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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 11/16. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — PNS
Dec 1 — Dec 81
Mon 12/1
Mon 12/8
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 30 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 November 1, 2025.

Most accurate provider

eDreams
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$116
(Cheapflightsfares)

One-way from

$55
(Kiwi.com)

Popular in

March

Cheapest in

January

Average price

$310
Provider with most accurate pricing for Chicago (CHI)-Valparaiso Destin-Ft Walton Beach flight deals.
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Provider most trusted by Cheapflights users for Chicago (CHI)-Valparaiso Destin-Ft Walton Beach flights.
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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. 25% potential increase in price ($108 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 November 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 November 1, 2025.

This Cheapflightsfares deal was found by Cheapflights users on 11/1. 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 12/186:54 pmMDW - VPS
Nonstop2h 13mAllegiant Air
Tue 12/301:01 pmVPS - MDW
Nonstop2h 19mAllegiant Air
Deal found 11/1$116
This Booking.com deal was found by Cheapflights users on 10/30. 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 Booking.com 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
Thu 11/205:24 pmVPS - MDW
Nonstop2h 19mAllegiant Air
Deal found 10/30$118
This Trip.com deal was found by Cheapflights users on 10/30. 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 11/1612:07 pmMDW - VPS
Nonstop2h 05mAllegiant Air
Sun 11/235:24 pmVPS - MDW
Nonstop2h 19mAllegiant Air
Deal found 10/30$156
This Kiwi.com deal was found by Cheapflights users on 10/30. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/136:30 amMDW - VPS
2 stops32h 58mMultiple Airlines
Thu 11/205:24 pmVPS - MDW
Nonstop2h 19mMultiple Airlines
Deal found 10/30$227
This Sun Country Air deal was found by Cheapflights users on 10/31. 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 Sun Country Air is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/1811:45 amORD - VPS
1 stop5h 44mSun Country Air
Mon 12/2211:26 amVPS - ORD
1 stop23h 00mSun Country Air
Deal found 10/31$264
This Kiwi.com deal was found by Cheapflights users on 11/1. 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 11/169:24 amORD - VPS
2 stops30h 02mMultiple Airlines
Thu 11/206:35 amVPS - ORD
1 stop6h 21mMultiple Airlines
Deal found 11/1$346
This Kiwi.com deal was found by Cheapflights users on 10/31. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/612:07 pmMDW - VPS
Nonstop2h 05mMultiple Airlines
Sat 11/87:53 pmVPS - MDW
3 stops40h 09mMultiple Airlines
Deal found 10/31$355
This Kiwi.com deal was found by Cheapflights users on 10/30. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/612:07 pmMDW - VPS
Nonstop2h 05mAllegiant Air
Wed 11/1210:11 amVPS - MDW
2 stops29h 32mAllegiant Air
Deal found 10/30$369
This Southwest deal was found by Cheapflights users on 10/30. 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.
Tue 12/25:00 amMDW - VPS
1 stop8h 15mSouthwest
Wed 12/32:00 pmVPS - MDW
1 stop7h 00mSouthwest
Deal found 10/30$392
This Southwest deal was found by Cheapflights users on 11/1. 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 12/21:45 pmORD - VPS
1 stop7h 25mSouthwest
Sat 12/67:00 amVPS - ORD
1 stop5h 15mSouthwest
Deal found 11/1$412
This American Airlines deal was found by Cheapflights users on 11/1. 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.
Tue 12/28:29 amORD - VPS
Nonstop2h 28mAmerican Airlines
Fri 12/511:29 amVPS - ORD
Nonstop2h 43mAmerican Airlines
Deal found 11/1$426
This American Airlines deal was found by Cheapflights users on 10/31. 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.
Wed 12/178:33 amORD - VPS
Nonstop2h 26mAmerican Airlines
Tue 12/307:29 pmVPS - ORD
1 stop14h 15mAmerican Airlines
Deal found 10/31$434

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 November 1, 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

