$99 Cheap Flights from Chicago (MDW) to Fort Walton Beach (VPS)

View $99 flight on Mon, Jul 28, 2025Opens in a new window

Popular airlines from Chicago Midway Airport (MDW) to Northwest Florida Regional Airport (VPS)

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Cheap Flights from Chicago to Fort Walton Beach (MDW-VPS)

Prices were available within the past 7 days and start at $99 for one-way flights and $197 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

Southwest Airlines
Wed, Jul 23 - Fri, Jul 25
MDW
Chicago
VPS
Fort Walton Beach
$197 Roundtrip, found 2 days ago
$197
Roundtrip
found 2 days ago
Select Southwest Airlines flight, departing Wed, Jul 23 from Chicago to Fort Walton Beach, returning Fri, Jul 25, priced at $197 found 2 days ago
Delta
Wed, Jul 23 - Fri, Jul 25
MDW
Chicago
VPS
Fort Walton Beach
$198 Roundtrip, found 2 days ago
$198
Roundtrip
found 2 days ago
Select Delta flight, departing Wed, Jul 23 from Chicago to Fort Walton Beach, returning Fri, Jul 25, priced at $198 found 2 days ago
Southwest Airlines
Mon, Jul 28 - Mon, Aug 4
MDW
Chicago
VPS
Fort Walton Beach
$199 Roundtrip, found 6 days ago
$199
Roundtrip
found 6 days ago
Select Southwest Airlines flight, departing Mon, Jul 28 from Chicago to Fort Walton Beach, returning Mon, Aug 4, priced at $199 found 6 days ago
Southwest Airlines
Mon, Jul 28 - Mon, Aug 4
MDW
Chicago
VPS
Fort Walton Beach
$206 Roundtrip, found 6 days ago
$206
Roundtrip
found 6 days ago
Select Southwest Airlines flight, departing Mon, Jul 28 from Chicago to Fort Walton Beach, returning Mon, Aug 4, priced at $206 found 6 days ago
Southwest Airlines
Thu, Sep 4 - Sat, Sep 6
MDW
Chicago
VPS
Fort Walton Beach
$219 Roundtrip, found 5 days ago
$219
Roundtrip
found 5 days ago
Select Southwest Airlines flight, departing Thu, Sep 4 from Chicago to Fort Walton Beach, returning Sat, Sep 6, priced at $219 found 5 days ago
Southwest Airlines
Mon, Sep 22 - Thu, Sep 25
MDW
Chicago
VPS
Fort Walton Beach
$222 Roundtrip, found 5 hours ago
$222
Roundtrip
found 5 hours ago
Select Southwest Airlines flight, departing Mon, Sep 22 from Chicago to Fort Walton Beach, returning Thu, Sep 25, priced at $222 found 5 hours ago
Southwest Airlines
Mon, Jul 21 - Thu, Jul 24
MDW
Chicago
VPS
Fort Walton Beach
$222 Roundtrip, found 5 hours ago
$222
Roundtrip
found 5 hours ago
Select Southwest Airlines flight, departing Mon, Jul 21 from Chicago to Fort Walton Beach, returning Thu, Jul 24, priced at $222 found 5 hours ago
Delta
Tue, Jul 22 - Fri, Jul 25
MDW
Chicago
VPS
Fort Walton Beach
$223 Roundtrip, found 14 hours ago
$223
Roundtrip
found 14 hours ago
Select Delta flight, departing Tue, Jul 22 from Chicago to Fort Walton Beach, returning Fri, Jul 25, priced at $223 found 14 hours ago
Southwest Airlines
Mon, Sep 1 - Sat, Sep 6
MDW
Chicago
VPS
Fort Walton Beach
$225 Roundtrip, found 12 hours ago
$225
Roundtrip
found 12 hours ago
Select Southwest Airlines flight, departing Mon, Sep 1 from Chicago to Fort Walton Beach, returning Sat, Sep 6, priced at $225 found 12 hours ago
Southwest Airlines
Mon, Sep 22 - Thu, Sep 25
MDW
Chicago
VPS
Fort Walton Beach
$228 Roundtrip, found 5 hours ago
$228
Roundtrip
found 5 hours ago
Select Southwest Airlines flight, departing Mon, Sep 22 from Chicago to Fort Walton Beach, returning Thu, Sep 25, priced at $228 found 5 hours ago

Find the cheapest month to fly from Chicago (MDW) to Fort Walton Beach (VPS)

July is typically the cheapest month to fly

From $155 - $670 per traveler.

Graph displaying average flight prices per month

Flights from Chicago (MDW) to Fort Walton Beach (VPS)
Origin airport
Midway Intl.
Destination airport
Northwest Florida Regional
Airlines serving
Delta, Southwest Airlines
Roundtrip price
$197
Distance
782 mi
Average flight time
2 hours 11 mins

Chicago to Fort Walton Beach Flights

The cheapest times to fly from Chicago to Fort Walton Beach

On average, Thursday can be the cheapest time to fly, according to data from the Airlines Reporting Corporation (ARC), one of the world's biggest databases for global airline sales. The data reveals that you could save up to 16% by flying on a Thursday—the cheapest day to travel on average—instead of a Sunday—the most expensive. Some of the most affordable flights from Chicago to Fort Walton Beach are during the month of July. You can find some of the cheapest flights from Chicago to Fort Walton Beach with Expedia's search tool and vast selection of airlines.

