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Cheap flights from Midway (MDW) to Destin (DSI)

MDW — DSI
Aug 23 — Aug 301
Sat 8/23
Sat 8/30
1 adult, Economy
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Cheap flight deals from Midway to Destin

Discover tips and strategies to find the most affordable flight options for your journey from Midway (MDW) to Destin (DSI). Learn about various techniques such as flexible date searches, comparing prices across and setting up price alerts. Use these methods to find the cheapest flights available for your travel needs. Data last updated August 18, 2025.

Popular in

October

Cheapest in

January

Average price

$414
Highest demand for flights based on searches. 8% potential increase in price ($36 potential increase over avg. RT price).
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Cheapest flight prices on average. 2% potential price decrease ($11 potential savings vs. average RT price).
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Average for round-trip flights in August 2025
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Best time to book a flight from Midway to Destin

Have a flexible travel schedule? Discover the best time to fly to Destin from Midway with our price prediction graph.
Estimated round-trip price
Rates are based on past data. Find the cheapest month and day to book your flight based on your travel requirements, then search for cheap deals.

Cheapflights Insights

Everything you need to know about your flight from Chicago Midway Airport to Destin

What is the cheapest month to book a flight from Chicago Midway Airport to Destin?

Currently, January is the cheapest month in which you can book a flight from Chicago Midway Airport to Destin (average of $240). Flying from Chicago Midway Airport to Destin in December is currently the most expensive (average of $424). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

Related info for your journey

Find useful and relevant information for your journey from Midway to Destin. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.

  • What airport do you fly into for flights to Destin from Chicago Midway?

    Destin (DSI), located 1.5 mi from the city center, is the airport you fly into when you book flights from Chicago Midway to Destin. 0 airlines have flights to Destin from Chicago Midway on a regular basis. Booking flights from Chicago Midway to Destin should not be difficult; the airport handles an average of 0 inbound flights from Chicago Midway per day.

  • Can I find deals for flights from Midway to Destin that include hotel bookings?

    Yes. In addition to deals on Midway to Destin flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from Midway to Destin?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Midway to Destin.

  • Can I find deals for business class flights from Midway to Destin?

    Yes. Cheapflights offers flight deals from Midway to Destin by cabin class. In addition to browsing deals, you can also filter by cabin class on the search results page after making a search.

  • What is the cheapest month to book a flight from Chicago Midway Airport to Destin?

    Currently, January is the cheapest month in which you can book a flight from Chicago Midway Airport to Destin (average of $240). Flying from Chicago Midway Airport to Destin in December is currently the most expensive (average of $424). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

See more FAQs

Traveling to a place near Destin?

Book flights to Destin if you plan to visit one of these locations
Miramar Beach
Santa Rosa Beach

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