$239+ 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 11/1. Fares are subject to change and may not be available on all flights or dates of travel.
HHH — CHI
Oct 18 — Oct 251
Round-trip
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
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
Cheapest
Best
Last-minute
One-way
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 September 18, 2026.
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 September 18, 2026.
This United Airlines deal was found by Cheapflights users on 9/15. 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 10/102:51 pm -
Nonstop3h 14m
Sat 10/2410:35 am -
Nonstop2h 35m
Deal found 9/15![United Airlines logo]()
$319
This American Airlines deal was found by Cheapflights users on 9/15. 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 11/611:04 am -
1 stop7h 36m
Sun 11/89:00 am -
1 stop7h 10m
Deal found 9/15![American Airlines logo]()
$339
This Delta deal was found by Cheapflights users on 9/17. 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 10/234:13 pm -
1 stop7h 04m
Tue 10/277:00 am -
2 stops7h 30m
Deal found 9/17![Delta logo]()
$344
This Delta deal was found by Cheapflights users on 9/13. 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 10/2812:23 pm -
2 stops9h 07m
Wed 11/46:00 am -
2 stops8h 30m
Deal found 9/13![Delta logo]()
$349
This American Airlines deal was found by Cheapflights users on 9/14. 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 10/211:07 am -
1 stop4h 58m
Mon 10/58:05 am -
1 stop5h 21m
Deal found 9/14![American Airlines logo]()
$359
This Delta deal was found by Cheapflights users on 9/14. 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 10/212:17 pm -
1 stop5h 20m
Mon 10/56:00 am -
2 stops8h 27m
Deal found 9/14![Delta logo]()
$364
This American Airlines deal was found by Cheapflights users on 9/14. 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.
Wed 10/146:08 pm -
1 stop5h 52m
Wed 10/216:29 am -
2 stops6h 57m
Deal found 9/14![American Airlines logo]()
$378
This American Airlines deal was found by Cheapflights users on 9/16. 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 10/111:07 am -
1 stop6h 11m
Mon 10/55:00 am -
1 stop5h 18m
Deal found 9/16![American Airlines logo]()
$379
This Delta deal was found by Cheapflights users on 9/16. 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 10/14:17 pm -
1 stop7h 01m
Mon 10/56:00 am -
2 stops8h 27m
Deal found 9/16![Delta logo]()
$384
This American Airlines deal was found by Cheapflights users on 9/17. 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 10/152:56 pm -
1 stop5h 55m
Sat 10/1712:05 pm -
1 stop4h 35m
Deal found 9/17![American Airlines logo]()
$402
Best flights from Hilton Head Island to ChicagoDiscover 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 September 18, 2026.
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 September 18, 2026.
This United Airlines deal was found by Cheapflights users on 9/15. 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 10/102:51 pm -
Nonstop3h 14m
Sat 10/2410:35 am -
Nonstop2h 35m
Deal found 9/15![United Airlines logo]()
$319
This American Airlines deal was found by Cheapflights users on 9/15. 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 11/611:04 am -
1 stop7h 36m
Sun 11/89:00 am -
1 stop7h 10m
Deal found 9/15![American Airlines logo]()
$339
This Delta deal was found by Cheapflights users on 9/13. 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 10/2812:23 pm -
1 stop5h 35m
Wed 11/48:05 am -
1 stop6h 25m
Deal found 9/13![Delta logo]()
$339
This American Airlines deal was found by Cheapflights users on 9/14. 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 10/96:08 pm -
1 stop7h 00m
Sun 10/115:00 am -
1 stop5h 05m
Deal found 9/14![American Airlines logo]()
$339
This Delta deal was found by Cheapflights users on 9/14. 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 10/212:17 pm -
1 stop5h 20m
Mon 10/56:00 am -
2 stops8h 27m
Deal found 9/14![Delta logo]()
$364
This American Airlines deal was found by Cheapflights users on 9/14. 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.
Wed 10/146:08 pm -
1 stop5h 52m
Wed 10/216:29 am -
2 stops6h 57m
Deal found 9/14![American Airlines logo]()
$378
This Delta deal was found by Cheapflights users on 9/17. 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 10/212:17 pm -
1 stop5h 20m
Tue 10/68:05 am -
1 stop6h 25m
Deal found 9/17![Delta logo]()
$379
This American Airlines deal was found by Cheapflights users on 9/16. 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 10/111:07 am -
1 stop6h 11m
Mon 10/55:00 am -
1 stop5h 18m
Deal found 9/16![American Airlines logo]()
$379
This Delta deal was found by Cheapflights users on 9/16. 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 10/112:17 pm -
2 stops7h 58m
Mon 10/56:00 am -
2 stops8h 27m
Deal found 9/16![Delta logo]()
$389
This American Airlines deal was found by Cheapflights users on 9/17. 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 10/152:56 pm -
1 stop5h 55m
Sat 10/1712:05 pm -
1 stop4h 35m
Deal found 9/17![American Airlines logo]()
$402
Last-minute flights from Hilton Head Island to ChicagoDiscover last-minute flight deals from Hilton Head Island to Chicago. Data last updated September 18, 2026 and is based on user searches.
