/24
ORD - HHH • Non-stop
Cheapest non-stop
$279
American Airlines
Tue 8/18Tue 8/25
ORD - HHH • Non-stop
Top airlines
Cheapest • from $279 (round-trip)
Best reviews • 7.4 score
Airline reviews
Airline reviews
+1
+1
Airline reviews
Airline reviews
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Nonstop flights
You can fly direct with American Airlines and United Airlines. Average duration is 2h 31m
Direct flights
Direct flights
+1
+1
Direct flights
Direct flights
+1
Top layover airports
Cheapest • Avg $334 (round-trip)
Shortest trip • 4h 52m (one-way)
Insights
Insights
Insights
Insights
When to book
in advance
Our data shows that travelers who book at least 4 weeks in advance save around 7% compared to booking last minute.
Insights
Insights
Insights
Insights
When to travel
Cheapest • 20% price drop
Most popular
Good to know
Good to know
+1
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Good to know
Good to know
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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

Fri, Aug 21 - Mon, Aug 24
United Airlines Logo
10:25 am - 2:03 pm
ORD
-
HHH
2h 38mnonstop
United Airlines Logo
2:58 pm - 5:15 pm
HHH
-
ORD
3h 17mnonstop
$279United Airlines
Tue, Aug 18 - Tue, Aug 25
American Airlines Logo
9:53 am - 1:17 pm
ORD
-
HHH
2h 24mnonstop
American Airlines Logo
1:52 pm - 3:30 pm
HHH
-
ORD
2h 38mnonstop
$279American Airlines
Fri, Aug 21 - Fri, Aug 28
American Airlines Logo
9:53 am - 1:17 pm
ORD
-
HHH
2h 24mnonstop
American Airlines Logo
1:52 pm - 3:30 pm
HHH
-
ORD
2h 38mnonstop
$279American Airlines
Sat, Aug 29 - Wed, Sep 2
American Airlines Logo
8:51 am - 12:15 pm
ORD
-
HHH
2h 24mnonstop
American Airlines Logo
1:52 pm - 3:30 pm
HHH
-
ORD
2h 38mnonstop
$279American Airlines
Fri, Aug 21 - Sun, Aug 23
United Airlines Logo
10:25 am - 2:03 pm
ORD
-
HHH
2h 38mnonstop
United Airlines Logo
2:58 pm - 5:15 pm
HHH
-
ORD
3h 17mnonstop
$294United Airlines
Tue, Sep 29 - Tue, Oct 6
Delta Logo
8:05 am - 3:27 pm
ORD
-
HHH
6h 22m
1 stop
Delta Logo
4:13 pm - 10:32 pm
HHH
-
ORD
7h 19m
1 stop
$299Delta
Thu, Sep 10 - Wed, Sep 16
Delta Logo
8:05 am - 3:27 pm
ORD
-
HHH
6h 22m
1 stop
Delta Logo
12:17 pm - 4:37 pm
HHH
-
ORD
5h 20m
1 stop
$299Delta
Wed, Sep 9 - Wed, Sep 16
Delta Logo
8:05 am - 3:27 pm
ORD
-
HHH
6h 22m
1 stop
Delta Logo
12:17 pm - 4:37 pm
HHH
-
ORD
5h 20m
1 stop
$299Delta
Wed, Aug 19 - Tue, Aug 25
United Airlines Logo
10:25 am - 2:03 pm
ORD
-
HHH
2h 38mnonstop
United Airlines Logo
2:58 pm - 5:15 pm
HHH
-
ORD
3h 17mnonstop
$299United Airlines
Thu, Aug 20 - Sun, Aug 23
United Airlines Logo
10:25 am - 2:03 pm
ORD
-
HHH
2h 38mnonstop
United Airlines Logo
2:58 pm - 5:15 pm
HHH
-
ORD
3h 17mnonstop
$314United 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.

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 August.

Flight prices are below average for this route right now.

Flights to Hilton Head Island from Chicago O'Hare Intl Airport usually cost between $427 and $785 in August.
The lowest price found in the past 5 days was $279 on United Airlines (Aug 21-Aug 24).

