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Valparaiso

$89+ Cheap flights from O'Hare Intl (ORD) to Valparaiso, FL (VPS)

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 9/14. Fares are subject to change and may not be available on all flights or dates of travel.
ORD — VPS
Aug 4 — Aug 111
Mon 8/4
Mon 8/11
1 adult, Economy
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Cheapflights Tip: The best prices from Chicago O'Hare Intl to Valparaiso Destin-Ft Walton Beach are usually found in September or August, booked 36 days in advance, depart on a Tuesday or Monday and return on a Wednesday

Cheap flight deals from O'Hare Intl to Valparaiso

Discover tips and strategies to find the most affordable flight options for your journey from O'Hare Intl (ORD) to Valparaiso (VPS). Learn about various techniques such as flexible date searches, comparing prices across and setting up price alerts. Use these methods to find the cheapest flights available for your travel needs. Data last updated July 30, 2025.

Round-trip from

$235
(Southwest)

One-way from

$89
(Mytrip)

Popular in

March

Cheapest in

September

Average price

$395

Good round-trip deal

$321 or less

Good one-way deal

$230 or less
From Chicago O'Hare Intl to Valparaiso Destin-Ft Walton Beach
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One-way flight from Chicago O'Hare Intl to Valparaiso Destin-Ft Walton Beach
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Highest demand for flights based on searches. 7% potential increase in price ($31 potential increase over avg. RT price).
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Cheapest flight prices on average. 1% potential price decrease ($7 potential savings vs. average RT price).
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Average for round-trip flights in July 2025
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Price to beat on a round-trip flight from Chicago O'Hare Intl to Valparaiso Destin-Ft Walton Beach.
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Price to beat on a one-way flight from Chicago O'Hare Intl to Valparaiso Destin-Ft Walton Beach.
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Find flight deals from O'Hare Intl to Valparaiso

Cheapest flights from O'Hare Intl to Valparaiso
Explore the most affordable flight options available from O'Hare Intl to Valparaiso. Find the lowest fares from popular airlines and budget airlines, with prices last updated on July 30, 2025.

This Southwest deal was found by Cheapflights users on 7/27. 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.
Sat 10/187:30 amORD - VPS
1 stop8h 05mSouthwest
Tue 10/212:00 pmVPS - ORD
1 stop7h 30mSouthwest
Deal found 7/27$235
This Sun Country Air deal was found by Cheapflights users on 7/30. 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.
Wed 11/2610:54 amORD - VPS
1 stop6h 32mSun Country Air
Fri 11/2810:11 amVPS - ORD
1 stop22h 51mSun Country Air
Deal found 7/30$248
This Mytrip deal was found by Cheapflights users on 7/28. 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 10/126:10 amORD - VPS
1 stop13h 32mMultiple Airlines
Fri 10/173:46 pmVPS - ORD
2 stops30h 12mMultiple Airlines
Deal found 7/28$266
This Delta deal was found by Cheapflights users on 7/28. 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.
Sat 9/2710:35 amORD - VPS
2 stops11h 14mDelta
Sat 10/412:55 pmVPS - ORD
1 stop8h 35mDelta
Deal found 7/28$316
This American Airlines deal was found by Cheapflights users on 7/29. 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.
Tue 8/1910:10 pmORD - VPS
1 stop12h 28mAmerican Airlines
Tue 8/267:00 amVPS - ORD
1 stop10h 10mAmerican Airlines
Deal found 7/29$366

Cheapflights Fare Finder

 
Customize your flight search to find flights from O'Hare Intl to Valparaiso 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 July 30, 2025.
Use the filters below to find and compare flights from Chicago O'Hare Intl Airport to Valparaiso that are best for you.

