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ORD - HHH

$209 Find Cheap Flights from Chicago to Hilton Head Island - Compare and Save

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1 adult, Economy, 0 bags

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Everything you should know

Cheapest round-trip
$329
Typical prices: $320-$508
American Airlines
Wed 12/12Sat 12/15
ORD - HHH • Non-stop
Cheapest non-stop
$339
Typical prices: $290-$502
American Airlines
Wed 10/24Wed 10/31
ORD - HHH • Non-stop
Nonstop flights
1 day a week
You can fly direct with American Airlines and United Airlines. Average duration is 2h 28m
Direct flights
+1
Direct flights
+1
When to book
15 weeks
in advance
Our data shows that travelers who book at least 15 weeks in advance save around 34% compared to booking last minute.
Insights
Insights
When to travel
August
Cheapest • 12% price drop
June
Most popular
Good to know
+1
Good to know
+1
Top layover airports
Atlanta Hartsfield-Jackson (ATL)
Cheapest • Avg $320 (round-trip)
Washington, D.C. Reagan-National (DCA)
Shortest trip • 4h 52m (one-way)
Insights
Insights
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Flight Deals

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

 
Discover the best prices for you by selecting your travel dates on KAYAK.

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

Sat, Oct 31 - Tue, Nov 3
American Airlines Logo
10:00 am - 1:25 pmORD  Chicago O'Hare Intl-HHH Hilton Head Island
2h 25mnonstop
American Airlines Logo
12:25 pm - 5:38 pmHHH  Hilton Head Island-ORD Chicago O'Hare Intl
6h 13m1 stop Charlotte Douglas
$329American Airlines
Sat, Dec 12 - Tue, Dec 15
American Airlines Logo
10:00 am - 1:29 pmORD  Chicago O'Hare Intl-HHH Hilton Head Island
2h 29mnonstop
American Airlines Logo
12:33 pm - 4:11 pmHHH  Hilton Head Island-ORD Chicago O'Hare Intl
4h 38m1 stop Charlotte Douglas
$329American Airlines
Sat, Dec 12 - Mon, Dec 14
American Airlines Logo
10:00 am - 1:29 pmORD  Chicago O'Hare Intl-HHH Hilton Head Island
2h 29mnonstop
American Airlines Logo
4:24 pm - 10:36 pmHHH  Hilton Head Island-ORD Chicago O'Hare Intl
7h 12m1 stop Charlotte Douglas
$329American Airlines
Thu, Oct 29 - Sat, Oct 31
American Airlines Logo
12:05 pm - 5:38 pmORD  Chicago O'Hare Intl-HHH Hilton Head Island
4h 33m1 stop Charlotte Douglas
American Airlines Logo
1:55 pm - 3:39 pmHHH  Hilton Head Island-ORD Chicago O'Hare Intl
2h 44mnonstop
$329American Airlines
Sat, Oct 24 - Sat, Oct 31
Delta Logo
8:05 am - 3:30 pmORD  Chicago O'Hare Intl-HHH Hilton Head Island
6h 25m1 stop Atlanta Hartsfield-Jackson
Delta Logo
12:23 pm - 8:30 pmHHH  Hilton Head Island-ORD Chicago O'Hare Intl
9h 07m2 stops Atlanta Hartsfield-Jackson Detroit Metropolitan Wayne County
$364Delta
Sat, Oct 24 - Sat, Oct 31
Delta Logo
7:00 am - 3:30 pmORD  Chicago O'Hare Intl-HHH Hilton Head Island
7h 30m2 stops Detroit Metropolitan Wayne County Atlanta Hartsfield-Jackson
Delta Logo
12:23 pm - 8:30 pmHHH  Hilton Head Island-ORD Chicago O'Hare Intl
9h 07m2 stops Atlanta Hartsfield-Jackson Detroit Metropolitan Wayne County
$369Delta
Sat, Oct 31 - Tue, Nov 3
Delta Logo
6:20 am - 3:30 pmORD  Chicago O'Hare Intl-HHH Hilton Head Island
8h 10m2 stops Minneapolis St Paul Atlanta Hartsfield-Jackson
Delta Logo
4:13 pm - 10:17 pmHHH  Hilton Head Island-ORD Chicago O'Hare Intl
7h 04m1 stop New York LaGuardia
$424Delta
Tue, Oct 20 - Sat, Oct 24
United Airlines Logo
6:00 am - 12:35 pmORD  Chicago O'Hare Intl-HHH Hilton Head Island
5h 35m1 stop Newark
United Airlines Logo
2:51 pm - 5:05 pmHHH  Hilton Head Island-ORD Chicago O'Hare Intl
3h 14mnonstop
$444United Airlines
Sat, Apr 3 - Sat, Apr 17
United Airlines Logo
10:50 am - 2:16 pmORD  Chicago O'Hare Intl-HHH Hilton Head Island
2h 26mnonstop
United Airlines Logo
3:05 pm - 4:49 pmHHH  Hilton Head Island-ORD Chicago O'Hare Intl
2h 44mnonstop
$663United Airlines
Sat, Apr 3 - Sat, Apr 17
United Airlines Logo
5:00 am - 11:12 amORD  Chicago O'Hare Intl-HHH Hilton Head Island
5h 12m1 stop Newark
United Airlines Logo
3:05 pm - 4:49 pmHHH  Hilton Head Island-ORD Chicago O'Hare Intl
2h 44mnonstop
$673United Airlines
Booking Insights

Price, demand and travel trends for Chicago O'Hare Intl Airport to Hilton Head Island flights

Use KAYAK data on prices, travel dates, airlines and seasonal trends to compare options and book flights with more confidence.

