Charlotte Amalie to Chicago (STT–MDW) — Airlines, Schedules & Connections

STT Airport Page →
2,103 mi airlines charter/private
On-time Some delays Frequent delays
Connecting Flight Schedule 5 1-stop flights Verified 3mos 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 5 hubs
ATL Atlanta 6h 36m DLVS → AFAMDL Atlanta (ATL) to Chicago flights
MCO Orlando 6h 48m WN → WN Orlando (MCO) to Chicago flights
CLT Charlotte 7h 6m AA → EJAWN Charlotte (CLT) to Chicago flights
MIA Miami 17h 56m AA → EJAWN Miami (MIA) to Chicago flights
IAH Houston ~8h 52m UA → UA Houston (IAH) to Chicago flights
✦ 1-STOP More options, longer trips
✧ 2-STOP Loading... Reach the hardest destinations
Charlotte Amalie to Chicago
Flown by charter / private operators — no scheduled airline service.
2,103 mi 4h 50m nonstop -1h behind

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

Also explore Browse available seat maps STT Routes MDW Routes STT Live Flights MDW Live Flights STT Delays MDW Delays
All flights from Chicago (MDW) Chicago to Charlotte Amalie flights
Connections

Connection Landscape

1-stop and 2-stop options for STT to MDW.
1-STOP
One-Stop Connections
5
Hubs
~6h
Fastest
~17h
Longest
ATL ~6h 36m MCO ~6h 48m CLT ~7h 6m IAH ~8h 52m MIA ~17h 56m
Verified with published schedule alignment and minimum connection time.
2-STOP
Two-Stop Connections
516
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
STT → MDW
100%
Generally reliable. Most flights run on time.
Departing
100%
Arriving
90%
Return
MDW → STT
91%
Generally reliable. Most flights run on time.
Departing
91%
Arriving
100%
OTP = percentage of flights arriving within 15 min of schedule. Based on airport-level delay snapshots. STT delays → MDW delays →
Alternatives

Other ways to reach Chicago from Charlotte Amalie

Nearby airports with service to Chicago Midway International Airport.
Metric STT→MDW EIS→MDW SJU→MDW
Distance from STT – 30 mi 68 mi
Nonstop airlines – 1 1
Weekly flights – – –
Flight time 4h 50m 4h 59m 4h 50m
Departure OTP 100% – –
Beef Island (EIS) to Chicago flights · San Juan (SJU) to Chicago flights · Sint Maarten (SXM) to Chicago flights
Airports within 200 miles of STT 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 Charlotte Amalie.
STT: AST · MDW: CDT

When it's 6:00 PM in Charlotte Amalie, it's 5:00 PM in Chicago.
Distance & Flight Time
2,103 mi / 3,384 km
Nonstop flight time is approximately 4h 50m gate to gate.
Facts

STT–MDW Quick Facts

Key statistics for the Charlotte Amalie to Chicago route.
Route details
Distance2,103 mi / 3,384 km
Flight time4h 50m
Time difference-1 hour
Airlines (nonstop)Charter / private
1-stop connectionsAvailable
Origin: STT
Full nameCyril E. King Airport
IATA / ICAOSTT / TIST
TimezoneAmerica/St_Thomas
Passengers/yr1.6M
Elevation23 ft / 7 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 STT to MDW flights.
Nonstop flights from Cyril E. King Airport to Chicago Midway International Airport take about 4h 50m gate to gate. The route covers 2,103 miles.
Yes, 1-stop connections are available, ranked by layover time. Common connecting points include Hartsfield Jackson Atlanta, Orlando and Charlotte Douglas.
On a single ticket, yes. Your bags are checked through to MDW and move between planes without you. On two separate tickets you collect your bags at the connecting airport and recheck them, so build in extra layover time.
Chicago is 1 hour behind Charlotte Amalie.
Yes, return flights from MDW to STT are available. Use the direction toggle at the top to view the return schedule.
Nearby alternatives include EIS, SJU and SXM. 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 STT to MDW

Cyril E. King Airport (STT) and Chicago Midway International Airport (MDW) are connected through multiple connecting hub airports.

STT to MDW Flight Duration and Schedule

Nonstop flight time from STT to MDW is about 4 hours 50 minutes gate to gate. The route covers a distance of 2,103 miles (3,384 km).

Connecting Options and Alternatives

1-stop connecting options are also available, commonly via Hartsfield Jackson Atlanta, Orlando and Charlotte Douglas. Two-stop connections are also available via intermediate hubs. Nearby alternative airports include Beef Island (EIS), San Juan (SJU) and Sint Maarten (SXM).