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$132+ 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 2/15. Fares are subject to change and may not be available on all flights or dates of travel.
PNS — CHI
Jan 17 — Jan 241
Sat 1/17
Sat 1/24
1 adult, Economy
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Cheap 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 December 18, 2025.

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.
Sun 12/2111:41 amVPS - ORD
Nonstop2h 41mAmerican Airlines
Wed 12/318:32 amORD - VPS
Nonstop2h 39mAmerican Airlines
Deal found 12/17$377
This American Airlines 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/306:50 amVPS - ORD
1 stop6h 54mAmerican Airlines
Sun 1/48:32 amORD - VPS
Nonstop2h 39mAmerican Airlines
Deal found 12/15$387
This American Airlines 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/2611:41 amVPS - ORD
Nonstop2h 41mAmerican Airlines
Mon 1/58:32 amORD - VPS
Nonstop2h 39mAmerican Airlines
Deal found 12/15$392
This Delta 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/267:24 pmVPS - ORD
1 stop4h 39mDelta
Mon 1/55:59 pmORD - VPS
1 stop4h 57mDelta
Deal found 12/15$411
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.
Tue 12/306:10 pmVPS - MDW
1 stop7h 00mSouthwest
Mon 1/52:55 pmMDW - VPS
1 stop6h 20mSouthwest
Deal found 12/15$411
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.
Tue 12/306:10 pmVPS - MDW
1 stop7h 00mSouthwest
Sun 1/45:25 amMDW - VPS
2 stops7h 55mSouthwest
Deal found 12/15$417
This Southwest 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/187:10 amVPS - MDW
1 stop8h 40mSouthwest
Sat 12/205:25 amMDW - VPS
1 stop5h 30mSouthwest
Deal found 12/16$443
This American Airlines 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/3011:39 amVPS - ORD
Nonstop2h 41mAmerican Airlines
Mon 1/58:32 amORD - VPS
Nonstop2h 39mAmerican Airlines
Deal found 12/15$454
This Southwest 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/177:15 amVPS - MDW
1 stop5h 30mSouthwest
Fri 12/1912:00 pmMDW - VPS
1 stop5h 25mSouthwest
Deal found 12/16$469
This Delta 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/315:30 pmVPS - ORD
1 stop6h 32mDelta
Mon 1/55:59 pmORD - VPS
1 stop4h 57mDelta
Deal found 12/15$494
This Delta 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/315:30 pmVPS - MDW
1 stop4h 52mDelta
Mon 1/55:31 pmMDW - VPS
1 stop5h 25mDelta
Deal found 12/15$494
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.
Tue 12/307:00 amVPS - ORD
2 stops14h 50mSouthwest
Mon 1/51:45 pmORD - VPS
1 stop7h 30mSouthwest
Deal found 12/15$505

Find 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 December 18, 2025.

Most accurate provider

eDreams
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$296
(American Airlines)

One-way from

$132
(Kiwi.com)

Popular in

March

Cheapest in

May

Average price

$194
Provider with most accurate pricing for Valparaiso Destin-Ft Walton Beach-Chicago (CHI) flight deals.
Search Deals
Provider most trusted by Cheapflights users for Valparaiso Destin-Ft Walton Beach-Chicago (CHI) flights.
Search Deals
From Fort Walton Beach to Chicago (CHI)
Search Deals
One-way flight from Fort Walton Beach to Chicago (CHI)
Search Deals
Highest demand for flights based on searches. 2% potential increase in price ($4 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 9% 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 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 December 18, 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 - ORD

