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 2h 45m. Your travel time can differ by up to 2h 59m. 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.

In terms of precipitation, rainfall in Chicago ranges from 1.7 - 4.9 inches per month. August is typically the wettest month, when rainfall can reach 4.9 in. January is typically the driest time to visit Chicago when rainfall is around 1.7 in.

If weather is an important factor for your trip to Chicago, use this chart to help with planning. For those seeking warmer temperatures, July is the ideal time of year to visit, when temperatures reach an average of 73.4 F. Travelers looking to avoid the cold should look outside of January, when temperatures are typically at their lowest (around 23.0 F).

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

Consider American Airlines (67%), Qatar Airways (67%) or Envoy Air (67%) when booking your flight. These represent the most reliable airlines when flying from Hilton Head Island to Chicago.

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

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.

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.

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.

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.

$215+ Flights from Hilton Head Island to Chicago

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1. Tell us where you want to go

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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 December 16, 2025.

Tue 12/302:46 pmHHH - ORD

1 stop5h 36mAmerican Airlines

Sat 1/35:00 amORD - HHH

1 stop4h 44mAmerican Airlines

Deal found 12/14

$526

Sun 12/2111:14 amHHH - ORD

1 stop5h 51mAmerican Airlines

Tue 12/235:00 amORD - HHH

1 stop4h 44mAmerican Airlines

Deal found 12/16

$742

Sun 12/212:46 pmHHH - ORD

1 stop5h 36mAmerican Airlines

Sat 12/275:00 amORD - HHH

1 stop4h 44mAmerican Airlines

Deal found 12/16

$785

Fri 12/196:13 pmHHH - ORD

1 stop5h 21mAmerican Airlines

Fri 12/265:00 amORD - HHH

1 stop4h 44mAmerican Airlines

Deal found 12/15

$839

Best flights from Hilton Head Island to Chicago
Discover carefully curated flight deals from Hilton Head Island to Chicago that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated December 16, 2025.

Wed 4/223:00 pmHHH - ORD

Nonstop2h 45mUnited Airlines

Wed 4/2910:35 amORD - HHH

Nonstop2h 26mUnited Airlines

Deal found 12/15

$249

Wed 4/2212:00 pmHHH - ORD

1 stop5h 44mDelta

Wed 4/299:30 amORD - HHH

1 stop4h 48mDelta

Deal found 12/15

$294

Wed 4/14:11 pmHHH - ORD

1 stop6h 11mAmerican Airlines

Wed 4/88:25 amORD - HHH

1 stop4h 55mAmerican Airlines

Deal found 12/16

$309

Wed 4/154:00 pmHHH - ORD

1 stop6h 48mDelta

Wed 4/227:10 amORD - HHH

1 stop7h 08mDelta

Deal found 12/15

$294

Wed 4/153:00 pmHHH - ORD

Nonstop2h 45mUnited Airlines

Wed 4/2210:35 amORD - HHH

Nonstop2h 26mUnited Airlines

Deal found 12/15

$297

Tue 2/1712:22 pmHHH - ORD

1 stop5h 17mAmerican Airlines

Tue 2/249:45 amORD - HHH

1 stop4h 20mAmerican Airlines

Deal found 12/16

$309

Sat 2/142:58 pmHHH - ORD

1 stop5h 50mAmerican Airlines

Tue 2/176:40 amORD - HHH

2 stops7h 25mAmerican Airlines

Deal found 12/15

$314

Sat 2/1411:02 amHHH - ORD

1 stop6h 04mAmerican Airlines

Sat 2/215:35 amORD - HHH

2 stops7h 52mAmerican Airlines

Deal found 12/16

$314

Last-minute flights from Hilton Head Island to Chicago
Discover last-minute flight deals from Hilton Head Island to Chicago. Data last updated December 16, 2025 and is based on user searches.