 

The best time to book a flight from Chicago to Fort Walton Beach

Sunday is one of the best days to book for cheap flights from Chicago to Fort Walton Beach: Tickets reserved on a Sunday cost between 6% and 13% less than those reserved on a Friday, according to ARC data. The data also suggests booking early can also lead to cheaper airfares. You could save 24% by buying your tickets for domestic flights at least a month in advance and 10% by booking international flights 2 months in advance.

 

How to find cheap round-trip tickets from Chicago to Fort Walton Beach

Being flexible with your dates and using Expedia's Price Drop Protection and Price Tracking features are some of the best ways of finding a cheap ticket from Chicago to Fort Walton Beach in 2025. You can also book with separate airlines for your outbound and return journeys, from $99 one-way. Expedia also offers Price Drop Protection, so if the cost of your airfare goes down after booking, you'll receive a credit for the difference*. This is available for a small fee, and is free to One Key Gold and Platinum tier members.

 

Expedia's Price Tracking feature means you can stay on top of airfares without manually checking every day. It sends you automated price alerts for cheap Chicago to Fort Walton Beach flights and uses historical data to indicate when the best time to book is. Download Expedia's free app to activate this handy tool in a few easy taps.

 

You could also save big by booking one of Expedia's vacation packages. Bundling together your Chicago to Fort Walton Beach airfare with your accommodations and car rental is often cheaper than booking everything separately. There’s also One Key, Expedia's generous rewards program. Join for free and you could earn One Key cash on most bookings to save on future adventures.

 

*Terms apply.

 

Disclaimer: ARC The statistics are based on average round-trip ticket prices between January and August 2023. The percentages you see are averages.

 

Frequently asked questions

How much does a flight from Midway Intl. Airport (MDW) to Northwest Florida Regional Airport (VPS) cost?
Discover the latest flight deals from MDW to VPS 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 VPS?
The cheapest flights from MDW to VPS 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 VPS?
Use the filter tool on Expedia to compare airlines and find the cheapest carrier that'll take you from MDW to VPS. 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 Northwest Florida Regional Airport (VPS)?
On average, Midway Intl. Airport (MDW) has 2 direct flights to Northwest Florida Regional Airport (VPS) weekly. For more choice, take advantage of Expedia's filters to find flights with layovers. Fit in a quick visit to another destination or just break up your journey.
What are the most popular departure times for flights from Midway Intl. Airport (MDW) to Northwest Florida Regional Airport (VPS)?
Flights between MDW and VPS are their busiest at 4 PM. If you'd like a quieter trip and potentially cheaper tickets, choose a departure outside the usual busy windows.
What day of the week has the most flights from MDW to VPS?
If you depart on a Thursday, you'll get the largest range of options for flights from Midway Intl. Airport (MDW) to Northwest Florida Regional Airport (VPS).
What is the earliest flight from Midway Intl. Airport (MDW) to Northwest Florida Regional Airport (VPS)?
Midway Intl. Airport (MDW)'s first flight to Northwest Florida Regional Airport (VPS) departs at approximately 4:31PM UTC-6. With a total journey time of 2h 26m, you'll touch down at around 6:57PM UTC-6.
How long does it take to fly from Midway Intl. Airport (MDW) to Northwest Florida Regional Airport (VPS)?
Flights from MDW to VPS have an average travel time of 2 hours and 26 minutes. The distance between the two airports is 780 mi.
What is the best time to fly from Midway Intl. Airport (MDW) to Northwest Florida Regional Airport (VPS)?
To arrive at Northwest Florida Regional Airport (VPS) on time, pick a flight that leaves from Midway Intl. Airport (MDW) before 3 PM. The chance 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 Fort Walton Beach from Midway Intl. Airport (MDW)?
Compare your flight options from Midway Intl. Airport (MDW) to Northwest Florida Regional Airport (VPS). This is the only Fort Walton Beach airport you can fly into if you're taking a direct flight.
Is it cheaper to buy a plane ticket from Midway Intl. Airport (MDW) to Northwest Florida Regional Airport (VPS) last-minute?
Last-minute bookings from MDW to VPS are generally more expensive. To secure the lowest prices, start looking for flights ahead of time. That said, if you're flexible with your travel plans, you may land a cheap ticket right before your trip.
Is it cheaper to book a MDW to VPS flight and hotel package?
Compared with arranging hotels and flights separately, booking a MDW to VPS flight and hotel package with Expedia could lead to significant savings. Better still, managing everything in one place takes the hassle out of travel planning. Just pick your flights and select from our extensive range of hotels, then customize your trip with extras like activities, tours and car rentals.
Can I cancel or change the date of my flight from Midway Intl. Airport (MDW) to Northwest Florida Regional Airport (VPS)?
Typically, you can cancel or reschedule your MDW to VPS flight. However, additional charges may apply, especially if you booked more than 24 hours ago. Check your itinerary for the airline's fees and policies on flight changes, or if you'd like further information, visit our Customer Service portal.

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*Available to One Key members.