St Simons Island to Chicago (SSI–MDW) — Airlines, Schedules & Connections

SSI Airport Page →
815 mi airlines charter/private ~1/wk
On-time Some delays Frequent delays
Connecting Flight Schedule 1 1-stop flight Verified 1w 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 1 hub
RSW Fort Myers ~5h 21m → WN Fort Myers (RSW) to Chicago flights
✦ 1-STOP More options, longer trips
✧ 2-STOP Loading... Reach the hardest destinations
St Simons Island to Chicago
Flown by charter / private operators — no scheduled airline service.
815 mi 1h 58m nonstop -1h behind

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

Also explore SSI Routes MDW Routes SSI Live Flights MDW Live Flights MDW Delays
All flights from Chicago (MDW) Chicago to St Simons Island flights
Connections

Connection Landscape

1-stop and 2-stop options for SSI to MDW.
1-STOP
One-Stop Connections
1
Hubs
~5h
Fastest
~5h
Longest
RSW ~5h 21m
Verified with published schedule alignment and minimum connection time.
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
SSI → MDW
70%
Moderate delays possible. Allow buffer time.
Arriving
70%
Return
MDW → SSI
28%
Frequent delays expected. Consider flexible booking.
Departing
28%
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 St Simons Island

Nearby airports with service to Chicago Midway International Airport.
Metric SSI→MDW JAX→MDW SAV→MDW
Distance from SSI – 49 mi 68 mi
Nonstop airlines – 3 4
Weekly flights ~1 15 10
Flight time 1h 58m 2h 20m 2h 10m
Jacksonville (JAX) to Chicago flights · Savannah (SAV) to Chicago flights · St Augustine (UST) to Chicago flights
Airports within 200 miles of SSI 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 St Simons Island.
SSI: EDT · MDW: CDT

When it's 6:00 PM in St Simons Island, it's 5:00 PM in Chicago.
Distance & Flight Time
815 mi / 1,311 km
Nonstop flight time is approximately 1h 58m gate to gate.
Facts

SSI–MDW Quick Facts

Key statistics for the St Simons Island to Chicago route.
Route details
Distance815 mi / 1,311 km
Flight time1h 58m
Time difference-1 hour
Airlines (nonstop)Charter / private
Weekly flights~1 out
1-stop connectionsAvailable
Origin: SSI
Full nameSt Simons Island Airport
IATA / ICAOSSI / KSSI
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 SSI to MDW flights.
Nonstop flights from St Simons Island Airport to Chicago Midway International Airport take about 1h 58m gate to gate. The route covers 815 miles.
Yes, 1-stop connections are available, ranked by layover time.
Chicago is 1 hour behind St Simons Island.
Yes, return flights from MDW to SSI are available. Use the direction toggle at the top to view the return schedule.
Nearby alternatives include JAX, SAV and UST. 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 SSI to MDW

St Simons Island Airport (SSI) and Chicago Midway International Airport (MDW) are connected through multiple connecting hub airports.

SSI to MDW Flight Duration and Schedule

Nonstop flight time from SSI to MDW is about 1 hours 58 minutes gate to gate. The route covers a distance of 815 miles (1,311 km).

Connecting Options and Alternatives

1-stop connecting options are also available. Nearby alternative airports include Jacksonville (JAX), Savannah (SAV) and St Augustine (UST).