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$223+ 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 1/26. Fares are subject to change and may not be available on all flights or dates of travel.
HHH — CHI
Nov 29 — Dec 61
Sat 11/29
Sat 12/6
1 adult, Economy
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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 October 30, 2025.

This American Airlines deal was found by Cheapflights users on 10/30. 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.
Sat 11/156:48 pmHHH - ORD
1 stop6h 10mAmerican Airlines
Wed 11/196:46 amORD - HHH
1 stop4h 43mAmerican Airlines
Deal found 10/30$369
This American Airlines deal was found by Cheapflights users on 10/30. 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.
Sat 11/1512:38 pmHHH - ORD
1 stop5h 15mAmerican Airlines
Sun 11/167:10 amORD - HHH
1 stop6h 09mAmerican Airlines
Deal found 10/30$397
This American Airlines deal was found by Cheapflights users on 10/29. 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 11/193:27 pmHHH - ORD
2 stops8h 06mAmerican Airlines
Sun 11/236:07 amORD - HHH
2 stops7h 12mAmerican Airlines
Deal found 10/29$407
This American Airlines deal was found by Cheapflights users on 10/29. 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.
Thu 11/132:51 pmHHH - ORD
1 stop5h 27mAmerican Airlines
Mon 11/178:20 amORD - HHH
1 stop5h 37mAmerican Airlines
Deal found 10/29$425
This American Airlines deal was found by Cheapflights users on 10/30. 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.
Thu 12/1811:14 amHHH - ORD
1 stop5h 51mAmerican Airlines
Sat 12/205:00 amORD - HHH
1 stop4h 44mAmerican Airlines
Deal found 10/30$427
This American Airlines deal was found by Cheapflights users on 10/30. 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 11/141:02 pmHHH - ORD
1 stop7h 24mAmerican Airlines
Sun 11/168:20 amORD - HHH
1 stop4h 59mAmerican Airlines
Deal found 10/30$495

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 October 30, 2025.

Most accurate provider

eDreams
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$369
(American Airlines)

One-way from

$223
(American Airlines)
Provider with most accurate pricing for Hilton Head Island-Chicago (CHI) flight deals.
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Provider most trusted by Cheapflights users for Hilton Head Island-Chicago (CHI) flights.
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From Hilton Head Island to Chicago (CHI)
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One-way flight from Hilton Head Island to Chicago (CHI)
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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 October 30, 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

Sat 11/15

6:48 pm-11:58 pm

1 stop6h 10m

Chicago O'Hare Intl

Wed 11/19

6:46 am-12:29 pm

1 stop4h 43m

$369

Hilton Head IslandChicago

HHH - ORD

HHHORD

Hilton Head Island

Wed 11/19

3:27 pm-7:18 pm

1 stop4h 51m

Chicago O'Hare Intl

Sun 11/23

8:20 am-2:19 pm

1 stop4h 59m

$397

Hilton Head IslandChicago

HHH - ORD

HHHORD

Hilton Head Island

Sat 11/15

12:38 pm-4:53 pm

1 stop5h 15m

Chicago O'Hare Intl

Sun 11/16

7:10 am-2:19 pm

1 stop6h 09m

$397

Hilton Head IslandChicago

HHH - ORD

HHHORD

Hilton Head Island

Thu 12/18

11:14 am-4:05 pm

1 stop5h 51m

Chicago O'Hare Intl

Sat 12/20

5:00 am-10:44 am

1 stop4h 44m

$427

Hilton Head IslandChicago

HHH - ORD

HHHORD

Hilton Head Island

Thu 11/13

2:51 pm-7:18 pm

1 stop5h 27m

Chicago O'Hare Intl

Mon 11/17

6:06 am-2:57 pm

2 stops7h 51m

$430

Hilton Head IslandChicago

HHH - ORD

HHHORD

Hilton Head Island

Thu 11/13

11:28 am-3:18 pm

1 stop4h 50m

Chicago O'Hare Intl

Sun 11/16

7:10 am-2:19 pm

1 stop6h 09m

$495

Hilton Head IslandChicago

HHH - ORD

HHHORD

Hilton Head Island

Mon 1/26

12:51 pm-10:51 am

2 stops23h 00m

$223

Hilton Head IslandChicago

HHH - ORD

HHHORD

Hilton Head Island

Tue 1/27

3:29 pm-10:50 am

2 stops20h 21m

$223

Hilton Head IslandChicago

HHH - ORD

HHHORD

Hilton Head Island

Wed 1/28

3:29 pm-10:50 am

2 stops20h 21m

$223

Hilton Head IslandChicago

HHH - ORD

HHHORD

Hilton Head Island

Tue 12/2

7:07 pm-8:47 am

2 stops14h 40m

$234

Flights are sorted by cheapest round-trip flights first.

Deals found on 10/29

Showing 1-10 of 13 results
1
2

Compare providers for flights from Hilton Head Island to Chicago

Provider information is updated monthly. Please note that these providers often have deals for this flight, but the availability may vary on a day-by-day basis on Cheapflights.
Use the table below to compare price accuracy, trust ratings, and cancellation policies for each provider offering flight deals from Hilton Head Island to Chicago in October.
ProviderPrice AccuracyTrust Score*
ExpediaPrice Accuracy2 starsTrust Score*3 stars
FlightHubPrice Accuracy3 starsTrust Score*1 star
eDreamsPrice Accuracy3 starsTrust Score*3 stars

*The Trust Score is based on feedback from users after their booking experience. It measures overall satisfaction, helping us identify issues like hidden fees, problems during the ticketing process, and the quality of customer service. This score is our best indicator of the provider's quality and reliability.

  • Most accurate provider: When it comes to deals on Hilton Head Island-Chicago flights, users find the pricing of eDreams to be most consistent on Cheapflights vs. eDreams Users can find the same prices on Hilton Head Island-Chicago flight deals on Cheapflights vs. eDreams >95% of the time. Price accuracy is based on data collected from Hilton Head Island-Chicago flight searches over the past month and is updated monthly.
  • Most trusted provider: When it comes to deals on Hilton Head Island-Chicago flights, Cheapflights users trust eDreams the most. eDreams has received a user feedback score of 3 out of 3 stars (3 being the best), meaning they have been trusted the most by Cheapflights users looking for Hilton Head Island-Chicago flight deals. Provider user feedback score is based on Cheapflights searches over the past month and is updated monthly.

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, April is the cheapest month in which you can book a flight from Hilton Head Island to Chicago (average of $76). Flying from Hilton Head Island to Chicago in January is currently the most expensive (average of $278). 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 October 30, 2025.

When flying from Hilton Head Island to Chicago, the time of day you decide to fly out makes little to no difference towards the overall price you’ll pay on tickets.

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 (83%), Qatar Airways (83%) or Envoy Air (83%) 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, April is the cheapest month in which you can book a flight from Hilton Head Island to Chicago (average of $76). Flying from Hilton Head Island to Chicago in January is currently the most expensive (average of $278). 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
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Alternative routes for Hilton Head Island to Chicago

See prices for flight routes from nearby airports that may be better suited for you.
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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 October 30, 2025.
AirlineCheapestAverageFlexibilityOn-time
American AirlinesCheapest$228Average$308FlexibilityNo cancel feeOn-time71%

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