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Fort Walton Beach

$54+ Cheap flights from Chicago (CHI) to Fort Walton Beach, FL

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 11/16. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — PNS
Oct 16 — Oct 231
Thu 10/16
Thu 10/23
1 adult, Economy
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Cheapflights Tip: The best prices from Chicago to Fort Walton Beach are usually found in January or October, booked 17 days in advance, depart on a Wednesday or Monday and return on a Thursday

Cheap flight deals from Chicago to Fort Walton Beach

Keep the following information in mind while searching for Chicago to Fort Walton Beach flight deals. Data was last updated September 16, 2025.

Round-trip from

$172
(Kiwi.com)

One-way from

$54
(Cheapflightsfares)

Popular in

March

Cheapest in

January

Average price

$263
From Chicago (CHI) to Fort Walton Beach
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One-way flight from Chicago (CHI) to Fort Walton Beach
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Highest demand for flights based on searches. 22% potential increase in price ($95 potential increase over avg. RT price).
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Cheapest flight prices on average. 6% potential price decrease ($20 potential savings vs. average RT price).
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Average for round-trip flights in September 2025
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Find flight deals from Chicago to Fort Walton Beach

Cheapest flights from Chicago to Fort Walton Beach
Explore the most affordable flight options available from Chicago to Fort Walton Beach. Find the lowest fares from popular airlines and budget airlines, with prices last updated on September 16, 2025.

This Kiwi.com deal was found by Cheapflights users on 9/14. 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.
Sun 11/912:07 pmMDW - VPS
Nonstop2h 05mAllegiant Air
Thu 11/139:00 amVPS - MDW
Nonstop2h 17mAllegiant Air
Deal found 9/14$172
This Trip.com deal was found by Cheapflights users on 9/15. 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 10/511:07 amMDW - VPS
Nonstop2h 05mAllegiant Air
Sun 10/128:00 amVPS - MDW
Nonstop2h 17mAllegiant Air
Deal found 9/15$194
This Cheapflightsfares deal was found by Cheapflights users on 9/15. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/1312:07 pmMDW - VPS
Nonstop2h 05mAllegiant Air
Sun 11/169:00 amVPS - MDW
Nonstop2h 17mAllegiant Air
Deal found 9/15$200
This Kiwi.com deal was found by Cheapflights users on 9/14. 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.
Sun 11/912:07 pmMDW - VPS
Nonstop2h 05mMultiple Airlines
Thu 11/136:35 amVPS - MDW
1 stop17h 20mMultiple Airlines
Deal found 9/14$215
This Cheapflightsfares deal was found by Cheapflights users on 9/15. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/2311:07 amMDW - VPS
Nonstop2h 05mAllegiant Air
Sun 10/268:00 amVPS - MDW
Nonstop2h 17mAllegiant Air
Deal found 9/15$221
This Kiwi.com deal was found by Cheapflights users on 9/14. 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.
Sun 11/912:07 pmMDW - VPS
Nonstop2h 05mAllegiant Air
Sun 11/169:00 amVPS - MDW
Nonstop2h 17mAllegiant Air
Deal found 9/14$230
This Kiwi.com deal was found by Cheapflights users on 9/14. 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.
Sun 11/912:07 pmMDW - VPS
Nonstop2h 05mMultiple Airlines
Sun 11/163:02 pmVPS - MDW
2 stops44h 36mMultiple Airlines
Deal found 9/14$271
This Kiwi.com deal was found by Cheapflights users on 9/15. 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 10/236:20 amMDW - VPS
2 stops13h 22mMultiple Airlines
Sun 10/268:00 amVPS - MDW
Nonstop2h 17mMultiple Airlines
Deal found 9/15$287
This Kiwi.com deal was found by Cheapflights users on 9/14. 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.
Sat 11/156:15 amMDW - VPS
2 stops12h 48mMultiple Airlines
Sun 11/169:00 amVPS - MDW
Nonstop2h 17mMultiple Airlines
Deal found 9/14$291
This Sun Country Air deal was found by Cheapflights users on 9/15. 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 Sun Country Air is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/188:08 pmORD - VPS
1 stop14h 21mSun Country Air
Mon 12/2211:26 amVPS - ORD
1 stop23h 00mSun Country Air
Deal found 9/15$298
This Kiwi.com deal was found by Cheapflights users on 9/14. 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.
Wed 11/127:05 pmORD - VPS
1 stop17h 45mMultiple Airlines
Mon 11/174:16 pmVPS - ORD
2 stops31h 56mMultiple Airlines
Deal found 9/14$299
This Southwest deal was found by Cheapflights users on 9/14. 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 10/73:10 pmORD - VPS
1 stop6h 00mSouthwest
Tue 10/142:00 pmVPS - ORD
1 stop7h 30mSouthwest
Deal found 9/14$315

Cheapflights Fare Finder

 
Customize your flight search to find flights from Chicago to Fort Walton Beach 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 September 16, 2025.
Use the filters below to find and compare flights from Chicago to Fort Walton Beach that are best for you.

