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$134+ 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 2/27. Fares are subject to change and may not be available on all flights or dates of travel.
HHH — CHI
Feb 28 — Mar 71
Sat 2/28
Sat 3/7
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 January 29, 2026.

This American Airlines deal was found by Cheapflights users on 1/28. 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 2/1211:03 am
HHH
-
ORD
1 stop5h 18m
American Airlines
Mon 2/165:00 am
ORD
-
HHH
1 stop4h 33m
American Airlines
Deal found 1/28$257
This American Airlines deal was found by Cheapflights users on 1/27. 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 2/33:29 pm
HHH
-
ORD
1 stop5h 21m
American Airlines
Tue 2/106:05 am
ORD
-
HHH
1 stop5h 15m
American Airlines
Deal found 1/27$312
This American Airlines deal was found by Cheapflights users on 1/28. 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 2/512:51 pm
HHH
-
ORD
2 stops10h 43m
American Airlines
Sun 2/810:10 am
ORD
-
HHH
1 stop3h 49m
American Airlines
Deal found 1/28$332
This American Airlines deal was found by Cheapflights users on 1/27. 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 2/1112:51 pm
HHH
-
ORD
1 stop6h 10m
American Airlines
Sat 2/1410:28 am
ORD
-
HHH
1 stop6h 16m
American Airlines
Deal found 1/27$333
This American Airlines deal was found by Cheapflights users on 1/27. 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.
Sun 2/13:29 pm
HHH
-
ORD
1 stop5h 21m
American Airlines
Sat 2/76:05 am
ORD
-
HHH
1 stop5h 15m
American Airlines
Deal found 1/27$417

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 January 29, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$257
(American Airlines)

One-way from

$134
(American Airlines)
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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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 January 29, 2026.
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

Thu 2/12

11:03 am-3:21 pm

1 stop5h 18m

Chicago O'Hare Intl

Mon 2/16

5:00 am-10:33 am

1 stop4h 33m

$257

Hilton Head IslandChicago

HHH - ORD

HHHORD

Hilton Head Island

Wed 2/11

12:51 pm-6:01 pm

1 stop6h 10m

Chicago O'Hare Intl

Sat 2/14

10:28 am-5:44 pm

1 stop6h 16m

$333

Hilton Head IslandChicago

HHH - ORD

HHHORD

Hilton Head Island

Sun 6/14

2:01 pm-3:38 pm

Nonstop2h 37m

Chicago O'Hare Intl

Sat 6/20

8:15 am-11:40 am

Nonstop2h 25m

$434

Hilton Head IslandChicago

HHH - ORD

HHHORD

Hilton Head Island

Mon 2/9

12:51 pm-6:01 pm

1 stop6h 10m

Chicago O'Hare Intl

Fri 2/13

6:35 pm-10:33 am

1 stop14h 58m

$779

Hilton Head IslandChicago

HHH - ORD

HHHORD

Hilton Head Island

Thu 7/23

3:00 pm-4:45 pm

Nonstop2h 45m

Chicago O'Hare Intl

Mon 7/27

10:35 am-2:01 pm

Nonstop2h 26m

$953

Hilton Head IslandChicago

HHH - ORD

HHHORD

Hilton Head Island

Tue 4/28

4:00 pm-4:42 pm

1 stop25h 42m

$191

Hilton Head IslandChicago

HHH - ORD

HHHORD

Hilton Head Island

Thu 4/23

4:00 pm-7:58 am

1 stop16h 58m

$191

Hilton Head IslandChicago

HHH - ORD

HHHORD

Hilton Head Island

Fri 4/24

4:00 pm-1:37 pm

1 stop22h 37m

$191

Hilton Head IslandChicago

HHH - ORD

HHHORD

Hilton Head Island

Mon 7/27

4:00 pm-9:09 am

1 stop18h 09m

$196

Hilton Head IslandChicago

HHH - ORD

HHHORD

Hilton Head Island

Tue 7/28

4:00 pm-7:22 pm

1 stop28h 22m

$196

Flights are sorted by cheapest round-trip flights first.

Deals found on 1/27

Showing 1-10 of 14 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 January.
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 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.

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 January 29, 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
7.2
Good
11,206 reviews

Boarding

7.5

Comfort

7.2

Crew

8.0

Entertainment

6.9

Overall

7.2

Food

6.4

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
11,206 reviews
American Airlines
7.2
Good
11,206 reviews

Boarding

7.5

Comfort

7.2

Crew

8.0

Entertainment

6.9

Overall

7.2

Food

6.4

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. 0 airlines have 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 5h 18m. Your travel time can differ by up to . There are 781 mi between Hilton Head Island and 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

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