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This weekend's flight prices found within the past 7 days, for the period specified. Prices and availability are subject to change. Additional terms apply.

Fares from $83 One Way, $157 Round Trip from Hilton Head to Chicago

Prices starting at $157 for return flights and $83 for one-way flights to Chicago were the cheapest prices found within the past 7 days, for the period specified. Prices and availability are subject to change. Additional terms apply.

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More About Flying To Chicago from Hilton Head

Route Information for Flights from Hilton Head to Chicago

Origin Airport IATA CodeSAV
Destination Airport IATA CodeCHI
Distance773 mi
Direct Flight AirlinesAmerican Airlines, Qatar Airways, Air Canada, Air New Zealand, United Airlines
Earliest Flight Arrival5:28PM UTC
Latest Flight Arrival10:53PM UTC

Flights Review

Dec 26, 2019

Seating was too crowded and close

Jan 12, 2019

Seats were not comfortable

Mar 15, 2018

We are really really upset about the 2 hour delay on the return flight from Savanna, which caused us to miss our connector from Chicago to Duluth. United put us up on squeaky, shaky cots in a hallway at the airport with 70 others. We heard loud announcements and reminders over the PA system all night, in a brightly light hallway, then were rousted out at 4 am so vendors and others could use the hallway. What a really rough, unpleasant experience. Wow. We landed in Duluth 12 hours after we were due here. Delays in Savanna were never explained to us, we were switched on planes, and we watched for 35 minutes waiting to refuel. We missed our connector by about 15 minutes. Bad news.

Feb 16, 2018

United staff at all levels very polite and helpful going out of their way to ensure everyone a comfortable flight, which was especially helpful to me as a senior citizen

Hilton Head to Chicago

Score low fares on flights from Hilton Head to Chicago with Orbitz. We make it easier than ever to find cheap Hilton Head to Chicago flights with our cutting-edge mobile tools and mobile website.

Book Discount Flights From Hilton Head to Chicago in Minutes

If you are looking for low cost Hilton Head to Chicago flights, just skip all of the other so-called bargain travel sites, because Orbitz offers guaranteed low fares. That means you don't have to constantly scan multiple sites and hover like a vulture at your computer, hoping to score better deals through last-minute sales.

Find Bargain Hilton Head to Chicago Flights With Our Convenient Tools

You benefit from more than just cheap flights from Hilton Head to Chicago. Orbitz is a convenient one-stop trip planner. Research weather, attractions, and transportation options for Chicago to help you plan your trip and decide what to pack and where to go.

Booking domestic or international air fare and accommodations with Orbitz is a snap. Use your iPad, iPhone or Android device to find discount flights from Hilton Head to Chicago even while on the move, and sign up for instant email and text alerts to stay up-to-date on any delays affecting your flight. Or access via your mobile device’s Web browser.

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Flights from Hilton Head to Chicago - Frequently Asked Questions

Are there non-stop flights from Hilton Head to Chicago?

United Airlines and American Airlines fly direct from Hilton Head Island, SC (HHH) to Chicago, IL (ORD-O'Hare Intl.), which means you won't need to worry about changing planes or being bored during a stopover.

What is the shortest flight from Hilton Head to Chicago?

The journey from Hilton Head to Chicago can be as quick as 2 hours and 20 minutes. With a short and sweet flight time like this, why not book an impromptu getaway?

What airlines fly from Hilton Head (and vicinity) to Chicago (and vicinity) most frequently?

If you're looking for the airline that offers the most flights from Hilton Head (and vicinity) to Chicago (and vicinity), American Airlines is the top pick. This popular airline operates 4 flights along this route every month.

If I am not able to travel due to COVID-19, can I cancel my flight to Chicago?

We get that traveling right now has its challenges, so it's good to know that many reservations booked through us are able to be cancelled or changed. If your travel plans to Chicago have been affected by COVID-19, a lot of airlines are making things easier by offering credits to use at a later date. Just sign in to your account and you'll quickly see what options are available. Our Customer Service Portal is the place to go for more information.

Are there flights to Chicago with flexible change policies?

In most cases you'll have the option to reschedule your flight to Chicago without a change fee. All you have to do then is pay the difference between the old flight and the new one. Look for the "no change fees" filter and book with confidence.

What is the cheapest day of the week to fly?

Consider flying out early in the week to save on your airfare. Orbitz data from 2019 shows that Tuesday is the cheapest day to depart, followed by Monday. Saturday showed the highest average ticket prices likely because many travelers prefer to start their vacation on a weekend.

What is the cheapest month to fly?

We won't keep you guessing, according to Orbitz data the cheapest month to fly is February. Perfect for those who need a weekend getaway, or just a fresh start to the new year. Be aware that the most expensive time to fly isn't the height of summer, as most people assume, but the festive month of December.

How can I save money on flights?

To really save big on your next vacation, think outside the box. Select two different airlines or fare types for your return trip and you'll generally get a much better deal. Those who tried this on Orbitz in 2019 saved over 50% on their airfares. Get mixing and matching today!

*According to flight demand on from January to December 2019. Savings are subject to change based on departure location, date and destination.

^Savings based on all package bookings with Flight + Hotel made on from January 1, 2019 to December 31, 2019 as compared to the price of the same components booked separately. Savings will vary based on origin/destination, length of trip, stay dates and selected travel supplier(s). Savings not available on all packages.