Discover last-minute flight deals from Hilton Head Island to Chicago. Data last updated September 18, 2026 and is based on user searches.
This American Airlines deal was found by Cheapflights users on 9/16. 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 10/111:07 am -
1 stop6h 11m
Mon 10/55:00 am -
1 stop5h 18m
Deal found 9/16![American Airlines logo]()
$379
This Delta deal was found by Cheapflights users on 9/16. 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 10/14:17 pm -
1 stop7h 01m
Mon 10/56:00 am -
2 stops8h 27m
Deal found 9/16![Delta logo]()
$384
This American Airlines deal was found by Cheapflights users on 9/14. 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 10/211:07 am -
1 stop4h 58m
Mon 10/58:05 am -
1 stop5h 21m
Deal found 9/14![American Airlines logo]()
$359
This Delta deal was found by Cheapflights users on 9/14. 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 10/212:17 pm -
1 stop5h 20m
Mon 10/56:00 am -
2 stops8h 27m
Deal found 9/14![Delta logo]()
$364
This American Airlines deal was found by Cheapflights users on 9/14. 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 10/96:08 pm -
1 stop7h 00m
Sun 10/115:00 am -
1 stop5h 05m
Deal found 9/14![American Airlines logo]()
$339
This United Airlines deal was found by Cheapflights users on 9/15. 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 10/102:51 pm -
Nonstop3h 14m
Sat 10/2410:35 am -
Nonstop2h 35m
Deal found 9/15![United Airlines logo]()
$319
This American Airlines deal was found by Cheapflights users on 9/14. 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.
Wed 10/146:08 pm -
1 stop5h 52m
Wed 10/216:29 am -
2 stops6h 57m
Deal found 9/14![American Airlines logo]()
$378
This American Airlines deal was found by Cheapflights users on 9/17. 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 10/152:56 pm -
1 stop5h 55m
Sat 10/1712:05 pm -
1 stop4h 35m
Deal found 9/17![American Airlines logo]()
$402
This Delta deal was found by Cheapflights users on 9/17. 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 10/234:13 pm -
1 stop7h 04m
Tue 10/277:00 am -
2 stops7h 30m
Deal found 9/17![Delta logo]()
$344
This Delta deal was found by Cheapflights users on 9/13. 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 10/2812:23 pm -
2 stops9h 07m
Wed 11/46:00 am -
2 stops8h 30m
Deal found 9/13![Delta logo]()
$349
One-way flights from Hilton Head Island to ChicagoSearch for one-way flight options from Hilton Head Island to Chicago. Find affordable one-way fares based on user searches. Data last updated September 18, 2026.
Search for one-way flight options from Hilton Head Island to Chicago. Find affordable one-way fares based on user searches. Data last updated September 18, 2026.
This American Airlines deal was found by Cheapflights users on 9/12. 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.
Sun 11/15:54 pm -
1 stop5h 38m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/12![American Airlines logo]()
$239
This American Airlines deal was found by Cheapflights users on 9/16. 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 11/141:55 pm -
Nonstop2h 42m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/16![American Airlines logo]()
$279
This Delta deal was found by Cheapflights users on 9/17. 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 10/154:13 pm -
1 stop7h 04m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/17![Delta logo]()
$289
This Delta deal was found by Cheapflights users on 9/16. 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 10/1312:23 pm -
2 stops10h 54m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/16![Delta logo]()
$294
This American Airlines deal was found by Cheapflights users on 9/16. 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 12/187:10 pm -
1 stop5h 49m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/16![American Airlines logo]()
$309
This American Airlines deal was found by Cheapflights users on 9/16. 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 3/136:22 pm -
1 stop5h 38m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/16![American Airlines logo]()
$319
This Delta deal was found by Cheapflights users on 9/13. 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 10/1412:23 pm -
2 stops9h 20m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/13![Delta logo]()
$325
This American Airlines deal was found by Cheapflights users on 9/16. 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.
Sun 3/1411:03 am -
1 stop4h 17m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/16![American Airlines logo]()
$339
This American Airlines deal was found by Cheapflights users on 9/16. 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 11/174:17 pm -
2 stops14h 53m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/16![American Airlines logo]()
$345
This American Airlines deal was found by Cheapflights users on 9/16. 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.
