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O'Hare Intl

$259+ Cheap flights from Hilton Head Island (HHH) to O'Hare Intl (ORD)

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 8/20. Fares are subject to change and may not be available on all flights or dates of travel.
HHH — ORD
Aug 31 — Sep 71
Mon 8/31
Mon 9/7
1 adult, Economy
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Cheap flight deals from Hilton Head Island to O'Hare Intl

Cheapest flights from Hilton Head Island to O'Hare Intl
Explore the most affordable flight options available from Hilton Head Island to O'Hare Intl. Find the lowest fares from popular airlines and budget airlines, with prices last updated on August 1, 2026.

This United Airlines deal was found by Cheapflights users on 7/30. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/272:58 pm
HHH
-
ORD
Nonstop3h 17m
United Airlines
Tue 9/110:25 am
ORD
-
HHH
Nonstop2h 38m
United Airlines
Deal found 7/30$279
This American Airlines deal was found by Cheapflights users on 7/27. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 8/2811:40 am
HHH
-
ORD
1 stop5h 20m
American Airlines
Tue 9/19:53 am
ORD
-
HHH
Nonstop2h 24m
American Airlines
Deal found 7/27$289
This United Airlines deal was found by Cheapflights users on 7/26. 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 10/173:00 pm
HHH
-
ORD
Nonstop3h 17m
United Airlines
Sat 10/2410:35 am
ORD
-
HHH
Nonstop2h 38m
United Airlines
Deal found 7/26$294
This Delta deal was found by Cheapflights users on 7/31. 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.
Fri 8/284:18 pm
HHH
-
ORD
1 stop7h 06m
Delta
Tue 9/18:05 am
ORD
-
HHH
1 stop6h 27m
Delta
Deal found 7/31$299
This Delta deal was found by Cheapflights users on 7/31. 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 8/2612:15 pm
HHH
-
ORD
2 stops9h 34m
Delta
Tue 9/18:05 am
ORD
-
HHH
1 stop6h 27m
Delta
Deal found 7/31$304
This American Airlines deal was found by Cheapflights users on 7/27. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/1310:57 am
HHH
-
ORD
1 stop7h 17m
American Airlines
Mon 8/179:53 am
ORD
-
HHH
Nonstop2h 24m
American Airlines
Deal found 7/27$309
This United Airlines deal was found by Cheapflights users on 7/28. 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.
Sun 8/302:58 pm
HHH
-
ORD
Nonstop3h 17m
United Airlines
Sun 9/610:25 am
ORD
-
HHH
Nonstop2h 38m
United Airlines
Deal found 7/28$314
This American Airlines deal was found by Cheapflights users on 7/28. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/1310:57 am
HHH
-
ORD
1 stop7h 17m
American Airlines
Sat 8/158:51 am
ORD
-
HHH
Nonstop2h 24m
American Airlines
Deal found 7/28$329
This American Airlines deal was found by Cheapflights users on 7/28. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 8/42:03 pm
HHH
-
ORD
Nonstop2h 36m
American Airlines
Sat 8/228:51 am
ORD
-
HHH
Nonstop2h 24m
American Airlines
Deal found 7/28$334
This American Airlines deal was found by Cheapflights users on 7/28. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 8/1410:57 am
HHH
-
ORD
1 stop7h 17m
American Airlines
Sun 8/166:49 am
ORD
-
HHH
1 stop6h 27m
American Airlines
Deal found 7/28$339

Find flight deals from Hilton Head Island to O'Hare Intl

Discover tips and strategies to find the most affordable flight options for your journey from Hilton Head Island (HHH) to O'Hare Intl (ORD). 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 August 1, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$279
(United Airlines)

One-way from

$259
(United Airlines)

Good round-trip deal

$343 or less

Good one-way deal

$280 or less
Provider with most accurate pricing for Hilton Head Island-Chicago O'Hare Intl flight deals.
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Provider most trusted by Cheapflights users for Hilton Head Island-Chicago O'Hare Intl flights.
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From Hilton Head Island to Chicago O'Hare Intl
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One-way flight from Hilton Head Island to Chicago O'Hare Intl
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Price to beat on a round-trip flight from Hilton Head Island to Chicago O'Hare Intl.
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Price to beat on a one-way flight from Hilton Head Island to Chicago O'Hare Intl.
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Cheapflights Fare Finder