Fly from

O'Hare Intl

Fly to

Valparaiso

Route

Depart

Return

Price

ChicagoValparaiso

ORD - VPS

ORDVPS

Chicago O'Hare Intl

Sat 10/18

7:30 am-3:35 pm

1 stop8h 05m

Valparaiso Destin-Ft Walton Beach

Tue 10/21

2:00 pm-9:30 pm

1 stop7h 30m

$235

ChicagoValparaiso

ORD - VPS

ORDVPS

Chicago O'Hare Intl

Sun 8/24

8:00 am-5:02 pm

1 stop9h 02m

Valparaiso Destin-Ft Walton Beach

Thu 8/28

6:08 pm-12:20 pm

1 stop18h 12m

$261

ChicagoValparaiso

ORD - VPS

ORDVPS

Chicago O'Hare Intl

Sun 10/12

6:10 am-7:42 pm

1 stop13h 32m

Valparaiso Destin-Ft Walton Beach

Fri 10/17

3:46 pm-9:58 pm

2 stops30h 12m

$266

ChicagoValparaiso

ORD - VPS

ORDVPS

Chicago O'Hare Intl

Sat 9/27

10:35 am-9:49 pm

2 stops11h 14m

Valparaiso Destin-Ft Walton Beach

Sat 10/4

12:55 pm-9:30 pm

1 stop8h 35m

$316

ChicagoValparaiso

ORD - VPS

ORDVPS

Chicago O'Hare Intl

Tue 8/19

10:10 pm-10:38 am

1 stop12h 28m

Valparaiso Destin-Ft Walton Beach

Tue 8/26

7:00 am-5:10 pm

1 stop10h 10m

$366

ChicagoValparaiso

ORD - VPS

ORDVPS

Chicago O'Hare Intl

Sun 9/14

6:10 am-7:56 pm

1 stop13h 46m

$89

ChicagoValparaiso

ORD - VPS

ORDVPS

Chicago O'Hare Intl

Sat 9/20

2:55 pm-6:45 pm

1 stop3h 50m

$118

ChicagoValparaiso

ORD - VPS

ORDVPS

Chicago O'Hare Intl

Fri 10/3

6:15 pm-9:55 am

1 stop15h 40m

$127

ChicagoValparaiso

ORD - VPS

ORDVPS

Chicago O'Hare Intl

Sat 8/30

1:42 pm-3:57 pm

Nonstop2h 15m

$169

Flights are sorted by cheapest round-trip flights first.

Deals found on 7/28

Best time to book a flight from O'Hare Intl to Valparaiso

Have a flexible travel schedule? Discover the best time to fly to Valparaiso from O'Hare Intl 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 O'Hare Intl Airport to Valparaiso

How far ahead should I book a flight from Chicago O'Hare Intl Airport to Valparaiso, Florida?

Use this chart to determine the optimal time to book a round-trip flight from O'Hare Intl to Valparaiso. Price data was last updated on July 25, 2025.

The price you pay for your flight from Chicago O'Hare Intl Airport to Valparaiso, Florida may vary depending on when you book. For the best chance of a lower fare, look to book 36 days in advance of your trip. Fares are likely to increase a fortnight or so before your departure date.

What is the cheapest month to book a flight from Chicago O'Hare Intl Airport to Valparaiso, Florida?

Currently, July is the cheapest month in which you can book a flight from Chicago O'Hare Intl Airport to Valparaiso, Florida (average of $294). Flying from Chicago O'Hare Intl Airport to Valparaiso, Florida in April is currently the most expensive (average of $386). 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 ORD to VPS?

Find hourly flight availability from O'Hare Intl to Valparaiso. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated July 30, 2025.

When flying from Chicago O'Hare Intl Airport to Valparaiso, Florida, the time of day you fly usually plays a role in the price. Save by searching for a flight in the afternoon, which can drop the price by up to 21% versus a flight in the morning.

