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Midway

$167+ Cheap flights from Fort Walton Beach, FL to Midway (MDW)

This is the cheapest one-way flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 6/17. Fares are subject to change and may not be available on all flights or dates of travel.
PNS — MDW
Feb 28 — Mar 71
Sat 2/28
Sat 3/7
1 adult, Economy
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Cheap flight deals from Fort Walton Beach to Midway

Cheapest flights from Fort Walton Beach to Midway
Explore the most affordable flight options available from Fort Walton Beach to Midway. Find the lowest fares from popular airlines and budget airlines, with prices last updated on January 29, 2026.

This Kiwi.com deal was found by Cheapflights users on 1/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 6/296:12 pm
VPS
-
MDW
Nonstop2h 21m
Allegiant Air
Fri 7/39:15 pm
MDW
-
VPS
Nonstop2h 14m
Allegiant Air
Deal found 1/28$194
This Kiwi.com deal was found by Cheapflights users on 1/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 8/76:14 pm
VPS
-
MDW
Nonstop2h 21m
Allegiant Air
Mon 8/109:25 pm
MDW
-
VPS
Nonstop2h 14m
Allegiant Air
Deal found 1/28$253
This Kiwi.com deal was found by Cheapflights users on 1/26. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 4/232:40 pm
VPS
-
MDW
Nonstop2h 17m
Multiple Airlines
Mon 4/279:14 am
MDW
-
VPS
3 stops23h 34m
Multiple Airlines
Deal found 1/26$299
This Southwest deal was found by Cheapflights users on 1/27. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 2/247:00 am
VPS
-
MDW
1 stop6h 25m
Southwest
Tue 3/38:15 am
MDW
-
VPS
1 stop5h 05m
Southwest
Deal found 1/27$333
This Kiwi.com deal was found by Cheapflights users on 1/27. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 3/1312:11 pm
VPS
-
MDW
3 stops33h 34m
Multiple Airlines
Sun 3/158:43 pm
MDW
-
VPS
Nonstop2h 08m
Multiple Airlines
Deal found 1/27$342
This Kiwi.com deal was found by Cheapflights users on 1/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 4/178:00 am
VPS
-
MDW
2 stops35h 31m
Multiple Airlines
Sun 4/195:47 pm
MDW
-
VPS
Nonstop2h 09m
Multiple Airlines
Deal found 1/28$351
This Delta deal was found by Cheapflights users on 1/26. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 4/236:00 am
VPS
-
MDW
1 stop6h 07m
Delta
Tue 4/285:21 pm
MDW
-
VPS
1 stop5h 58m
Delta
Deal found 1/26$355
This Southwest deal was found by Cheapflights users on 1/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/812:15 pm
VPS
-
MDW
1 stop8h 05m
Southwest
Tue 8/116:30 am
MDW
-
VPS
1 stop7h 00m
Southwest
Deal found 1/28$368

Find flight deals from Fort Walton Beach to Midway

Keep the following information in mind while searching for Fort Walton Beach to Midway flight deals. Data was last updated January 29, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$194
(Kiwi.com)

One-way from

$167
(Southwest)

Popular in

December

Cheapest in

May

Average price

$376
Provider with most accurate pricing for Valparaiso Destin-Ft Walton Beach-Chicago (CHI) flight deals.
Search Deals
Provider most trusted by Cheapflights users for Valparaiso Destin-Ft Walton Beach-Chicago (CHI) flights.
Search Deals
From Fort Walton Beach to Chicago Midway
Search Deals
One-way flight from Fort Walton Beach to Chicago Midway
Search Deals
Highest demand for flights based on searches. 27% potential increase in price ($82 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 7% potential price decrease ($16 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in January 2026
Search Deals

Cheapflights Fare Finder

 
Customize your flight search to find flights from Fort Walton Beach to Midway that fit within your specific budget. Explore options based on user searches and filter the results based on your desired price range. Find flights that match your budget for a cost-effective journey. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated January 29, 2026.
Use the filters below to find and compare flights from Fort Walton Beach to Chicago Midway Airport that are best for you.

