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$51 Cheap Flights from Chicago Midway to Destin-Ft Walton Beach

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      Travellers and cabin class, 1 Adult, Economy
      Allegiant Air

      Compare Chicago Midway to Destin-Ft Walton Beach flight deals

      Find the cheapest month or even day of the year to fly to Destin-Ft Walton Beach

      Book the best Destin-Ft Walton Beach fare with no extra fees

      Flight deals from Chicago Midway to Destin-Ft Walton Beach

      Looking for a cheap last-minute deal or the best return flight from Chicago Midway Airport to Destin-Ft Walton Beach Airport? If you want to travel next month, return fares start from $177. Find the lowest prices on one-way and return tickets right here.
      Destin.$51 per passenger.Departing Mon, 2 Nov.One-way flight with Allegiant Air.Outbound direct flight with Allegiant Air departs from Chicago Midway on Mon, 2 Nov, arriving in Destin-Ft Walton Beach.Price includes taxes and charges.From $51, select.
      Destin.$77 per passenger.Departing Fri, 23 Oct.One-way flight with Allegiant Air.Outbound direct flight with Allegiant Air departs from Chicago Midway on Fri, 23 Oct, arriving in Destin-Ft Walton Beach.Price includes taxes and charges.From $77, select.
      Destin.$111 per passenger.Departing Thu, 31 Dec.One-way flight with Allegiant Air.Outbound direct flight with Allegiant Air departs from Chicago Midway on Thu, 31 Dec, arriving in Destin-Ft Walton Beach.Price includes taxes and charges.From $111, select.
      Destin.$112 per passenger.Departing Sun, 3 Jan.One-way flight with Allegiant Air.Outbound direct flight with Allegiant Air departs from Chicago Midway on Sun, 3 Jan, arriving in Destin-Ft Walton Beach.Price includes taxes and charges.From $112, select.
      Destin.$147 per passenger.Departing Thu, 1 Apr.One-way flight with Allegiant Air.Outbound direct flight with Allegiant Air departs from Chicago Midway on Thu, 1 Apr, arriving in Destin-Ft Walton Beach.Price includes taxes and charges.From $147, select.
      How did we find these deals? The deals you see here are the lowest prices for flight tickets from Chicago Midway to Destin-Ft Walton Beach found in the last 4 days, and are subject to change and availability.

      Find the cheapest month to fly from Chicago Midway to Destin-Ft Walton Beach

      We’re always keeping an eye on fares, so you can find the best one in seconds. It looks like Chicago Midway to Destin-Ft Walton Beach flights are currently cheapest in November.
      Sep
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      Oct
      from $77
      Nov
      from $51
      Dec
      from $111
      Jan
      from $112
      Feb
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      Mar
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      Apr
      from $147
      May
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      Jun
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      Jul
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      Aug
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      Direct flights from Chicago Midway to Destin-Ft Walton Beach

      Allegiant Air

      Chicago Midway to Destin-Ft Walton Beach: Alternative routes

      Compare routes from Chicago Midway to Destin below. You may find an airport to fly into that's cheaper, faster, or easier than Destin-Ft Walton Beach.

      Destin Executive

      3km from central Destin
      Closest
      Search flights

      Destin-Ft Walton Beach

      11km from central Destin
      Cheapest
      from $51
      Search flights

      Pensacola

      67km from central Destin
      from $186
      Search flights

      Northwest Florida Beaches International

      68km from central Destin
      from $215
      Search flights

      Chicago to Destin: Flight information

      The things to know before you go.
      Cheapest flight found$51
      Cheapest month to flyNovember
      Average flight time2 hrs, 10 mins
      Most popular airlineAllegiant Air
      Average flights per week2

      Finding cheap flights from Chicago Midway to Destin-Ft Walton Beach: Frequently asked questions

      The best price we found for a return flight from Chicago Midway to Destin-Ft Walton Beach is $118. This is an estimate based on information collected from different airlines and travel providers over the last 4 days and is subject to change and availability.
      2 hours and 10 minutes is the average flight time from Chicago Midway to Destin-Ft Walton Beach.
      Allegiant Air flies direct from Chicago Midway to Destin-Ft Walton Beach.
      As of September 2026, there are 2 flights per week flying from Chicago Midway to Destin-Ft Walton Beach.
      The cheapest month to fly from Chicago Midway to Destin-Ft Walton Beach is usually November.
      After crunching the numbers on our flight calendar, we found that it's currently cheapest to fly from Chicago Midway Airport to Destin-Ft Walton Beach Airport on Monday, 2 November 2026.
      Yes – the average flight time is 2 hours and 10 minutes.
      We show every price from over 1,200 airlines and travel agents, comparing them all so you don’t have to. If you know you want to fly to Destin-Ft Walton Beach but you’re not ready to book, set up a Price Alert. We’ll track prices for you, and let you know when they rise or fall.

      We crunched all the numbers in our flight calendar and it looks like the cheapest time to book a flight to Destin is around 40 days in advance, so don’t leave your flight to the last minute.

