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

HHH Airport Page →
766 mi airlines 1/wk
On-time Some delays Frequent delays
Flight Schedule 0 flights Verified 1w ago
Nonstop 1-Stop 2-Stop Hide separate tickets Hide overnight
  Flight Airline AC Dep Arr Dur OTP Sched  

No flights match your filters.

No nonstop flights on this route. connecting options below.

✦ 1-STOP
✧ 2-STOP Loading...
Hilton Head Island to Chicago
Connecting service available through multiple hubs.
1 Flights/wk 766 mi 2h 21m nonstop -1h behind 17 1-stop hubs

While no nonstop service exists between HHH and MDW, connecting options are available through 17 hubs.

Also explore HHH Routes MDW Routes HHH Live Flights MDW Live Flights MDW Delays
Connections

Connection Landscape

Beyond nonstop. 1-stop and 2-stop options for HHH to MDW.
1-STOP
One-Stop Connections
17
Hubs
~3h
Fastest
~24h
Longest
STL ~3h 19m TYS ~3h 56m CLE ~4h 31m MCO ~5h 3m APF ~5h 25m
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
HHH → MDW
96%
Generally reliable. Most flights run on time.
Arriving
96%
Return
MDW → HHH
52%
Frequent delays expected. Consider flexible booking.
Departing
52%
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 0 1 1
Weekly flights 1 17 15
Flight time 2h 21m 2h 15m 1h 51m
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 2h 21m.
Facts

HHH–MDW Quick Facts

Key statistics for the Hilton Head Island to Chicago route.
Route details
Distance766 mi / 1,233 km
Flight time2h 21m
Time difference-1 hour
Airlines (nonstop)0
Weekly flights1 out
1-stop connections17 hubs
Origin: HHH
Full nameHilton Head Airport
IATA / ICAOHHH / KHXD
TimezoneAmerica/Kentucky/Monticello
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 approximately 2h 21m. The route covers 766 miles.
There are approximately 1 nonstop flights per week from HHH to MDW.
Yes, 1-stop connections are available through STL, TYS, CLE, MCO, APF, RSW, PHL, BOS, FLL, MIA, DAL, ATL, CLT, DCA, LGA, EWR and ORD. These options provide additional schedule flexibility.
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 ranges from 2 hours 21 minutes. The route covers a distance of 766 miles (1,233 km).

Connecting Options and Alternatives

17 one-stop connections are available, with the fastest taking approximately 3 hours via STL. Two-stop connections are also available via intermediate hubs. Nearby alternative airports include Savannah (SAV), Charleston (CHS) and Augusta (AGS).