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

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Frequently asked questions

How much does a flight from Midway Intl. Airport (MDW) to Destin-Fort Walton Beach Airport (DSI) cost?
Discover the latest flight deals from MDW 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 MDW to DSI?
The cheapest flights from MDW 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 MDW to DSI?
Use the filter tool on Expedia to compare airlines and find the cheapest carrier that’ll take you from MDW to DSI. Sort your results by “Price (lowest to highest)” to snap up a great deal.
How many flights per day from Midway Intl. Airport (MDW) to Destin-Fort Walton Beach Airport (DSI)?
There are no daily nonstop flights available from Midway Intl. Airport (MDW) to Destin-Fort Walton Beach Airport (DSI). But you can opt for flights with layovers. Filter your search results on Expedia to include one or two stops, and you’ll be on your way in no time.
What day of the week has the most flights from MDW to DSI?
Usually you’ll find the greatest selection of flight options on a Friday. Tuesdays tend to be the quietest.* But this can vary depending on the airline, season and other factors.*Busiest/quietest day to travel is based on Expedia flight demand through January to December 2024.
What is the best time to fly from Midway Intl. Airport (MDW) to Destin-Fort Walton Beach Airport (DSI)?
To arrive at Destin-Fort Walton Beach Airport (DSI) on time, book a flight that leaves from Midway Intl. Airport (MDW) before 3 PM. The likelihood of cancellations is 22% higher, on average, for departures after this hour.**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 Midway Intl. Airport (MDW)?
Northwest Florida Regional Airport (VPS) is the only airport in Destin with direct flights from Midway Intl. Airport (MDW). Explore the available options and find cheap fares on Expedia.
Is it cheaper to buy a plane ticket from Midway Intl. Airport (MDW) to Destin-Fort Walton Beach Airport (DSI) last-minute?
Last-minute fares from MDW to DSI are usually more expensive. For the cheapest rates, start searching for flights well in advance. That said, if you’re flexible with your travel plans, you may score a cheap fare right before your journey.
Is it cheaper to book a MDW to DSI flight and hotel package?
Opting for a MDW to DSI flight and hotel package is typically cheaper than booking separately. With Expedia, you can enjoy the convenience of organizing your trip all in one place. Select from our extensive range of accommodations and then add car rentals, activities and flights to your booking. Bundle it all together, and you could save hundreds of dollars.
Can I cancel or change the date of my flight from Midway Intl. Airport (MDW) to Destin-Fort Walton Beach Airport (DSI)?
Typically, you can cancel or modify your MDW to DSI flight. However, there may be additional charges, especially if you booked more than 24 hours ago. Check your itinerary for the airline’s fees and guidelines on flight changes, or if you want further information, go to our Customer Service portal.
*Available to One Key members.