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$55+ 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 12/1. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — PNS
Aug 5 — Aug 121
Tue 8/5
Tue 8/12
1 adult, Economy
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Cheapflights Tip: The best prices from Chicago to Fort Walton Beach are usually found in January or February, booked 85 days in advance, depart on a Wednesday or Monday and return on a Wednesday

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 July 31, 2025.

Round-trip from

$235
(Southwest)

One-way from

$59
(Cheapflightsfares)

Popular in

March

Cheapest in

January

Average price

$276
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. 21% potential increase in price ($86 potential increase over avg. RT price).
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Cheapest flight prices on average. 7% potential price decrease ($21 potential savings vs. average RT price).
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Average for round-trip flights in July 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 July 31, 2025.

This Mytrip deal was found by Cheapflights users on 7/31. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/267:50 pmMDW - VPS
1 stop14h 17mAllegiant Air
Thu 10/28:00 amVPS - MDW
Nonstop2h 17mAllegiant Air
Deal found 7/31$167
This Southwest deal was found by Cheapflights users on 7/30. 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 8/232:55 pmORD - VPS
1 stop3h 50mSouthwest
Wed 8/277:00 amVPS - ORD
1 stop5h 45mSouthwest
Deal found 7/30$235
This Southwest deal was found by Cheapflights users on 7/31. 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.
Thu 8/215:10 amMDW - VPS
1 stop6h 05mSouthwest
Tue 8/262:00 pmVPS - MDW
1 stop5h 45mSouthwest
Deal found 7/31$235
This Sun Country Air deal was found by Cheapflights users on 7/30. 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.
Wed 11/2610:54 amORD - VPS
1 stop6h 32mSun Country Air
Fri 11/2810:11 amVPS - ORD
1 stop22h 51mSun Country Air
Deal found 7/30$248
This American Airlines deal was found by Cheapflights users on 7/31. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 8/227:08 amORD - VPS
Nonstop2h 12mAmerican Airlines
Mon 8/2510:00 amVPS - ORD
Nonstop2h 35mAmerican Airlines
Deal found 7/31$296
This Mytrip deal was found by Cheapflights users on 7/29. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/215:16 pmORD - VPS
2 stops18h 24mMultiple Airlines
Sun 8/246:00 pmVPS - ORD
1 stop15h 14mMultiple Airlines
Deal found 7/29$311
This Delta deal was found by Cheapflights users on 7/30. 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.
Sat 9/277:10 amORD - VPS
2 stops14h 39mDelta
Sat 10/412:55 pmVPS - ORD
1 stop8h 35mDelta
Deal found 7/30$316
This Delta deal was found by Cheapflights users on 7/29. 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.
Tue 9/99:30 amMDW - VPS
2 stops12h 24mDelta
Sat 9/136:00 amVPS - MDW
2 stops12h 35mDelta
Deal found 7/29$330

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 July 31, 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

