Cheap Flights from Destin-Ft Walton Beach to Chicago Midway

Compare Destin-Ft Walton Beach to Chicago Midway flight deals

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

Book the best Chicago Midway fare with no extra fees

Flight deals from Destin-Ft Walton Beach to Chicago Midway

Looking for a cheap last-minute deal or the best return flight from Destin-Ft Walton Beach Airport to Chicago Midway Airport? If you want to travel next month, return fares start from $243. Find the lowest prices on one-way and return tickets right here.

Chicago.$160 per passenger.Departing Fri, 16 Oct, returning Mon, 26 Oct.Return flight with Allegiant Air.Outbound direct flight with Allegiant Air departs from Destin-Ft Walton Beach on Fri, 16 Oct, arriving in Chicago Midway.Inbound direct flight with Allegiant Air departs from Chicago Midway on Mon, 26 Oct, arriving in Destin-Ft Walton Beach.Price includes taxes and charges.From $160, select.

Chicago.$167 per passenger.Departing Mon, 2 Nov, returning Fri, 13 Nov.Return flight with Allegiant Air.Outbound direct flight with Allegiant Air departs from Destin-Ft Walton Beach on Mon, 2 Nov, arriving in Chicago Midway.Inbound direct flight with Allegiant Air departs from Chicago Midway on Fri, 13 Nov, arriving in Destin-Ft Walton Beach.Price includes taxes and charges.From $167, select.

Chicago.$176 per passenger.Departing Fri, 30 Oct, returning Fri, 13 Nov.Return flight with Allegiant Air.Outbound direct flight with Allegiant Air departs from Destin-Ft Walton Beach on Fri, 30 Oct, arriving in Chicago Midway.Inbound direct flight with Allegiant Air departs from Chicago Midway on Fri, 13 Nov, arriving in Destin-Ft Walton Beach.Price includes taxes and charges.From $176, select.

Chicago.$243 per passenger.Departing Fri, 7 Aug, returning Mon, 17 Aug.Return flight with Allegiant Air.Outbound direct flight with Allegiant Air departs from Destin-Ft Walton Beach on Fri, 7 Aug, arriving in Chicago Midway.Inbound direct flight with Allegiant Air departs from Chicago Midway on Mon, 17 Aug, arriving in Destin-Ft Walton Beach.Price includes taxes and charges.From $243, select.

Chicago.$319 per passenger.Departing Thu, 24 Dec, returning Sun, 3 Jan.Return flight with Allegiant Air.Outbound direct flight with Allegiant Air departs from Destin-Ft Walton Beach on Thu, 24 Dec, arriving in Chicago Midway.Inbound 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 $319, select.

Chicago.$359 per passenger.Departing Fri, 31 Jul, returning Mon, 17 Aug.Return flight with Allegiant Air.Outbound direct flight with Allegiant Air departs from Destin-Ft Walton Beach on Fri, 31 Jul, arriving in Chicago Midway.Inbound direct flight with Allegiant Air departs from Chicago Midway on Mon, 17 Aug, arriving in Destin-Ft Walton Beach.Price includes taxes and charges.From $359, select.

Chicago.$498 per passenger.Departing Mon, 30 Nov, returning Sun, 20 Dec.Return flight with Allegiant Air.Outbound direct flight with Allegiant Air departs from Destin-Ft Walton Beach on Mon, 30 Nov, arriving in Chicago Midway.Inbound direct flight with Allegiant Air departs from Chicago Midway on Sun, 20 Dec, arriving in Destin-Ft Walton Beach.Price includes taxes and charges.From $498, select.

Chicago.$542 per passenger.Departing Thu, 24 Dec, returning Sun, 27 Dec.Return flight with Allegiant Air.Outbound direct flight with Allegiant Air departs from Destin-Ft Walton Beach on Thu, 24 Dec, arriving in Chicago Midway.Inbound direct flight with Allegiant Air departs from Chicago Midway on Sun, 27 Dec, arriving in Destin-Ft Walton Beach.Price includes taxes and charges.From $542, select.

Chicago.$554 per passenger.Departing Sat, 5 Sep, returning Tue, 8 Sep.Return flight with Southwest Airlines.Outbound indirect flight with Southwest Airlines, departs from Destin-Ft Walton Beach on Sat, 5 Sep, arriving in Chicago Midway.Inbound indirect flight with Southwest Airlines, departs from Chicago Midway on Tue, 8 Sep, arriving in Destin-Ft Walton Beach.Price includes taxes and charges.From $554, select.

Chicago.$679 per passenger.Departing Sun, 30 Aug, returning Tue, 15 Sep.Return flight with Southwest Airlines.Outbound indirect flight with Southwest Airlines, departs from Destin-Ft Walton Beach on Sun, 30 Aug, arriving in Chicago Midway.Inbound indirect flight with Southwest Airlines, departs from Chicago Midway on Tue, 15 Sep, arriving in Destin-Ft Walton Beach.Price includes taxes and charges.From $679, select.

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

We’re always keeping an eye on fares, so you can find the best one in seconds. It looks like Destin-Ft Walton Beach to Chicago Midway flights are currently cheapest in October.

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Direct flights from Destin-Ft Walton Beach to Chicago Midway

Destin-Ft Walton Beach to Chicago Midway: Alternative routes

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

Destin to Chicago: Flight information

The things to know before you go.

Cheapest flight found	$160
Cheapest month to fly	October
Average flight time	2 hrs, 21 mins
Most popular airline	Allegiant Air
Average flights per week	2

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

How much are return flights from Destin-Ft Walton Beach to Chicago Midway?

