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

DSI Airport Page →
790 mi airlines 1/wk
On-time Some delays Frequent delays
Connecting Flight Schedule 27 1-stop flights Verified 6h 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
Destin to Chicago
Connecting service available through multiple hubs.
1 Flights/wk 790 mi 1h 59m nonstop 27 1-stop hubs

While no nonstop service exists between DSI and MDW, connecting options are available through 27 hubs.

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

Connection Landscape

Beyond nonstop. 1-stop and 2-stop options for DSI to MDW.
1-STOP
One-Stop Connections
27
Hubs
~4h
Fastest
~19h
Longest
Verified with published schedule alignment and minimum connection time.
2-STOP
Two-Stop Connections
110
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 Chicago from Destin

Nearby airports with service to Chicago Midway International Airport.
Metric DSI→MDW VPS→MDW ECP→MDW
Distance from DSI – 6 mi 40 mi
Nonstop airlines 0 1 4
Weekly flights 1 3 6
Flight time 1h 59m 2h 17m 2h 20m
Valparaiso (VPS) to Chicago flights · Panama City Beach (ECP) to Chicago flights · Pensacola (PNS) to Chicago flights
Airports within 200 miles of DSI with service to Chicago Midway International Airport.
Know before you go

Travel Essentials

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

When it's 6:00 PM in Destin, it's 6:00 PM in Chicago.
Distance & Flight Time
790 mi / 1,271 km
Nonstop flight time is approximately 1h 59m.
Facts

DSI–MDW Quick Facts

Key statistics for the Destin to Chicago route.
Route details
Distance790 mi / 1,271 km
Flight time1h 59m
Time difference0 hours
Airlines (nonstop)0
Weekly flights1 out / 1 return
1-stop connections27 hubs
Origin: DSI
Full nameDestin Executive Airport
IATA / ICAODSI / KDTS
TimezoneAmerica/Chicago
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 DSI to MDW flights.
Nonstop flights from Destin Executive Airport to Chicago Midway International Airport take approximately 1h 59m. The route covers 790 miles.
There are approximately 1 nonstop flights per week from DSI to MDW. The return direction has about 1 weekly flights.
Yes, 1-stop connections are available through BNA, MSY, TYS, PIE, IAD, SSI, MEM, OKC, OMA, HOU, CLT, MSP, DFW, EYW, TPA, PBI, MCO, MIA, IAH, FLL, ASE, NAS, YYZ, TUS, ABQ, SLC and DAL. These options provide additional schedule flexibility.
Yes, return flights from MDW to DSI are available. Use the direction toggle at the top to view the return schedule.
Nearby alternatives include VPS, ECP and PNS. 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 DSI to MDW

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

DSI to MDW Flight Duration and Schedule

Nonstop flight time from DSI to MDW ranges from 1 hours 59 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

27 one-stop connections are available, with the fastest taking approximately 4 hours via BNA. Two-stop connections are also available via intermediate hubs. Nearby alternative airports include Valparaiso (VPS), Panama City Beach (ECP) and Pensacola (PNS).