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Fort Walton Beach

$127+ 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 2/18. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — PNS
Jan 17 — Jan 241
Sat 1/17
Sat 1/24
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

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 December 18, 2025.

This Cheapflightsfares deal was found by Cheapflights users on 12/17. 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
Sun 12/213:45 pmVPS - MDW
Nonstop2h 19mAllegiant Air
Deal found 12/17$223
This American Airlines deal was found by Cheapflights users on 12/16. 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 12/304:05 pmORD - VPS
1 stop5h 27mAmerican Airlines
Sat 1/1012:30 pmVPS - ORD
Nonstop2h 40mAmerican Airlines
Deal found 12/16$372
This American Airlines deal was found by Cheapflights users on 12/16. 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 12/248:32 amORD - VPS
Nonstop2h 39mAmerican Airlines
Sun 12/2811:41 amVPS - ORD
Nonstop2h 41mAmerican Airlines
Deal found 12/16$377
This Southwest deal was found by Cheapflights users on 12/14. 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.
Thu 12/256:35 amMDW - VPS
1 stop3h 45mSouthwest
Mon 12/296:10 pmVPS - MDW
1 stop7h 00mSouthwest
Deal found 12/14$384
This American Airlines deal was found by Cheapflights users on 12/16. 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.
Sat 12/201:16 pmORD - VPS
1 stop5h 34mAmerican Airlines
Mon 12/2211:41 amVPS - ORD
Nonstop2h 41mAmerican Airlines
Deal found 12/16$387
This American Airlines deal was found by Cheapflights users on 12/17. 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.
Thu 12/189:00 amORD - VPS
Nonstop2h 38mAmerican Airlines
Mon 12/2211:41 amVPS - ORD
Nonstop2h 41mAmerican Airlines
Deal found 12/17$392
This Southwest deal was found by Cheapflights users on 12/17. 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 12/256:35 amMDW - VPS
1 stop3h 45mSouthwest
Sun 12/286:10 pmVPS - MDW
1 stop7h 00mSouthwest
Deal found 12/17$404
This Delta deal was found by Cheapflights users on 12/16. 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 12/186:00 amORD - VPS
1 stop6h 12mDelta
Sun 12/212:43 pmVPS - ORD
1 stop6h 31mDelta
Deal found 12/16$411
This Delta deal was found by Cheapflights users on 12/16. 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 12/185:26 pmMDW - VPS
1 stop5h 46mDelta
Sun 12/214:41 pmVPS - MDW
1 stop5h 41mDelta
Deal found 12/16$411
This Trip.com deal was found by Cheapflights users on 12/16. 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.
Tue 12/304:10 pmMDW - VPS
Nonstop2h 13mAllegiant Air
Sat 1/311:01 amVPS - MDW
Nonstop2h 19mAllegiant Air
Deal found 12/16$430
This American Airlines deal was found by Cheapflights users on 12/17. 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.
Thu 12/258:32 amORD - VPS
Nonstop2h 39mAmerican Airlines
Mon 12/2911:41 amVPS - ORD
Nonstop2h 41mAmerican Airlines
Deal found 12/17$433
This Southwest deal was found by Cheapflights users on 12/15. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 12/293:35 pmMDW - VPS
1 stop5h 35mSouthwest
Mon 1/56:05 pmVPS - MDW
1 stop6h 05mSouthwest
Deal found 12/15$440

Find 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 December 18, 2025.

Most accurate provider

eDreams
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$202
(Kiwi.com)

One-way from

$127
(Kiwi.com)

Popular in

March

Cheapest in

January

Average price

$365
Provider with most accurate pricing for Chicago (CHI)-Valparaiso Destin-Ft Walton Beach flight deals.
Search Deals
Provider most trusted by Cheapflights users for Chicago (CHI)-Valparaiso Destin-Ft Walton Beach flights.
Search Deals
From Chicago (CHI) to Fort Walton Beach
Search Deals
One-way flight from Chicago (CHI) to Fort Walton Beach
Search Deals
Highest demand for flights based on searches. 24% potential increase in price ($103 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 6% potential price decrease ($19 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in December 2025
Search Deals

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 December 18, 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