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, Sunday is the most expensive day to fly from Chicago to Hilton Head Island. For your return ticket, we recommend flying on a Wednesday 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 April, where tickets cost $369 (return) on average. On the other hand, the most expensive months are March and August, where the average cost of round-trip tickets is $633 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 $359, 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 4 weeks before departure, which saves you about 7% compared to booking last minute. For the absolute cheapest price, our data suggests you should book 25 weeks before departure.

Good to know

Low season

January

Cheapest flight

$190
Best time to beat the crowds with an average 16% drop in price.
Most popular time to fly with an average 2% 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 5 days, the lowest price for a flight from Chicago O'Hare Intl Airport to Hilton Head Island was $190 for a one-way ticket and $279 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 $426 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 $467 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 $346 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 10062 reviews
7.3Comfort
6.7Food
7.1Entertainment
8.1Crew
7.7Boarding
Airline reviews

It was hot and not as comfortable as the flight to Chicago. Must have been a different plane that needs to be worked on or replaced.

8.0 ExcellentArmedrest, Jul 2026
ORD - PAH
Read more United Airlines reviews

It was hot and not as comfortable as the flight to Chicago. Must have been a different plane that needs to be worked on or replaced.

The SFO lounge closes at 12 midnight. My flight took off at 2AM

It was extremely hot in the cabin the entire flight, vent air was worn

Have not had a flight out or returning to Norfolk that has not required maintenance, and a gate delay. Properly staff the crew so maintenance can be performed without last minute emergencies on each flight and there is enough staff to have gates prepared for inbound flights. Staff to ensure the safety and on time service vs. profit.

My original flight was cancelled and that affected my trip and my plans and I got no compensation and customer service was hard to reach as well

The flight was delayed by a hour and I wish they had communicated it sooner. No issues on the plane, it did take a while for food to come.

Know that the movies that you are going to be offered are the oldest be rated movies they could possibly get. They may have one or two new movies that they keep advertising but when you’re flying 15 hours, there is nothing to see past the first new movie.

Great experience. Boarding was fast, staff were very nice and funny, everything at the seat worked well.

Horrible! Several delays and then was cancelled! I spent over 24 hours in the airport and was unable to get a hotel or food voucher.

Awful. No counter attendants. No dinner offered due to delays.

I had my flight of Cedar Rapids. THen Chicago to Boston. Flight out of Cedar rapids was delayed by 12 hrs. Had to drive to Chicago to catch my flight

Long delays to board due to mechanical issues with plane.

Flight was delayed, boarded, sat at the gate for more than 30 minutes, left the gate then waited on the pad for another 30 to 60 minutes then returned to the gate, deboarded and was cancelled... alternative flight was not booked automatically. Waited in line for 30 minutes but fortunately an alternate flight to a different destination was found ... no thanks to the travel agent used by kayak

The flight from Milwaukee to Dallas was great the staff absolutely amazing. After that EVERYTHING WENT DOWN HILL!!! ABSOLUTELY HORRIBLE!!! WILL NOT FLY THIS AIRLINE AGAIN

I was very unhappy with the lack of communication from the cockpit. It took close to a half an hour before we took off after the doors were closed, and we got no announcements as to progress. It would be nice to get some acknowledgement of the situation and updates as to when we are taking off.

The seat was not even cleaned. It has full of cookie crums probably from last flight's passenger. Its basic expectation that, seats are clean.

Very turbulent flight, no drinks, very little service, unorganized boarding, gate changed multiple times

The flight was delayed significantly. Communication during the flight was abrupt and caused some panic as we were navigating turbulence. It was also too loud and every announcement felt startling. The flight attendants did not offer any assurances and I felt unsettled most of the flight. The seats, floor and tray table was very dirty. The seat next to me was broken and the passenger sitting there was very uncomfortable. He had a spring in his back and his seat made terrible squeaking noises through the flight.

Significant delays on my trip to Chicago and my trip back to NY

In-flight Wi-Fi didn’t work and the flight was 25 minutes late. The Embraer plane I was on was pretty old and the tray table was broken.

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

Information on your arrival and departure airports