What are the cheapest airlines to fly from Hilton Head Island to Chicago one-way?

The cheapest airline one-way is Delta, with whom users have recently found tickets for as low as $188. However, be on the lookout for offers from American Airlines and United Airlines, as they are both options that can get you from Hilton Head Island to Chicago for a low price.

What is the cheapest day to fly from Hilton Head Island to Chicago?

Travelers seeking maximum savings on their Hilton Head Island to Chicago flight should consider departing on Friday mornings when fares are most often at their lowest. Sunday mornings flights should be avoided if possible as fares are typically the most expensive at this time.

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

Flights from Hilton Head Island to Chicago are found to be more expensive on Saturday. This shouldn't discourage you from searching as you can still find great deals by being flexible with your options. Use our search form to find deals on tickets 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 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 22% versus a flight at noon.

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.

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.

$188+ 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

Most accurate provider	FlightHub 3 stars
Most trusted provider	FlightHub 3 stars
Round-trip from	$249 (Delta)
One-way from	$188 (Delta)

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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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 April 1, 2025.

Wed 8/63:58 pmHHH - ORD

1 stop7h 48mDelta

Tue 8/129:30 amORD - HHH

1 stop4h 52mDelta

Deal found 3/31

$249

Fri 5/96:20 pmHHH - ORD

1 stop6h 51mAmerican Airlines

Sun 5/118:05 amORD - HHH

1 stop5h 38mAmerican Airlines

Deal found 4/1

$289

Thu 8/712:02 pmHHH - ORD

2 stops22h 26mUnited Airlines

Tue 8/123:48 pmORD - HHH

2 stops18h 29mUnited Airlines

Deal found 4/1

$580

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 April 1, 2025.

Wed 5/74:00 pmHHH - ORD

1 stop7h 41mDelta

Wed 5/149:39 amORD - HHH

1 stop4h 41mDelta

Deal found 4/1

$249

Thu 5/296:20 pmHHH - ORD

1 stop6h 51mAmerican Airlines

Mon 6/27:00 amORD - HHH

1 stop6h 43mAmerican Airlines

Deal found 3/31

$289

Thu 8/712:02 pmHHH - ORD

2 stops21h 03mUnited Airlines

Tue 8/123:48 pmORD - HHH

2 stops18h 29mUnited Airlines

Deal found 4/1

$580

Last-minute flights from Hilton Head Island to Chicago
Discover last-minute flight deals from Hilton Head Island to Chicago. Data last updated April 1, 2025 and is based on user searches.

Wed 5/74:00 pmHHH - ORD

1 stop7h 41mDelta

Wed 5/149:39 amORD - HHH

1 stop4h 41mDelta

Deal found 4/1

$249

Fri 5/96:20 pmHHH - ORD

1 stop6h 51mAmerican Airlines

Sun 5/118:05 amORD - HHH

1 stop5h 38mAmerican Airlines

Deal found 4/1

$289

Thu 5/2911:17 amHHH - ORD

2 stops21h 29mUnited Airlines

Mon 6/29:30 pmORD - HHH

2 stops12h 34mUnited Airlines

Deal found 3/31

$611

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 April 1, 2025.

Wed 5/2812:05 pmHHH - ORD

2 stops11h 36mDelta

Deal found 3/31

$188

Thu 6/195:50 pmHHH - ORD

1 stop4h 35mAmerican Airlines

Deal found 4/1

$234

Sat 6/285:00 pmHHH - ORD

Nonstop2h 35mUnited Airlines

Deal found 3/30

$359

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 8/6

3:58 pm-10:46 pm

1 stop7h 48m

Chicago O'Hare Intl

Tue 8/12

9:30 am-3:22 pm

1 stop4h 52m

$249

Hilton Head IslandChicago

HHH - ORD

HHHORD

Hilton Head Island

Fri 5/9

6:20 pm-12:11 am

1 stop6h 51m

Chicago O'Hare Intl

Sun 5/11

8:05 am-2:43 pm

1 stop5h 38m

$289

Hilton Head IslandChicago

HHH - ORD

HHHORD

Hilton Head Island

Thu 8/7

12:02 pm-9:28 am

2 stops22h 26m

Chicago O'Hare Intl

Tue 8/12

3:48 pm-11:17 am

2 stops18h 29m

$580

Hilton Head IslandChicago

HHH - ORD

HHHORD

Hilton Head Island

Wed 5/28

12:05 pm-10:41 pm

2 stops11h 36m

$188

Hilton Head IslandChicago

HHH - ORD

HHHORD

Hilton Head Island

Thu 6/19

5:50 pm-9:25 pm

1 stop4h 35m

$234

Hilton Head IslandChicago

HHH - ORD

HHHORD

Hilton Head Island

Sat 6/28

5:00 pm-6:35 pm

Nonstop2h 35m

$359

Flights are sorted by cheapest round-trip flights first.

Deals found on 3/31

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 April.

Provider	Price Accuracy	Trust Score*
Expedia	Price Accuracy1 star	Trust Score*3 stars
FlightHub	Price Accuracy3 stars	Trust Score*3 stars
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 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, 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 $323). 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.

Rainfall in Chicago by month

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.

Temperature in Chicago by month

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).

Reviews of airlines servicing Chicago

Delta

8.0

Very good

7,898 reviews

Reviews

1 / 20

10.0

Excellent

Aaron,Oct 2024

TUS - LAX

Delta has consistently been the best U.S. airline for my travels and this flight was no exception

Delta

8.0

Very good

7,898 reviews

Delta

8.0

Very good

7,898 reviews

Reviews

1 / 20

10.0

Excellent

Aaron,Oct 2024

TUS - LAX

Delta has consistently been the best U.S. airline for my travels and this flight was no exception

United Airlines

7.4

Good

8,615 reviews

Delta

8.0

Very good

7,898 reviews

Reviews

1 / 20

10.0

Excellent

Aaron,Oct 2024

TUS - LAX

Delta has consistently been the best U.S. airline for my travels and this flight was no exception

American Airlines

7.2

Good

10,000 reviews

Delta

8.0

Very good

7,898 reviews

Reviews

1 / 20

10.0

Excellent

Aaron,Oct 2024

TUS - LAX

Delta has consistently been the best U.S. airline for my travels and this flight was no exception

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.
What are the cheapest airlines to fly from Hilton Head Island to Chicago one-way?
The cheapest airline one-way is Delta, with whom users have recently found tickets for as low as $188. However, be on the lookout for offers from American Airlines and United Airlines, as they are both options that can get you from Hilton Head Island to Chicago for a low price.
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 $323). 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

Merrillville

New Buffalo

Hammond

Benton Harbor

Porter

Lansing

Valparaiso

Chesterton

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Top airline flying from Hilton Head Island to Chicago

Airline	Cheapest	Average	Flexibility	On-time
American Airlines	Cheapest$228	Average$336	FlexibilityNo cancel fee	On-time71%

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$188+ 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 5/28. 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

Most accurate provider

Most trusted provider

Round-trip from

One-way from

Find 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 April 1, 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 April 1, 2025.

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 April.

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?

Rainfall in Chicago by month

Plan your trip to Chicago by taking into account the average rainfall totals by month.

Temperature in Chicago by month

Plan your trip to Chicago by taking into account the average temperature totals by month.

Reviews of airlines servicing 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?

What are the cheapest airlines to fly from Hilton Head Island to Chicago one-way?

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 Hilton Head Island?

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.

Top airline flying from Hilton Head Island to Chicago

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Book with Flexibility

Travel Smart

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 April 1, 2025.