Cheap Flights from Hilton Head Island to Chicago
Cheap Flights from Hilton Head Island to Chicago
Looking for cheap flights from Hilton Head Island to Chicago? 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 Hilton Head Island to Chicago 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 Hilton Head Island to Chicago for specific travel dates.
2026-11-05
HHH - ORD
Economy | 1 Stop | 9+ left
From 7,500 Pts + $25.6
2026-11-06
HHH - ORD
Economy | 1 Stop | 9+ left
From 7,500 Pts + $25.6
2026-11-12
HHH - ORD
Economy | 1 Stop | 9+ left
From 7,500 Pts + $25.6
2026-11-13
HHH - ORD
Economy | 1 Stop | 9+ left
From 7,500 Pts + $25.6
2026-11-14
HHH - ORD
Economy | Non stop | 9+ left
From 7,500 Pts + $25.6
2026-11-18
HHH - ORD
Economy | 1 Stop | 8 left
From 7,500 Pts + $25.6
Hilton Head Island to Chicago 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
Chicago is 1 hour behind Hilton Head Island.
Airports in Hilton Head Island
HHH · Hilton Head
Airports in Chicago
DPA · Dupage
MDW · Chicago Midway Intl
ORD · Chicago O'Hare Intl
Nearby airport alternatives
Flights Savannah - Chicago · Savannah is 30 mi from Hilton Head Island
Flights Charleston - Chicago · Charleston is 60 mi from Hilton Head Island
Flights Hilton Head Island - Milwaukee · Milwaukee is 73 mi from Chicago
Flights Bush Field - Chicago · Bush Field is 108 mi from Hilton Head Island
Flights Columbia - Chicago · Columbia is 121 mi from Hilton Head Island
Flights Jacksonville - Chicago · Jacksonville is 133 mi from Hilton Head Island
Premium cabin flights from Hilton Head Island to Chicago
Premium cabin
2026-11-10
HHH - ORD
First | 1 Stop | 5 left
From 15,000 Pts + $25.6
Premium cabin
2026-11-19
HHH - ORD
First | 1 Stop | 7 left
From 15,000 Pts + $25.6
Premium cabin
2026-11-20
HHH - ORD
First | 1 Stop | 4 left
From 15,000 Pts + $25.6
Premium cabin
2026-11-21
HHH - ORD
First | 1 Stop | 3 left
From 15,000 Pts + $25.6
Premium cabin
2026-11-22
HHH - ORD
First | 1 Stop | 2 left
From 15,000 Pts + $25.6
Premium cabin
2026-11-23
HHH - ORD
First | 1 Stop | 2 left
From 15,000 Pts + $25.6
Selected hotels for your next stay
Chicago (United States)
Chicago Athletic Association
From 15,000 Pts or $236
Chicago (USA)
ACME Hotel Chicago, Outset Collection by Hilton
From 28,000 Pts or $75
Chicago, IL (USA)
Waldorf Astoria Chicago
From 95,000 Pts or $407
Frequently Asked Questions
The cheapest route from Hilton Head Island to Chicago 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 Hilton Head Island to Chicago.
Yes. Searching metro codes when available helps compare nearby airport combinations for flights from Hilton Head Island to Chicago.
Hilton Head Island and Chicago 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.
Chicago is 1 hour behind Hilton Head Island.
Departures from Hilton Head Island: Hilton Head (HHH). Arrivals in Chicago: Dupage (DPA), Chicago Midway Intl (MDW), Chicago O'Hare Intl (ORD).
Travelers searching this route also look at other popular routes into Chicago, plus the return trip when we track it. Fares and award space change daily.
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