Cheap Flights from Chicago (ORD) to Destin (DSI)

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Frequently asked questions

How much does a flight from O'Hare Intl. Airport (ORD) to Destin-Fort Walton Beach Airport (DSI) cost?
Discover the latest flight deals from ORD to DSI by entering your preferred travel dates and searching on Expedia. Easily compare prices by departure date if you have flexibility with your schedule and use handy filters to explore prices for your preferred journey. As a member of One Key™, our free loyalty program, you can use Price Tracking to watch fares and receive notifications if prices go up or down.
What is the cheapest month to fly from ORD to DSI?
The cheapest flights from ORD to DSI are usually during off-peak season, when demand is lower. To save money, avoid flying during public holidays, school breaks and major local events.
What is the cheapest airline that flies from ORD to DSI?
Use the filter tool on Expedia to compare airlines and find the cheapest carrier that’ll take you from ORD to DSI. Sort your results by “Price (lowest to highest)” to snap up a great deal.
How many flights per day from O'Hare Intl. Airport (ORD) to Destin-Fort Walton Beach Airport (DSI)?
Direct flights from O’Hare Intl. Airport (ORD) to Destin-Fort Walton Beach Airport (DSI) aren’t available daily, so you’ll have to take a flight with a layover. Explore your options with Expedia’s filter tool. Enter your travel dates and click on either “1 Stop” or “2+ Stops.”
What day of the week has the most flights from ORD to DSI?
You’ll usually find Tuesday the quietest day for flights, while Fridays are often the busiest.* However this can vary from season to season and during public holidays or peak travel times.*Busiest/quietest day to travel is based on Expedia flight demand through January to December 2024.
What is the best time to fly from O'Hare Intl. Airport (ORD) to Destin-Fort Walton Beach Airport (DSI)?
To avoid possible delays on the O’Hare Intl. Airport (ORD) to Destin-Fort Walton Beach Airport (DSI) route, travel before 3 PM. Later departures have a 22% higher chance of being canceled.**Most reliable time of the day and month to travel recommendation is based on January through August 2024 flight status data sourced from OAG’s global flight data platform.
What airports do you fly into for Destin from O'Hare Intl. Airport (ORD)?
Compare your flight options from O’Hare Intl. Airport (ORD) to Pensacola Intl. Airport (PNS). This is the only airport in Destin you can jet into if you’re taking a direct flight.
Is it cheaper to buy a plane ticket from O'Hare Intl. Airport (ORD) to Destin-Fort Walton Beach Airport (DSI) last-minute?
Last-minute bookings from ORD to DSI are typically more expensive. To lock in the best prices, start looking for flights as soon as possible. That said, if you’re flexible with your travel dates, you may land a cheap fare right before your trip.
Is it cheaper to book an ORD to DSI flight and hotel package?
Compared with arranging hotels and flights separately, booking an ORD to DSI flight and hotel package with Expedia could lead to significant savings. Better still, having everything in one easy place takes the hassle out of travel planning. Simply secure your flights and choose from our extensive range of hotels, then personalize your trip with other add-ons like tours, car rentals and activities.
Can I cancel or change the date of my flight from O'Hare Intl. Airport (ORD) to Destin-Fort Walton Beach Airport (DSI)?
Generally, it’s possible to cancel or reschedule your ORD to DSI flight. However, if the booking was made more than 24 hours ago, additional charges may apply. Check your airline’s policies in your itinerary to see what changes are possible and if any costs are involved. You’ll also find more information on our Customer Service portal.
*Available to One Key members.