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Valparaiso

$54+ Cheap flights from Chicago (CHI) 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 5/11. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — VPS
Apr 2 — Apr 91
Wed 4/2
Wed 4/9
1 adult, Economy
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Cheapflights Tip: The best prices from Chicago to Valparaiso Destin-Ft Walton Beach are usually found in January or February, booked 85 days in advance, depart on a Monday or Friday and return on a Sunday

Cheap flight deals from Chicago to Valparaiso

Discover tips and strategies to find the most affordable flight options for your journey from Chicago (CHI) 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 March 28, 2025.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$164
(Cheapflightsfares)

One-way from

$54
(Cheapflightsfares)

Popular in

March

Cheapest in

January

Average price

$532

Good round-trip deal

$122 or less

Good one-way deal

$64 or less
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 Valparaiso Destin-Ft Walton Beach
Search Deals
One-way flight from Chicago (CHI) to Valparaiso Destin-Ft Walton Beach
Search Deals
Highest demand for flights based on searches. 18% potential increase in price ($70 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 7% potential price decrease ($21 potential savings vs. average RT price).
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Average for round-trip flights in March 2025
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Price to beat on a round-trip flight from Chicago (CHI) to Valparaiso Destin-Ft Walton Beach.
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Price to beat on a one-way flight from Chicago (CHI) to Valparaiso Destin-Ft Walton Beach.
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Find flight deals from Chicago to Valparaiso

Cheapest flights from Chicago to Valparaiso
Explore the most affordable flight options available from Chicago to Valparaiso. Find the lowest fares from popular airlines and budget airlines, with prices last updated on March 28, 2025.

This Cheapflightsfares deal was found by Cheapflights users on 3/27. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 4/242:19 pmMDW - VPS
Nonstop2h 10mAllegiant Air
Thu 5/111:16 amVPS - MDW
Nonstop2h 13mAllegiant Air
Deal found 3/27$164
This American Airlines deal was found by Cheapflights users on 3/27. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/247:25 amORD - VPS
Nonstop2h 28mAmerican Airlines
Tue 5/2711:08 amVPS - ORD
Nonstop2h 29mAmerican Airlines
Deal found 3/27$225
This Delta deal was found by Cheapflights users on 3/26. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 4/157:05 amORD - VPS
1 stop6h 55mDelta
Wed 4/235:05 pmVPS - ORD
1 stop6h 54mDelta
Deal found 3/26$252
This Sun Country Air deal was found by Cheapflights users on 3/27. 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 Sun Country Air is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 4/247:15 pmORD - VPS
1 stop22h 00mSun Country Air
Thu 5/16:10 pmVPS - ORD
1 stop24h 59mSun Country Air
Deal found 3/27$254
This Delta deal was found by Cheapflights users on 3/25. 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 5/1012:53 pmMDW - VPS
1 stop5h 40mDelta
Tue 5/136:00 amVPS - MDW
1 stop5h 53mDelta
Deal found 3/25$294
This Mytrip deal was found by Cheapflights users on 3/27. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 5/48:05 pmORD - VPS
1 stop15h 01mMultiple Airlines
Thu 5/86:35 amVPS - ORD
2 stops17h 30mMultiple Airlines
Deal found 3/27$306
This Southwest deal was found by Cheapflights users on 3/25. 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 5/106:40 amMDW - VPS
2 stops9h 15mSouthwest
Tue 5/136:25 pmVPS - MDW
1 stop4h 45mSouthwest
Deal found 3/25$335
This Southwest deal was found by Cheapflights users on 3/26. 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.
Wed 6/111:50 pmORD - VPS
2 stops7h 30mSouthwest
Sun 6/157:00 amVPS - ORD
1 stop5h 45mSouthwest
Deal found 3/26$384

Cheapflights Fare Finder

Customize your flight search to find flights from Chicago 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 March 28, 2025.
Use the filters below to find and compare flights from Chicago to Valparaiso that are best for you.