 
Customize your flight search to find flights from Hilton Head Island to O'Hare Intl 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 August 1, 2026.
Use the filters below to find and compare flights from Hilton Head Island to Chicago O'Hare Intl Airport 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

Fri 9/4

2:58 pm-5:15 pm

Nonstop3h 17m

Chicago O'Hare Intl

Mon 9/7

10:25 am-2:03 pm

Nonstop2h 38m

$279

Hilton Head IslandChicago

HHH - ORD

HHHORD

Hilton Head Island

Thu 8/27

2:58 pm-5:15 pm

Nonstop3h 17m

Chicago O'Hare Intl

Tue 9/1

10:25 am-2:03 pm

Nonstop2h 38m

$279

Hilton Head IslandChicago

HHH - ORD

HHHORD

Hilton Head Island

Sat 10/17

1:50 pm-3:34 pm

Nonstop2h 44m

Chicago O'Hare Intl

Sat 10/24

9:02 am-2:26 pm

1 stop4h 24m

$289

Hilton Head IslandChicago

HHH - ORD

HHHORD

Hilton Head Island

Sat 10/17

3:00 pm-5:17 pm

Nonstop3h 17m

Chicago O'Hare Intl

Sat 10/24

10:35 am-2:13 pm

Nonstop2h 38m

$294

Hilton Head IslandChicago

HHH - ORD

HHHORD

Hilton Head Island

Thu 8/27

12:15 pm-4:51 pm

1 stop5h 36m

Chicago O'Hare Intl

Tue 9/1

6:00 am-3:32 pm

2 stops8h 32m

$304

Hilton Head IslandChicago

HHH - ORD

HHHORD

Hilton Head Island

Fri 8/28

4:18 pm-10:24 pm

1 stop7h 06m

Chicago O'Hare Intl

Tue 9/1

6:59 am-3:32 pm

2 stops7h 33m

$344

Hilton Head IslandChicago

HHH - ORD

HHHORD

Hilton Head Island

Fri 8/14

12:15 pm-6:49 pm

1 stop7h 34m

Chicago O'Hare Intl

Wed 8/19

6:00 am-3:32 pm

2 stops8h 32m

$354

Hilton Head IslandChicago

HHH - ORD

HHHORD

Hilton Head Island

Fri 8/28

3:27 pm-9:57 pm

1 stop7h 30m

Chicago O'Hare Intl

Tue 9/1

9:53 am-1:17 pm

Nonstop2h 24m

$369
Cheapest one-way
Quickest one-way

Hilton Head IslandChicago

HHH - ORD

HHHORD

Hilton Head Island

Mon 8/24

2:58 pm-5:15 pm

Nonstop3h 17m

$259

Hilton Head IslandChicago

HHH - ORD

HHHORD

Hilton Head Island

Mon 9/14

2:48 pm-5:05 pm

Nonstop3h 17m

$259

Flights are sorted by cheapest round-trip flights first.

Deals found on 7/30

Showing 1-10 of 19 resultsSorted by cheapest first
1
2

Compare providers for flights from Hilton Head Island to O'Hare Intl

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 O'Hare Intl in August.
ProviderPrice AccuracyTrust Score*
ExpediaPrice Accuracy1 starTrust Score*3 stars
FlightHubPrice 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 O'Hare Intl Airport 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 O'Hare Intl Airport flight deals on Cheapflights vs. FlightHub >95% of the time. Price accuracy is based on data collected from Hilton Head Island-Chicago O'Hare Intl Airport flight searches over the past month and is updated monthly.
  • Most trusted provider: When it comes to deals on Hilton Head Island-Chicago O'Hare Intl Airport 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 O'Hare Intl Airport 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 O'Hare Intl

Have a flexible travel schedule? Discover the best time to fly to O'Hare Intl 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 O'Hare Intl Airport

What is the cheapest time of day to fly from HHH to ORD?

Find hourly flight availability from Hilton Head Island to O'Hare Intl. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated August 1, 2026.

Regardless of the time of day you decide to fly, the ticket price will remain around the same. Book flights from Hilton Head Island to Chicago O'Hare Intl Airport as you normally would.

