Nonstop flights from Destin to Chicago

2 airlines fly from Destin (VPS) to 2 Chicago airports (MDW and ORD), with up to 2 flights a day.

VPSMDW

Routes

2 airport pairs

Destin time

6:30a6:16pFirst departure 6:30 AM, last 6:16 PM

Two in the morning, 6:30 AM to 11:28 AM, then one afternoon flight at 3:37 PM, then two in the evening, 5:54 PM to 6:16 PM.

Earliest first

6:30 AM→8:54 AMVPS to MDWAllegiant AirUntil Nov 30, back Dec 17Airbus A319Thu, Sat
6:30 AM→8:54 AMVPS to MDWAllegiant AirUntil Nov 30, back Dec 17Airbus A319Sun
11:28 AM→2:13 PMVPS to ORDAmerican AirlinesResumes Oct 10Embraer 175Mon, Tue, Wed, Thu, Sat, Sun
3:37 PM→6:01 PMVPS to MDWAllegiant AirUntil Nov 30, back Dec 17Airbus A319Tue
5:54 PM→8:12 PMVPS to MDWAllegiant AirUntil Nov 30, back Dec 17Airbus A319Mon
6:16 PM→8:34 PMVPS to MDWAllegiant AirUntil Nov 30, back Dec 17Airbus A319Fri

Schedules last checked Sep 22, 2026. Times are local.

Allegiant Air flies 6 times a week on the Airbus A319. American Airlines flies 6 times a week on the Embraer 175.

There are 1 or 2 flights every day of the week. The first arrival in Chicago is at 8:54 AM and the last at 8:34 PM.

VPS to MDW is the busiest airport pair, with 6 flights a week, then VPS to ORD with 6.

On VPS to MDW, Allegiant Air flies it until Nov 30 and is back on Dec 17. On VPS to ORD, American Airlines is back on Oct 10.

Flying back, Chicago to Destin has 12 nonstop flights a week.

Schedules as of Oct 9, 2026.