Fly from

Chicago

Fly to

Valparaiso

Route

Depart

Return

Price

ChicagoValparaiso

MDW - VPS

MDWVPS

Chicago Midway

Thu 4/24

2:19 pm-4:29 pm

Nonstop2h 10m

Valparaiso Destin-Ft Walton Beach

Thu 5/1

11:16 am-1:29 pm

Nonstop2h 13m

$164

ChicagoValparaiso

ORD - VPS

ORDVPS

Chicago O'Hare Intl

Sat 5/24

7:25 am-9:53 am

Nonstop2h 28m

Valparaiso Destin-Ft Walton Beach

Tue 5/27

11:08 am-1:37 pm

Nonstop2h 29m

$225

ChicagoValparaiso

ORD - VPS

ORDVPS

Chicago O'Hare Intl

Tue 4/15

7:05 am-2:00 pm

1 stop6h 55m

Valparaiso Destin-Ft Walton Beach

Wed 4/23

5:05 pm-11:59 pm

1 stop6h 54m

$252

ChicagoValparaiso

ORD - VPS

ORDVPS

Chicago O'Hare Intl

Thu 4/24

7:15 pm-5:15 pm

1 stop22h 00m

Valparaiso Destin-Ft Walton Beach

Thu 5/1

6:10 pm-7:09 pm

1 stop24h 59m

$254

ChicagoValparaiso

MDW - VPS

MDWVPS

Chicago Midway

Sat 5/10

12:53 pm-6:33 pm

1 stop5h 40m

Valparaiso Destin-Ft Walton Beach

Tue 5/13

6:00 am-11:53 am

1 stop5h 53m

$294

ChicagoValparaiso

ORD - VPS

ORDVPS

Chicago O'Hare Intl

Sun 5/4

8:05 pm-11:06 am

1 stop15h 01m

Valparaiso Destin-Ft Walton Beach

Thu 5/8

6:35 am-12:05 am

2 stops17h 30m

$306

ChicagoValparaiso

MDW - VPS

MDWVPS

Chicago Midway

Sat 5/10

6:40 am-3:55 pm

2 stops9h 15m

Valparaiso Destin-Ft Walton Beach

Tue 5/13

6:25 pm-11:10 pm

1 stop4h 45m

$335

ChicagoValparaiso

ORD - VPS

ORDVPS

Chicago O'Hare Intl

Wed 6/11

1:50 pm-9:20 pm

2 stops7h 30m

Valparaiso Destin-Ft Walton Beach

Sun 6/15

7:00 am-12:45 pm

1 stop5h 45m

$384

ChicagoValparaiso

MDW - VPS

MDWVPS

Chicago Midway

Sun 5/11

2:19 pm-4:29 pm

Nonstop2h 10m

$54

ChicagoValparaiso

ORD - VPS

ORDVPS

Chicago O'Hare Intl

Tue 7/22

4:00 pm-9:20 pm

1 stop5h 20m

$90

Flights are sorted by cheapest round-trip flights first.

Deals found on 3/27

Showing 1-10 of 16 results
1
2

Compare providers for flights from Chicago 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 Chicago to Valparaiso in March.
ProviderPrice AccuracyTrust Score*
ExpediaPrice Accuracy1 starTrust Score*3 stars
FlightHubPrice Accuracy3 starsTrust Score*3 stars
eDreamsPrice Accuracy3 starsTrust Score*3 stars
CheapflightsfaresPrice Accuracy3 starsTrust Score*2 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-Valparaiso, Florida flights, users find the pricing of FlightHub to be most consistent on Cheapflights vs. FlightHub Users can find the same prices on Chicago-Valparaiso, Florida flight deals on Cheapflights vs. FlightHub >95% of the time. Price accuracy is based on data collected from Chicago-Valparaiso, Florida flight searches over the past month and is updated monthly.
  • Most trusted provider: When it comes to deals on Chicago-Valparaiso, Florida flights, Cheapflights users trust FlightHub the most. FlightHub 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-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 Chicago to Valparaiso

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

How far ahead should I book a flight from Chicago to Valparaiso, Florida?

Use this chart to determine the optimal time to book a round-trip flight from Chicago to Valparaiso. Price data was last updated on March 21, 2025.

Booking 85 days in advance of your planned departure date is, on average, the best time to get cheap flights from Chicago to Valparaiso, Florida. The general trend is that the closer you book to the departure date, the more expensive your flight will be.

