HomeSearch by dateVacation packagesHotelsFlight dealsCar rentalTravel tips & news
Chicago

$218+ Cheap flights from Hilton Head Island (HHH) to Chicago (CHI)

This is the cheapest one-way flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 11/14. Fares are subject to change and may not be available on all flights or dates of travel.
HHH — CHI
Oct 15 — Oct 221
Wed 10/15
Wed 10/22
1 adult, Economy
We work with more than 300 partners to bring you better travel deals

Find cheap flights from Hilton Head Island to Chicago with Cheapflights

1. Tell us where you want to go

Enter your travel information like dates, passengers, trip type (one-way or round trip), and preferred cabin class then click “Find deals”

2. Select your favorite providers

We find the providers serving your travel needs. Choose up to four travel providers to compare side-by-side for flights, hotels, or car rentals.

3. Compare prices and book

Review each provider’s pricing and select the best option for you! Book through your favorite provider’s website for a seamless experience.

Cheap flight deals from Hilton Head Island to Chicago

Discover tips and strategies to find the most affordable flight options for your journey from Hilton Head Island (HHH) to Chicago (CHI). Learn about various techniques such as flexible date searches, comparing prices across and setting up price alerts. Use these methods to find the cheapest flights available for your travel needs. Data last updated September 15, 2025.

Round-trip from

$309
(American Airlines)

One-way from

$218
(American Airlines)
From Hilton Head Island to Chicago (CHI)
Search Deals
One-way flight from Hilton Head Island to Chicago (CHI)
Search Deals

Find flight deals from Hilton Head Island to Chicago

Cheapest flights from Hilton Head Island to Chicago
Explore the most affordable flight options available from Hilton Head Island to Chicago. Find the lowest fares from popular airlines and budget airlines, with prices last updated on September 15, 2025.

This American Airlines deal was found by Cheapflights users on 9/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/312:52 pmHHH - ORD
1 stop6h 10mAmerican Airlines
Wed 12/106:45 amORD - HHH
1 stop7h 12mAmerican Airlines
Deal found 9/14$309
This Delta deal was found by Cheapflights users on 9/13. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/194:05 pmHHH - ORD
1 stop7h 18mDelta
Mon 9/229:50 amORD - HHH
1 stop4h 35mDelta
Deal found 9/13$324
This American Airlines deal was found by Cheapflights users on 9/15. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/305:20 pmHHH - ORD
1 stop4h 07mAmerican Airlines
Sat 10/411:26 amORD - HHH
1 stop6h 28mAmerican Airlines
Deal found 9/15$339
This American Airlines deal was found by Cheapflights users on 9/13. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/173:02 pmHHH - ORD
1 stop7h 22mAmerican Airlines
Mon 10/207:10 amORD - HHH
1 stop6h 22mAmerican Airlines
Deal found 9/13$363
This American Airlines deal was found by Cheapflights users on 9/13. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/1911:04 amHHH - ORD
1 stop7h 19mAmerican Airlines
Sun 9/215:00 amORD - HHH
1 stop5h 30mAmerican Airlines
Deal found 9/13$395
This American Airlines deal was found by Cheapflights users on 9/13. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/195:20 pmHHH - ORD
2 stops7h 28mAmerican Airlines
Mon 9/227:00 amORD - HHH
2 stops6h 56mAmerican Airlines
Deal found 9/13$405

Cheapflights Fare Finder

 
Customize your flight search to find flights from Hilton Head Island to Chicago that fit within your specific budget. Explore options based on user searches and filter the results based on your desired price range. Find flights that match your budget for a cost-effective journey. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated September 15, 2025.
Use the filters below to find and compare flights from Hilton Head Island to Chicago that are best for you.