Fri 12/196:13 pmHHH - ORD

1 stop5h 21mAmerican Airlines

Fri 12/265:00 amORD - HHH

1 stop4h 44mAmerican Airlines

Deal found 12/15

$839

Sun 12/2111:14 amHHH - ORD

1 stop5h 51mAmerican Airlines

Tue 12/235:00 amORD - HHH

1 stop4h 44mAmerican Airlines

Deal found 12/16

$742

Sun 12/2111:14 amHHH - ORD

1 stop5h 51mAmerican Airlines

Sat 12/275:00 amORD - HHH

1 stop4h 44mAmerican Airlines

Deal found 12/15

$785

Tue 12/302:46 pmHHH - ORD

1 stop5h 36mAmerican Airlines

Sat 1/35:00 amORD - HHH

1 stop4h 44mAmerican Airlines

Deal found 12/14

$526

Mon 1/52:46 pmHHH - ORD

1 stop5h 36mAmerican Airlines

Mon 1/126:05 amORD - HHH

1 stop5h 15mAmerican Airlines

Deal found 12/15

$425

Fri 1/163:29 pmHHH - ORD

1 stop5h 21mAmerican Airlines

Mon 1/1910:10 amORD - HHH

1 stop3h 49mAmerican Airlines

Deal found 12/16

$363

One-way flights from Hilton Head Island to Chicago
Search for one-way flight options from Hilton Head Island to Chicago. Find affordable one-way fares based on user searches. Data last updated December 16, 2025.

Sat 1/173:29 pmHHH - ORD

2 stops20h 21mAmerican Airlines

Deal found 12/16

$215

Fri 1/163:29 pmHHH - ORD

2 stops17h 22mAmerican Airlines

Deal found 12/16

$219

Sat 3/142:50 pmHHH - ORD

Nonstop2h 35mUnited Airlines

Deal found 12/16

$224

Mon 1/123:29 pmHHH - ORD

2 stops20h 22mAmerican Airlines

Deal found 12/16

$228

Thu 1/153:29 pmHHH - ORD

2 stops20h 22mAmerican Airlines

Deal found 12/15

$229

Sun 1/113:29 pmHHH - ORD

2 stops20h 21mAmerican Airlines

Deal found 12/15

$233

Tue 2/173:35 pmHHH - ORD

2 stops18h 37mAmerican Airlines

Deal found 12/16

$234

Wed 2/184:15 pmHHH - ORD

2 stops17h 57mAmerican Airlines

Deal found 12/16

$243

Tue 3/175:19 pmHHH - ORD

2 stops18h 27mAmerican Airlines

Deal found 12/15

$258

Fri 6/123:00 pmHHH - ORD

Nonstop2h 45mUnited Airlines

Deal found 12/15

$259

Sat 6/133:00 pmHHH - ORD

Nonstop2h 45mUnited Airlines

Deal found 12/16

$279

Mon 2/162:58 pmHHH - ORD

2 stops19h 12mAmerican Airlines

Deal found 12/16

$287

Find flight deals from Hilton Head Island to Chicago

Most accurate provider	eDreams 3 stars
Most trusted provider	eDreams 3 stars
Round-trip from	$249 (United Airlines)
One-way from	$215 (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)

