Cheap Flights from Chicago to Hilton Head Island
Cheap Flights from Chicago to Hilton Head Island
Looking for cheap flights from Chicago to Hilton Head Island? PointsYeah scans award availability across major airline and bank transfer programs in one place, so travelers can compare the lowest points and cash routes faster. Instead of searching each airline separately, users can see pricing from programs like Chase, Amex, Capital One, Citi, and Bilt side by side.
Award prices from Chicago to Hilton Head Island vary by season, cabin, and date, but available award flights can start around 7,500 points one way, with premium cabins available at higher mileage levels. The live search above allows filtering by cabin, airline, stops, or maximum points to find the best award flights from Chicago to Hilton Head Island for specific travel dates.
2026-11-07
ORD - HHH
Economy | Non stop | 5 left
From 7,500 Pts + $25.6
2026-11-08
ORD - HHH
Economy | 1 Stop | 9+ left
From 7,500 Pts + $25.6
2026-11-10
ORD - HHH
Economy | 1 Stop | 9+ left
From 7,500 Pts + $25.6
2026-11-14
ORD - HHH
Economy | Non stop | 9+ left
From 7,500 Pts + $25.6
2026-11-15
ORD - HHH
Economy | 1 Stop | 9+ left
From 7,500 Pts + $25.6
2026-11-09
ORD - HHH
Economy | 1 Stop | 2 left
From 7,500 Pts + $31.2
Chicago to Hilton Head Island flight facts
Distance
778 mi
1,252 km in a straight line
Estimated flight time
about 2h
In the air, for the straight-line distance
Time difference
+1h
Hilton Head Island is 1 hour ahead of Chicago.
Airports in Chicago
DPA · Dupage
MDW · Chicago Midway Intl
ORD · Chicago O'Hare Intl
Airports in Hilton Head Island
HHH · Hilton Head
Nearby airport alternatives
Flights Chicago - Savannah · Savannah is 30 mi from Hilton Head Island
Flights Chicago - Charleston · Charleston is 60 mi from Hilton Head Island
Flights Chicago - Bush Field · Bush Field is 108 mi from Hilton Head Island
Flights Chicago - Columbia · Columbia is 121 mi from Hilton Head Island
Flights Chicago - Jacksonville · Jacksonville is 133 mi from Hilton Head Island
Flights Chicago - Myrtle Beach · Myrtle Beach is 144 mi from Hilton Head Island
Premium cabin flights from Chicago to Hilton Head Island
Premium cabin
2026-11-13
ORD - HHH
First | 1 Stop | 3 left
From 15,000 Pts + $25.6
Premium cabin
2026-11-16
ORD - HHH
First | 1 Stop | 1 left
From 15,000 Pts + $25.6
Premium cabin
2026-11-17
ORD - HHH
First | 1 Stop | 3 left
From 15,000 Pts + $25.6
Premium cabin
2026-11-06
ORD - HHH
First | 1 Stop | 4 left
From 15,000 Pts + $31.2
Premium cabin
2026-11-22
ORD - HHH
First | 1 Stop
From 29,500 Pts + $5.6
Premium cabin
2026-11-22
ORD - HHH
First | 1 Stop
From 29,500 Pts + $5.6
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Frequently Asked Questions
The cheapest route from Chicago to Hilton Head Island depends on award space, transfer bonuses, and travel dates. PointsYeah compares bank and airline programs in one place so you can find the best points and cash combinations faster.
Yes. Transferable points from Chase, Amex, Capital One, Citi, and Bilt can often be moved to airline partners for flights from Chicago to Hilton Head Island.
Yes. Searching metro codes when available helps compare nearby airport combinations for flights from Chicago to Hilton Head Island.
Chicago and Hilton Head Island are about 778 miles (1,252 km) apart in a straight line.
Flying the 778-mile straight-line distance takes about 2h in the air, estimated from typical cruising speed. Actual travel time depends on the routing; itineraries with connections take longer.
Hilton Head Island is 1 hour ahead of Chicago.
Departures from Chicago: Dupage (DPA), Chicago Midway Intl (MDW), Chicago O'Hare Intl (ORD). Arrivals in Hilton Head Island: Hilton Head (HHH).
Travelers searching this route also look at other popular routes into Hilton Head Island, plus the return trip when we track it. Fares and award space change daily.
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