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Cheap flight tickets from Destin to Chicago

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      Travellers and cabin class, 1 Adult, Economy
      American Airlines
      Qatar Airways
      Alaska Airlines
      Allegiant Air

      Compare Destin to Chicago flight deals

      Find the cheapest month or even day of the year to fly to Chicago

      Book the best Chicago fare with no extra fees

      Flight deals from Destin to Chicago

      Looking for a cheap last-minute deal or the best return flight from Destin to Chicago? If you want to travel next month, return fares start from RM1,410. Find the lowest prices on one-way and return tickets right here.
      Chicago.RM195 per passenger.Departing Fri, 2 Oct.One-way flight with Allegiant Air.Outbound direct flight with Allegiant Air departs from Destin-Ft Walton Beach on Fri, 2 Oct, arriving in Chicago Midway.Price includes taxes and charges.From RM195, select.
      Chicago.RM211 per passenger.Departing Fri, 13 Nov.One-way flight with Allegiant Air.Outbound direct flight with Allegiant Air departs from Destin-Ft Walton Beach on Fri, 13 Nov, arriving in Chicago Midway.Price includes taxes and charges.From RM211, select.
      Chicago.RM299 per passenger.Departing Thu, 17 Dec.One-way flight with Allegiant Air.Outbound direct flight with Allegiant Air departs from Destin-Ft Walton Beach on Thu, 17 Dec, arriving in Chicago Midway.Price includes taxes and charges.From RM299, select.
      Chicago.RM500 per passenger.Departing Thu, 18 Mar.One-way flight with Allegiant Air.Outbound direct flight with Allegiant Air departs from Destin-Ft Walton Beach on Thu, 18 Mar, arriving in Chicago Midway.Price includes taxes and charges.From RM500, select.
      Chicago.RM688 per passenger.Departing Sun, 9 May.One-way flight with Allegiant Air.Outbound direct flight with Allegiant Air departs from Destin-Ft Walton Beach on Sun, 9 May, arriving in Chicago Midway.Price includes taxes and charges.From RM688, select.
      Chicago.RM720 per passenger.Departing Sat, 26 Sep.One-way flight with Southwest Airlines.Outbound indirect flight with Southwest Airlines, departs from Destin-Ft Walton Beach on Sat, 26 Sep, arriving in Chicago Midway.Price includes taxes and charges.From RM720, select.
      Chicago.RM742 per passenger.Departing Tue, 5 Jan.One-way flight with Southwest Airlines.Outbound indirect flight with Southwest Airlines, departs from Destin-Ft Walton Beach on Tue, 5 Jan, arriving in Chicago Midway.Price includes taxes and charges.From RM742, select.
      Chicago.RM1,030 per passenger.Departing Sun, 3 Jan.One-way flight with Allegiant Air.Outbound direct flight with Allegiant Air departs from Destin-Ft Walton Beach on Sun, 3 Jan, arriving in Chicago Midway.Price includes taxes and charges.From RM1,030, select.
      Chicago.RM1,041 per passenger.Departing Mon, 31 Aug.One-way flight with Southwest Airlines.Outbound indirect flight with Southwest Airlines, departs from Destin-Ft Walton Beach on Mon, 31 Aug, arriving in Chicago Midway.Price includes taxes and charges.From RM1,041, select.
      Chicago.RM1,189 per passenger.Departing Sun, 4 Apr.One-way flight with Allegiant Air.Outbound direct flight with Allegiant Air departs from Destin-Ft Walton Beach on Sun, 4 Apr, arriving in Chicago Midway.Price includes taxes and charges.From RM1,189, select.

      Find the cheapest month to fly from Destin to Chicago

      We’re always keeping an eye on fares, so you can find the best one in seconds. It looks like Destin to Chicago flights are currently cheapest in October.
      Aug
      from RM1,041
      Sep
      from RM720
      Oct
      from RM195
      Nov
      from RM211
      Dec
      from RM299
      Jan
      from RM742
      Feb
      Find prices
      Mar
      from RM500
      Apr
      from RM1,189
      May
      from RM688
      Jun
      Find prices
      Jul
      Find prices

      Direct flights from Destin to Chicago

      Alaska Airlines
      Allegiant Air
      American Airlines
      Qatar Airways

      Alternative Destin to Chicago routes

      Looking for the cheapest, fastest or easiest route from Destin to Chicago? You could fly into the following airports instead.