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

Round-trip flights from Chicago O'Hare Intl Airport to Hilton Head Island typically range from $320 to $508. The lowest price found in the past 5 days was $329, on American Airlines.

What's the cheapest day of the week to fly from Chicago O'Hare Intl Airport to Hilton Head Island?

Based on deals KAYAK users found in the last 12 months, Tuesday is the cheapest day of the week to fly from Chicago O'Hare Intl Airport to Hilton Head Island. It’s 28% cheaper than the average day, while Sunday is the most expensive, with prices 19% higher.

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

•August is the cheapest month to fly from Chicago O'Hare Intl Airport to Hilton Head Island at $364 round-trip.
•November ($605) and March ($469) are the most expensive months.
•The price difference between flying in the cheapest and most expensive months is 66% on average.
This is based on KAYAK aggregated and averaged internal data over the past 12 months.

When are flights from Chicago O'Hare Intl Airport to Hilton Head Island the cheapest?

Flights from Chicago O'Hare Intl Airport to Hilton Head Island are cheapest 15 weeks before departure. Booking in this window typically costs about 34% less than the average last-minute fare (within 2 weeks of the flight), based on KAYAK data.

Find deals

Key details for Chicago O'Hare Intl Airport to Hilton Head Island flights

Low season

December

Cheapest flight

$209
Beat the crowds with an average 77% drop in travelers.
The most popular month to fly with an average 135% increase in travelers.
One-way flight from Chicago O'Hare Intl Airport 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

Your Chicago O'Hare Intl Airport to Hilton Head Island flight questions, answered

Find helpful answers about this route, including flight times, airports, airlines and booking tips.

  • What are the earliest and latest flights from Chicago O'Hare Intl Airport to Hilton Head Island?

    These are the earliest and latest flight times available from Chicago O'Hare Intl Airport to Hilton Head Island:

    • Earliest: departs at 9:55 am and lands at 12:23 pm
    • Latest: departs at 10:35 am and lands at 1:03 pm.

    The flight takes about 2h 28m.

  • What cabin classes can I book on flights from Chicago O'Hare Intl Airport to Hilton Head Island?

    Two cabin classes are available on flights from Chicago O'Hare Intl Airport to Hilton Head Island:

    • Economy Class
    • First Class

  • How long is a flight from Chicago O'Hare Intl Airport to Hilton Head Island?

    A nonstop flight from Chicago O'Hare Intl Airport to Hilton Head Island takes 2h 28m, covering 781 miles.

  • Do I need a passport to fly from Chicago O'Hare Intl Airport to Hilton Head Island?

    No, a passport is not required for this domestic route, but you will need a real ID-compliant driver's license, a state ID or another TSA-accepted form of identification.

  • How much should I expect to pay for a Chicago O'Hare Intl Airport to Hilton Head Island flight?

    Round-trip flights from Chicago O'Hare Intl Airport to Hilton Head Island range from $320 to $508, with an average of $412 over the past 12 months. Anything below $320 counts as a good deal.

  • How expensive are last-minute Chicago O'Hare Intl Airport to Hilton Head Island flights?

    Last-minute fares on this route (booked within two weeks of departure) run 20% above the $412 route average. Book 15 weeks before departure for the lowest fares.

  • How much can I save by taking a layover when flying from Chicago O'Hare Intl Airport to Hilton Head Island?

    On this route, layover flights are cheaper than nonstop options on average. Layover fares average $320 round-trip via Atlanta Hartsfield-Jackson (ATL), compared to $378 for nonstop.

  • What is the standard checked-bag allowance on flights from Chicago O'Hare Intl Airport to Hilton Head Island?

    There is no standard. Checked-bag policies vary by airline on this route. Most carriers charge $40–$100 for the first checked bag in economy. Premium fares and elite-status bookings typically include a free checked bag.

  • Which aircraft model is used most often on flights from Chicago O'Hare Intl Airport to Hilton Head Island?

    The Embraer 175 (Enhanced Winglets) family is used most often on this route, operated mainly by United Airlines. Other aircraft seen on the route include Embraer 175 variants.

  • Have flight prices from Chicago O'Hare Intl Airport to Hilton Head Island changed much recently?

    Yes. Based on fares seen in the past 5 days, round-trip prices on this route showed a wide range, from about $319 to $1,400. That means the highest observed fare was about 4x higher than the lowest one.

  • Which airlines offer Wi-Fi on Chicago O'Hare Intl Airport to Hilton Head Island flights?

    American Airlines is the only airline on the Chicago O'Hare Intl Airport to Hilton Head Island route offering in-flight Wi-Fi. Pricing depends on fare class.

