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

HHH Airport Page →
766 mi airlines charter/private ~1/wk
On-time Some delays Frequent delays
Connecting Flight Schedule 9 1-stop flights Verified 3w 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 9 hubs
ATL Atlanta 4h 27m DL → AFAMDL Atlanta (ATL) to Chicago flights
CLT Charlotte 5h 23m AAEJA → WN Charlotte (CLT) to Chicago flights
PHL Philadelphia 5h 41m AA → EJAWN Philadelphia (PHL) to Chicago flights
DCA Washington 6h 25m AA → WN Washington (DCA) to Chicago flights
LGA New York 7h 40m DL → WN New York (LGA) to Chicago flights
BOS Boston 18h 31m AA → WN Boston (BOS) to Chicago flights
EWR Newark 23h 11m UA → UA Newark (EWR) to Chicago flights
ORF Norfolk ~5h 49m DL → WN Norfolk (ORF) to Chicago flights
MIA Miami ~6h 7m → EJAWN Miami (MIA) to Chicago flights
✦ 1-STOP More options, longer trips
✧ 2-STOP Loading... Reach the hardest destinations
Hilton Head Island to Chicago
Flown by charter / private operators — no scheduled airline service.
766 mi 1h 49m nonstop -1h behind

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

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

Connection Landscape

1-stop and 2-stop options for HHH to MDW.
1-STOP
One-Stop Connections
9
Hubs
~4h
Fastest
~23h
Longest
ATL ~4h 27m CLT ~5h 23m PHL ~5h 41m ORF ~5h 49m MIA ~6h 7m
Verified with published schedule alignment and minimum connection time.
2-STOP
Two-Stop Connections
484
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
HHH → MDW
48%
Frequent delays expected. Consider flexible booking.
Arriving
48%
Return
MDW → HHH
38%
Frequent delays expected. Consider flexible booking.
Departing
38%
OTP = percentage of flights arriving within 15 min of schedule. Based on airport-level delay snapshots. MDW delays →
Alternatives

Other ways to reach Chicago from Hilton Head Island

Nearby airports with service to Chicago Midway International Airport.
Metric HHH→MDW SAV→MDW CHS→MDW
Distance from HHH – 30 mi 60 mi
Nonstop airlines – 4 6
Weekly flights ~1 10 14
Flight time 1h 49m 2h 10m 2h 10m
Savannah (SAV) to Chicago flights · Charleston (CHS) to Chicago flights · Augusta (AGS) to Chicago flights
Airports within 200 miles of HHH with service to Chicago Midway International Airport.
Know before you go

Travel Essentials

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

When it's 6:00 PM in Hilton Head Island, it's 5:00 PM in Chicago.
Distance & Flight Time
766 mi / 1,233 km
Nonstop flight time is approximately 1h 49m gate to gate.
Facts

HHH–MDW Quick Facts

Key statistics for the Hilton Head Island to Chicago route.
Route details
Distance766 mi / 1,233 km
Flight time1h 49m
Time difference-1 hour
Airlines (nonstop)Charter / private
Weekly flights~1 out / ~1 return
1-stop connectionsAvailable
Origin: HHH
Full nameHilton Head Airport
IATA / ICAOHHH / KHXD
TimezoneAmerica/New_York
Elevation19 ft / 6 m
Destination: MDW
Full nameChicago Midway International Airport
IATA / ICAOMDW / KMDW
TimezoneAmerica/Chicago
Passengers/yr20.7M
Elevation620 ft / 189 m
FAQ

Frequently Asked Questions

Common questions about HHH to MDW flights.
Nonstop flights from Hilton Head Airport to Chicago Midway International Airport take about 1h 49m gate to gate. The route covers 766 miles.
Yes, 1-stop connections are available, ranked by layover time. Common connecting points include Hartsfield Jackson Atlanta, Charlotte Douglas and Philadelphia.
Chicago is 1 hour behind Hilton Head Island.
Yes, return flights from MDW to HHH are available. Use the direction toggle at the top to view the return schedule.
Nearby alternatives include SAV, CHS and AGS. 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 HHH to MDW

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

HHH to MDW Flight Duration and Schedule

Nonstop flight time from HHH to MDW is about 1 hours 49 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 Hartsfield Jackson Atlanta, Charlotte Douglas and Philadelphia. Two-stop connections are also available via intermediate hubs. Nearby alternative airports include Savannah (SAV), Charleston (CHS) and Augusta (AGS).