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$51+ Cheap flights from Fort Walton Beach, FL to Chicago (CHI)

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 12/21. Fares are subject to change and may not be available on all flights or dates of travel.
PNS — CHI
Nov 29 — Dec 61
Sat 11/29
Sat 12/6
1 adult, Economy
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Cheap flight deals from Fort Walton Beach to Chicago

Keep the following information in mind while searching for Fort Walton Beach to Chicago flight deals. Data was last updated October 30, 2025.

Most accurate provider

eDreams
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$127
(Mytrip)

One-way from

$51
(Cheapflightsfares)

Popular in

March

Cheapest in

May

Average price

$191
Provider with most accurate pricing for Valparaiso Destin-Ft Walton Beach-Chicago (CHI) flight deals.
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Provider most trusted by Cheapflights users for Valparaiso Destin-Ft Walton Beach-Chicago (CHI) flights.
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From Fort Walton Beach to Chicago (CHI)
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One-way flight from Fort Walton Beach to Chicago (CHI)
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High demand for flights, 7% potential price rise
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Cheapest flight prices on average. 7% potential price decrease ($16 potential savings vs. average RT price).
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Average for round-trip flights in October 2025
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Find flight deals from Fort Walton Beach to Chicago

Cheapest flights from Fort Walton Beach to Chicago
Explore the most affordable flight options available from Fort Walton Beach to Chicago. Find the lowest fares from popular airlines and budget airlines, with prices last updated on October 30, 2025.

This Mytrip 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/231:01 pmVPS - MDW
Nonstop2h 19mAllegiant Air
Tue 12/304:10 pmMDW - VPS
Nonstop2h 13mAllegiant Air
Deal found 10/30$127
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.
Sun 11/235:24 pmVPS - MDW
Nonstop2h 19mAllegiant Air
Sat 11/299:09 amMDW - VPS
Nonstop2h 13mAllegiant Air
Deal found 10/30$138
This Cheapflightsfares deal was found by Cheapflights users on 10/29. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/231:01 pmVPS - MDW
Nonstop2h 19mAllegiant Air
Sat 1/32:10 pmMDW - VPS
Nonstop2h 13mAllegiant Air
Deal found 10/29$142
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.
Tue 12/301:01 pmVPS - MDW
Nonstop2h 19mMultiple Airlines
Thu 1/17:44 amMDW - VPS
1 stop7h 11mMultiple Airlines
Deal found 10/30$222
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.
Tue 12/231:01 pmVPS - MDW
Nonstop2h 19mMultiple Airlines
Tue 12/306:14 amMDW - VPS
2 stops36h 00mMultiple Airlines
Deal found 10/30$236
This Kiwi.com deal was found by Cheapflights users on 10/29. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 11/2312:00 pmVPS - MDW
2 stops34h 43mMultiple Airlines
Sat 11/299:09 amMDW - VPS
Nonstop2h 13mMultiple Airlines
Deal found 10/29$281
This Mytrip 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 11/236:35 amVPS - ORD
1 stop6h 21mMultiple Airlines
Sat 11/298:22 pmORD - VPS
1 stop12h 46mMultiple Airlines
Deal found 10/30$383
This Sun Country Air 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 Sun Country Air is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 11/234:56 pmVPS - ORD
1 stop17h 43mSun Country Air
Sat 11/2910:00 amORD - VPS
1 stop23h 08mSun Country Air
Deal found 10/30$384
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.
Tue 12/308:35 amVPS - ORD
1 stop23h 56mMultiple Airlines
Thu 1/16:00 amORD - VPS
2 stops37h 57mMultiple Airlines
Deal found 10/30$385
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 12/307:00 amVPS - ORD
1 stop5h 15mSouthwest
Thu 1/11:45 pmORD - VPS
1 stop7h 25mSouthwest
Deal found 10/30$398
This American Airlines deal was found by Cheapflights users on 10/29. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/1111:29 amVPS - ORD
Nonstop2h 43mAmerican Airlines
Sun 12/148:33 amORD - VPS
Nonstop2h 26mAmerican Airlines
Deal found 10/29$426
This American Airlines deal was found by Cheapflights users on 10/29. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/246:37 amVPS - ORD
1 stop15h 46mAmerican Airlines
Tue 12/28:29 amORD - VPS
Nonstop2h 28mAmerican Airlines
Deal found 10/29$427

Cheapflights Fare Finder

 
Customize your flight search to find flights from Fort Walton Beach to Chicago 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 October 30, 2025.
Use the filters below to find and compare flights from Fort Walton Beach to Chicago that are best for you.

