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

MDW Airport Page →
766 mi airlines charter/private ~1/wk
On-time Some delays Frequent delays
Connecting Flight Schedule 7 1-stop flights Verified 2w ago
Charter / private route. No scheduled airline service — operated by charter & private 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 7 hubs
CLT Charlotte 4h 39m WN → AA Charlotte (CLT) to Hilton Head Island flights
LGA New York 5h 18m WN → DL New York (LGA) to Hilton Head Island flights
ATL Atlanta 5h 28m AFAMDL → AFDL Atlanta (ATL) to Hilton Head Island flights
DCA Washington 6h 29m WN → AA Washington (DCA) to Hilton Head Island flights
BOS Boston 8h 49m WN → AA Boston (BOS) to Hilton Head Island flights
PHL Philadelphia 15h 50m EJAWN → AA Philadelphia (PHL) to Hilton Head Island flights
SAV Savannah ~17h WN → DLUA Savannah (SAV) 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
7
Hubs
~4h
Fastest
~17h
Longest
CLT ~4h 39m LGA ~5h 18m ATL ~5h 28m DCA ~6h 29m BOS ~8h 49m
Verified with published schedule alignment and minimum connection time.
2-STOP
Two-Stop Connections
510
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
76%
Generally reliable. Most flights run on time.
Departing
76%
Return
HHH → MDW
79%
Generally reliable. Most flights run on time.
Arriving
79%
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 – 3 1
Weekly flights ~1 14 1
Flight time 1h 47m 2h 27m 1h 37m
Departure OTP 76% – –
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
Weekly flights~1 out / ~1 return
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, LaGuardia and Hartsfield Jackson Atlanta.
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, LaGuardia and Hartsfield Jackson Atlanta. Two-stop connections are also available via intermediate hubs. Nearby alternative airports include Chicago (ORD), South Bend (SBN) and Milwaukee (MKE).