      Chicago Midway

      14km from central Chicago
      ClosestCheapest
      from RM195
      Search flights

      Chicago O'Hare International

      25km from central Chicago
      from RM1,949
      Search flights

      Chicago Rockford

      127km from central Chicago
      Search flights

      Destin to Chicago: Flight information

      The things to know before you go.
      Cheapest flight foundRM195
      Cheapest month to flyOctober
      Average flight time2 hrs, 33 mins
      Most popular airlineAmerican Airlines
      Average flights per week27

      Finding cheap flights from Destin to Chicago: Frequently asked questions

      There are 3 airports in Chicago: Chicago Midway, Chicago O'Hare International and Chicago Rockford.
      The best price we found for a return flight from Destin to Chicago is RM388. 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 33 minutes is the average flight time from Destin to Chicago.
      American Airlines, Qatar Airways and Alaska Airlines fly direct from Destin to Chicago.
      As of August 2026, there are 27 flights per week flying from Destin to Chicago.
      The cheapest month to fly from Destin to Chicago is usually November.
      If you're flying from Destin, the cheapest airport near Chicago is Chicago Midway – which is 14.5 km away from the centre of Chicago. We've found flights into this airport from RM388.
      After crunching the numbers on our flight calendar, we found that it is currently cheapest to fly from Destin to Chicago on Friday, 13 November 2026.
      Yes – the average flight time is 2 hours and 33 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 Chicago 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 Chicago is around 40 days in advance, so don’t leave your flight to the last minute.

      In August, the average temperature is usually around 22°C. July is typically the warmest month in Chicago, when it usually averages around 26°C. You can expect the least rain in January. The coldest month is January, with temperatures averaging -8°C. The rainiest month is August.
      The cheapest airline that flies to Chicago is Allegiant Air .

      How to find cheap flights from Destin to Chicago

      Looking for cheap flight tickets from Destin to Chicago? Whether you are aiming to find one-way or return flights, here are a few tips on how to secure the best ticket price and make your journey as smooth as possible.

      • Simply hit 'search'. We've compared tickets from all major online travel agents and airlines flying from Destin-Chicago to find the cheapest flights. And with us there are no hidden extras - what you see is what you pay.

      • Flex your dates to find the flight price for your Destin-Chicago flight. If your travel dates are flexible, use Skyscanner's 'Whole month' tool to find the cheapest month, and even day to fly to Chicago from Destin.

      • Set up a Price Alert. You can easily track the price of your flight from Destin to Chicago by creating an alert. Whenever prices go down or up, you'll get a push notification or e-mail to help you get the best flight deal.

      • Look for non-stop flights. Only interested in direct flights between Destin and Chicago ? Make sure to tick 'Direct flights only' when performing a search. If there are flights without stops available, these will appear in the results.

      • Include nearby airports in your search. Widen your search for Destin to Chicago flight deals by selecting the "add nearby airports" option. This will allow you to see flight prices for all the nearest airports at your departure point and your destination and could help you save on your next trip.

      • Find the cheapest Business class flights from Destin to Chicago. Check the difference in price of your Destin-Chicago air ticket when travelling in Economy, Premium economy, Business or First class. Note that not all cabin classes are available on every route or airline.

      • Search for cheap flights when out and about. To get the best flight booking experience regardless of where you are, download our app and search for flight tickets from Destin to Chicago on the go.

      Book flight tickets from Destin to Chicago with peace of mind

      • Find flexible flights. Your airline might be offering flexible tickets from Destin to Chicago , which means you won't lose out if your flight has to be changed or cancelled.

      • Add travel cost protection. Avoid travel pitfalls and choose travel cost protection - it's available at the checkout as you book your Destin-Chicago flight with us.

      • Reduce your carbon footprint by selecting a greener flight option. To check whether there are any lower emissions flights available on the route Destin-Chicago , simply check the “only show flights with lower CO₂ emissions” box later on in your search.

      Combine your flight to Chicago with hotels and car hire

      Once you've secured your flight booking from Destin to Chicago, we will help you discover the best prices and exclusive rates for cheap hotels in Chicago or nearby. And if you're looking for car hire, we've got you covered too. We allow you to compare hundreds of car hire companies in one search and find the best price on car rental in Chicago.

      Compare Destin-Chicago tickets with other routes

      Not entirely set on flying from Destin to Chicago yet? You can easily browse other destinations by searching flights to 'Everywhere' - this will allow you to find the cheapest place to travel from your chosen departure point in Malaysia or abroad.


      Plan the rest of your trip from Destin to Chicago

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