Chicago to Hilton Head Island (MDW–HHH) — Airlines, Schedules & Connections

MDW Airport Page →
766 mi airlines charter/private
On-time Some delays Frequent delays
Connecting Flight Schedule 6 1-stop flights Verified 1mo ago
Charter / private route. No scheduled airline service — operated by NetJets Aviation.
Nonstop Charter / private 1-Stop 2-Stop Hide separate tickets Hide overnight Hide codeshares
  Flight Airline AC Dep Arr Dur OTP Sched  
✈ Nonstop

No flights match your filters.

No scheduled airline flights on this route — it's flown by charter / private operators (). No nonstop flights on this route. connecting options below.

✦ 1-Stop connections via 6 hubs
CLT Charlotte 4h 21m EJAWN → AA Charlotte (CLT) to Hilton Head Island flights
ATL Atlanta 4h 39m AFAMDL → DL Atlanta (ATL) to Hilton Head Island flights
LGA New York 5h 14m WN → DL New York (LGA) to Hilton Head Island flights
DCA Washington 6h 37m WN → AA Washington (DCA) to Hilton Head Island flights
BOS Boston 7h 55m WN → AA Boston (BOS) to Hilton Head Island flights
PHL Philadelphia 16h 12m WN → AA Philadelphia (PHL) to Hilton Head Island flights
✦ 1-STOP More options, longer trips
✧ 2-STOP Loading... Reach the hardest destinations
Chicago to Hilton Head Island
Flown by charter / private operators — no scheduled airline service.
766 mi 1h 47m nonstop +1h ahead

MDW–HHH has no scheduled airline service; it is flown by charter / private operators. 1-stop connecting options are also available.

Also explore MDW Routes HHH Routes MDW Live Flights HHH Live Flights MDW Delays
All flights from Hilton Head Island (HHH) Hilton Head Island to Chicago flights
Connections

Connection Landscape

1-stop and 2-stop options for MDW to HHH.
1-STOP
One-Stop Connections
6
Hubs
~4h
Fastest
~16h
Longest
CLT ~4h 21m ATL ~4h 39m LGA ~5h 14m DCA ~6h 37m BOS ~7h 55m
Verified with published schedule alignment and minimum connection time.
2-STOP
Two-Stop Connections
482
Candidates
Two-stop connections loaded in the connections tab above.
Connections computed from published schedules with minimum connection time verification. Use the interactive explorer above the fold to filter by airline, tier, and layover time.
Reliability

On-Time Performance

What to expect at each end of your journey.
Outbound
MDW → HHH
51%
Frequent delays expected. Consider flexible booking.
Departing
51%
Return
HHH → MDW
68%
Moderate delays possible. Allow buffer time.
Arriving
68%
OTP = percentage of flights arriving within 15 min of schedule. Based on airport-level delay snapshots. MDW delays →
Alternatives

Other ways to reach Hilton Head Island from Chicago

Nearby airports with service to Hilton Head Airport.
Metric MDW→HHH ORD→HHH SBN→HHH
Distance from MDW – 15 mi 74 mi
Nonstop airlines – 5 1
Weekly flights – 21 –
Flight time 1h 47m 2h 24m 1h 37m
Departure OTP 51% – –
Chicago (ORD) to Hilton Head Island flights · South Bend (SBN) to Hilton Head Island flights · Milwaukee (MKE) to Hilton Head Island flights
Airports within 200 miles of MDW with service to Hilton Head Airport.
Know before you go

Travel Essentials

Practical planning for this route.
Time Difference
+1h
Hilton Head Island is 1 hour ahead of Chicago.
MDW: CDT · HHH: EDT

When it's 6:00 PM in Chicago, it's 7:00 PM in Hilton Head Island.
Distance & Flight Time
766 mi / 1,233 km
Nonstop flight time is approximately 1h 47m gate to gate.
Facts

MDW–HHH Quick Facts

Key statistics for the Chicago to Hilton Head Island route.
Route details
Distance766 mi / 1,233 km
Flight time1h 47m
Time difference+1 hour
Airlines (nonstop)Charter / private
1-stop connectionsAvailable
Origin: MDW
Full nameChicago Midway International Airport
IATA / ICAOMDW / KMDW
TimezoneAmerica/Chicago
Passengers/yr20.7M
Elevation620 ft / 189 m
Destination: HHH
Full nameHilton Head Airport
IATA / ICAOHHH / KHXD
TimezoneAmerica/New_York
Elevation19 ft / 6 m
FAQ

Frequently Asked Questions

Common questions about MDW to HHH flights.
Nonstop flights from Chicago Midway International Airport to Hilton Head Airport take about 1h 47m gate to gate. The route covers 766 miles.
Yes, 1-stop connections are available, ranked by layover time. Common connecting points include Charlotte Douglas, Hartsfield Jackson Atlanta and LaGuardia.
Hilton Head Island is 1 hour ahead of Chicago.
Yes, return flights from HHH to MDW are available. Use the direction toggle at the top to view the return schedule.
Nearby alternatives include ORD, SBN and MKE. See the Alternatives section for a full comparison.
Click the 'Search Flights' button to check availability and prices on Google Flights. You can also compare airlines and schedules on this page to find the best option.
See the On-Time Performance section for the latest delay data at both airports. This shows departure and arrival reliability to help you plan.
Route data is updated regularly from official airline schedules. On-time performance data comes from recent airport delay snapshots.

Flights from MDW to HHH

Chicago Midway International Airport (MDW) and Hilton Head Airport (HHH) are connected through multiple connecting hub airports.

MDW to HHH Flight Duration and Schedule

Nonstop flight time from MDW to HHH is about 1 hours 47 minutes gate to gate. The route covers a distance of 766 miles (1,233 km).

Connecting Options and Alternatives

1-stop connecting options are also available, commonly via Charlotte Douglas, Hartsfield Jackson Atlanta and LaGuardia. Two-stop connections are also available via intermediate hubs. Nearby alternative airports include Chicago (ORD), South Bend (SBN) and Milwaukee (MKE).