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Valparaiso

$121+ 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 4/20. Fares are subject to change and may not be available on all flights or dates of travel.
ORD — VPS
Nov 29 — Dec 61
Sat 11/29
Sat 12/6
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 February or July, booked 36 days in advance, depart on a Tuesday or Monday and return on a Wednesday

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 October 30, 2025.

This Sun Country Air deal was found by Cheapflights users on 10/28. 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 Sun Country Air is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/1811:45 amORD - VPS
1 stop22h 44mSun Country Air
Mon 12/2211:26 amVPS - ORD
1 stop23h 00mSun Country Air
Deal found 10/28$244
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.
Sun 12/142:36 pmORD - VPS
2 stops28h 32mMultiple Airlines
Fri 12/1911:26 amVPS - ORD
1 stop7h 12mMultiple Airlines
Deal found 10/30$305
This Kiwi.com deal was found by Cheapflights users on 10/28. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/1811:45 amORD - VPS
1 stop5h 44mMultiple Airlines
Tue 12/308:35 amVPS - ORD
1 stop28h 22mMultiple Airlines
Deal found 10/28$323
This American Airlines deal was found by Cheapflights users on 10/28. 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 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
Tue 12/3011:39 amVPS - ORD
Nonstop2h 41mAmerican Airlines
Deal found 10/28$426
This American Airlines deal was found by Cheapflights users on 10/28. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/128:33 amORD - VPS
Nonstop2h 26mAmerican Airlines
Mon 12/156:28 amVPS - ORD
1 stop15h 50mAmerican Airlines
Deal found 10/28$434
This American Airlines deal was found by Cheapflights users on 10/28. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/187:11 amORD - VPS
1 stop5h 12mAmerican Airlines
Mon 12/2211:41 amVPS - ORD
Nonstop2h 41mAmerican Airlines
Deal found 10/28$436
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.
Sun 12/141:45 pmORD - VPS
1 stop7h 30mSouthwest
Fri 12/197:00 amVPS - ORD
1 stop5h 15mSouthwest
Deal found 10/30$441
This American Airlines deal was found by Cheapflights users on 10/28. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 11/168:29 amORD - VPS
Nonstop2h 28mAmerican Airlines
Wed 11/1911:27 amVPS - ORD
Nonstop2h 40mAmerican Airlines
Deal found 10/28$478
This Southwest deal was found by Cheapflights users on 10/28. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/186:05 amORD - VPS
2 stops15h 10mSouthwest
Tue 12/307:00 amVPS - ORD
2 stops8h 25mSouthwest
Deal found 10/28$485

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 October 30, 2025.

Most accurate provider

eDreams
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$244
(Sun Country Air)

One-way from

$121
(Booking.com)

Popular in

October

Cheapest in

February

Average price

$502

Good round-trip deal

$425 or less
Provider with most accurate pricing for Chicago O'Hare Intl-Valparaiso Destin-Ft Walton Beach flight deals.
Search Deals
Provider most trusted by Cheapflights users for Chicago O'Hare Intl-Valparaiso Destin-Ft Walton Beach flights.
Search Deals
From Chicago O'Hare Intl to Valparaiso Destin-Ft Walton Beach
Search Deals
One-way flight from Chicago O'Hare Intl to Valparaiso Destin-Ft Walton Beach
Search Deals
Highest demand for flights based on searches. 6% potential increase in price ($29 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 1% potential price decrease ($7 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in October 2025
Search Deals
Price to beat on a round-trip flight from Chicago O'Hare Intl to Valparaiso Destin-Ft Walton Beach.
Search Deals

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 October 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