VPSORD

Valparaiso Destin-Ft Walton Beach

Sat 2/14

12:15 pm-2:59 pm

Nonstop2h 44m

Chicago O'Hare Intl

Tue 2/17

9:15 am-11:45 am

Nonstop2h 30m

$302

ValparaisoChicago

VPS - ORD

VPSORD

Valparaiso Destin-Ft Walton Beach

Wed 1/21

11:00 am-6:01 pm

1 stop7h 01m

Chicago O'Hare Intl

Wed 1/28

10:30 am-1:01 pm

Nonstop2h 31m

$306

ValparaisoChicago

VPS - ORD

VPSORD

Valparaiso Destin-Ft Walton Beach

Sun 1/18

5:12 pm-11:59 pm

1 stop6h 47m

Chicago O'Hare Intl

Sat 1/31

7:05 am-11:15 am

1 stop4h 10m

$315

ValparaisoChicago

VPS - ORD

VPSORD

Valparaiso Destin-Ft Walton Beach

Wed 1/21

7:00 am-12:15 pm

1 stop5h 15m

Chicago O'Hare Intl

Wed 1/28

1:45 pm-6:55 pm

1 stop5h 10m

$315

ValparaisoChicago

VPS - ORD

VPSORD

Valparaiso Destin-Ft Walton Beach

Sat 1/24

6:00 am-10:13 am

1 stop4h 13m

Chicago O'Hare Intl

Wed 1/28

9:55 am-4:40 pm

1 stop6h 45m

$315

ValparaisoChicago

VPS - ORD

VPSORD

Valparaiso Destin-Ft Walton Beach

Sat 2/14

3:00 pm-7:19 pm

1 stop4h 19m

Chicago O'Hare Intl

Wed 2/18

9:52 am-4:03 pm

1 stop6h 11m

$315

ValparaisoChicago

VPS - ORD

VPSORD

Valparaiso Destin-Ft Walton Beach

Sun 1/18

6:00 am-10:07 am

1 stop4h 07m

Chicago O'Hare Intl

Tue 1/27

5:30 am-11:15 am

1 stop5h 45m

$315

ValparaisoChicago

VPS - ORD

VPSORD

Valparaiso Destin-Ft Walton Beach

Sat 1/24

1:02 pm-9:43 pm

1 stop8h 41m

Chicago O'Hare Intl

Sat 1/31

7:05 am-11:15 am

1 stop4h 10m

$315

ValparaisoChicago

VPS - MDW

VPSMDW

Valparaiso Destin-Ft Walton Beach

Tue 1/27

12:15 pm-6:05 pm

1 stop5h 50m

Chicago Midway

Fri 1/30

6:00 am-11:40 am

1 stop5h 40m

$334

ValparaisoChicago

VPS - MDW

VPSMDW

Valparaiso Destin-Ft Walton Beach

Tue 1/13

5:12 pm-10:07 pm

1 stop4h 55m

Chicago Midway

Tue 1/20

12:48 pm-4:40 pm

1 stop3h 52m

$348

Flights are sorted by cheapest round-trip flights first.

Deals found on 12/17

Showing 1-10 of 28 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 December is currently the most expensive (average of $228). 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 December 18, 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 in the afternoon tend to be the most expensive. A flight in the evening could potentially save you up to 33% 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 December 18, 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
7.9
Good
4,252 reviews

Comfort

8.0

Entertainment

7.5

Boarding

8.1

Crew

8.6

Overall

7.9

Food

7.0

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
7.9
Good
4,252 reviews
Southwest
7.9
Good
4,252 reviews

Comfort

8.0

Entertainment

7.5

Boarding

8.1

Crew

8.6

Overall

7.9

Food

7.0

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
11,054 reviews
Southwest
7.9
Good
4,252 reviews

Comfort

8.0

Entertainment

7.5

Boarding

8.1

Crew

8.6

Overall

7.9

Food

7.0

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
700 reviews
Southwest
7.9
Good
4,252 reviews

Comfort

8.0

Entertainment

7.5

Boarding

8.1

Crew

8.6

Overall

7.9

Food

7.0

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 40m. There are 797 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 Allegiant Air ($47), American Airlines ($169), and Delta ($217).

  • 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: Lufthansa (82%), Qatar Airways (80%), Envoy Air (79%).

  • 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 $402, our data indicates the cheapest price to be $122. The most popular route (Valparaiso Destin-Ft Walton Beach - Chicago O'Hare Intl), is priced around $315.

  • 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 December is currently the most expensive (average of $228). 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
Lansing
Merrillville
Hammond
Porter
Benton Harbor

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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 December 18, 2025.
AirlineCheapestAverageFlexibilityOn-time
Allegiant AirCheapest$84Average$144FlexibilityNo cancel feeOn-time88%
Spirit AirlinesCheapest$155Average$213FlexibilityNo cancel feeOn-time65%
American AirlinesCheapest$157Average$358FlexibilityNo cancel feeOn-time71%
SouthwestCheapest$173Average$350FlexibilityNo cancel feeOn-time63%
DeltaCheapest$194Average$304FlexibilityNo cancel feeOn-timeN/A
United AirlinesCheapest$209Average$329FlexibilityNo cancel feeOn-time69%

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