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

MDW Airport Page →
790 mi airlines 1/wk
On-time Some delays Frequent delays
Connecting Flight Schedule 31 1-stop flights Verified 12h ago
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  Flight Airline AC Dep Arr Dur OTP Sched  
✈ Nonstop

No flights match your filters.

No nonstop flights on this route. connecting options below.

✦ 1-STOP More options, longer trips
✧ 2-STOP Loading... Reach the hardest destinations
Chicago to Destin
Connecting service available through multiple hubs.
1 Flights/wk 790 mi 1h 57m nonstop 31 1-stop hubs

While no nonstop service exists between MDW and DSI, connecting options are available through 31 hubs.

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

Connection Landscape

Beyond nonstop. 1-stop and 2-stop options for MDW to DSI.
1-STOP
One-Stop Connections
31
Hubs
~3h
Fastest
~28h
Longest
Verified with published schedule alignment and minimum connection time.
2-STOP
Two-Stop Connections
119
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.
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 0 1
Weekly flights 1 –
Flight time 1h 57m 0h 56m
Departure OTP 80% –
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.
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)0
Weekly flights1 out / 1 return
1-stop connections31 hubs
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 approximately 1h 57m. The route covers 790 miles.
There are approximately 1 nonstop flights per week from MDW to DSI. The return direction has about 1 weekly flights.
Yes, 1-stop connections are available through IND, ORD, BNA, PDK, ECP, LIT, MEM, GSO, IAD, CLE, MSY, RDU, TUL, ABQ, ATL, CLT, OMA, PBI, GNV, HOU, FLL, SLC, MIA, SNA, VNY, TPA, DAL, TYS, AUS, MCO and DFW. These options provide additional schedule flexibility.
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 ranges from 1 hours 57 minutes. The route covers a distance of 790 miles (1,271 km). There are approximately 1 weekly flights outbound and 1 return, totaling 2 flights per week in both directions.

Connecting Options and Alternatives

31 one-stop connections are available, with the fastest taking approximately 3 hours via IND. Two-stop connections are also available via intermediate hubs. Nearby alternative airports include Chicago (ORD).