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$259+ 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 8/20. Fares are subject to change and may not be available on all flights or dates of travel.
HHH — CHI
Sep 1 — Sep 81
Tue 9/1
Tue 9/8
1 adult, Economy
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Cheap 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 August 2, 2026.

This United Airlines deal was found by Cheapflights users on 7/29. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/42:58 pm
HHH
-
ORD
Nonstop3h 17m
United Airlines
Mon 9/710:25 am
ORD
-
HHH
Nonstop2h 38m
United Airlines
Deal found 7/29$279
This American Airlines deal was found by Cheapflights users on 7/29. 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.
Fri 9/43:27 pm
HHH
-
ORD
1 stop7h 30m
American Airlines
Mon 9/79:53 am
ORD
-
HHH
Nonstop2h 24m
American Airlines
Deal found 7/29$289
This American Airlines deal was found by Cheapflights users on 7/31. 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.
Mon 9/1411:07 am
HHH
-
ORD
1 stop7h 21m
American Airlines
Mon 9/216:29 am
ORD
-
HHH
1 stop4h 46m
American Airlines
Deal found 7/31$297
This Delta deal was found by Cheapflights users on 7/31. 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.
Wed 8/2612:15 pm
HHH
-
ORD
2 stops9h 34m
Delta
Tue 9/18:05 am
ORD
-
HHH
1 stop6h 27m
Delta
Deal found 7/31$304
This American Airlines deal was found by Cheapflights users on 7/28. 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 8/131:52 pm
HHH
-
ORD
Nonstop2h 38m
American Airlines
Tue 8/186:49 am
ORD
-
HHH
1 stop7h 08m
American Airlines
Deal found 7/28$309
This United Airlines deal was found by Cheapflights users on 7/28. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 8/302:58 pm
HHH
-
ORD
Nonstop3h 17m
United Airlines
Sun 9/610:25 am
ORD
-
HHH
Nonstop2h 38m
United Airlines
Deal found 7/28$314
This American Airlines deal was found by Cheapflights users on 7/28. 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 8/1310:57 am
HHH
-
ORD
1 stop7h 17m
American Airlines
Sat 8/158:51 am
ORD
-
HHH
Nonstop2h 24m
American Airlines
Deal found 7/28$329
This American Airlines deal was found by Cheapflights users on 7/28. 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 8/1410:57 am
HHH
-
ORD
1 stop7h 17m
American Airlines
Sun 8/166:49 am
ORD
-
HHH
1 stop6h 27m
American Airlines
Deal found 7/28$339
This American Airlines deal was found by Cheapflights users on 8/2. 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 8/121:52 pm
HHH
-
ORD
Nonstop2h 38m
American Airlines
Wed 8/199:53 am
ORD
-
HHH
Nonstop2h 24m
American Airlines
Deal found 8/2$354

Find 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 August 2, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$279
(United Airlines)

One-way from

$259
(United Airlines)

Good round-trip deal

$279 or less

Good one-way deal

$280 or less
Provider with most accurate pricing for Hilton Head Island-Chicago (CHI) flight deals.
Search Deals
Provider most trusted by Cheapflights users for Hilton Head Island-Chicago (CHI) flights.
Search Deals
From Hilton Head Island to Chicago (CHI)
Search Deals
One-way flight from Hilton Head Island to Chicago (CHI)
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Price to beat on a round-trip flight from Hilton Head Island to Chicago (CHI).
Search Deals
Price to beat on a one-way flight from Hilton Head Island to Chicago (CHI).
Search Deals

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 August 2, 2026.
Use the filters below to find and compare flights from Hilton Head Island to Chicago that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip

