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$182+ 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 7/27. Fares are subject to change and may not be available on all flights or dates of travel.
HHH — CHI
Jun 1 — Jun 81
Mon 6/1
Mon 6/8
1 adult, Economy
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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 May 2, 2026.

This United Airlines deal was found by Cheapflights users on 4/27. 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.
Wed 5/203:08 pm
HHH
-
ORD
Nonstop2h 41m
United Airlines
Wed 5/2710:45 am
ORD
-
HHH
Nonstop2h 36m
United Airlines
Deal found 4/27$269
This Delta deal was found by Cheapflights users on 4/27. 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.
Thu 6/1112:13 pm
HHH
-
ORD
1 stop5h 51m
Delta
Tue 6/168:08 am
ORD
-
HHH
1 stop6h 24m
Delta
Deal found 4/27$289
This Delta deal was found by Cheapflights users on 4/27. 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.
Wed 5/2012:18 pm
HHH
-
ORD
1 stop7h 23m
Delta
Wed 5/276:00 am
ORD
-
HHH
2 stops8h 33m
Delta
Deal found 4/27$294
This United Airlines deal was found by Cheapflights users on 4/28. 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.
Wed 5/133:08 pm
HHH
-
ORD
Nonstop2h 41m
United Airlines
Sun 5/1710:45 am
ORD
-
HHH
Nonstop2h 26m
United Airlines
Deal found 4/28$309
This Delta deal was found by Cheapflights users on 4/29. 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.
Mon 6/812:13 pm
HHH
-
ORD
1 stop5h 51m
Delta
Wed 7/15:45 pm
ORD
-
HHH
1 stop16h 46m
Delta
Deal found 4/29$321
This Delta deal was found by Cheapflights users on 4/28. 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.
Wed 5/134:16 pm
HHH
-
ORD
1 stop7h 20m
Delta
Sun 5/177:07 am
ORD
-
HHH
1 stop7h 26m
Delta
Deal found 4/28$329
This Delta deal was found by Cheapflights users on 4/29. 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.
Mon 6/812:13 pm
HHH
-
ORD
1 stop7h 29m
Delta
Mon 7/68:08 am
ORD
-
HHH
1 stop6h 24m
Delta
Deal found 4/29$344
This Delta deal was found by Cheapflights users on 4/29. 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.
Wed 6/1012:13 pm
HHH
-
ORD
2 stops9h 18m
Delta
Mon 7/68:08 am
ORD
-
HHH
1 stop6h 24m
Delta
Deal found 4/29$349
This American Airlines deal was found by Cheapflights users on 5/1. 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.
Tue 6/232:43 pm
HHH
-
ORD
1 stop6h 02m
American Airlines
Tue 7/1410:00 am
ORD
-
HHH
Nonstop2h 33m
American Airlines
Deal found 5/1$359
This Delta deal was found by Cheapflights users on 4/29. 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.
Thu 5/1412:18 pm
HHH
-
ORD
1 stop5h 38m
Delta
Mon 5/188:10 am
ORD
-
HHH
1 stop6h 23m
Delta
Deal found 4/29$364

Find 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 May 2, 2026.

Most accurate provider

Expedia
1 star

Most trusted provider

Expedia
3 stars

Round-trip from

$269
(United Airlines)

One-way from

$182
(Delta)

Good round-trip deal

$309 or less

Good one-way deal

$213 or less
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)
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Price to beat on a round-trip flight from Hilton Head Island to Chicago (CHI).
Search Deals
Price to beat on a one-way flight from Hilton Head Island to Chicago (CHI).
Search Deals

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 May 2, 2026.
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