Fri 9/26

7:50 pm-10:07 am

1 stop14h 17m

Valparaiso Destin-Ft Walton Beach

Thu 10/2

8:00 am-10:17 am

Nonstop2h 17m

$167

ChicagoValparaiso

ORD - VPS

ORDVPS

Chicago O'Hare Intl

Sat 8/23

2:55 pm-6:45 pm

1 stop3h 50m

Valparaiso Destin-Ft Walton Beach

Wed 8/27

7:00 am-12:45 pm

1 stop5h 45m

$235

ChicagoValparaiso

MDW - VPS

MDWVPS

Chicago Midway

Thu 8/21

5:10 am-11:15 am

1 stop6h 05m

Valparaiso Destin-Ft Walton Beach

Tue 8/26

2:00 pm-7:45 pm

1 stop5h 45m

$235

ChicagoValparaiso

ORD - VPS

ORDVPS

Chicago O'Hare Intl

Sun 8/24

8:00 am-5:02 pm

1 stop9h 02m

Valparaiso Destin-Ft Walton Beach

Thu 8/28

6:08 pm-12:20 pm

1 stop18h 12m

$261

ChicagoValparaiso

ORD - VPS

ORDVPS

Chicago O'Hare Intl

Fri 8/22

7:08 am-9:20 am

Nonstop2h 12m

Valparaiso Destin-Ft Walton Beach

Mon 8/25

10:00 am-12:35 pm

Nonstop2h 35m

$296

ChicagoValparaiso

ORD - VPS

ORDVPS

Chicago O'Hare Intl

Thu 8/21

5:16 pm-11:40 am

2 stops18h 24m

Valparaiso Destin-Ft Walton Beach

Sun 8/24

6:00 pm-9:14 am

1 stop15h 14m

$311

ChicagoValparaiso

ORD - VPS

ORDVPS

Chicago O'Hare Intl

Sat 9/27

7:10 am-9:49 pm

2 stops14h 39m

Valparaiso Destin-Ft Walton Beach

Sat 10/4

12:55 pm-9:30 pm

1 stop8h 35m

$316

ChicagoValparaiso

MDW - VPS

MDWVPS

Chicago Midway

Tue 9/9

9:30 am-9:54 pm

2 stops12h 24m

Valparaiso Destin-Ft Walton Beach

Mon 9/15

7:06 pm-8:40 am

2 stops13h 34m

$330

ChicagoValparaiso

MDW - VPS

MDWVPS

Chicago Midway

Mon 12/1

9:24 am-11:37 am

Nonstop2h 13m

$55

ChicagoValparaiso

ORD - VPS

ORDVPS

Chicago O'Hare Intl

Thu 9/11

6:10 am-8:40 pm

1 stop14h 30m

$92

Flights are sorted by cheapest round-trip flights first.

Deals found on 7/29

Showing 1-10 of 16 results
1
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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 July 25, 2025.

The best time to book flights from Chicago to Fort Walton Beach is 61 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 $306). Flying from Chicago to Fort Walton Beach in March is currently the most expensive (average of $417). 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 July 31, 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.

Weekly flight availability from Chicago to Fort Walton Beach

Explore weekly flight availability from Chicago to Fort Walton Beach. Discover flights operating on different days of the week, giving you the flexibility to choose a travel day that best fits your plans. Compare info to find the most convenient option for your journey. Data last updated July 31, 2025.

The most flights from CHI to FO9 are scheduled on a Monday (4 on average). You will have fewer flight options on Tuesday, which is when the least amount of flights are scheduled (2 on average).

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 July 31, 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
4,246 reviews

Food

7.0

Entertainment

7.5

Boarding

8.1

Overall

8.0

Crew

8.6

Comfort

8.0

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
4,246 reviews
Southwest
8.0
Very good
4,246 reviews

Food

7.0

Entertainment

7.5

Boarding

8.1

Overall

8.0

Crew

8.6

Comfort

8.0

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
7,981 reviews
Southwest
8.0
Very good
4,246 reviews

Food

7.0

Entertainment

7.5

Boarding

8.1

Overall

8.0

Crew

8.6

Comfort

8.0

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
4,246 reviews

Food

7.0

Entertainment

7.5

Boarding

8.1

Overall

8.0

Crew

8.6

Comfort

8.0

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
702 reviews
Southwest
8.0
Very good
4,246 reviews

Food

7.0

Entertainment

7.5

Boarding

8.1

Overall

8.0

Crew

8.6

Comfort

8.0

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.
Sun Country Air
6.9
Okay
334 reviews
Southwest
8.0
Very good
4,246 reviews

Food

7.0

Entertainment

7.5

Boarding

8.1

Overall

8.0

Crew

8.6

Comfort

8.0

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.

  • What are the cheapest airlines to fly from Chicago to Fort Walton Beach one-way?

    The cheapest airlines for a one-way flight from Chicago to Fort Walton Beach are Allegiant Air ($59), American Airlines ($109), and Southwest ($118).

  • 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 Envoy Air (83%).

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

    Looking at all options, your cheapest flight can be booked for $166. While the most popular route (Chicago O'Hare Intl - Valparaiso Destin-Ft Walton Beach) can be booked for $235 on average our data indicates $332 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 $306). Flying from Chicago to Fort Walton Beach in March is currently the most expensive (average of $417). 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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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 July 31, 2025.
AirlineCheapestAverageFlexibilityOn-time
Allegiant AirCheapest$85Average$162FlexibilityNo cancel feeOn-time88%
Spirit AirlinesCheapest$118Average$211FlexibilityNo cancel feeOn-time65%
DeltaCheapest$196Average$341FlexibilityNo cancel feeOn-timeN/A
SouthwestCheapest$212Average$387FlexibilityNo cancel feeOn-time63%
American AirlinesCheapest$228Average$367FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$235Average$442FlexibilityNo cancel feeOn-time69%

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