Hilton Head IslandChicago

HHH - ORD

HHHORD

Hilton Head Island

Thu 8/27

2:58 pm-5:15 pm

Nonstop3h 17m

Chicago O'Hare Intl

Tue 9/1

10:25 am-2:03 pm

Nonstop2h 38m

$279

Hilton Head IslandChicago

HHH - ORD

HHHORD

Hilton Head Island

Fri 9/4

2:58 pm-5:15 pm

Nonstop3h 17m

Chicago O'Hare Intl

Mon 9/7

10:25 am-2:03 pm

Nonstop2h 38m

$279

Hilton Head IslandChicago

HHH - ORD

HHHORD

Hilton Head Island

Thu 8/27

12:15 pm-4:51 pm

1 stop5h 36m

Chicago O'Hare Intl

Tue 9/1

6:00 am-3:32 pm

2 stops8h 32m

$304

Hilton Head IslandChicago

HHH - ORD

HHHORD

Hilton Head Island

Wed 8/26

12:15 pm-8:49 pm

2 stops9h 34m

Chicago O'Hare Intl

Tue 9/1

6:00 am-3:32 pm

2 stops8h 32m

$309
Quickest round-trip

Hilton Head IslandChicago

HHH - ORD

HHHORD

Hilton Head Island

Wed 8/12

1:52 pm-3:30 pm

Nonstop2h 38m

Chicago O'Hare Intl

Wed 8/19

9:53 am-1:17 pm

Nonstop2h 24m

$354

Hilton Head IslandChicago

HHH - ORD

HHHORD

Hilton Head Island

Fri 8/14

12:15 pm-6:49 pm

1 stop7h 34m

Chicago O'Hare Intl

Wed 8/19

6:00 am-3:32 pm

2 stops8h 32m

$354

Hilton Head IslandChicago

HHH - ORD

HHHORD

Hilton Head Island

Fri 8/28

2:58 pm-5:15 pm

Nonstop3h 17m

Chicago O'Hare Intl

Tue 9/1

10:25 am-2:03 pm

Nonstop2h 38m

$359

Hilton Head IslandChicago

HHH - ORD

HHHORD

Hilton Head Island

Fri 8/28

3:27 pm-9:57 pm

1 stop7h 30m

Chicago O'Hare Intl

Tue 9/1

9:53 am-1:17 pm

Nonstop2h 24m

$369

Hilton Head IslandChicago

HHH - ORD

HHHORD

Hilton Head Island

Wed 8/12

12:15 pm-8:49 pm

2 stops9h 34m

Chicago O'Hare Intl

Wed 8/19

8:05 am-3:32 pm

1 stop6h 27m

$379
Cheapest one-way
Quickest one-way

Hilton Head IslandChicago

HHH - ORD

HHHORD

Hilton Head Island

Mon 9/14

2:48 pm-5:05 pm

Nonstop3h 17m

$259

Flights are sorted by cheapest round-trip flights first.

Deals found on 7/30

Showing 1-10 of 17 resultsSorted by cheapest first
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 August.
ProviderPrice AccuracyTrust Score*
ExpediaPrice Accuracy1 starTrust Score*3 stars
FlightHubPrice 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 FlightHub to be most consistent on Cheapflights vs. FlightHub Users can find the same prices on Hilton Head Island-Chicago flight deals on Cheapflights vs. FlightHub >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 FlightHub the most. FlightHub 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 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 August 2, 2026.

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.

Weekly flight availability from Hilton Head Island to Chicago

Explore weekly flight availability from Hilton Head Island to Chicago. Discover flights operating on different days of the week, giving you the flexibility to choose a travel day that best fits your plans. Compare info to find the most convenient option for your journey. Data last updated August 2, 2026.

The most flights from HHH to CHI are scheduled on a Monday (2 on average). You will have fewer flight options on Wednesday, which is when the least amount of flights are scheduled (1 on average).

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 August 2, 2026.
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
7.1
Good
11,845 reviews

Crew

7.9

Overall

7.1

Comfort

7.2

Entertainment

6.8

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
7.1
Good
11,845 reviews
American Airlines
7.1
Good
11,845 reviews

Crew

7.9

Overall

7.1

Comfort

7.2

Entertainment

6.8

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 1 outbound flight 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?

    United Airlines and Delta can get you from Hilton Head Island to Chicago in just under 3h 17m. Your travel time can differ by up to 2h 19m. There are 781 mi between Hilton Head Island and Chicago. When browsing for deals, the options you’ll see will be for both nonstop flights and flights with stops.

  • What is the cheapest airline to fly from Hilton Head Island to Chicago round-trip?

    Cheapflights users have booked flights from Hilton Head Island to Chicago round-trip from $229.

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

    Consider United Airlines (72%), Envoy Air (66%) or Republic Airways (36%) when booking your flight. These represent the most reliable airlines when flying from Hilton Head Island to Chicago.

  • What are the cheapest flights from Hilton Head Island to Chicago?

    While on average a flight from Hilton Head Island to Chicago is generally $390, our data shows the cheapest flight currently is $263. When looking at the most popular route, (Hilton Head Island - Chicago O'Hare Intl), you can expect to pay $279 for that flight.

  • 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.

See more FAQs

Traveling to a place near Chicago?

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

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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 August 2, 2026.
AirlineCheapestAverageFlexibilityOn-time
United AirlinesCheapest$229Average$355FlexibilityNo cancel feeOn-time69%

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