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Valparaiso

$938+ Cheap flights from Oakland, CA to Valparaiso, FL (OAK - VPS)

This is the cheapest round-trip flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 10/3. Fares are subject to change and may not be available on all flights or dates of travel.
OAK — VPS
Feb 28 — Mar 71
Sat 2/28
Sat 3/7
1 adult, Economy
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Cheap flight deals from Oakland to Valparaiso

Cheapest flights from Oakland to Valparaiso
Explore the most affordable flight options available from Oakland to Valparaiso. Find the lowest fares from popular airlines and budget airlines, with prices last updated on January 29, 2026.

This Delta deal was found by Cheapflights users on 1/28. 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 10/35:05 pm
OAK
-
VPS
2 stops13h 28m
Delta
Sun 10/42:40 pm
VPS
-
OAK
2 stops11h 09m
Delta
Deal found 1/28$938
This Southwest deal was found by Cheapflights users on 1/27. 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 1/315:30 am
OAK
-
VPS
2 stops9h 50m
Southwest
Mon 2/22:00 pm
VPS
-
OAK
2 stops9h 25m
Southwest
Deal found 1/27$1,086
This Southwest deal was found by Cheapflights users on 1/26. 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 1/266:55 pm
OAK
-
VPS
2 stops14h 45m
Southwest
Fri 1/302:00 pm
VPS
-
OAK
2 stops9h 45m
Southwest
Deal found 1/26$1,092

Find flight deals from Oakland to Valparaiso

Discover tips and strategies to find the most affordable flight options for your journey from Oakland (OAK) 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 January 29, 2026.

Most accurate provider

Expedia
1 star

Most trusted provider

Expedia
3 stars

Popular in

November

Cheapest in

September

Average price

$541
Provider with most accurate pricing for Oakland-Valparaiso Destin-Ft Walton Beach flight deals.
Search Deals
Provider most trusted by Cheapflights users for Oakland-Valparaiso Destin-Ft Walton Beach flights.
Search Deals
Highest demand for flights based on searches. 30% potential increase in price ($257 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 11% potential price decrease ($59 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in January 2026
Search Deals
  • Most accurate provider: When it comes to deals on Oakland, California-Valparaiso, Florida flights, users find the pricing of Expedia to be most consistent on Cheapflights vs. Expedia Users can find the same prices on Oakland, California-Valparaiso, Florida flight deals on Cheapflights vs. Expedia <90% of the time. Price accuracy is based on data collected from Oakland, California-Valparaiso, Florida flight searches over the past month and is updated monthly.
  • Most trusted provider: When it comes to deals on Oakland, California-Valparaiso, Florida flights, Cheapflights users trust Expedia the most. Expedia 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 Oakland, California-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 Oakland to Valparaiso

Have a flexible travel schedule? Discover the best time to fly to Valparaiso from Oakland 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 Oakland to Valparaiso

What is the cheapest month to book a flight from Oakland, California to Valparaiso, Florida?

Currently, January is the cheapest month in which you can book a flight from Oakland, California to Valparaiso, Florida (average of $102). Flying from Oakland, California to Valparaiso, Florida in December is currently the most expensive (average of $430). 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.

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 January 29, 2026.
Read reviews from past customers who have flown Southwest from Oakland to Valparaiso. Users can see the overall rating for each airline as well as how each is rated in terms of entertainment options, comfort, food, crew/service, and boarding process.
Southwest
8.0
Very good
4,267 reviews

Overall

8.0

Entertainment

7.5

Food

7.0

Crew

8.6

Boarding

8.1

Comfort

8.0

Reviews

1 / 20
10.0
Excellent

William Drew,Nov 2025

SJC - HNL

Flight crew was amazing! Usually they're very good on Southwest, but this crew went above and beyond. I have never ever seen so many rounds of drink service on a flight before.
Southwest
8.0
Very good
4,267 reviews
Southwest
8.0
Very good
4,267 reviews

Overall

8.0

Entertainment

7.5

Food

7.0

Crew

8.6

Boarding

8.1

Comfort

8.0

Reviews

1 / 20
10.0
Excellent

William Drew,Nov 2025

SJC - HNL

Flight crew was amazing! Usually they're very good on Southwest, but this crew went above and beyond. I have never ever seen so many rounds of drink service on a flight before.

Related info for your journey

Find useful and relevant information for your journey from Oakland to Valparaiso. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.

  • What is the cheapest airline to fly from Oakland, California to Valparaiso, Florida round-trip?

    According to our current data, Southwest ($419), offers the cheapest pricing from Oakland, California to Valparaiso, Florida.

  • Can I find deals for flights from Oakland to Valparaiso that include hotel bookings?

    Yes. In addition to deals on Oakland to Valparaiso flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from Oakland to Valparaiso?

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

  • Can I find deals for business class flights from Oakland to Valparaiso?

    Yes. Cheapflights offers flight deals from Oakland 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 Oakland, California to Valparaiso, Florida?

    Currently, January is the cheapest month in which you can book a flight from Oakland, California to Valparaiso, Florida (average of $102). Flying from Oakland, California to Valparaiso, Florida in December is currently the most expensive (average of $430). 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 airline flying from Oakland to Valparaiso

Discover the top airline that operate flights from Oakland 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 January 29, 2026.
AirlineCheapestAverageFlexibilityOn-time
SouthwestCheapest$419Average$546FlexibilityNo cancel feeOn-time63%

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