Search Deals

Cheapflights Fare Finder

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

Hilton Head IslandChicago

HHH - ORD

HHHORD

Hilton Head Island

Wed 4/22

3:00 pm-4:45 pm

Nonstop2h 45m

Chicago O'Hare Intl

Wed 4/29

10:35 am-2:01 pm

Nonstop2h 26m

$249

Hilton Head IslandChicago

HHH - ORD

HHHORD

Hilton Head Island

Wed 4/22

12:00 pm-4:44 pm

1 stop5h 44m

Chicago O'Hare Intl

Wed 4/29

9:30 am-3:18 pm

1 stop4h 48m

$294

Hilton Head IslandChicago

HHH - ORD

HHHORD

Hilton Head Island

Wed 4/15

4:00 pm-9:48 pm

1 stop6h 48m

Chicago O'Hare Intl

Wed 4/22

7:10 am-3:18 pm

1 stop7h 08m

$294

Hilton Head IslandChicago

HHH - ORD

HHHORD

Hilton Head Island

Wed 4/15

3:00 pm-4:45 pm

Nonstop2h 45m

Chicago O'Hare Intl

Wed 4/22

10:35 am-2:01 pm

Nonstop2h 26m

$297

Hilton Head IslandChicago

HHH - ORD

HHHORD

Hilton Head Island

Wed 4/1

4:11 pm-9:22 pm

1 stop6h 11m

Chicago O'Hare Intl

Wed 4/8

8:25 am-2:20 pm

1 stop4h 55m

$309

Hilton Head IslandChicago

HHH - ORD

HHHORD

Hilton Head Island

Tue 2/17

12:22 pm-4:39 pm

1 stop5h 17m

Chicago O'Hare Intl

Tue 2/24

9:45 am-3:05 pm

1 stop4h 20m

$309

Hilton Head IslandChicago

HHH - ORD

HHHORD

Hilton Head Island

Sat 2/14

2:58 pm-7:48 pm

1 stop5h 50m

Chicago O'Hare Intl

Tue 2/17

6:40 am-3:05 pm

2 stops7h 25m

$314

Hilton Head IslandChicago

HHH - ORD

HHHORD

Hilton Head Island

Sat 2/14

11:02 am-4:06 pm

1 stop6h 04m

Chicago O'Hare Intl

Sat 2/21

5:35 am-2:27 pm

2 stops7h 52m

$314

Hilton Head IslandChicago

HHH - ORD

HHHORD

Hilton Head Island

Sat 1/17

3:29 pm-10:50 am

2 stops20h 21m

$215

Hilton Head IslandChicago

HHH - ORD

HHHORD

Hilton Head Island

Sat 3/7

2:50 pm-4:25 pm

Nonstop2h 35m

$224

Flights are sorted by cheapest round-trip flights first.

Deals found on 12/15

Showing 1-10 of 16 results

Compare providers for flights from Hilton Head Island to Chicago

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 December.

Provider	Price Accuracy	Trust Score*
Expedia	Price Accuracy2 stars	Trust Score*3 stars
FlightHub	Price Accuracy3 stars	Trust Score*1 star
eDreams	Price Accuracy3 stars	Trust 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.

Related info for your journey

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?
United Airlines and Delta can get you from Hilton Head Island to Chicago in just under 2h 45m. Your travel time can differ by up to 2h 59m. 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 are the most reliable airlines from Hilton Head Island to Chicago?
Consider American Airlines (67%), Qatar Airways (67%) or Envoy Air (67%) 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

Lansing

Merrillville

Hammond

Porter

Benton Harbor

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Top airline flying from Hilton Head Island to Chicago

Airline	Cheapest	Average	Flexibility	On-time
American Airlines	Cheapest$228	Average$308	FlexibilityNo cancel fee	On-time71%

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$215+ 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 1/17. Fares are subject to change and may not be available on all flights or dates of travel.

Find cheap flights from Hilton Head Island to Chicago with Cheapflights

1. Tell us where you want to go

2. Select your favorite providers

3. Compare prices and book

Cheap flight deals from Hilton Head Island to Chicago

Cheapest flights from Hilton Head Island to ChicagoExplore 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 December 16, 2025.

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 December 16, 2025.

Find flight deals from Hilton Head Island to Chicago

Most accurate provider

Most trusted provider

Round-trip from

One-way from

Cheapflights Fare Finder

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

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 December.

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.

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?

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?

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

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

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

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

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

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

Traveling to a place near Chicago?

Browse thousands of different options on Cheapflights for your next trip

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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.

Top airline flying from Hilton Head Island to Chicago

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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 December 16, 2025.