  • How are flight prices from Chicago O'Hare Intl Airport to Hilton Head Island looking right now?

    One-way fares from Chicago O'Hare Intl Airport to Hilton Head Island are currently lower than usual. Average one-way flight prices are about $256, which is 19% below the typical average for this route.

  • What car rental options are available at Hilton Head Island Airport (HHH)?

    Hilton Head Island Airport (HHH) hosts 5 major car rental companies, with daily rates starting from around $29 for economy cars. Top options include:

    • Budget
    • Thrifty
    • Alamo
    • Avis
    • Enterprise Rent-A-Car

  • Which airports can I use when flying from Chicago O'Hare Intl Airport to Hilton Head Island?

    Flights from Chicago O'Hare Intl Airport to Hilton Head Island usually depart from Chicago O'Hare Intl (ORD) and arrive at Hilton Head Island (HHH).

  • Which airports do connecting flights from Chicago O'Hare Intl Airport to Hilton Head Island pass through?

    One-stop flights from Chicago O'Hare Intl Airport to Hilton Head Island most commonly connect through:

    • Charlotte Douglas (CLT) - 90% of one-stop connections
    • Atlanta Hartsfield-Jackson (ATL) - 7% of one-stop connections
    • Washington, D.C. Reagan-National (DCA) - 3% of one-stop connections

  • Can I save money by using flexible dates for flights from Chicago O'Hare Intl Airport to Hilton Head Island?

    Yes. Flexible dates can save you up to 40% on flights from Chicago O'Hare Intl Airport to Hilton Head Island. Tuesday is the cheapest departure day at $299 round-trip on average, while Sunday is the most expensive at $492, a difference of $193.

    KAYAK's flexible dates feature shows options up to 3 days before and after your selected dates, making it easier to compare nearby fares.

  • What airlines fly from Chicago O'Hare Intl Airport to Hilton Head Island?

    2 airlines operate flights between Chicago O'Hare Intl Airport and Hilton Head Island. The airlines offering nonstop flights on this route include:

    • American Airlines
    • United Airlines

  • How much time can I save by choosing a different layover airport from Chicago O'Hare Intl Airport to Hilton Head Island?

    Flying via Washington, D.C. Reagan-National (DCA) gives the shortest average 1-stop total travel time at 4h 52m, compared with 5h 05m via Charlotte Douglas (CLT) and 5h 34m via Atlanta Hartsfield-Jackson (ATL).

  • What is the time difference between Chicago O'Hare Intl Airport and Hilton Head Island?

    Hilton Head Island is 1 hour ahead of Chicago O'Hare Intl Airport (Eastern Time vs Central Time). Plan for the time shift when scheduling connections or first-day activities.

  • Which airlines offer extra legroom and free seat selection on Chicago O'Hare Intl Airport to Hilton Head Island flights?

    Among airlines operating Chicago O'Hare Intl Airport to Hilton Head Island flights:

    • United Airlines: offers extra legroom; offers free seat selection
    • American Airlines: offers free seat selection

    Extra legroom and free seat selection availability depends on fare class and route.

  • Which airlines include bags at no extra cost on Chicago O'Hare Intl Airport to Hilton Head Island flights?

    Here are some options for this route, based on selected ticket types and cabin classes:

    • United Airlines: a cabin bag and a checked bag in Economy Class
    • American Airlines: a cabin bag and a checked bag in First Class

    Bag allowance can vary by ticket type, cabin class, route and airline, so always check the fare details before booking.

Your guide to booking Chicago O'Hare Intl Airport to Hilton Head Island flights

Get tips on when to book, when to fly and what to know before your trip.
  • If your dates are flexible, aim for a Tuesday departure and avoid flying on Sunday. On this route, Tuesday flights average $299, about $193 less than Sunday fares (39% savings) based on the last 12 months.
  • For the best chance at a low fare, aim to book around 15 weeks before you fly. On this route, that window historically saves about 34% versus last-minute pricing (KAYAK booking data, last 12 months).
  • If you can choose when to travel, plan your Chicago O'Hare Intl Airport to Hilton Head Island trip for August. Fares historically average $364 round-trip in that month - typically $241 less than the most expensive month, which is November (based on the last 12 months).
  • If you have the time, taking a 1-stop flight through Atlanta Hartsfield-Jackson Airport (ATL) can be cheaper than flying direct. The cheapest layover option averages $320 round-trip on this route - about $58 less than direct flights (based on the last 12 months).
  • If you're arriving late at night and need somewhere to stay, check out these hotels close to Hilton Head Island Airport.

    • Hampton Inn Hilton Head
    • Simple Rewards Inn
    • Marriott's Barony Beach Club

Prefer to fly direct from Chicago 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

Saturday

American Airlines

American Airlines

See more direct flights

Direct returns

Hilton Head Island to Chicago O'Hare Intl

Saturday

American Airlines

American Airlines

See more direct flights

More options for your flight from Chicago to Hilton Head Island

Complete your trip to Hilton Head Island with a hotel stay or car rental

Car rentals in Hilton Head Island
Hotels in Hilton Head Island
Vacations in Hilton Head Island