Fly from

Fort Walton Beach

Fly to

Chicago

Route

Depart

Return

Price

ValparaisoChicago

VPS - MDW

VPSMDW

Valparaiso Destin-Ft Walton Beach

Tue 12/23

1:01 pm-3:20 pm

Nonstop2h 19m

Chicago Midway

Tue 12/30

4:10 pm-6:23 pm

Nonstop2h 13m

$127

ValparaisoChicago

VPS - MDW

VPSMDW

Valparaiso Destin-Ft Walton Beach

Sun 11/23

5:24 pm-7:43 pm

Nonstop2h 19m

Chicago Midway

Sat 11/29

9:09 am-11:22 am

Nonstop2h 13m

$138

ValparaisoChicago

VPS - MDW

VPSMDW

Valparaiso Destin-Ft Walton Beach

Tue 12/23

1:01 pm-3:20 pm

Nonstop2h 19m

Chicago Midway

Sat 1/3

2:10 pm-4:23 pm

Nonstop2h 13m

$142

ValparaisoChicago

VPS - MDW

VPSMDW

Valparaiso Destin-Ft Walton Beach

Tue 12/30

1:01 pm-3:20 pm

Nonstop2h 19m

Chicago Midway

Thu 1/1

7:44 am-2:55 pm

1 stop7h 11m

$222

ValparaisoChicago

VPS - MDW

VPSMDW

Valparaiso Destin-Ft Walton Beach

Tue 12/23

1:01 pm-3:20 pm

Nonstop2h 19m

Chicago Midway

Tue 12/30

6:14 am-6:14 pm

2 stops36h 00m

$236

ValparaisoChicago

VPS - MDW

VPSMDW

Valparaiso Destin-Ft Walton Beach

Sun 11/23

12:00 pm-10:43 pm

2 stops34h 43m

Chicago Midway

Sat 11/29

9:09 am-11:22 am

Nonstop2h 13m

$281

ValparaisoChicago

VPS - ORD

VPSORD

Valparaiso Destin-Ft Walton Beach

Sun 11/23

4:56 pm-10:39 am

1 stop17h 43m

Chicago O'Hare Intl

Sat 11/29

10:00 am-9:08 am

1 stop23h 08m

$384

ValparaisoChicago

VPS - ORD

VPSORD

Valparaiso Destin-Ft Walton Beach

Tue 12/30

8:35 am-8:31 am

1 stop23h 56m

Chicago O'Hare Intl

Thu 1/1

6:00 am-7:57 pm

2 stops37h 57m

$385

ValparaisoChicago

VPS - ORD

VPSORD

Valparaiso Destin-Ft Walton Beach

Tue 12/30

7:00 am-12:15 pm

1 stop5h 15m

Chicago O'Hare Intl

Thu 1/1

1:45 pm-9:10 pm

1 stop7h 25m

$398

ValparaisoChicago

VPS - ORD

VPSORD

Valparaiso Destin-Ft Walton Beach

Thu 12/11

11:29 am-2:12 pm

Nonstop2h 43m

Chicago O'Hare Intl

Sun 12/14

8:33 am-10:59 am

Nonstop2h 26m

$426

Flights are sorted by cheapest round-trip flights first.

Deals found on 10/29

Showing 1-10 of 38 results
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Best time to book a flight from Fort Walton Beach to Chicago

Have a flexible travel schedule? Discover the best time to fly to Chicago 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

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

Currently, June is the cheapest month in which you can book a flight from Fort Walton Beach to Chicago (average of $99). Flying from Fort Walton Beach to Chicago in April is currently the most expensive (average of $221). 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 CHI?

Find hourly flight availability from Fort Walton Beach to Chicago. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated October 30, 2025.

One of the essential ways to save on airfare from Fort Walton Beach to Chicago is to remain as flexible as possible. Flights that are at noon tend to be the most expensive. A flight in the evening could potentially save you up to 34% on airfare.

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

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

Travelers seeking maximum savings on their Fort Walton Beach to Chicago flight should consider departing on Monday mornings when fares are most often at their lowest. Sunday evenings 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 Fort Walton Beach to Chicago?