Fly from

Fort Walton Beach

Fly to

Midway

Route

Depart

Return

Price

ValparaisoChicago

VPS - MDW

VPSMDW

Valparaiso Destin-Ft Walton Beach

Mon 6/29

6:12 pm-8:33 pm

Nonstop2h 21m

Chicago Midway

Fri 7/3

9:15 pm-11:29 pm

Nonstop2h 14m

$194

ValparaisoChicago

VPS - MDW

VPSMDW

Valparaiso Destin-Ft Walton Beach

Thu 4/23

2:40 pm-4:57 pm

Nonstop2h 17m

Chicago Midway

Mon 4/27

9:14 am-8:48 am

3 stops23h 34m

$299

ValparaisoChicago

VPS - MDW

VPSMDW

Valparaiso Destin-Ft Walton Beach

Tue 2/24

7:00 am-1:25 pm

1 stop6h 25m

Chicago Midway

Tue 3/3

8:15 am-1:20 pm

1 stop5h 05m

$333

ValparaisoChicago

VPS - MDW

VPSMDW

Valparaiso Destin-Ft Walton Beach

Fri 3/13

8:42 pm-8:21 pm

2 stops23h 39m

Chicago Midway

Sun 3/15

8:43 pm-10:51 pm

Nonstop2h 08m

$354

ValparaisoChicago

VPS - MDW

VPSMDW

Valparaiso Destin-Ft Walton Beach

Fri 3/13

7:20 am-11:55 am

1 stop4h 35m

Chicago Midway

Mon 3/16

4:05 pm-9:05 pm

1 stop5h 00m

$370

ValparaisoChicago

VPS - MDW

VPSMDW

Valparaiso Destin-Ft Walton Beach

Fri 4/17

4:59 pm-10:28 pm

1 stop5h 29m

Chicago Midway

Sun 4/19

6:00 am-12:48 pm

1 stop6h 48m

$374

ValparaisoChicago

VPS - MDW

VPSMDW

Valparaiso Destin-Ft Walton Beach

Wed 7/1

6:00 am-9:51 am

1 stop3h 51m

Chicago Midway

Thu 7/9

6:00 am-10:11 am

1 stop4h 11m

$377

ValparaisoChicago

VPS - MDW

VPSMDW

Valparaiso Destin-Ft Walton Beach

Wed 6/17

4:00 pm-12:05 am

1 stop8h 05m

$167

ValparaisoChicago

VPS - MDW

VPSMDW

Valparaiso Destin-Ft Walton Beach

Mon 4/6

4:00 pm-9:20 pm

1 stop5h 20m

$183

ValparaisoChicago

VPS - MDW

VPSMDW

Valparaiso Destin-Ft Walton Beach

Fri 3/13

6:00 pm-12:05 am

1 stop6h 05m

$186

Flights are sorted by cheapest round-trip flights first.

Deals found on 1/27

Showing 1-10 of 15 results
1
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Best time to book a flight from Fort Walton Beach to Midway

Have a flexible travel schedule? Discover the best time to fly to Midway from Fort Walton Beach 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 Fort Walton Beach to Chicago Midway Airport

What is the cheapest month to book a flight from Fort Walton Beach to Chicago Midway Airport?

Currently, June is the cheapest month in which you can book a flight from Fort Walton Beach to Chicago Midway Airport (average of $108). Flying from Fort Walton Beach to Chicago Midway Airport in July is currently the most expensive (average of $284). 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.

What is the cheapest time of day to fly from FO9 to MDW?

Find hourly flight availability from Fort Walton Beach to Midway. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated January 29, 2026.

It’s typically best to fly out from Fort Walton Beach to Chicago Midway Airport at noon. Doing so could potentially save you 38% on the flight price compared to flying in the evening, which is usually more expensive.

Reviews of airlines servicing Midway

Get insights into the airlines that provide service to Midway. Read reviews, discover amenities, and learn about the overall travel experience offered by airlines. Use this information to make informed decisions when choosing an airline for your flight to Midway. Reviews last updated January 29, 2026.
Read through reviews of airlines operating flights from Fort Walton Beach to Chicago Midway Airport, such as Allegiant Air. Reviews also offer insight into each airline's entertainment options, comfort, food, crew/service, and boarding process.
Allegiant Air
7.2
Good
706 reviews

Food

5.9

Boarding

7.6

Comfort

6.8

Overall

7.2

Crew

8.1

Entertainment

5.5

Reviews

1 / 20
4.0
Okay

Sara,Nov 2025

PSC - AZA

We were delayed and then couldn’t get off due to lightening.
Allegiant Air
7.2
Good
706 reviews
Allegiant Air
7.2
Good
706 reviews

Food

5.9

Boarding

7.6

Comfort

6.8

Overall

7.2

Crew

8.1

Entertainment

5.5

Reviews

1 / 20
4.0
Okay

Sara,Nov 2025

PSC - AZA

We were delayed and then couldn’t get off due to lightening.

Related info for your journey

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

  • How long is the flight from Fort Walton Beach to Chicago Midway Airport?

    Airlines like Allegiant Air and Southwest fly from Fort Walton Beach to Chicago Midway Airport in about 2h 21m. The time it takes to get you to your destination can typically vary by up to 4h 04m. The distance between Fort Walton Beach and Chicago Midway Airport is about 783 mi. This flight may include one or multiple stops.

  • Can I find deals for flights from Fort Walton Beach to Midway that include hotel bookings?

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

  • How can I find direct flights from Fort Walton Beach to Midway?

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

  • Can I find deals for business class flights from Fort Walton Beach to Midway?

    Yes. Cheapflights offers flight deals from Fort Walton Beach to Midway 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 Fort Walton Beach to Chicago Midway Airport?

    Currently, June is the cheapest month in which you can book a flight from Fort Walton Beach to Chicago Midway Airport (average of $108). Flying from Fort Walton Beach to Chicago Midway Airport in July is currently the most expensive (average of $284). 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 Chicago Midway Airport?

Book flights to Chicago Midway Airport if you plan to visit one of these locations
Lansing
Merrillville
Hammond
Porter
Benton Harbor

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Top 3 airlines flying from Fort Walton Beach to Midway

Discover the top 3 airlines that operate flights from Fort Walton Beach to Midway. Compare their services, reliability, and customer satisfaction ratings to choose the airline that best suits your travel preferences and needs. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated January 29, 2026.
AirlineCheapestAverageFlexibilityOn-time
Allegiant AirCheapest$86Average$144FlexibilityNo cancel feeOn-time88%
DeltaCheapest$89Average$296FlexibilityNo cancel feeOn-timeN/A
SouthwestCheapest$216Average$355FlexibilityNo cancel feeOn-time63%

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