Cheap flights from Chicago to Hilton Head Island

Chicago FSS
CHI
Hilton Head
HHH

Flight deals from Chicago to Hilton Head Island

Below you can see the best deals on flights Chicago — Hilton Head Island for upcoming dates. Direct and connecting flights from various airlines — compare prices and choose the right ticket.

The lowest price for the next 2 months is on 12 September, from $185.

Top 10 cheap flights from Chicago to Hilton Head Island

About the Chicago — Hilton Head Island flight

Looking for cheap flights from Chicago to Hilton Head Island? Compare fares from different airlines, check the flight schedule and travel time — and book your Chicago — Hilton Head Island ticket online at the best price.

The route has direct flights — around 25 flights per week, flights are operated by United Airlines, American Airlines, a nonstop flight takes about 2 h 33 min, the distance between the cities is around 1,233 km.

Planning your trip? You may find our Hilton Head Island travel guide, how to get from the airport into town and Hilton Head Island weather forecast useful. To catch a low fare, use the low-price calendar and the monthly price chart on this page.

Facts about this route

from $185Min. price
SeptemberCheapest
SeptemberPeak season
YesDirect flights
1,233 kmDistance
2 h 33 minTravel time
2Airlines
25 / wkFlights

Flight schedule from Chicago to Hilton Head Island

The table shows direct flights from Chicago to Hilton Head Island on the selected date. The flight takes approximately 2 h 33 min. Regular flights are operated by United Airlines and American Airlines. Departures from O'Hare International Airport, Chicago Midway International Airport and Midway International Airport airports, arrivals at Hilton Head Airport.

For each flight, the following details are shown: departure time (local), arrival city and airport, flight number and airline, terminal or gate, and status. Click on a flight to open its details and go to ticket search. To view flights on a different day, change the date above the table.

Today
Any time
Last update: 01 Sep 2026

Flight ticket prices by day: Chicago — Hilton Head Island

Below is a calendar of the lowest flight ticket prices for Chicago — Hilton Head Island by day. Pick a convenient date and instantly see the fare. The cheapest flights on this route start from $185 in September, and the most expensive are around $185 in September. If your travel dates are flexible, the calendar will help you find the best price for your preferred period. To view round-trip fares, switch to the "Round trip" tab above the calendar, select your departure date — and the right-hand calendar will highlight the lowest prices for return flights on each day.

 
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Prices by month

Average one-way fares from Chicago to Hilton Head Island by month. Tickets are usually cheapest in August (around $232) and priciest in July (about $397) — use the table and chart below to pick the best time to fly.

MonthAverage priceLevelMonthAverage priceLevelMonthAverage priceLevel
Jan$254lowMay$309mediumSep$287medium
Feb$243lowJun$375highOct$276medium
Mar$287mediumJul$397highNov$254low
Apr$353highAug$232lowDec$342high

Some values are estimated based on seasonality.

When to fly

Weather in Hilton Head Island: it is warmest in July (up to 32 °C on average) and coolest in January (around 16 °C). The driest month is January.

Tickets are usually cheapest in September and most expensive in September. Compare prices and weather by month in the charts below to pick the best time to fly.

Temperature · Hilton Head Island

Dry and wet days · Hilton Head Island

Wind speed and direction · Hilton Head Island

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How to get the best deal on a Chicago — Hilton Head Island ticket

  • Book ahead: fares for Chicago — Hilton Head Island are usually lower 3–8 weeks before departure than at the last minute.
  • Play with your dates — Tuesday, Wednesday and Saturday departures are often cheaper than Friday and Sunday.
  • Chicago is served by more than one airport — compare fares and travel time to each before you book.
  • The cheapest month to fly to Hilton Head Island is usually September — plan your trip around it if your dates are flexible.
  • Compare direct and connecting flights: nonstop is faster, while a connection is sometimes noticeably cheaper.
  • Watch the low-price calendar and the monthly price trend on this page — they make it easier to catch a good date.
  • Travelling light? Pick a cabin-baggage-only fare — tickets without checked luggage are noticeably cheaper.
  • Get to the airport in good time — about 2–3 hours before an international departure and roughly an hour before a domestic one.