      Currently, Allegiant Air offers the cheapest flight tickets to Destin-Ft Walton Beach.

      Travelling from Chicago Midway Airport (MDW) to Destin-Ft Walton Beach Airport (VPS): what you need to know

      • The average duration of a direct flight from Chicago Midway Airport to Destin-Ft Walton Beach Airport is 2 hours 10 minutes.

      • Arriving two hours before an international flight and one hour ahead of a domestic departure are golden rules for stress-free travel. Show up at the airport on time to catch your MDW to VPS flight.

      • During popular months such as July, it's best to get to the airport even earlier. Arrive two hours before a domestic departure and four hours ahead of an international flight when you travel during a peak period in general.

      • Allegiant Air is your gateway to discovering Destin (and perhaps some other exciting parts of the United States!). Check out the direct flights from Chicago Midway Airport to Destin-Ft Walton Beach Airport offered by this popular airline.

      • The majority of passengers choose to fly with Allegiant Air on this route.

      • The most punctual carrier that operates MDW to VPS flights is Allegiant Air. Its services arrive as scheduled 70.97% of the time.

      • If you want to include a stop along the way, simply deselect 'Direct flights only' when searching for your ticket from Chicago Midway Airport to Destin-Ft Walton Beach Airport. Here are the most popular stopovers between MDW and VPS:

        • Atlanta Hartsfield-Jackson Airport

        • Nashville Airport

        • Pittsburgh International Airport

      How to find the cheapest flights from Chicago Midway Airport (MDW) to Destin-Ft Walton Beach Airport (VPS)

      • Currently, $51 is the lowest price we've found for a one-way Chicago Midway Airport to Destin-Ft Walton Beach Airport flight. The best price for a return plane ticket is $118. Bear in mind that fares may change due to availability when booking.

      • To pick up cheap tickets from MDW to VPS, book in advance. Airlines tend to offer lower fares when flights are first made available.

      • The cheapest month for flights from Chicago Midway Airport to Destin-Ft Walton Beach Airport is May. Use the 'Whole month' tool to find the lowest airfares if you have a flexible schedule.

      • You don't need to check every day to find out if fares have dropped when you set up a Price Alert. We'll update you the moment a special offer becomes available on cheap flights from MDW to VPS.

      • Select your ideal arrival and departure times, number of stops and airlines with the filters. Or sort your results by 'Cheapest' to see the best deals on flights from Chicago Midway Airport to Destin-Ft Walton Beach Airport.

      Handy information about Chicago Midway Airport (MDW)

      • The address for MDW is 5700 South Cicero.

      • When it comes to Chicago Midway Airport's on-time performance, 76% of flights arrive within the expected timeframe.

      • Chicago Midway Airport is around 16 kilometres from central Chicago. If you're ride-sharing, catching a taxi or driving from the centre, it'll take you 25 minutes or so to arrive, depending on the traffic.

      • You can expect a journey time of around 30 minutes when using public transport.

      • Booked an early flight from Chicago Midway Airport to Destin-Ft Walton Beach Airport? Avoid the stress of rushing to the airport (and enjoy a little extra shut-eye) by choosing one of these stays close to MDW:

      Arriving at Destin-Ft Walton Beach Airport (VPS)

      • Step off your Chicago Midway Airport to Destin-Ft Walton Beach Airport flight and be snoozing in your hotel bed soon after. If you're looking for a handy option that's not too far from VPS, check out TownePlace Suites Fort Walton Beach-Eglin AFB.

      • Pick up a Destin-Ft Walton Beach Airport rental car and explore Destin and beyond with your own set of wheels. Dollar, Budget and Hertz are leading providers to choose from here.

      • Reserving your vehicle from Destin-Ft Walton Beach Airport around two weeks in advance gives you the best shot at securing a great deal.

      When to fly to Destin-Ft Walton Beach Airport (VPS)

      • It's time to pick your trip dates for your flight from Chicago Midway Airport to Destin-Ft Walton Beach Airport. July is the busiest month to head to Destin. If you like a more laid-back vibe, go in March.

      • Book your flight from Chicago Midway Airport to Destin-Ft Walton Beach Airport for August if you want to visit Destin during its warmest month. Expect temperatures of between 25ºC (77ºF) and 33ºC (91ºF).

      • January sees average temperatures of between 4ºC (39ºF) and 18ºC (64ºF). Look for cheap tickets from MDW to VPS sometime around then if you like cooler conditions.

      Explore more of the United States

      • You've seen Destin, now it's time to discover other parts of the United States. Travel about 467 kilometres east to Jacksonville to tick off its leading sights. From St. John's Cathedral to Museum of Contemporary Art Jacksonville and The Cummer Museum of Art & Gardens, your itinerary will be busy.

      • Atlanta is another sought-after destination in the United States and is around 418 kilometres north-east of Destin. No journey is complete without visiting Georgia Aquarium, Birth Home of Martin Luther King, Jr and Fox Theatre.

      Prices shown on this page are estimated lowest prices only. Found in the last 12 days.