Fly from

Hilton Head Island

Fly to

Chicago

Route

Depart

Return

Price

Hilton Head IslandChicago

HHH - ORD

HHHORD

Hilton Head Island

Wed 12/3

12:52 pm-6:02 pm

1 stop6h 10m

Chicago O'Hare Intl

Wed 12/10

6:45 am-2:57 pm

1 stop7h 12m

$309

Hilton Head IslandChicago

HHH - ORD

HHHORD

Hilton Head Island

Tue 9/30

11:04 am-3:50 pm

1 stop5h 46m

Chicago O'Hare Intl

Sat 10/4

10:00 am-1:27 pm

Nonstop2h 27m

$329

Hilton Head IslandChicago

HHH - ORD

HHHORD

Hilton Head Island

Fri 10/17

3:02 pm-9:24 pm

1 stop7h 22m

Chicago O'Hare Intl

Mon 10/20

7:10 am-2:32 pm

1 stop6h 22m

$363

Hilton Head IslandChicago

HHH - ORD

HHHORD

Hilton Head Island

Fri 10/17

3:02 pm-9:24 pm

1 stop7h 22m

Chicago O'Hare Intl

Sun 10/19

5:22 am-11:32 am

1 stop5h 10m

$363

Hilton Head IslandChicago

HHH - ORD

HHHORD

Hilton Head Island

Fri 11/14

7:07 pm-10:49 am

2 stops16h 42m

$218

Hilton Head IslandChicago

HHH - ORD

HHHORD

Hilton Head Island

Wed 10/15

4:10 pm-9:43 am

2 stops18h 33m

$223

Hilton Head IslandChicago

HHH - ORD

HHHORD

Hilton Head Island

Wed 12/10

12:52 pm-7:20 am

2 stops19h 28m

$223

Hilton Head IslandChicago

HHH - ORD

HHHORD

Hilton Head Island

Mon 11/17

3:27 pm-7:45 am

2 stops17h 18m

$223

Hilton Head IslandChicago

HHH - ORD

HHHORD

Hilton Head Island

Tue 12/9

7:08 pm-7:50 am

2 stops13h 42m

$223

Hilton Head IslandChicago

HHH - ORD

HHHORD

Hilton Head Island

Tue 11/11

7:07 pm-12:18 pm

2 stops18h 11m

$223

Flights are sorted by cheapest round-trip flights first.

Deals found on 9/12

Showing 1-10 of 13 results
1
2

Best time to book a flight from Hilton Head Island to Chicago

Have a flexible travel schedule? Discover the best time to fly to Chicago from Hilton Head Island with our price prediction graph.
Estimated round-trip price
Rates are based on past data. Find the cheapest month and day to book your flight based on your travel requirements, then search for cheap deals.

Cheapflights Insights

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

What is the cheapest month to book a flight from Hilton Head Island to Chicago?

Currently, August is the cheapest month in which you can book a flight from Hilton Head Island to Chicago (average of $245). Flying from Hilton Head Island to Chicago in March is currently the most expensive (average of $321). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

What is the cheapest time of day to fly from HHH to CHI?

Find hourly flight availability from Hilton Head Island to Chicago. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated September 15, 2025.

When flying from Hilton Head Island to Chicago, the time of day you fly usually plays a role in the price. Save by searching for a flight in the morning, which can drop the price by up to 10% versus a flight at noon.

Reviews of airlines servicing Chicago

Get insights into the airlines that provide service to Chicago. Read reviews, discover amenities, and learn about the overall travel experience offered by airlines. Use this information to make informed decisions when choosing an airline for your flight to Chicago. Reviews last updated September 15, 2025.
See what other customers who have flown with American Airlines from Hilton Head Island to Chicago have to say. You can also see how each airline compares in terms of entertainment options, comfort, food, crew/service, and boarding process.
American Airlines
7.2
Good
10,000 reviews

Entertainment

6.9

Crew

8.0

Comfort

7.2

Overall

7.2

Food

6.4

Boarding

7.5

Reviews

1 / 20
2.0
Mediocre

Anonymous,Aug 2025

BNA - ORD

My flight was 8 hours delayed, so I missed my connecting flight to Dublin. I understand it’s not the staff’s fault but the lack of sympathy and apology was appalling. I had been sat in the airport since 4am until 3pm and they did not seem understanding. Not good. Need better customer service.
American Airlines
7.2
Good
10,000 reviews
American Airlines
7.2
Good
10,000 reviews

Entertainment

6.9

Crew

8.0

Comfort

7.2

Overall

7.2

Food

6.4

Boarding

7.5

Reviews

1 / 20
2.0
Mediocre

Anonymous,Aug 2025

BNA - ORD

My flight was 8 hours delayed, so I missed my connecting flight to Dublin. I understand it’s not the staff’s fault but the lack of sympathy and apology was appalling. I had been sat in the airport since 4am until 3pm and they did not seem understanding. Not good. Need better customer service.

Related info for your journey

Find useful and relevant information for your journey from Hilton Head Island to Chicago. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.

  • What airport do you fly from for flights from Hilton Head Island to Chicago?

