Private charter · MDW → DSI
Chicago to Destin
790 miles. One price for the whole airplane.
Price your flight from Chicago to Destin
The trip
Chicago to Destin, door to door faster.
Trade about 17 hours on the road for about a short flight in the air. Bluebird flies you direct from Chicago Midway International Airport in Chicago to Destin Executive Airport in Destin, 790 miles in a private jet with two pilots up front. Need a different size of aircraft? We'll source one sized for the trip. The price is for the whole aircraft, with every fee and tax shown before you book.
- Distance
- 790 mi
- Flight
- —
- Driving
- 17 hours
- Passengers
- Up to 1
Departing Chicago
Airports in Chicago
MDW
Major airportChicago Midway International Airport
Chicago · KMDW
- From downtown
- 9 mi
- Longest runway
- 6,522 ft
ORD
Major airportChicago O'Hare International Airport
Chicago · KORD
- From downtown
- 16 mi
- Longest runway
- 13,000 ft
PWK
Commercial airportChicago Executive Airport
Chicago/Prospect Heights/Wheeling · KPWK
- From downtown
- 21 mi
- Longest runway
- 5,001 ft
GYY
Commercial airportGary/Chicago International Airport
Gary · KGYY
- From downtown
- 21 mi
- Longest runway
- 8,859 ft
Arriving Destin
Airports in Destin
DSI
Commercial airportDestin Executive Airport
Destin · KDTS
- From downtown
- 1 mi
- Longest runway
- 5,001 ft
VPS
Commercial airportDestin-Fort Walton Beach Airport
Valparaiso · KVPS
- From downtown
- 7 mi
- Longest runway
- 12,004 ft
CEW
Commercial airportBob Sikes Airport
Crestview · KCEW
- From downtown
- 27 mi
- Longest runway
- 8,006 ft
When you land
Things to do in Destin
Destin grew from a small fishing village into the Panhandle's best-known beach destination, and it still calls itself the World's Luckiest Fishing Village. The 100-fathom curve comes unusually close to shore here, so charter boats reach deep water quickly for snapper, grouper, amberjack and billfish, and the harbor is lined with restaurants, marinas and one of the largest charter fleets on the Gulf.
- 01
Destin Harbor Boardwalk
A waterfront walk lined with seafood restaurants, bars and shops, and the departure point for fishing charters, dolphin cruises and sunset sails.
- 02
Henderson Beach State Park
A protected stretch of dunes and white-sand beach right in town, with boardwalk trails, picnic areas, camping and calm Gulf swimming.
- 03
Crab Island
A shallow sandbar near the Destin bridge where boats anchor in clear, waist-deep water, creating a floating gathering spot popular with families and groups in summer.
- 04
Scenic Highway 30A
East of Destin, this coastal road links planned beach towns like Seaside, Rosemary Beach and Alys Beach, known for their architecture, bike paths and rare coastal dune lakes.
- 05
Grayton Beach State Park
Along 30A, this park protects tall dunes, a coastal dune lake and pine flatwoods trails, and its beach has topped national best-beach rankings.
- 06
Gulfarium Marine Adventure Park
Founded in 1955 on Okaloosa Island in neighboring Fort Walton Beach, the Gulfarium is one of the oldest marine parks in the country, with dolphins, sea lions and penguins.
Questions
Chicago to Destin flights
How long is a private flight from Chicago to Destin?
About a short flight in a private jet, for 790 miles direct. Driving the same trip takes about 17 hours.
Which airports do flights from Chicago to Destin use?
You can depart from Chicago Midway International Airport (MDW), Chicago O'Hare International Airport (ORD), or Chicago Executive Airport (PWK) and arrive at Destin Executive Airport (DSI), Destin-Fort Walton Beach Airport (VPS), or Bob Sikes Airport (CEW). Pick whichever is closest to where you're starting and where you're headed.
How much does a private charter from Chicago to Destin cost?
The price depends on the date, departure time, aircraft and where the airplane is positioned. Enter your trip above to see an instant price for the whole airplane, with every tax and fee included.
Can I book a round trip between Chicago and Destin?
Yes. Choose round trip when you search, and pick your return date and time. Flights from Destin back to Chicago are priced the same way.
Return flight
Destin to Chicago
More flights from Chicago
More flights to Destin
Explore Chicago private charter and Destin private charter, airports and things to do. Arriving at Destin Executive Airport (DSI).
Chicago to Destin, on your schedule
Choose your departure time and see a price for the whole aircraft. Bring up to 1 passengers for the same price.
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