Nonstop flights from Chicago to Destin

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

MDWVPS

Routes

2 airport pairs

Chicago time

8:25a9:24pFirst departure 8:25 AM, last 9:24 PM

Two in the morning, 8:25 AM to 9:44 AM, then three in the evening, 6:51 PM to 9:24 PM.

Earliest first

8:25 AM→10:53 AMORD to VPSAmerican AirlinesResumes Oct 10Embraer 175Mon, Tue, Wed, Thu, Sat, Sun
9:44 AM→11:49 AMMDW to VPSAllegiant AirUntil Nov 30, back Dec 17Airbus A319Thu, Sat
9:44 AM→11:49 AMMDW to VPSAllegiant AirUntil Nov 30, back Dec 17Airbus A319Sun
6:51 PM→8:56 PMMDW to VPSAllegiant AirUntil Nov 30, back Dec 17Airbus A319Tue
9:02 PM→11:13 PMMDW to VPSAllegiant AirUntil Nov 30, back Dec 17Airbus A319Mon
9:24 PM→11:35 PMMDW to VPSAllegiant 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 Destin is at 10:53 AM and the last at 11:35 PM.

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

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

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

Schedules as of Oct 9, 2026.