Chicago to Destin (MDW–DSI) — Airlines, Schedules & Connections

MDW Airport Page →
790 mi airlines charter/private
On-time Some delays Frequent delays
Connecting Flight Schedule 1 1-stop flight Verified 1mo 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
DAL Dallas 5h 30m EJAKOWWN → XE Dallas (DAL) to Destin flights
✦ 1-STOP More options, longer trips
✧ 2-STOP Loading... Reach the hardest destinations
Chicago to Destin
Flown by charter / private operators — no scheduled airline service.
790 mi 1h 57m nonstop

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

Also explore MDW Routes DSI Routes MDW Live Flights DSI Live Flights MDW Delays
All flights from Destin (DSI) Destin to Chicago flights
Connections

Connection Landscape

1-stop and 2-stop options for MDW to DSI.
1-STOP
One-Stop Connections
1
Hubs
~5h
Fastest
~5h
Longest
DAL ~5h 30m
Verified with published schedule alignment and minimum connection time.
2-STOP
Two-Stop Connections
63
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 → DSI
48%
Frequent delays expected. Consider flexible booking.
Departing
48%
Return
DSI → MDW
72%
Moderate delays possible. Allow buffer time.
Arriving
72%
OTP = percentage of flights arriving within 15 min of schedule. Based on airport-level delay snapshots. MDW delays →
Alternatives

Other ways to reach Destin from Chicago

Nearby airports with service to Destin Executive Airport.
Metric MDW→DSI ORD→DSI
Distance from MDW – 15 mi
Nonstop airlines – 1
Weekly flights – –
Flight time 1h 57m 0h 56m
Departure OTP 48% –
Chicago (ORD) to Destin flights
Airports within 200 miles of MDW with service to Destin Executive Airport.
Know before you go

Travel Essentials

Practical planning for this route.
Time Difference
0h
Destin is 0 hours the same as Chicago.
MDW: CDT · DSI: CDT

When it's 6:00 PM in Chicago, it's 6:00 PM in Destin.
Distance & Flight Time
790 mi / 1,271 km
Nonstop flight time is approximately 1h 57m gate to gate.
Facts

MDW–DSI Quick Facts

Key statistics for the Chicago to Destin route.
Route details
Distance790 mi / 1,271 km
Flight time1h 57m
Time difference0 hours
Airlines (nonstop)Charter / private
1-stop connectionsAvailable
Origin: MDW
Full nameChicago Midway International Airport
IATA / ICAOMDW / KMDW
TimezoneAmerica/Chicago
Passengers/yr20.7M
Elevation620 ft / 189 m
Destination: DSI
Full nameDestin Executive Airport
IATA / ICAODSI / KDTS
TimezoneAmerica/Chicago
Elevation23 ft / 7 m
FAQ

Frequently Asked Questions

Common questions about MDW to DSI flights.
Nonstop flights from Chicago Midway International Airport to Destin Executive Airport take about 1h 57m gate to gate. The route covers 790 miles.
Yes, 1-stop connections are available, ranked by layover time. Common connecting points include Dallas Love Field.
Yes, return flights from DSI to MDW are available. Use the direction toggle at the top to view the return schedule.
Nearby alternatives include ORD. 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 DSI

Chicago Midway International Airport (MDW) and Destin Executive Airport (DSI) are connected through multiple connecting hub airports.

MDW to DSI Flight Duration and Schedule

Nonstop flight time from MDW to DSI is about 1 hours 57 minutes gate to gate. The route covers a distance of 790 miles (1,271 km).

Connecting Options and Alternatives

1-stop connecting options are also available, commonly via Dallas Love Field. Two-stop connections are also available via intermediate hubs. Nearby alternative airports include Chicago (ORD).