Mon 11/164:17 pm -
2 stops19h 53m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/16![American Airlines logo]()
$358
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 September 18, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $319 (United Airlines) |
One-way from | $239 (American Airlines) |
Good round-trip deal | $347 or less |
Good one-way deal | $314 or less |
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 7,457,451 searches. Data last updated September 18, 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
Cheapest round-trip
Hilton Head IslandChicago
HHH Hilton Head Island - ORD Chicago O'Hare Intl
HHHORD
Hilton Head Island
Thu 10/15
4:13 pm-10:17 pm
1 stop7h 04m
Chicago O'Hare Intl
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$289
Hilton Head IslandChicago
HHH Hilton Head Island - ORD Chicago O'Hare Intl
HHHORD
Hilton Head Island
Tue 10/13
12:23 pm-10:17 pm
2 stops10h 54m
Chicago O'Hare Intl
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$294
Hilton Head IslandChicago
HHH Hilton Head Island - ORD Chicago O'Hare Intl
HHHORD
Hilton Head Island
Wed 10/14
12:23 pm-7:20 pm
2 stops7h 57m
Chicago O'Hare Intl
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$294
Hilton Head IslandChicago
HHH Hilton Head Island - ORD Chicago O'Hare Intl
HHHORD
Hilton Head Island
Tue 10/27
12:23 pm-8:30 pm
2 stops9h 07m
Chicago O'Hare Intl
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$294
Quickest round-trip
Hilton Head IslandChicago
HHH Hilton Head Island - ORD Chicago O'Hare Intl
HHHORD
Hilton Head Island
Sat 10/10
2:51 pm-5:05 pm
Nonstop3h 14m
Chicago O'Hare Intl
Sat 10/24
10:35 am-2:10 pm
Nonstop2h 35m
$319
Hilton Head IslandChicago
HHH Hilton Head Island - ORD Chicago O'Hare Intl
HHHORD
Hilton Head Island
Fri 10/9
12:23 pm-9:27 pm
2 stops10h 04m
Chicago O'Hare Intl
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$325
Hilton Head IslandChicago
HHH Hilton Head Island - ORD Chicago O'Hare Intl
HHHORD
Hilton Head Island
Sun 11/1
2:51 pm-9:29 pm
2 stops7h 38m
Chicago O'Hare Intl
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$330
Hilton Head IslandChicago
HHH Hilton Head Island - ORD Chicago O'Hare Intl
HHHORD
Hilton Head Island
Fri 11/6
11:04 am-5:40 pm
1 stop7h 36m
Chicago O'Hare Intl
Sun 11/8
9:00 am-5:10 pm
1 stop7h 10m
$339
Hilton Head IslandChicago
HHH Hilton Head Island - ORD Chicago O'Hare Intl
HHHORD
Hilton Head Island
Wed 10/28
12:23 pm-4:58 pm
1 stop5h 35m
Chicago O'Hare Intl
Wed 11/4
8:05 am-3:30 pm
1 stop6h 25m
$339
Hilton Head IslandChicago
HHH Hilton Head Island - ORD Chicago O'Hare Intl
HHHORD
Hilton Head Island
Fri 10/9
6:08 pm-12:08 am
1 stop7h 00m
Chicago O'Hare Intl
Sun 10/11
5:00 am-11:05 am
1 stop5h 05m
$339
Showing 1-10 of 16 resultsSorted by cheapest first
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 September.
| Provider | Price Accuracy | Trust Score* |
|---|---|---|
| Price Accuracy1 star | Trust Score*3 stars | |
| Price Accuracy3 stars | Trust Score*3 stars |
- 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.
HHH-CHI
HHH-ORD
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
HHH-CHI
HHH-ORD
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 September 18, 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 September 18, 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).
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 September 18, 2026.
See what other customers who have flown with 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.
Boarding
7.7
Food
6.7
Comfort
7.3
Crew
8.1
Overall
7.4
Entertainment
7.1
Reviews
1 / 20
4.0
OkayChris,Aug 2026
MIA - ORD
Boarding
7.7
Food
6.7
Comfort
7.3
Crew
8.1
Overall
7.4
Entertainment
7.1
Reviews
1 / 20
4.0
OkayChris,Aug 2026
MIA - ORD
Boarding
7.7
Food
6.7
Comfort
7.3
Crew
8.1
Overall
7.4
Entertainment
7.1
Reviews
1 / 20
4.0
OkayChris,Aug 2026
MIA - ORD
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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.
Traveling to a place near Chicago?
Book flights to Chicago if you plan to visit one of these locationsBenton Harbor
Lansing
Merrillville
Valparaiso
Hammond
Saint Joseph
Porter
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Hilton Head Island and Chicago flights
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Top airline flying from Hilton Head Island to Chicago
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| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$229 | Average$355 | FlexibilityNo cancel fee | On-time69% |