HomeSearch by dateVacation packagesHotelsFlight dealsCar rentalTravel tips & news
Chicago

$224+ Cheap flights from Hilton Head Island (HHH) to Chicago (CHI)

This is the cheapest round-trip flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 1/8. Fares are subject to change and may not be available on all flights or dates of travel.
HHH — CHI
Nov 5 — Nov 121
Tue 11/5
Tue 11/12
1 adult, Economy
We work with more than 300 partners to bring you better travel deals

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

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 October 31, 2024.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$224
(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

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 October 31, 2024.

This American Airlines deal was found by Cheapflights users on 10/30. 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.
Sat 11/166:55 pmHHH - ORD
1 stop4h 31mAmerican Airlines
Wed 11/205:00 amORD - HHH
1 stop4h 37mAmerican Airlines
Deal found 10/30$279

Find flights from Hilton Head Island to Chicago within your budget

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 2,570,725 searches. Data last updated October 31, 2024.

Fly from

Any airport

Fly to

Any airport

Route

Depart

Return

Price

Hilton Head IslandChicago

HHH - ORD

HHHORD

Hilton Head Island

Mon 4/28

5:30 pm-10:42 pm

1 stop6h 12m

$229

Hilton Head IslandChicago

HHH - ORD

HHHORD

Hilton Head Island

Fri 1/31

6:05 pm-7:05 am

2 stops14h 00m

$271

Hilton Head IslandChicago

HHH - ORD

HHHORD

Hilton Head Island

Sun 4/27

4:19 pm-8:04 am

2 stops16h 45m

$482

Hilton Head IslandChicago

HHH - ORD

HHHORD

Hilton Head Island

Wed 1/8

6:05 pm-12:09 am

1 stop7h 04m

Chicago O'Hare Intl

Sat 1/11

10:28 am-5:35 pm

1 stop6h 07m

$224

Flights are sorted by cheapest first

Deals found on 10/31

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 October.
ProviderPrice AccuracyTrust Score*Cancellation Policy
FlightHubPrice Accuracy3 starsTrust Score*3 starsCancellation PolicyAirline Policy
ExpediaPrice Accuracy1 starTrust Score*3 starsCancellation PolicyAirline Policy
eDreamsPrice Accuracy3 starsTrust Score*3 starsCancellation PolicyAirline Policy

*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.

Travel insights for flights from Hilton Head Island to Chicago

Get recent, data-driven insights about flights from Hilton Head Island to Chicago including ideal travel times, pricing trends, and more.

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

Currently, September is the cheapest month in which you can book a flight from Hilton Head Island to Chicago (average of $232). Flying from Hilton Head Island to Chicago in June is currently the most expensive (average of $308). 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

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 October 31, 2024.
Delta
8.0
Very good
8,835 reviews

Boarding

8.2

Overall

8.0

Crew

8.5

Comfort

7.9

Entertainment

7.9

Food

7.3

Reviews

1 / 10

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

Delta
8.0
Very good
8,835 reviews
Delta
8.0
Very good
8,835 reviews

Boarding

8.2

Overall

8.0

Crew

8.5

Comfort

7.9

Entertainment

7.9

Food

7.3

Reviews

1 / 10

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

United Airlines
7.4
Good
9,240 reviews
Delta
8.0
Very good
8,835 reviews

Boarding

8.2

Overall

8.0

Crew

8.5

Comfort

7.9

Entertainment

7.9

Food

7.3

Reviews

1 / 10

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
8,835 reviews

Boarding

8.2

Overall

8.0

Crew

8.5

Comfort

7.9

Entertainment

7.9

Food

7.3

Reviews

1 / 10

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.

  • Can I find flights from Hilton Head Island to Chicago for under $300 on Cheapflights?

    Yes, there are multiple flights from Hilton Head Island to Chicago for under $300. The cheapest flight booked recently is on American Airlines for just $224, but on average you can expect to pay $224.