Fly from

Chicago

Fly to

Fort Walton Beach

Route

Depart

Return

Price

ChicagoValparaiso

MDW - VPS

MDWVPS

Chicago Midway

Sun 11/9

12:07 pm-2:12 pm

Nonstop2h 05m

Valparaiso Destin-Ft Walton Beach

Thu 11/13

6:35 am-6:39 pm

2 stops12h 04m

$246

ChicagoValparaiso

MDW - VPS

MDWVPS

Chicago Midway

Tue 12/2

5:00 am-1:15 pm

1 stop8h 15m

Valparaiso Destin-Ft Walton Beach

Wed 12/3

2:00 pm-7:25 pm

1 stop5h 25m

$315

ChicagoValparaiso

ORD - VPS

ORDVPS

Chicago O'Hare Intl

Sat 10/18

10:30 am-9:58 pm

2 stops11h 28m

Valparaiso Destin-Ft Walton Beach

Thu 10/23

6:00 am-4:11 pm

2 stops10h 11m

$316

ChicagoValparaiso

MDW - VPS

MDWVPS

Chicago Midway

Fri 11/7

12:14 pm-7:03 pm

3 stops30h 49m

Valparaiso Destin-Ft Walton Beach

Sun 11/9

9:00 am-11:17 am

Nonstop2h 17m

$319

ChicagoValparaiso

MDW - VPS

MDWVPS

Chicago Midway

Tue 10/7

3:00 pm-9:10 pm

2 stops6h 10m

Valparaiso Destin-Ft Walton Beach

Tue 10/14

7:15 am-1:25 pm

1 stop6h 10m

$321

ChicagoValparaiso

MDW - VPS

MDWVPS

Chicago Midway

Wed 11/12

5:00 am-1:15 pm

1 stop8h 15m

Valparaiso Destin-Ft Walton Beach

Sat 11/15

11:00 am-7:05 pm

1 stop8h 05m

$332

ChicagoValparaiso

MDW - VPS

MDWVPS

Chicago Midway

Thu 12/11

5:35 am-10:20 am

1 stop4h 45m

Valparaiso Destin-Ft Walton Beach

Wed 12/17

11:20 am-4:00 pm

1 stop4h 40m

$332

ChicagoValparaiso

ORD - VPS

ORDVPS

Chicago O'Hare Intl

Tue 10/14

6:58 pm-3:18 pm

2 stops20h 20m

Valparaiso Destin-Ft Walton Beach

Tue 10/21

6:30 am-12:45 pm

1 stop30h 15m

$346

ChicagoValparaiso

MDW - VPS

MDWVPS

Chicago Midway

Mon 10/13

6:00 am-9:40 am

1 stop3h 40m

Valparaiso Destin-Ft Walton Beach

Mon 10/20

6:30 pm-12:45 am

1 stop6h 15m

$349

ChicagoValparaiso

ORD - VPS

ORDVPS

Chicago O'Hare Intl

Sat 10/18

10:30 am-9:58 pm

2 stops11h 28m

Valparaiso Destin-Ft Walton Beach

Fri 10/24

7:00 am-6:14 pm

2 stops11h 14m

$353

Flights are sorted by cheapest round-trip flights first.

Deals found on 9/14

Showing 1-10 of 35 results
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Best time to book a flight from Chicago to Fort Walton Beach

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

How far ahead should I book a flight from Chicago to Fort Walton Beach?

Use this chart to determine the optimal time to book a round-trip flight from Chicago to Fort Walton Beach. Price data was last updated on September 12, 2025.

The best time to book flights from Chicago to Fort Walton Beach is 17 days before your desired departure date. The cost of your flight will likely increase significantly if you book two weeks in advance of your flight.

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

Currently, September is the cheapest month in which you can book a flight from Chicago to Fort Walton Beach (average of $303). Flying from Chicago to Fort Walton Beach in March is currently the most expensive (average of $415). 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 CHI to FO9?

Find hourly flight availability from Chicago to Fort Walton Beach. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated September 16, 2025.

When flying from Chicago to Fort Walton Beach, the time of day you decide to fly out makes little to no difference towards the overall price you’ll pay on tickets.

What is the cheapest day to fly from Chicago to Fort Walton Beach?

Use this chart to determine the cheapest time to fly round-trip from Chicago to Fort Walton Beach. Price data was last updated on December 16, 2024.

Travelers seeking maximum savings on their Chicago to Fort Walton Beach flight should consider departing on Sunday afternoons when fares are most often at their lowest. Sunday mornings flights should be avoided if possible as fares are typically the most expensive at this time.