Thu 12/18

11:45 am-10:29 am

1 stop22h 44m

Valparaiso Destin-Ft Walton Beach

Mon 12/22

11:26 am-10:26 am

1 stop23h 00m

$244

ChicagoValparaiso

ORD - VPS

ORDVPS

Chicago O'Hare Intl

Sun 12/14

2:36 pm-7:08 pm

2 stops28h 32m

Valparaiso Destin-Ft Walton Beach

Fri 12/19

11:26 am-6:38 pm

1 stop7h 12m

$305

ChicagoValparaiso

ORD - VPS

ORDVPS

Chicago O'Hare Intl

Thu 12/18

11:45 am-5:29 pm

1 stop5h 44m

Valparaiso Destin-Ft Walton Beach

Tue 12/30

8:35 am-12:57 pm

1 stop28h 22m

$323

ChicagoValparaiso

ORD - VPS

ORDVPS

Chicago O'Hare Intl

Thu 1/15

9:29 am-12:00 pm

Nonstop2h 31m

Valparaiso Destin-Ft Walton Beach

Mon 1/19

12:30 pm-3:10 pm

Nonstop2h 40m

$426

ChicagoValparaiso

ORD - VPS

ORDVPS

Chicago O'Hare Intl

Thu 12/18

9:00 am-11:38 am

Nonstop2h 38m

Valparaiso Destin-Ft Walton Beach

Tue 12/30

11:39 am-2:20 pm

Nonstop2h 41m

$426

ChicagoValparaiso

ORD - VPS

ORDVPS

Chicago O'Hare Intl

Fri 12/12

8:33 am-10:59 am

Nonstop2h 26m

Valparaiso Destin-Ft Walton Beach

Mon 12/15

11:29 am-2:12 pm

Nonstop2h 43m

$426

ChicagoValparaiso

ORD - VPS

ORDVPS

Chicago O'Hare Intl

Sun 12/14

8:33 am-10:59 am

Nonstop2h 26m

Valparaiso Destin-Ft Walton Beach

Fri 12/19

12:11 pm-2:52 pm

Nonstop2h 41m

$426

ChicagoValparaiso

ORD - VPS

ORDVPS

Chicago O'Hare Intl

Sat 1/17

10:19 am-9:26 pm

1 stop11h 07m

Valparaiso Destin-Ft Walton Beach

Fri 2/27

3:52 pm-10:26 pm

1 stop6h 34m

$437

ChicagoValparaiso

ORD - VPS

ORDVPS

Chicago O'Hare Intl

Sun 12/14

1:45 pm-9:15 pm

1 stop7h 30m

Valparaiso Destin-Ft Walton Beach

Fri 12/19

7:00 am-12:15 pm

1 stop5h 15m

$441

ChicagoValparaiso

ORD - VPS

ORDVPS

Chicago O'Hare Intl

Wed 1/28

6:00 pm-1:09 pm

2 stops19h 09m

$164

Flights are sorted by cheapest round-trip flights first.

Deals found on 10/28

Showing 1-10 of 16 results
1
2

Compare providers for flights from O'Hare Intl to Valparaiso

Provider information is updated monthly. Please note that these providers often have deals for this flight, but the availability may vary on a day-by-day basis on Cheapflights.
Use the table below to compare price accuracy, trust ratings, and cancellation policies for each provider offering flight deals from O'Hare Intl to Valparaiso in October.
ProviderPrice AccuracyTrust Score*
ExpediaPrice Accuracy2 starsTrust Score*3 stars
FlightHubPrice Accuracy3 starsTrust Score*1 star
eDreamsPrice Accuracy3 starsTrust Score*3 stars

*The Trust Score is based on feedback from users after their booking experience. It measures overall satisfaction, helping us identify issues like hidden fees, problems during the ticketing process, and the quality of customer service. This score is our best indicator of the provider's quality and reliability.

  • Most accurate provider: When it comes to deals on Chicago O'Hare Intl Airport-Valparaiso, Florida flights, users find the pricing of eDreams to be most consistent on Cheapflights vs. eDreams Users can find the same prices on Chicago O'Hare Intl Airport-Valparaiso, Florida flight deals on Cheapflights vs. eDreams >95% of the time. Price accuracy is based on data collected from Chicago O'Hare Intl Airport-Valparaiso, Florida flight searches over the past month and is updated monthly.
  • Most trusted provider: When it comes to deals on Chicago O'Hare Intl Airport-Valparaiso, Florida flights, Cheapflights users trust eDreams the most. eDreams has received a user feedback score of 3 out of 3 stars (3 being the best), meaning they have been trusted the most by Cheapflights users looking for Chicago O'Hare Intl Airport-Valparaiso, Florida flight deals. Provider user feedback score is based on Cheapflights searches over the past month and is updated monthly.