Airlines

Flights on the Chicago — Hilton Head Island route are operated by 2 airlines; United Airlines runs the most flights (around 56% of all flights). Compare carriers, flight shares and schedules below.

  • United AirlinesUA
    5x/week
    WebsiteFleet: 956165M pax/year
    • Direct flight ORD → HHH5x/week
      Duration
      2h 38m
      Days
      MTWTFSS
    56.0%Open →
  • American AirlinesAA
    4x/week
    WebsiteFleet: 965211M pax/year
    • Direct flight ORD → HHH4x/week
      Duration
      2h 24m
      Days
      MTWTFSS
    44.0%Open →

Cities and airports on the Chicago — Hilton Head Island route

Flights Chicago — Hilton Head Island depart from O'Hare International Airport, Chicago Midway International Airport, Midway International Airport and Chicago Rockford International Airport and arrive at Hilton Head Airport. Below are pages for the cities, countries, and airports on the route: airlines, schedules, and travel guides.

Departure

Chicago

CHI
United States
About the cityHow to get thereWeatherAll about the country United States
Arrival

Hilton Head Island

HHH
United States
About the cityHow to get thereWeatherAll about the country United States
Departure airports
Arrival airports

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Frequently asked questions about the Chicago — Hilton Head Island flight

How long is the flight from Chicago to Hilton Head Island?

A nonstop Chicago — Hilton Head Island flight takes about 2 h 33 min — the distance between the cities is around 1,233 km.

How far is it from Chicago to Hilton Head Island?

The distance from Chicago to Hilton Head Island is about 1,233 km, which a nonstop flight covers in around 2 h 33 min.

Are there direct flights from Chicago to Hilton Head Island?

Yes, there are nonstop flights Chicago — Hilton Head Island — around 25 flights per week.

Which airlines fly from Chicago to Hilton Head Island?

Airlines operating Chicago — Hilton Head Island include United Airlines, American Airlines. See the full list with schedules in the "Airlines" section on this page.

Which airports do Chicago — Hilton Head Island flights use?

Flights from Chicago depart from O'Hare International Airport, Chicago Midway International Airport, Midway International Airport, and arrive at Hilton Head Airport. If a city has more than one airport, check which one your ticket uses before you travel.

How much is a ticket from Chicago to Hilton Head Island?

The price of a Chicago — Hilton Head Island ticket depends on your travel date, season and demand: it is usually cheapest to fly in September, and most expensive in September. Check the current lowest fare and low-price calendar on this page.

When is the best time to book flights Chicago — Hilton Head Island?

Flights Chicago — Hilton Head Island are usually cheaper when booked in advance — a few weeks before departure and away from peak dates; the most budget-friendly month to fly is September. Compare prices by month in the price trend chart on this page.

How can I find the cheapest flights from Chicago to Hilton Head Island?

To catch a low fare Chicago — Hilton Head Island, book a few weeks in advance, keep your dates flexible, and compare airlines and connecting options. The low-price calendar and monthly price chart on this page show the cheapest days and months at a glance: the most budget-friendly month to fly is usually September.

How early should I arrive at the airport?

For international flights, plan to be at the airport about 2–3 hours before departure, and around an hour before a domestic flight. Allow extra time during busy travel seasons and at large hubs, where check-in and security lines can be longer.

Where else you can fly from Chicago

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Where else you can fly from Hilton Head Island

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New York CityAtlantaCharlotteWashington, D.C.PhiladelphiaBostonOrlandoGreensboroTampaWest Palm BeachBirminghamHuntsvilleSarasotaLexingtonRoanokeMobileMiamiPensacolaEvansvilleMontgomeryJacksonManhattanDothan

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