Reviews of airlines servicing Fort Walton Beach

Get insights into the airlines that provide service to Fort Walton Beach. 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 Fort Walton Beach. Reviews last updated September 16, 2025.
Read through reviews of airlines operating flights from Chicago to Fort Walton Beach, such as Southwest, Delta, and American Airlines. Reviews also offer insight into each airline's entertainment options, comfort, food, crew/service, and boarding process.
Southwest
8.0
Very good
4,242 reviews

Food

7.0

Boarding

8.1

Comfort

8.0

Crew

8.6

Overall

8.0

Entertainment

7.5

Reviews

1 / 20
10.0
Excellent

Sarah,Aug 2024

MDW - AUS

My first time, surprisingly good! It was a good ride overall. Coming from Singapore, this budget flight is better than the budget airline for our national carrier Singapore Airlines.
Southwest
8.0
Very good
4,242 reviews
Southwest
8.0
Very good
4,242 reviews

Food

7.0

Boarding

8.1

Comfort

8.0

Crew

8.6

Overall

8.0

Entertainment

7.5

Reviews

1 / 20
10.0
Excellent

Sarah,Aug 2024

MDW - AUS

My first time, surprisingly good! It was a good ride overall. Coming from Singapore, this budget flight is better than the budget airline for our national carrier Singapore Airlines.
Delta
8.0
Very good
7,954 reviews
Southwest
8.0
Very good
4,242 reviews

Food

7.0

Boarding

8.1

Comfort

8.0

Crew

8.6

Overall

8.0

Entertainment

7.5

Reviews

1 / 20
10.0
Excellent

Sarah,Aug 2024

MDW - AUS

My first time, surprisingly good! It was a good ride overall. Coming from Singapore, this budget flight is better than the budget airline for our national carrier Singapore Airlines.
American Airlines
7.2
Good
10,000 reviews
Southwest
8.0
Very good
4,242 reviews

Food

7.0

Boarding

8.1

Comfort

8.0

Crew

8.6

Overall

8.0

Entertainment

7.5

Reviews

1 / 20
10.0
Excellent

Sarah,Aug 2024

MDW - AUS

My first time, surprisingly good! It was a good ride overall. Coming from Singapore, this budget flight is better than the budget airline for our national carrier Singapore Airlines.
Allegiant Air
7.2
Good
699 reviews
Southwest
8.0
Very good
4,242 reviews

Food

7.0

Boarding

8.1

Comfort

8.0

Crew

8.6

Overall

8.0

Entertainment

7.5

Reviews

1 / 20
10.0
Excellent

Sarah,Aug 2024

MDW - AUS

My first time, surprisingly good! It was a good ride overall. Coming from Singapore, this budget flight is better than the budget airline for our national carrier Singapore Airlines.

Related info for your journey

Find useful and relevant information for your journey from Chicago to Fort Walton Beach. 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 Chicago to Fort Walton Beach?

    Southwest and Delta can get you from Chicago to Fort Walton Beach in just under 8h 15m. Your travel time can differ by up to 3h 13m. Airlines will cover a distance of 783 mi. Both multi-stop and nonstop flights can be found to your destination and back.

  • What are the most reliable airlines from Chicago to Fort Walton Beach?

    The top 3 most reliable airlines when flying from Chicago to Fort Walton Beach are United Airlines (90%), Air New Zealand (90%) and American Airlines (80%).

  • What are the cheapest flights from Chicago to Fort Walton Beach?

    Looking at all options, your cheapest flight can be booked for $107. While the most popular route (Chicago O'Hare Intl - Valparaiso Destin-Ft Walton Beach) can be booked for $298 on average, our data indicates $368 when flying from Chicago to Fort Walton Beach.

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

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

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

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

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

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

    Currently, September is the cheapest month in which you can book a flight from Chicago to Fort Walton Beach (average of $303). Flying from Chicago to Fort Walton Beach in March is currently the most expensive (average of $415). 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

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Alternative routes for Chicago to Fort Walton Beach

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Top 6 airlines flying from Chicago to Fort Walton Beach

Discover the top 6 airlines that operate flights from Chicago to Fort Walton Beach. 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 September 16, 2025.
AirlineCheapestAverageFlexibilityOn-time
Allegiant AirCheapest$82Average$138FlexibilityNo cancel feeOn-time88%
Spirit AirlinesCheapest$118Average$212FlexibilityNo cancel feeOn-time65%
DeltaCheapest$196Average$338FlexibilityNo cancel feeOn-timeN/A
SouthwestCheapest$212Average$390FlexibilityNo cancel feeOn-time63%
American AirlinesCheapest$225Average$372FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$227Average$429FlexibilityNo cancel feeOn-time69%

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