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 October 24, 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, April is the cheapest month in which you can book a flight from Chicago O'Hare Intl Airport to Valparaiso, Florida (average of $137). Flying from Chicago O'Hare Intl Airport to Valparaiso, Florida 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 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 October 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 evening, which can drop the price by up to 78% 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 October 30, 2025.
Read through reviews of airlines operating flights from Chicago O'Hare Intl Airport to Valparaiso, such as Delta and American Airlines. Reviews also offer insight into each airline's entertainment options, comfort, food, crew/service, and boarding process.
Delta
7.9
Good
7,998 reviews

Entertainment

7.9

Crew

8.5

Boarding

8.2

Overall

7.9

Food

7.3

Comfort

7.9

Reviews

1 / 20
2.0
Mediocre

Joseph,Aug 2023

MSP - MCO

Even if you have delta comfort plus, they will move your overhead bag. One of the perks for upgrading is that you have dedicated space for your carry on with comfort plus with delta. They moved my carry on luggage (3) compartments back and put in bags for other passengers that should have gone under their respective seats. When deboarding the plane, there was no help from anyone to retrieve my luggage back several rows. Delta is turning into pure garbage.
Delta
7.9
Good
7,998 reviews
Delta
7.9
Good
7,998 reviews

Entertainment

7.9

Crew

8.5

Boarding

8.2

Overall

7.9

Food

7.3

Comfort

7.9

Reviews

1 / 20
2.0
Mediocre

Joseph,Aug 2023

MSP - MCO

Even if you have delta comfort plus, they will move your overhead bag. One of the perks for upgrading is that you have dedicated space for your carry on with comfort plus with delta. They moved my carry on luggage (3) compartments back and put in bags for other passengers that should have gone under their respective seats. When deboarding the plane, there was no help from anyone to retrieve my luggage back several rows. Delta is turning into pure garbage.
American Airlines
7.2
Good
11,035 reviews
Delta
7.9
Good
7,998 reviews

Entertainment

7.9

Crew

8.5

Boarding

8.2

Overall

7.9

Food

7.3

Comfort

7.9

Reviews

1 / 20
2.0
Mediocre

Joseph,Aug 2023

MSP - MCO

Even if you have delta comfort plus, they will move your overhead bag. One of the perks for upgrading is that you have dedicated space for your carry on with comfort plus with delta. They moved my carry on luggage (3) compartments back and put in bags for other passengers that should have gone under their respective seats. When deboarding the plane, there was no help from anyone to retrieve my luggage back several rows. Delta is turning into pure garbage.

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 2 airlines. Valparaiso Destin-Ft Walton Beach is conveniently located just 3.1 mi from Valparaiso’s city center.

  • How long is the flight from Chicago O'Hare Intl Airport to Valparaiso, Florida?

    Airlines like Sun Country Air and American Airlines fly from Chicago O'Hare Intl Airport to Valparaiso, Florida in about 2h 31m. The time it takes to get you to your destination can typically vary by up to 20h 13m. There are 797 mi between Chicago O'Hare Intl Airport and Valparaiso, Florida. When browsing for deals, the options you’ll see will be for both nonstop flights and flights with stops.

  • 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 $207. Another airline that can offer you cheap pricing is American Airlines. Delta is priced at 52% lower than the current average price of a flight leaving 3 months from now.

  • 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 $594, our data shows the cheapest flight currently is $425. When looking at the most popular route, (Chicago O'Hare Intl - Valparaiso Destin-Ft Walton Beach), you can expect to pay $244 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, April is the cheapest month in which you can book a flight from Chicago O'Hare Intl Airport to Valparaiso, Florida (average of $137). Flying from Chicago O'Hare Intl Airport to Valparaiso, Florida 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 Valparaiso?

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

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Top 2 airlines flying from O'Hare Intl to Valparaiso

Discover the top 2 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 October 30, 2025.
AirlineCheapestAverageFlexibilityOn-time
DeltaCheapest$207Average$495FlexibilityNo cancel feeOn-timeN/A
American AirlinesCheapest$238Average$420FlexibilityNo cancel feeOn-time71%

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