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$54+ 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 6/4. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — PNS
May 6 — May 131
Tue 5/6
Tue 5/13
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 Monday or Friday 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 May 1, 2025.

Most accurate provider

FlightHub
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$118
(Kiwi.com)

One-way from

$54
(Booking.com)

Popular in

March

Cheapest in

January

Average price

$242
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. 20% potential increase in price ($78 potential increase over avg. RT price).
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Cheapest flight prices on average. 7% potential price decrease ($22 potential savings vs. average RT price).
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Average for round-trip flights in May 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 May 1, 2025.

This Kiwi.com deal was found by Cheapflights users on 4/29. 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.
Wed 6/114:27 pmMDW - VPS
Nonstop2h 11mAllegiant Air
Fri 6/206:00 amVPS - MDW
Nonstop2h 22mAllegiant Air
Deal found 4/29$118
This American Airlines deal was found by Cheapflights users on 4/29. 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.
Wed 6/117:43 amORD - VPS
Nonstop2h 16mAmerican Airlines
Fri 6/207:30 pmVPS - ORD
1 stop5h 29mAmerican Airlines
Deal found 4/29$178
This Delta deal was found by Cheapflights users on 4/29. 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.
Thu 6/59:39 amORD - VPS
1 stop6h 35mDelta
Tue 6/106:00 amVPS - ORD
1 stop4h 09mDelta
Deal found 4/29$217
This Southwest deal was found by Cheapflights users on 4/30. 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.
Mon 6/25:20 amMDW - VPS
2 stops8h 15mSouthwest
Wed 6/46:25 pmVPS - MDW
1 stop4h 45mSouthwest
Deal found 4/30$258
This Delta deal was found by Cheapflights users on 4/30. 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.
Fri 5/3012:48 pmMDW - VPS
1 stop5h 40mDelta
Fri 6/64:59 pmVPS - MDW
1 stop4h 28mDelta
Deal found 4/30$261
This Mytrip deal was found by Cheapflights users on 4/30. 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.
Sat 6/149:28 pmORD - VPS
1 stop17h 17mMultiple Airlines
Sat 6/218:00 amVPS - ORD
2 stops15h 45mMultiple Airlines
Deal found 4/30$286
This Sun Country Air deal was found by Cheapflights users on 4/29. 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 Sun Country Air is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 5/226:18 pmORD - VPS
1 stop22h 42mSun Country Air
Sun 5/256:10 pmVPS - ORD
1 stop25h 59mSun Country Air
Deal found 4/29$294
This Southwest deal was found by Cheapflights users on 4/29. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 8/17:30 amORD - VPS
2 stops9h 45mSouthwest
Tue 8/57:00 amVPS - ORD
1 stop5h 45mSouthwest
Deal found 4/29$342

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 May 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

