Cheap flights from Chicago to Hilton Head Island from $229
This is the cheapest round-trip flight price found by a momondo user in the last 72 hours by searching for a flight from Chicago to Hilton Head Island departing on 8/12. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.
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American Airlines flights from Chicago to Hilton Head Island
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United Airlines flights from Chicago to Hilton Head Island
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How to get the cheapest flight ticket from Chicago to Hilton Head Island
Look no further. We've gone through all the searches for this route on momondo so you have the important information and insights to find the cheapest flight ticket for your trip
What is the cheapest month to fly to Hilton Head Island?
If you don’t want to visit Hilton Head Island in August, then you should wait until January to fly from Chicago, when ticket prices are also cheap, with an average price of $328.
What is the cheapest day to depart on your flight to Hilton Head Island?
The cheapest day to depart from Chicago to Hilton Head Island is on a Tuesday. Travelers who choose to depart for Hilton Head Island on a Tuesday will often find tickets for as low as $361. On the other hand, Saturday is the most expensive day to depart from Chicago because it is more convenient for both business and leisure travelers. As a result, prices tend to be around $537.
What is the cheapest Chicago to Hilton Head Island flight route?
Fly from Chicago O'Hare Intl to Hilton Head Island for the best Chicago - Hilton Head Island flight prices
How far in advance should I book a flight to Hilton Head Island?
You are more likely to see cheaper flights to Hilton Head Island from Chicago when booking weeks ahead of your departure date. In general, you can expect to find flights to Hilton Head Island for around $428 when searching weeks out. However, flight prices might be lower outside of this timeframe. For example, people recently found flights to Hilton Head Island from Chicago for as low as $350 on momondo.
What cabin class options are available on Chicago to Hilton Head Island flights?
There are 1 cabin classes available to choose from on Chicago to Hilton Head Island flights. Cabin price and availability will vary by airline so perform a search above to find the right deals for you.
Can stopping save me money on Chicago to Hilton Head Island flights?
You could potentially save up to 59% on your flight if you consider stops on a Chicago to Hilton Head Island flight.
What is the cheapest airline that flies from Chicago to Hilton Head Island?
Delta, United Airlines, and American Airlines are the most popular carriers operating from Chicago to Hilton Head Island
What airlines fly to Hilton Head Island?
United Airlines, American Airlines and Southwest are the top three most popular airlines that fly to Hilton Head Island from Chicago according to our data. United Airlines is the first choice among our users, with 55% of people opting to fly with this airline when traveling to Hilton Head Island. Keep in mind that there are 6 different airlines that fly to Hilton Head Island on a routine basis, so you have a few additional options to choose from.
When to book flights from Chicago to Hilton Head Island
Cheap Chicago to Hilton Head Island (CHI to HHH) flight deals and tips
Find info about flight duration, direct flights, and airports for your flight from Chicago to Hilton Head Island
Best Price Found | $234 |
|---|---|
Fastest flight time | 2h 20m |
Direct flights | Sun |
Airports in Hilton Head Island | 1 airport |
How far is Chicago to Hilton Head Island by plane?
There are 766.4 mi between Chicago and Hilton Head Island. By plane, this route typically takes 2h 20m.
When did momondo last update prices for flights from Chicago to Hilton Head Island Airport?
Prices for flights from Chicago to Hilton Head Island Airport are updated daily.
How many operators does momondo search for flights from Chicago to Hilton Head Island Airport?
The number of operators available for flights from Chicago to Hilton Head Island Airport is 2 as of July 2025.
How old do you have to be to fly from Chicago to Hilton Head Island Airport?
Although the minimum age for a child to fly alone is five, airlines that offer an unaccompanied minor (UMNR) service may have their own age limits, which could be impacted by factors such as flight length, timing, and layovers. It is recommended that you verify with the airline you are booking with for travel from Chicago to Hilton Head Island Airport.
What documentation or ID do you need to fly to Hilton Head Island Airport?
The travel and health documents you'll need for your trip to Hilton Head Island Airport may differ based on your itinerary and personal situation. Typically, you should have several documents on hand, such as a national ID card or driver's license and a passport that is valid for six months after your intended arrival at Hilton Head Island Airport. It is always advisable to seek advice from your airline or a trusted third party, such as IATA.
What is the most popular plane model from Chicago to Hilton Head Island?
momondo data reveals that the most frequently booked plane model on the route from Chicago to Hilton Head Island is Embraer 170, representing 39.13% of all bookings. The subsequent popular models are Embraer 175 (Enhanced Winglets) at 32.61%, Airbus A319 at 8.70%, and Embraer 175 at 6.52%.
What is the most popular airline from Chicago to Hilton Head Island?
Based on momondo bookings for this flight route, the most popular airline on flight routes from Chicago to Hilton Head Island is American Airlines (78% of total bookings). The next most popular airlines are United Airlines (13%) and Delta (9%).
Best airlines flying from Chicago to Hilton Head Island
Compare and see reviews for airlines that fly from Chicago to Hilton Head Island with momondo
| Airline | Rating | Free Cancellation | Price | ||
|---|---|---|---|---|---|
| PriceFrom $239 | Free Cancellation | Rating 7.2 10,000 reviews | |||
| PriceFrom $273 | Free Cancellation | Rating 7.4 8,861 reviews |
Traveling to a place near Hilton Head Island?
Book flights to Hilton Head Island if you plan to visit one of these locationsWhy use momondo?
Why should I use momondo to find a flight deal from Chicago to Hilton Head Island?
Finding the right flight to Hilton Head Island from Chicago is quick and easy when you have a range of options in front of you, from reputable agents and recognisable airlines. Options that can then be filtered down to find the best fit. That is what momondo does. We make finding flights to Hilton Head Island quick and easy, saving you time and money.
Can I find flights from Chicago to Hilton Head Island with flexible booking policies on momondo?
Yes. momondo allows you to filter the results for Chicago to Hilton Head Island flights to just show those with flexible booking policies.
How can momondo help me find flights from Chicago to Hilton Head Island?
momondo helps you find the best flight between Chicago and Hilton Head Island by providing filters to narrow your choice of flights to those matching your criteria. You can select flights based on numerous factors such as price, departure and landing times, airport and airline.
I’m not ready to book a flight from Chicago to Hilton Head Island right now. Can momondo alert me if prices change?
Yes. momondo can track prices for Chicago to Hilton Head Island flights and alert you when they change. Perform a search to set up the price alert. All that is required is a valid email address.