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$202+ 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 5/20. Fares are subject to change and may not be available on all flights or dates of travel.
HHH — CHI
Apr 27 — May 41
Sun 4/27
Sun 5/4
1 adult, Economy
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Find cheap flights from Hilton Head Island to Chicago with Cheapflights

1. Tell us where you want to go

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Cheap 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 April 22, 2025.

Most accurate provider

FlightHub
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$229
(Delta)

One-way from

$202
(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 22, 2025.

This Delta deal was found by Cheapflights users on 4/21. 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.
Tue 5/204:00 pmHHH - ORD
1 stop5h 46mDelta
Wed 5/289:39 amORD - HHH
1 stop4h 41mDelta
Deal found 4/21$229
This American Airlines deal was found by Cheapflights users on 4/22. 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 6/125:50 pmHHH - ORD
1 stop4h 35mAmerican Airlines
Tue 6/179:22 amORD - HHH
1 stop6h 32mAmerican Airlines
Deal found 4/22$331
This United Airlines deal was found by Cheapflights users on 4/22. 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.
Sat 4/265:11 pmHHH - ORD
Nonstop2h 44mUnited Airlines
Tue 4/298:50 amORD - HHH
1 stop5h 47mUnited Airlines
Deal found 4/22$709

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 April 22, 2025.
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

Tue 5/20

4:00 pm-8:46 pm

1 stop5h 46m

Chicago O'Hare Intl

Wed 5/28

9:39 am-3:20 pm

1 stop4h 41m

$229

Hilton Head IslandChicago

HHH - ORD

HHHORD

Hilton Head Island

Thu 6/12

5:50 pm-9:25 pm

1 stop4h 35m

Chicago O'Hare Intl

Tue 6/17

9:22 am-4:54 pm

1 stop6h 32m

$331

Hilton Head IslandChicago

HHH - ORD

HHHORD

Hilton Head Island

Tue 5/20

4:00 pm-10:12 am

1 stop19h 12m

$202

Hilton Head IslandChicago

HHH - ORD

HHHORD

Hilton Head Island

Sat 7/19

5:00 pm-6:35 pm

Nonstop2h 35m

$259

Hilton Head IslandChicago

HHH - ORD

HHHORD

Hilton Head Island

Sat 6/21

3:33 pm-6:54 am

1 stop16h 21m

$274

Flights are sorted by cheapest round-trip flights first.

Deals found on 4/22

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.
ProviderPrice AccuracyTrust Score*
ExpediaPrice Accuracy1 starTrust Score*3 stars
FlightHubPrice Accuracy3 starsTrust Score*2 stars
eDreamsPrice 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 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, 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?

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 April 22, 2025.

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.

Rainfall in Chicago by month

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

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

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 April 22, 2025.
Delta
8.0
Very good
7,920 reviews

Entertainment

7.9

Crew

8.5

Food

7.3

Boarding

8.2

Comfort

7.9

Overall

8.0

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
7,920 reviews
Delta
8.0
Very good
7,920 reviews

Entertainment

7.9

Crew

8.5

Food

7.3

Boarding

8.2

Comfort

7.9

Overall

8.0

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
8,683 reviews
Delta
8.0
Very good
7,920 reviews

Entertainment

7.9

Crew

8.5

Food

7.3

Boarding

8.2

Comfort

7.9

Overall

8.0

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
7,920 reviews

Entertainment

7.9

Crew

8.5

Food

7.3

Boarding

8.2

Comfort

7.9

Overall

8.0

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

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. 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 $202. 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 $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

Traveling to a place near Hilton Head Island?

Book flights to Hilton Head Island if you plan to visit one of these locations
Merrillville
Hammond
Benton Harbor
Porter
Lansing
Valparaiso
Chesterton

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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.
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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 April 22, 2025.
AirlineCheapestAverageFlexibilityOn-time
American AirlinesCheapest$228Average$358FlexibilityNo cancel feeOn-time71%

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