Wed 6/11

4:27 pm-6:38 pm

Nonstop2h 11m

Valparaiso Destin-Ft Walton Beach

Fri 6/20

6:00 am-8:22 am

Nonstop2h 22m

$118

ChicagoValparaiso

ORD - VPS

ORDVPS

Chicago O'Hare Intl

Wed 6/11

7:43 am-9:59 am

Nonstop2h 16m

Valparaiso Destin-Ft Walton Beach

Fri 6/20

7:30 pm-12:59 am

1 stop5h 29m

$178

ChicagoValparaiso

ORD - VPS

ORDVPS

Chicago O'Hare Intl

Thu 6/5

9:39 am-4:14 pm

1 stop6h 35m

Valparaiso Destin-Ft Walton Beach

Tue 6/10

6:00 am-10:09 am

1 stop4h 09m

$217

ChicagoValparaiso

MDW - VPS

MDWVPS

Chicago Midway

Mon 6/2

5:20 am-1:35 pm

2 stops8h 15m

Valparaiso Destin-Ft Walton Beach

Wed 6/4

6:25 pm-11:10 pm

1 stop4h 45m

$258

ChicagoValparaiso

MDW - VPS

MDWVPS

Chicago Midway

Fri 5/30

12:48 pm-6:28 pm

1 stop5h 40m

Valparaiso Destin-Ft Walton Beach

Fri 6/6

4:59 pm-9:27 pm

1 stop4h 28m

$261

ChicagoValparaiso

ORD - VPS

ORDVPS

Chicago O'Hare Intl

Sat 6/14

9:28 pm-2:45 pm

1 stop17h 17m

Valparaiso Destin-Ft Walton Beach

Sat 6/21

8:00 am-11:45 pm

2 stops15h 45m

$286

ChicagoValparaiso

ORD - VPS

ORDVPS

Chicago O'Hare Intl

Thu 5/22

6:18 pm-5:00 pm

1 stop22h 42m

Valparaiso Destin-Ft Walton Beach

Sun 5/25

6:10 pm-8:09 pm

1 stop25h 59m

$294

ChicagoValparaiso

ORD - VPS

ORDVPS

Chicago O'Hare Intl

Fri 6/27

7:00 am-7:10 pm

2 stops12h 10m

Valparaiso Destin-Ft Walton Beach

Wed 7/2

7:00 am-5:55 pm

2 stops10h 55m

$392

ChicagoValparaiso

MDW - VPS

MDWVPS

Chicago Midway

Wed 6/4

4:27 pm-6:38 pm

Nonstop2h 11m

$54

ChicagoValparaiso

ORD - VPS

ORDVPS

Chicago O'Hare Intl

Wed 6/18

4:00 pm-9:20 pm

1 stop5h 20m

$90

Flights are sorted by cheapest round-trip flights first.

Deals found on 4/30

Showing 1-10 of 17 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 April 25, 2025.

The best time to book flights from Chicago to Fort Walton Beach is 85 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 $418). 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 May 1, 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. Saturday mornings flights should be avoided if possible as fares are typically the most expensive at this time.

Rainfall in Fort Walton Beach by month

Plan your trip to Fort Walton Beach by taking into account the average rainfall totals by month.

In terms of precipitation, rainfall in Fort Walton Beach ranges from 3.1 - 7.5 inches per month. July is typically the wettest month, when rainfall can reach 7.5 in. October is typically the driest time to visit Fort Walton Beach when rainfall is around 3.1 in.

Temperature in Fort Walton Beach by month

Plan your trip to Fort Walton Beach by taking into account the average temperature totals by month.

If weather is an important factor for your trip to Fort Walton Beach, use this chart to help with planning. For those seeking warmer temperatures, July is the ideal time of year to visit, when temperatures reach an average of 80.6 F. Travelers looking to avoid the cold should look outside of January, when temperatures are typically at their lowest (around 50.0 F).

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 May 1, 2025.
To help decide which airline to fly from Chicago to Fort Walton Beach, see what other customers have to say about Southwest, Delta and Allegiant Air. You can also see how each airline compares in terms of entertainment options, comfort, food, crew/service, and boarding process.
Southwest
8.0
Very good
4,294 reviews

Boarding

8.2

Comfort

8.0

Food

7.1

Entertainment

7.6

Crew

8.6

Overall

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
4,294 reviews
Southwest
8.0
Very good
4,294 reviews

Boarding

8.2

Comfort

8.0

Food

7.1

Entertainment

7.6

Crew

8.6

Overall

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
7,934 reviews
Southwest
8.0
Very good
4,294 reviews

Boarding

8.2

Comfort

8.0

Food

7.1

Entertainment

7.6

Crew

8.6

Overall

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
7.3
Good
734 reviews
Southwest
8.0
Very good
4,294 reviews

Boarding

8.2

Comfort

8.0

Food

7.1

Entertainment

7.6

Crew

8.6

Overall

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
4,294 reviews

Boarding

8.2

Comfort

8.0

Food

7.1

Entertainment

7.6

Crew

8.6

Overall

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
346 reviews
Southwest
8.0
Very good
4,294 reviews

Boarding

8.2

Comfort

8.0

Food

7.1

Entertainment

7.6

Crew

8.6

Overall

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 ($54), Southwest ($90), and Sun Country Air ($140).

  • 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 American Airlines (100%), Envoy Air (100%) and Spirit Airlines (89%).

  • 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 $177 on average our data indicates $315 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 $418). 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.

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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 May 1, 2025.
AirlineCheapestAverageFlexibilityOn-time
Allegiant AirCheapest$92Average$167FlexibilityNo cancel feeOn-time88%
Spirit AirlinesCheapest$118Average$205FlexibilityNo cancel feeOn-time65%
DeltaCheapest$199Average$331FlexibilityNo cancel feeOn-timeN/A
SouthwestCheapest$222Average$390FlexibilityNo cancel feeOn-time63%
American AirlinesCheapest$228Average$369FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$239Average$454FlexibilityNo cancel feeOn-time69%

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