ORD - VPS

ORDVPS

Chicago O'Hare Intl

Tue 1/27

1:45 pm-6:55 pm

1 stop5h 10m

Valparaiso Destin-Ft Walton Beach

Tue 2/3

7:00 am-12:15 pm

1 stop5h 15m

$315

ChicagoValparaiso

ORD - VPS

ORDVPS

Chicago O'Hare Intl

Sat 3/14

5:59 pm-11:02 pm

1 stop5h 03m

Valparaiso Destin-Ft Walton Beach

Sat 3/21

6:00 am-1:18 pm

1 stop7h 18m

$315

ChicagoValparaiso

ORD - VPS

ORDVPS

Chicago O'Hare Intl

Wed 2/11

5:30 am-10:59 am

1 stop5h 29m

Valparaiso Destin-Ft Walton Beach

Sat 2/14

6:00 am-10:07 am

1 stop4h 07m

$315

ChicagoValparaiso

MDW - VPS

MDWVPS

Chicago Midway

Wed 2/11

6:00 am-10:59 am

1 stop4h 59m

Valparaiso Destin-Ft Walton Beach

Sat 2/14

6:00 am-10:06 am

1 stop4h 06m

$315

ChicagoValparaiso

ORD - VPS

ORDVPS

Chicago O'Hare Intl

Fri 1/30

10:30 am-1:01 pm

Nonstop2h 31m

Valparaiso Destin-Ft Walton Beach

Mon 2/2

1:31 pm-4:11 pm

Nonstop2h 40m

$334

ChicagoValparaiso

ORD - VPS

ORDVPS

Chicago O'Hare Intl

Wed 2/11

5:30 am-10:59 am

1 stop5h 29m

Valparaiso Destin-Ft Walton Beach

Sun 2/15

5:12 pm-11:57 pm

1 stop6h 45m

$334

ChicagoValparaiso

ORD - VPS

ORDVPS

Chicago O'Hare Intl

Sat 1/17

5:30 am-10:43 am

1 stop5h 13m

Valparaiso Destin-Ft Walton Beach

Fri 1/23

7:13 pm-11:55 pm

1 stop4h 42m

$334

ChicagoValparaiso

MDW - VPS

MDWVPS

Chicago Midway

Sat 1/17

6:45 am-10:43 am

1 stop3h 58m

Valparaiso Destin-Ft Walton Beach

Fri 1/23

1:02 pm-6:36 pm

1 stop5h 34m

$334

ChicagoValparaiso

MDW - VPS

MDWVPS

Chicago Midway

Wed 2/18

12:46 pm-6:19 pm

1 stop5h 33m

Valparaiso Destin-Ft Walton Beach

Sun 2/22

6:00 am-9:56 am

1 stop3h 56m

$334

ChicagoValparaiso

MDW - VPS

MDWVPS

Chicago Midway

Fri 2/20

10:53 am-4:03 pm

1 stop5h 10m

Valparaiso Destin-Ft Walton Beach

Tue 2/24

6:00 am-11:59 am

1 stop5h 59m

$334

Flights are sorted by cheapest round-trip flights first.

Deals found on 12/16

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 December 12, 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 $208). 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 December 18, 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 41% 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.

How much does it cost to fly round-trip from Chicago to Fort Walton Beach?

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 December 18, 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
7.9
Good
4,249 reviews

Entertainment

7.5

Crew

8.6

Overall

7.9

Boarding

8.1

Food

7.0

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
7.9
Good
4,249 reviews
Southwest
7.9
Good
4,249 reviews

Entertainment

7.5

Crew

8.6

Overall

7.9

Boarding

8.1

Food

7.0

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
7.9
Good
8,006 reviews
Southwest
7.9
Good
4,249 reviews

Entertainment

7.5

Crew

8.6

Overall

7.9

Boarding

8.1

Food

7.0

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
11,053 reviews
Southwest
7.9
Good
4,249 reviews

Entertainment

7.5

Crew

8.6

Overall

7.9

Boarding

8.1

Food

7.0

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
700 reviews
Southwest
7.9
Good
4,249 reviews

Entertainment

7.5

Crew

8.6

Overall

7.9

Boarding

8.1

Food

7.0

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.

  • 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 5h 03m. Your travel time can differ by up to 07m. Airlines will cover a distance of 797 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 (83%), Air New Zealand (76%) and Envoy Air (71%).

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

    Looking at all options, your cheapest flight can be booked for $153. While the most popular route (Chicago O'Hare Intl - Valparaiso Destin-Ft Walton Beach) can be booked for $283 on average, our data indicates $311 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 $208). 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 December 18, 2025.
AirlineCheapestAverageFlexibilityOn-time
Allegiant AirCheapest$82Average$151FlexibilityNo cancel feeOn-time88%
Spirit AirlinesCheapest$118Average$211FlexibilityNo cancel feeOn-time65%
DeltaCheapest$177Average$313FlexibilityNo cancel feeOn-timeN/A
SouthwestCheapest$212Average$377FlexibilityNo cancel feeOn-time63%
United AirlinesCheapest$214Average$427FlexibilityNo cancel feeOn-time69%
American AirlinesCheapest$218Average$377FlexibilityNo cancel feeOn-time71%

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