Reviews of airlines servicing Valparaiso

Get insights into the airlines that provide service to Valparaiso. 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 Valparaiso. Reviews last updated July 30, 2025.
Read through reviews of airlines operating flights from Chicago O'Hare Intl Airport to Valparaiso, 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

Boarding

8.1

Comfort

8.0

Food

7.0

Entertainment

7.5

Overall

8.0

Crew

8.6

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

Boarding

8.1

Comfort

8.0

Food

7.0

Entertainment

7.5

Overall

8.0

Crew

8.6

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
7,980 reviews
Southwest
8.0
Very good
4,241 reviews

Boarding

8.1

Comfort

8.0

Food

7.0

Entertainment

7.5

Overall

8.0

Crew

8.6

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
4,241 reviews

Boarding

8.1

Comfort

8.0

Food

7.0

Entertainment

7.5

Overall

8.0

Crew

8.6

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
334 reviews
Southwest
8.0
Very good
4,241 reviews

Boarding

8.1

Comfort

8.0

Food

7.0

Entertainment

7.5

Overall

8.0

Crew

8.6

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 O'Hare Intl to Valparaiso. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.

  • What airport do you fly into for flights to Valparaiso from Chicago O'Hare Intl?

    Most people fly into Valparaiso Destin-Ft Walton Beach (VPS) if they book a flight to Valparaiso from Chicago O'Hare Intl. On average, Destin-Ft Walton Beach has 0 inbound flights from Chicago O'Hare Intl per day from 3 airlines. Valparaiso Destin-Ft Walton Beach is conveniently located just 3.1 mi from Valparaiso’s city center.

  • What are the cheapest airlines flying from Chicago O'Hare Intl Airport to Valparaiso, Florida round-trip?

    Cheapflights users have booked flights from Chicago O'Hare Intl Airport to Valparaiso, Florida round-trip from $235. Other airlines that can offer you cheap pricing are Sun Country Air, from $248, and Delta, from $316. Southwest is priced at 42% lower than the current average price of a flight leaving 3 months from now.

  • What are the cheapest airlines to fly from Chicago O'Hare Intl Airport to Valparaiso, Florida one-way?

    To fly one-way, consider booking your trip with Southwest, which is currently one of the cheapest options available, starting at $118. Sun Country Air flights start at $127 while deals on American Airlines start at $169 one-way.

  • What are the cheapest flights from Chicago O'Hare Intl Airport to Valparaiso, Florida?

    While on average a flight from Chicago O'Hare Intl Airport to Valparaiso, Florida is generally $476, our data shows the cheapest flight currently is $198. When looking at the most popular route, (Chicago O'Hare Intl - Valparaiso Destin-Ft Walton Beach), you can expect to pay $241 for that flight.

  • Can I find deals for flights from O'Hare Intl to Valparaiso that include hotel bookings?

    Yes. In addition to deals on O'Hare Intl to Valparaiso flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from O'Hare Intl to Valparaiso?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from O'Hare Intl to Valparaiso.

  • Can I find deals for business class flights from O'Hare Intl to Valparaiso?

    Yes. Cheapflights offers flight deals from O'Hare Intl to Valparaiso 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 O'Hare Intl Airport to Valparaiso, Florida?

    Currently, July is the cheapest month in which you can book a flight from Chicago O'Hare Intl Airport to Valparaiso, Florida (average of $294). Flying from Chicago O'Hare Intl Airport to Valparaiso, Florida in April is currently the most expensive (average of $386). 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 Valparaiso?

Book flights to Valparaiso if you plan to visit one of these locations
Crestview
Andalusia
Niceville

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Top 3 airlines flying from O'Hare Intl to Valparaiso

Discover the top 3 airlines that operate flights from O'Hare Intl to Valparaiso. 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 July 30, 2025.
AirlineCheapestAverageFlexibilityOn-time
American AirlinesCheapest$235Average$413FlexibilityNo cancel feeOn-time71%
DeltaCheapest$236Average$437FlexibilityNo cancel feeOn-timeN/A
SouthwestCheapest$366Average$380FlexibilityNo cancel feeOn-time63%

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