The best price we found for a return flight from Destin-Ft Walton Beach to Chicago Midway is $160. 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.

How long does it take to fly from Destin-Ft Walton Beach to Chicago Midway?

2 hours and 21 minutes is the average flight time from Destin-Ft Walton Beach to Chicago Midway.

Which airlines fly direct from Destin-Ft Walton Beach to Chicago Midway?

Allegiant Air flies direct from Destin-Ft Walton Beach to Chicago Midway.

How many flights are there a week from Destin-Ft Walton Beach to Chicago Midway?

As of July 2026, there are 2 flights per week flying from Destin-Ft Walton Beach to Chicago Midway.

When is the cheapest time to fly from Destin-Ft Walton Beach to Chicago Midway?

The cheapest month to fly from Destin-Ft Walton Beach to Chicago Midway is usually October.

Which upcoming date is cheapest to fly from Destin-Ft Walton Beach Airport to Chicago Midway Airport on?

After crunching the numbers on our flight calendar, we found that it's currently cheapest to fly from Destin-Ft Walton Beach Airport to Chicago Midway Airport on Friday, 16 October 2026.

Can I get a direct flight from Destin-Ft Walton Beach Airport to Chicago Midway Airport?

Yes – the average flight time is 2 hours and 21 minutes.

How can I find the best flight deal to Chicago Midway?

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 Midway 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.

When is the best time to book flights to Chicago?

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.

Which is the cheapest airline to fly from Destin-Ft Walton Beach Airport to Chicago Midway with?

Currently, Allegiant Air offers the cheapest flight tickets to Chicago Midway.

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

Around 2 hours 20 minutes is how long you can expect to be in the air on a direct flight from Destin-Ft Walton Beach Airport to Chicago Midway Airport.
Chicago's timezone is UTC-6, which is the same as Destin.
Your VPS to MDW flight won't wait if you're running late, so show up at the airport on time. Arrive up to one hour in advance for domestic flights and two hours ahead for international travel.
Be prepared for longer queues during popular months such as July. Arriving up to four hours ahead of an international flight and two hours for a domestic departure is a wise move.
Jetting into Chicago (and then seeing more of the United States!) is easy with Allegiant Air. This popular carrier has direct flights from Destin-Ft Walton Beach Airport to Chicago Midway Airport.
Most passengers choose to travel with Allegiant Air on this route.
With 77.42% of its services landing as planned, Allegiant Air is the most punctual carrier operating VPS to MDW flights.

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

$74 is currently the best price for a one-way Destin-Ft Walton Beach Airport to Chicago Midway Airport flight. A return flight starts from $160. These fares may change depending on demand.
To get your hands on cheap tickets from VPS to MDW, book as early as you can. Airlines typically offer lower fares when flights are first made available.
The 'Whole month' tool shows you the cheapest flights from Destin-Ft Walton Beach Airport to Chicago Midway Airport throughout the entire month. It's a great way to find a bargain if your trip dates are flexible.
Save time looking for cheap flights from VPS to MDW by creating a Price Alert. You'll get an email or push notification on the app when a new low fare is offered.
Select your ideal arrival and departure times, number of stops and airlines with the filters. Alternatively, sort your results by 'Cheapest' to see the best deals on flights from Destin-Ft Walton Beach Airport to Chicago Midway Airport.

Handy information about Destin-Ft Walton Beach Airport (VPS)

82% of flights leaving Destin-Ft Walton Beach Airport touch down at their destination according to schedule. Given its strong on-time performance, you're unlikely to face delays when flying out of VPS.
Destin-Ft Walton Beach Airport is around 13 kilometres from central Destin. To work out how to get there, use Google Maps. This useful travel app will show you the quickest route and your public transport options.
Get your flight from Destin-Ft Walton Beach Airport to Chicago Midway Airport off to a stress-free start. Only a quick drive from VPS, book a night at TownePlace Suites Fort Walton Beach-Eglin AFB and you'll be well-rested for the trip ahead.

Arriving at Chicago Midway Airport (MDW)

If you have a late Destin-Ft Walton Beach Airport to Chicago Midway Airport flight, nothing beats the convenience of staying near the terminal. Grab your bags from the carousel and then be resting not long after at one of these accommodation options near MDW:
Grab a Chicago Midway Airport rental car and discover Chicago and beyond with your own set of wheels. Dollar, Hertz and Budget are popular outlets to choose from here.
Get the best deal by booking your vehicle from Chicago Midway Airport around four weeks ahead of your trip.

When to fly to Chicago Midway Airport (MDW)

It's time to work out your dates for your flight from Destin-Ft Walton Beach Airport to Chicago Midway Airport. July is the most popular month to head to Chicago. If you like a quieter vibe, go in December.
When booking your flight from Destin-Ft Walton Beach Airport to Chicago Midway Airport, think about the kind of weather you enjoy. July is the warmest month in Chicago, with temperatures ranging from 16ºC to 28ºC.
If you'd rather travel in cooler conditions, look for a cheap ticket from VPS to MDW in January. Average temperatures are between -12ºC and 3ºC then.

Explore more of the United States

Chicago has plenty to offer, but there are so many other corners of the United States waiting to be discovered. About 451 kilometres south-east of Chicago, a trip to Columbus will keep your itinerary busy. Don't miss top attractions like Franklin Park Conservatory and Botanical Gardens, Whetstone Park / Park of Roses and Ohio Theatre.
If there's time to check out another well-known destination in the United States, head for Indianapolis, about 257 kilometres south-east of Chicago. Lucas Oil Stadium, Eiteljorg Museum and The Children's Museum of Indianapolis are key reasons to visit.