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

    Cheapflights users have booked flights from Hilton Head Island to Chicago round-trip from $224.

  • 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 $229. 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 does HHH to ORD mean?

    This is defined as Hilton Head Island Airport (HHH) and Chicago O'Hare Intl Airport (ORD). Codes like Chicago O'Hare Intl Airport are often used to just call airports uniquely. Chicago Midway Airport (MDW), Chicago Greater Rockford Airport (RFD) are other airports near this flight route and their unique identifiers/IATA codes.

  • Can I find deals for flights from Hilton Head Island to Chicago that include extra baggage allowance?

    The amount of baggage you can bring on your Hilton Head Island to Chicago flight depends on the airline and the type of fare you've chosen. After entering your flight details, you'll be able to view the specific baggage policies for each deal in the search results. Keep in mind that certain deals may offer additional baggage allowance.

  • Can I find deals on flights from Hilton Head Island to Chicago with specific airlines?

    Yes, Cheapflights allows you to browse and filter Hilton Head Island to Chicago flight deals by airline. After entering your origin and destination, use the available filters to view flights offered by airlines.

  • 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.

  • Can I find deals for flights from Hilton Head Island to Chicago that allow pets onboard?

    Many airlines flying from Hilton Head Island to Chicago offer the option to travel with pets. After selecting a flight deal, you can find more information about the airline's pet policy on their official website or by contacting the airline directly. Please note that additional fees and restrictions may apply.

  • Can I find deals on last-minute flights from Hilton Head Island to Chicago?

    Yes, you can often find last-minute deals on Hilton Head Island to Chicago flights on Cheapflights. However, these deals can vary and may not always be available. We recommend checking back frequently or signing up for price alerts for the most up-to-date deals.

  • How recently were the Hilton Head Island to Chicago flight deals updated?

    The Hilton Head Island to Chicago flight deals you see on this page were last updated on 10/30.

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

    Currently, September is the cheapest month in which you can book a flight from Hilton Head Island to Chicago (average of $232). Flying from Hilton Head Island to Chicago in June is currently the most expensive (average of $308). 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

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.
Charlotte to O'Hare Intl flights
Charleston to O'Hare Intl flights
Charlotte to Midway flights
Savannah to O'Hare Intl flights
Greenville to O'Hare Intl flights
Charlotte to St. Louis flights
Columbia to O'Hare Intl flights
Charleston to Midway flights
Savannah to Midway flights
Myrtle Beach to Midway flights
Columbia to Midway flights
Greenville to Midway flights
Myrtle Beach to O'Hare Intl flights
Columbia to St. Louis flights
Charlotte to Moline flights
Charlotte to Peoria flights
Savannah to St. Louis flights
Greenville to St. Louis flights
Augusta to O'Hare Intl flights
Charlotte to Evansville flights
Augusta to Midway flights
Charleston to Moline flights
Charleston to St. Louis flights
Charlotte to Bloomington flights
Savannah to Peoria flights
Myrtle Beach to St. Louis flights
Augusta to St. Louis flights
Greenville to Peoria flights
Columbia to Bloomington flights
Charleston to Peoria flights
Myrtle Beach to Moline flights
Hilton Head Island to St. Louis flights
Myrtle Beach to Peoria flights
Greenville to Moline flights
Columbia to Moline flights
Columbia to Peoria flights
Charleston to Rockford flights
Augusta to Moline flights
Florence to St. Louis flights
Greenville to Bloomington flights
Hilton Head Island to O'Hare Intl flights
Greenville to Champaign flights
Charlotte to Dubuque flights
Charlotte to Springfield flights
Columbia to Evansville flights
Augusta to Bloomington flights
Savannah to Rockford flights
Charlotte to Champaign flights
Columbia to Springfield flights
Greenville to Evansville flights

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 2,570,725 searches. Data last updated October 31, 2024.
AirlineCheapestAverageFlexibilityOn-time
American AirlinesCheapest$180Average$433FlexibilityNo cancel feeOn-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.
View all available airlines