Reviews of airlines servicing O'Hare Intl

Get insights into the airlines that provide service to O'Hare Intl. 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 O'Hare Intl. Reviews last updated August 1, 2026.
Peruse reviews from past customers who have flown with United Airlines from Hilton Head Island to Chicago O'Hare Intl Airport to help guide your decision. You can also see how each airline stacks up in terms of entertainment options, comfort, food, crew/service, and boarding process.
United Airlines
7.4
Good
10,053 reviews

Crew

8.1

Overall

7.4

Comfort

7.3

Boarding

7.7

Entertainment

7.1

Food

6.7

Reviews

1 / 20
2.0
Mediocre

Deb,Jan 2025

MKE - ORD

It was terrible! So much to say, but in a nutshell we used vouchers from United because our last trip with them was awful with many mishaps and errors made. Unfortunately, this trip was even worse!
United Airlines
7.4
Good
10,053 reviews
United Airlines
7.4
Good
10,053 reviews

Crew

8.1

Overall

7.4

Comfort

7.3

Boarding

7.7

Entertainment

7.1

Food

6.7

Reviews

1 / 20
2.0
Mediocre

Deb,Jan 2025

MKE - ORD

It was terrible! So much to say, but in a nutshell we used vouchers from United because our last trip with them was awful with many mishaps and errors made. Unfortunately, this trip was even worse!

Related info for your journey

Find useful and relevant information for your journey from Hilton Head Island to O'Hare Intl. 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 O'Hare Intl?

    Hilton Head Island (HHH), located 3.3 mi from the city center, is the airport you fly out of when you book flights from Hilton Head Island to Chicago O'Hare Intl. 1 airline have flights from Hilton Head to Chicago O'Hare Intl on a regular basis. Booking flights from Hilton Head Island to Chicago O'Hare Intl should not be difficult; the airport handles an average of 1 outbound flight to Chicago O'Hare Intl per day.

  • How long is the flight from Hilton Head Island to Chicago O'Hare Intl Airport?

    Departing from Hilton Head Island to Chicago O'Hare Intl Airport will take you 2h 44m. Hilton Head Island and Chicago O'Hare Intl Airport are separated by a distance of 781 mi. Generally, flights for this route are nonstop.

  • What is the cheapest airline to fly from Hilton Head Island to Chicago O'Hare Intl Airport round-trip?

    Flying on United Airlines is currently your cheapest option to Chicago O'Hare Intl Airport, with prices starting at $229.

  • What are the most reliable airlines from Hilton Head Island to Chicago O'Hare Intl Airport?

    Consider United Airlines (74%), Envoy Air (65%) or Republic Airways (37%) when booking your flight. These represent the most reliable airlines when flying from Hilton Head Island to Chicago O'Hare Intl Airport.

  • What are the cheapest flights from Hilton Head Island to Chicago O'Hare Intl Airport?

    Looking at all options, your cheapest flight can be booked for $263. While the most popular route (Hilton Head Island - Chicago O'Hare Intl) can be booked for $279 on average, our data indicates $390 when flying from Hilton Head Island to Chicago O'Hare Intl Airport.

  • Can I find deals for flights from Hilton Head Island to O'Hare Intl that include hotel bookings?

    Yes. In addition to deals on Hilton Head Island to O'Hare Intl flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from Hilton Head Island to O'Hare Intl?

    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 O'Hare Intl.

  • Can I find deals for business class flights from Hilton Head Island to O'Hare Intl?

    Yes. Cheapflights offers flight deals from Hilton Head Island to O'Hare Intl 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 O'Hare Intl Airport?

Book flights to Chicago O'Hare Intl Airport if you plan to visit one of these locations
Benton Harbor
Rosemont
Schaumburg
Naperville
Lake Geneva
Oak Brook
Delavan
Oakbrook Terrace
Gurnee
South Holland
Libertyville
Orland Park
Hoffman Estates
Beloit
Downers Grove
Rockford
Aurora
Racine
Great Lakes
Janesville

Browse thousands of different options on Cheapflights for your next trip

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Top airline flying from Hilton Head Island to O'Hare Intl

Discover the top airline that operate flights from Hilton Head Island to O'Hare Intl. 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 August 1, 2026.
AirlineCheapestAverageFlexibilityOn-time
United AirlinesCheapest$229Average$355FlexibilityNo cancel feeOn-time69%

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