Cheapest round-trip
Quickest round-trip

Hilton Head IslandChicago

HHH - ORD

HHHORD

Hilton Head Island

Tue 5/12

3:08 pm-4:49 pm

Nonstop2h 41m

Chicago O'Hare Intl

Tue 5/19

10:45 am-2:11 pm

Nonstop2h 26m

$289

Hilton Head IslandChicago

HHH - ORD

HHHORD

Hilton Head Island

Thu 6/11

12:13 pm-5:04 pm

1 stop5h 51m

Chicago O'Hare Intl

Thu 6/18

8:08 am-3:32 pm

1 stop6h 24m

$289

Hilton Head IslandChicago

HHH - ORD

HHHORD

Hilton Head Island

Thu 5/14

3:08 pm-4:49 pm

Nonstop2h 41m

Chicago O'Hare Intl

Mon 5/18

10:45 am-2:11 pm

Nonstop2h 26m

$309

Hilton Head IslandChicago

HHH - ORD

HHHORD

Hilton Head Island

Wed 5/13

12:18 pm-10:36 pm

2 stops11h 18m

Chicago O'Hare Intl

Sun 5/17

7:07 am-3:33 pm

1 stop7h 26m

$334

Hilton Head IslandChicago

HHH - ORD

HHHORD

Hilton Head Island

Wed 6/10

3:05 pm-4:51 pm

Nonstop2h 46m

Chicago O'Hare Intl

Sun 7/5

10:45 am-2:21 pm

Nonstop2h 36m

$369

Hilton Head IslandChicago

HHH - ORD

HHHORD

Hilton Head Island

Fri 5/29

12:18 pm-6:35 pm

1 stop7h 17m

Chicago O'Hare Intl

Sun 5/31

7:07 am-3:33 pm

1 stop7h 26m

$384

Hilton Head IslandChicago

HHH - ORD

HHHORD

Hilton Head Island

Wed 9/23

12:00 pm-10:43 pm

2 stops11h 43m

Chicago O'Hare Intl

Thu 10/1

7:10 am-3:20 pm

1 stop7h 10m

$389

Hilton Head IslandChicago

HHH - ORD

HHHORD

Hilton Head Island

Mon 6/8

12:13 pm-6:42 pm

1 stop7h 29m

Chicago O'Hare Intl

Sun 7/5

8:08 am-3:32 pm

1 stop6h 24m

$444

Hilton Head IslandChicago

HHH - ORD

HHHORD

Hilton Head Island

Tue 6/30

12:13 pm-9:25 pm

2 stops10h 12m

Chicago O'Hare Intl

Sun 7/5

8:08 am-3:32 pm

1 stop6h 24m

$449
Cheapest one-way

Hilton Head IslandChicago

HHH - ORD

HHHORD

Hilton Head Island

Mon 7/27

4:12 pm-6:03 pm

1 stop26h 51m

$182

Flights are sorted by cheapest round-trip flights first.

Deals found on 5/1

Showing 1-10 of 20 resultsSorted by cheapest first
1
2
  • Most accurate provider: When it comes to deals on Hilton Head Island-Chicago flights, users find the pricing of Expedia to be most consistent on Cheapflights vs. Expedia Users can find the same prices on Hilton Head Island-Chicago flight deals on Cheapflights vs. Expedia <90% 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 Expedia the most. Expedia 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 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 May 2, 2026.

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.

Weekly flight availability from Hilton Head Island to Chicago

Explore weekly flight availability from Hilton Head Island to Chicago. Discover flights operating on different days of the week, giving you the flexibility to choose a travel day that best fits your plans. Compare info to find the most convenient option for your journey. Data last updated May 2, 2026.

The most flights from HHH to CHI are scheduled on a Monday (1 on average). You will have fewer flight options on Monday, which is when the least amount of flights are scheduled (1 on average).

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 1 outbound flight 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 41m. Your travel time can differ by up to 3h 10m. 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 cheapest flights from Hilton Head Island to Chicago?

    While on average a flight from Hilton Head Island to Chicago is generally $336, our data shows the cheapest flight currently is $155. When looking at the most popular route, (Hilton Head Island - Chicago O'Hare Intl), you can expect to pay $289 for that flight.

  • 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.

See more FAQs

Traveling to a place near Chicago?

Book flights to Chicago if you plan to visit one of these locations
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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 May 2, 2026.
AirlineCheapestAverageFlexibilityOn-time
United AirlinesCheapest$223Average$355FlexibilityNo cancel feeOn-time69%

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