Thu 11/13

12:07 pm-2:12 pm

Nonstop2h 05m

Valparaiso Destin-Ft Walton Beach

Thu 11/20

5:24 pm-7:43 pm

Nonstop2h 19m

$126

ChicagoValparaiso

MDW - VPS

MDWVPS

Chicago Midway

Thu 11/13

12:07 pm-2:12 pm

Nonstop2h 05m

Valparaiso Destin-Ft Walton Beach

Thu 11/20

11:59 am-1:05 am

3 stops37h 06m

$239

ChicagoValparaiso

ORD - VPS

ORDVPS

Chicago O'Hare Intl

Thu 12/18

11:45 am-5:29 pm

1 stop5h 44m

Valparaiso Destin-Ft Walton Beach

Mon 12/22

11:26 am-10:26 am

1 stop23h 00m

$264

ChicagoValparaiso

ORD - VPS

ORDVPS

Chicago O'Hare Intl

Sun 11/16

9:24 am-3:26 pm

2 stops30h 02m

Valparaiso Destin-Ft Walton Beach

Thu 11/20

6:35 am-12:56 pm

1 stop6h 21m

$346

ChicagoValparaiso

MDW - VPS

MDWVPS

Chicago Midway

Thu 1/15

5:25 am-10:30 am

1 stop5h 05m

Valparaiso Destin-Ft Walton Beach

Tue 1/20

2:00 pm-8:40 pm

1 stop6h 40m

$349

ChicagoValparaiso

MDW - VPS

MDWVPS

Chicago Midway

Tue 1/20

9:34 am-11:05 pm

2 stops13h 31m

Valparaiso Destin-Ft Walton Beach

Mon 1/26

12:05 pm-5:32 pm

1 stop5h 27m

$390

ChicagoValparaiso

MDW - VPS

MDWVPS

Chicago Midway

Tue 1/20

9:34 am-11:05 pm

2 stops13h 31m

Valparaiso Destin-Ft Walton Beach

Thu 1/22

5:12 pm-10:26 pm

1 stop5h 14m

$390

ChicagoValparaiso

MDW - VPS

MDWVPS

Chicago Midway

Tue 1/27

9:34 am-11:05 pm

2 stops13h 31m

Valparaiso Destin-Ft Walton Beach

Fri 1/30

1:02 pm-6:36 pm

1 stop5h 34m

$390

ChicagoValparaiso

MDW - VPS

MDWVPS

Chicago Midway

Tue 1/20

9:34 am-11:05 pm

2 stops13h 31m

Valparaiso Destin-Ft Walton Beach

Tue 1/27

12:05 pm-5:32 pm

1 stop5h 27m

$390

ChicagoValparaiso

ORD - VPS

ORDVPS

Chicago O'Hare Intl

Tue 1/27

10:35 am-11:05 pm

2 stops12h 30m

Valparaiso Destin-Ft Walton Beach

Wed 1/28

12:05 pm-4:54 pm

1 stop4h 49m

$390

Flights are sorted by cheapest round-trip flights first.

Deals found on 10/30

Showing 1-10 of 44 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 October 31, 2025.

The best time to book flights from Chicago to Fort Walton Beach is 30 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, July is the cheapest month in which you can book a flight from Chicago to Fort Walton Beach (average of $81). Flying from Chicago to Fort Walton Beach in December is currently the most expensive (average of $200). 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 November 1, 2025.

One of the essential ways to save on airfare from Chicago to Fort Walton Beach is to remain as flexible as possible. Flights that are in the afternoon tend to be the most expensive. A flight in the evening could potentially save you up to 42% on airfare.

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 mornings when fares are most often at their lowest. Monday at noon 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 November 1, 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
4,241 reviews

Overall

8.0

Crew

8.6

Food

7.0

Boarding

8.1

Comfort

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
4,241 reviews
Southwest
8.0
Very good
4,241 reviews

Overall

8.0

Crew

8.6

Food

7.0

Boarding

8.1

Comfort

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
7.9
Good
7,995 reviews
Southwest
8.0
Very good
4,241 reviews

Overall

8.0

Crew

8.6

Food

7.0

Boarding

8.1

Comfort

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
11,030 reviews
Southwest
8.0
Very good
4,241 reviews

Overall

8.0

Crew

8.6

Food

7.0

Boarding

8.1

Comfort

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
694 reviews
Southwest
8.0
Very good
4,241 reviews

Overall

8.0

Crew

8.6

Food

7.0

Boarding

8.1

Comfort

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?

    Allegiant Air, Sun Country Air, and Southwest can get you from Chicago to Fort Walton Beach in just under 2h 05m. Your travel time can differ by up to 3h 39m. 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 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 ($76), Sun Country Air ($128), and Delta ($164).

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

    Looking at all options, your cheapest flight can be booked for $104. While the most popular route (Chicago O'Hare Intl - Valparaiso Destin-Ft Walton Beach) can be booked for $264 on average, our data indicates $269 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, July is the cheapest month in which you can book a flight from Chicago to Fort Walton Beach (average of $81). Flying from Chicago to Fort Walton Beach in December is currently the most expensive (average of $200). 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

See prices for flight routes from nearby airports that may be better suited for you.
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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 November 1, 2025.
AirlineCheapestAverageFlexibilityOn-time
Allegiant AirCheapest$85Average$163FlexibilityNo cancel feeOn-time88%
Spirit AirlinesCheapest$118Average$210FlexibilityNo cancel feeOn-time65%
DeltaCheapest$177Average$322FlexibilityNo cancel feeOn-timeN/A
SouthwestCheapest$212Average$391FlexibilityNo cancel feeOn-time63%
American AirlinesCheapest$217Average$379FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$219Average$421FlexibilityNo cancel feeOn-time69%

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