Reviews of airlines servicing Chicago

Get insights into the airlines that provide service to Chicago. 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 Chicago. Reviews last updated October 30, 2025.
Read through reviews of airlines operating flights from Fort Walton Beach to Chicago, such as Southwest, American Airlines, and Allegiant Air. Reviews also offer insight into each airline's entertainment options, comfort, food, crew/service, and boarding process.
Southwest
8.0
Very good
4,243 reviews

Food

7.0

Crew

8.6

Comfort

8.0

Overall

8.0

Boarding

8.1

Entertainment

7.5

Reviews

1 / 20
2.0
Mediocre

Anonymous,Feb 2025

MCO - STL

Cancelled at last minute, SWA unable to assist in formulating alternate plans. Wound up renting a car and driving 13 hours to beat bad weather forecast at home. Not SWA’s fault that there was significant bad weather across the country.
Southwest
8.0
Very good
4,243 reviews
Southwest
8.0
Very good
4,243 reviews

Food

7.0

Crew

8.6

Comfort

8.0

Overall

8.0

Boarding

8.1

Entertainment

7.5

Reviews

1 / 20
2.0
Mediocre

Anonymous,Feb 2025

MCO - STL

Cancelled at last minute, SWA unable to assist in formulating alternate plans. Wound up renting a car and driving 13 hours to beat bad weather forecast at home. Not SWA’s fault that there was significant bad weather across the country.
American Airlines
7.2
Good
11,035 reviews
Southwest
8.0
Very good
4,243 reviews

Food

7.0

Crew

8.6

Comfort

8.0

Overall

8.0

Boarding

8.1

Entertainment

7.5

Reviews

1 / 20
2.0
Mediocre

Anonymous,Feb 2025

MCO - STL

Cancelled at last minute, SWA unable to assist in formulating alternate plans. Wound up renting a car and driving 13 hours to beat bad weather forecast at home. Not SWA’s fault that there was significant bad weather across the country.
Allegiant Air
7.2
Good
694 reviews
Southwest
8.0
Very good
4,243 reviews

Food

7.0

Crew

8.6

Comfort

8.0

Overall

8.0

Boarding

8.1

Entertainment

7.5

Reviews

1 / 20
2.0
Mediocre

Anonymous,Feb 2025

MCO - STL

Cancelled at last minute, SWA unable to assist in formulating alternate plans. Wound up renting a car and driving 13 hours to beat bad weather forecast at home. Not SWA’s fault that there was significant bad weather across the country.

Related info for your journey

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

    Departing from Fort Walton Beach to Chicago will take you 2h 19m. There are 783 mi between Fort Walton Beach and Chicago. This flight may include one or multiple stops.

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

    The cheapest airlines for a one-way flight from Fort Walton Beach to Chicago are Delta ($162), Sun Country Air ($167), and Southwest ($174).

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

    Looking for the most reliable airlines to get you to your destination on time? Our data shows these are most likely to get you from Fort Walton Beach to Chicago on time: United Airlines (88%), Lufthansa (86%), Emirates (85%).

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

    Looking for the cheapest flight from Fort Walton Beach to Chicago? While on average our users pay $265, our data indicates the cheapest price to be $104. The most popular route (Valparaiso Destin-Ft Walton Beach - Chicago O'Hare Intl), is priced around $364.

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

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

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

    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 Chicago.

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

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

    Currently, June is the cheapest month in which you can book a flight from Fort Walton Beach to Chicago (average of $99). Flying from Fort Walton Beach to Chicago in April is currently the most expensive (average of $221). 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?

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

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Alternative routes for Fort Walton Beach to Chicago

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Top 6 airlines flying from Fort Walton Beach to Chicago

Discover the top 6 airlines that operate flights from Fort Walton Beach to Chicago. 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 October 30, 2025.
AirlineCheapestAverageFlexibilityOn-time
Allegiant AirCheapest$84Average$178FlexibilityNo cancel feeOn-time88%
Spirit AirlinesCheapest$155Average$213FlexibilityNo cancel feeOn-time65%
American AirlinesCheapest$157Average$353FlexibilityNo cancel feeOn-time71%
SouthwestCheapest$173Average$335FlexibilityNo cancel feeOn-time63%
DeltaCheapest$194Average$323FlexibilityNo cancel feeOn-timeN/A
United AirlinesCheapest$209Average$340FlexibilityNo cancel feeOn-time69%

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