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

The cheapest airline one-way is American Airlines, with whom users have recently found tickets for as low as $177. However, be on the lookout for offers from Delta 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. Saturday afternoons flights should be avoided if possible as fares are typically the most expensive at this time.

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 Qatar Airways (75%), United Airlines (75%) or Republic Airways (75%) when booking your flight. These represent the most reliable airlines when flying from Hilton Head Island to Chicago.

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 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.

$177+ Flights from Hilton Head Island to Chicago

Home Search by date Vacation packages Hotels Flight deals Car rental Travel tips & news

Find cheap flights from Hilton Head Island to Chicago with Cheapflights

1. Tell us where you want to go

Enter your travel information like dates, passengers, trip type (one-way or round trip), and preferred cabin class then click “Find deals”

2. Select your favorite providers

We find the providers serving your travel needs. Choose up to four travel providers to compare side-by-side for flights, hotels, or car rentals.

3. Compare prices and book

Review each provider’s pricing and select the best option for you! Book through your favorite provider’s website for a seamless experience.

Cheap flight deals from Hilton Head Island to Chicago

Round-trip from	$308 (American Airlines)
One-way from	$177 (American Airlines)

From Hilton Head Island to Chicago (CHI)

Search Deals

One-way flight from Hilton Head Island to Chicago (CHI)

Search Deals

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 July 31, 2025.

Sat 10/255:57 pmHHH - ORD

1 stop4h 32mAmerican Airlines

Tue 10/289:20 amORD - HHH

1 stop6h 31mAmerican Airlines

Deal found 7/31

$308

Thu 8/2112:11 pmHHH - ORD

1 stop5h 17mDelta

Tue 8/266:00 amORD - HHH

2 stops8h 22mDelta

Deal found 7/30

$319

Thu 9/1812:06 pmHHH - ORD

2 stops20h 28mUnited Airlines

Sun 9/2110:35 amORD - HHH

2 stops23h 50mUnited Airlines

Deal found 7/28

$617

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 July 31, 2025.

Sat 10/255:57 pmHHH - ORD

1 stop4h 32mAmerican Airlines

Tue 10/289:20 amORD - HHH

1 stop6h 31mAmerican Airlines

Deal found 7/31

$308

Thu 8/2112:11 pmHHH - ORD

1 stop5h 17mDelta

Tue 8/266:00 amORD - HHH

2 stops8h 22mDelta

Deal found 7/30

$319

Thu 9/1812:06 pmHHH - ORD

2 stops20h 28mUnited Airlines

Sun 9/2110:35 amORD - HHH

2 stops23h 50mUnited Airlines

Deal found 7/28

$617

Last-minute flights from Hilton Head Island to Chicago
Discover last-minute flight deals from Hilton Head Island to Chicago. Data last updated July 31, 2025 and is based on user searches.

Sat 8/96:15 pmHHH - ORD

1 stop6h 33mAmerican Airlines

Wed 8/136:03 amORD - HHH

1 stop4h 56mAmerican Airlines

Deal found 7/30

$727

Wed 8/1311:19 amHHH - ORD

1 stop5h 09mAmerican Airlines

Tue 8/198:37 amORD - HHH

1 stop7h 18mAmerican Airlines

Deal found 7/30

$345

Thu 8/2112:11 pmHHH - ORD

1 stop5h 17mDelta

Tue 8/269:47 amORD - HHH

1 stop4h 35mDelta

Deal found 7/30

$314

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 July 31, 2025.

Sat 8/303:41 pmHHH - ORD

1 stop16h 43mAmerican Airlines

Deal found 7/31

$177

Mon 9/294:05 pmHHH - ORD

2 stops19h 14mDelta

Deal found 7/31

$181

Sat 9/2712:21 pmHHH - ORD

1 stop7h 13mUnited Airlines

Deal found 7/31

$322

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

Sat 10/25

5:57 pm-9:29 pm

1 stop4h 32m

Chicago O'Hare Intl

Tue 10/28

9:20 am-4:51 pm

1 stop6h 31m

$308

Hilton Head IslandChicago

HHH - ORD

HHHORD

Hilton Head Island

Thu 8/21

12:11 pm-4:28 pm

1 stop5h 17m

Chicago O'Hare Intl

Tue 8/26

6:00 am-3:22 pm

2 stops8h 22m

$319

Hilton Head IslandChicago

HHH - ORD

HHHORD

Hilton Head Island

Thu 9/18

12:06 pm-7:34 am

2 stops20h 28m

Chicago O'Hare Intl

Sun 9/21

10:35 am-11:25 am

2 stops23h 50m

$617

Hilton Head IslandChicago

HHH - ORD

HHHORD

Hilton Head Island

Sat 8/30

3:41 pm-7:24 am

1 stop16h 43m

$177

Hilton Head IslandChicago

HHH - ORD

HHHORD

Hilton Head Island

Mon 9/29

4:05 pm-10:19 am

2 stops19h 14m

$181

Hilton Head IslandChicago

HHH - ORD

HHHORD

Hilton Head Island

Sat 9/27

12:21 pm-6:34 pm

1 stop7h 13m

$322

Flights are sorted by cheapest round-trip flights first.

Deals found on 7/31

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 $321). 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?

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 10% versus a flight at noon.

Reviews of airlines servicing Chicago

See what other customers who have flown with Delta, United Airlines, and 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.

Delta

8.0

Very good

7,981 reviews

Reviews

1 / 20

10.0

Excellent

Kim,May 2025

PIH - SLC

This trip was fine even with delay I had plenty of time to get connection flight!

Delta

8.0

Very good

7,981 reviews

Delta

8.0

Very good

7,981 reviews

Reviews

1 / 20

10.0

Excellent

Kim,May 2025

PIH - SLC

This trip was fine even with delay I had plenty of time to get connection flight!

United Airlines

7.4

Good

8,900 reviews

Delta

8.0

Very good

7,981 reviews

Reviews

1 / 20

10.0

Excellent

Kim,May 2025

PIH - SLC

This trip was fine even with delay I had plenty of time to get connection flight!

American Airlines

7.2

Good

10,000 reviews

Delta

8.0

Very good

7,981 reviews

Reviews

1 / 20

10.0

Excellent

Kim,May 2025

PIH - SLC

This trip was fine even with delay I had plenty of time to get connection flight!

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 American Airlines, with whom users have recently found tickets for as low as $177. However, be on the lookout for offers from Delta and United Airlines, as they are both options that can get you from Hilton Head Island to Chicago for a low price.
What are the most reliable airlines from Hilton Head Island to Chicago?
Consider Qatar Airways (75%), United Airlines (75%) or Republic Airways (75%) 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, 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 $321). 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

Lansing

Hammond

Benton Harbor

Porter

Valparaiso

Chesterton

Browse thousands of different options on Cheapflights for your next trip

Top airline flying from Hilton Head Island to Chicago

Airline	Cheapest	Average	Flexibility	On-time
American Airlines	Cheapest$228	Average$358	FlexibilityNo cancel fee	On-time71%

100% Free

Cheapflights is completely free to use, so you can start saving the moment you arrive.

Book with Flexibility

Our users can plan ahead with confidence and find flights with no change fees

Travel Smart

Millions of people come to us for their flight needs every year. We help make travel planning easy by providing useful insights and data-driven graphs that can inform your decisions.

$177+ 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 8/30. 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

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 July 31, 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 July 31, 2025.

Cheapflights Fare Finder

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

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?

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 July 31, 2025.

Reviews of airlines servicing Chicago

See what other customers who have flown with Delta, United Airlines, and 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.

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?

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

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

100% Free

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 July 31, 2025.