    For a flight from Hilton Head Island to Chicago, you will be flying from Hilton Head. Hilton Head Island (HHH) is just 3.3 mi from the center of the city. Hilton Head is the only Hilton Head Island airport and it handles 0 outbound flights to Chicago per day. 1 airline has flights to Chicago from Hilton Head Island on a regular basis.

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

    American Airlines can get you from Hilton Head Island to Chicago in just under 6h 10m. Your travel time can differ by up to . There are 781 mi between Hilton Head Island and Chicago.

  • What are the most reliable airlines from Hilton Head Island to Chicago?

    Consider American Airlines (60%), Qatar Airways (60%) or Envoy Air (60%) when booking your flight. These represent the most reliable airlines when flying from Hilton Head Island to Chicago.

  • Can I find deals for flights from Hilton Head Island to Chicago that include hotel bookings?

    Yes. In addition to deals on Hilton Head Island to Chicago flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from Hilton Head Island to Chicago?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Hilton Head Island to Chicago.

  • Can I find deals for business class flights from Hilton Head Island to Chicago?

    Yes. Cheapflights offers flight deals from Hilton Head Island to Chicago by cabin class. In addition to browsing deals, you can also filter by cabin class on the search results page after making a search.

  • What is the cheapest month to book a flight from Hilton Head Island to Chicago?

    Currently, August is the cheapest month in which you can book a flight from Hilton Head Island to Chicago (average of $245). Flying from Hilton Head Island to Chicago in March is currently the most expensive (average of $321). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

See more FAQs

Traveling to a place near Chicago?

Book flights to Chicago if you plan to visit one of these locations
Merrillville
Lansing
Hammond
Benton Harbor
Porter
Chesterton

Browse thousands of different options on Cheapflights for your next trip

Toggle through the tabs below to find thousands of options on Cheapflights for your next trip.

Alternative routes for Hilton Head Island to Chicago

See prices for flight routes from nearby airports that may be better suited for you.
Charlotte to O'Hare Intl flights
Charleston to O'Hare Intl flights
Charlotte to Midway flights
Greenville to O'Hare Intl flights
Savannah to O'Hare Intl flights
Charleston to Midway flights
Columbia to O'Hare Intl flights
Myrtle Beach to O'Hare Intl flights
Charlotte to St. Louis flights
Myrtle Beach to Midway flights
Charleston to St. Louis flights
Greenville to Midway flights
Columbia to St. Louis flights
Columbia to Moline flights
Savannah to St. Louis flights
Savannah to Midway flights
Columbia to Midway flights
Columbia to Peoria flights
Augusta to Moline flights
Greenville to St. Louis flights
Charleston to Peoria flights
Augusta to St. Louis flights
Charlotte to Evansville flights
Savannah to Peoria flights
Columbia to Bloomington flights
Myrtle Beach to St. Louis flights
Hilton Head Island to O'Hare Intl flights
Greenville to Peoria flights
Charlotte to Moline flights
Myrtle Beach to Moline flights
Charleston to Moline flights
Charlotte to Peoria flights
Augusta to O'Hare Intl flights
Florence to O'Hare Intl flights
Columbia to Springfield flights
Greenville to Bloomington flights
Augusta to Midway flights
Charleston to Evansville flights
Myrtle Beach to Peoria flights
Charlotte to Bloomington flights
Greenville to Evansville flights
Augusta to Bloomington flights
Hilton Head Island to St. Louis flights
Charlotte to Dubuque flights
Columbia to Evansville flights
Charlotte to Champaign flights
Greenville to Moline flights
Greenville to Decatur flights
Charleston to Rockford flights
Columbia to Dubuque flights

Top airline flying from Hilton Head Island to Chicago

Discover the top airline that operate flights from Hilton Head Island to Chicago. Compare their services, reliability, and customer satisfaction ratings to choose the airline that best suits your travel preferences and needs. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated September 15, 2025.
AirlineCheapestAverageFlexibilityOn-time
American AirlinesCheapest$228Average$308FlexibilityNo cancel feeOn-time71%

100% Free

Cheapflights is completely free to use, so you can start saving the moment you arrive.

Book with Flexibility

Our users can plan ahead with confidence and find flights with no change fees

Travel Smart

Millions of people come to us for their flight needs every year. We help make travel planning easy by providing useful insights and data-driven graphs that can inform your decisions.