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

Currently, January is the cheapest month in which you can book a flight from Chicago to Valparaiso, Florida (average of $299). Flying from Chicago to Valparaiso, Florida in March is currently the most expensive (average of $388). 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 VPS?

Find hourly flight availability from Chicago 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 March 28, 2025.

A simple way to save on the total cost of your ticket is to fly from Chicago to Valparaiso, Florida in the afternoon. If you’re flexible enough to do this you can expect to save up to 60% on your trip compared to booking a flight in the morning.

Rainfall in Valparaiso by month

Plan your trip to Valparaiso by taking into account the average rainfall totals by month.

In terms of precipitation, rainfall in Valparaiso, Florida 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 Valparaiso, Florida when rainfall is around 3.1 in.

Temperature in Valparaiso by month

Plan your trip to Valparaiso by taking into account the average temperature totals by month.

If weather is an important factor for your trip to Valparaiso, Florida, 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 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 March 28, 2025.
Get a feel of what it's like to fly with Southwest, Delta and Allegiant Air from Chicago to Valparaiso by reading reviews from past customers. Users have also rated airlines in terms of entertainment options, comfort, food, crew/service, and boarding process.
Southwest
8.1
Very good
4,273 reviews

Crew

8.6

Boarding

8.2

Overall

8.1

Food

7.1

Comfort

8.1

Entertainment

7.6

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
8.1
Very good
4,273 reviews
Southwest
8.1
Very good
4,273 reviews

Crew

8.6

Boarding

8.2

Overall

8.1

Food

7.1

Comfort

8.1

Entertainment

7.6

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
7,896 reviews
Southwest
8.1
Very good
4,273 reviews

Crew

8.6

Boarding

8.2

Overall

8.1

Food

7.1

Comfort

8.1

Entertainment

7.6

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.
Allegiant Air
7.3
Good
731 reviews
Southwest
8.1
Very good
4,273 reviews

Crew

8.6

Boarding

8.2

Overall

8.1

Food

7.1

Comfort

8.1

Entertainment

7.6

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
8.1
Very good
4,273 reviews

Crew

8.6

Boarding

8.2

Overall

8.1

Food

7.1

Comfort

8.1

Entertainment

7.6

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
348 reviews
Southwest
8.1
Very good
4,273 reviews

Crew

8.6

Boarding

8.2

Overall

8.1

Food

7.1

Comfort

8.1

Entertainment

7.6

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 Chicago 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?

    Most people fly into Valparaiso Destin-Ft Walton Beach (VPS) if they book a flight to Valparaiso from Chicago. On average, Destin-Ft Walton Beach has 0 inbound flights from Chicago 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 to Valparaiso, Florida round-trip?

    Currently priced at $164, Allegiant Air will fly you from Chicago to Valparaiso, Florida and back. In addition to Allegiant Air, many other airlines offer competitively priced options for your trip. Search Cheapflights for deals from American Airlines and Delta - these airlines can fly you to your destination from $225 and $252, respectively. Allegiant Air is 46% cheaper than the average price of flights available within the next 90 days to this destination.

  • What are the cheapest airlines to fly from Chicago to Valparaiso, Florida one-way?

    To fly one-way, consider booking your trip with Allegiant Air, which is currently one of the cheapest options available, starting at $54. Southwest flights start at $90 while deals on Sun Country Air start at $120 one-way.

  • What are the cheapest flights from Chicago to Valparaiso, Florida?

    The cheapest flight price from Chicago to Valparaiso, Florida is $198. On average you can expect to pay $332. The most popular route, (Chicago O'Hare Intl - Valparaiso Destin-Ft Walton Beach), can usually be booked for $252.

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

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

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

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

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

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

    Currently, January is the cheapest month in which you can book a flight from Chicago to Valparaiso, Florida (average of $299). Flying from Chicago to Valparaiso, Florida in March is currently the most expensive (average of $388). 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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Alternative routes for Chicago to Valparaiso

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Top 3 airlines flying from Chicago to Valparaiso

Discover the top 3 airlines that operate flights from Chicago 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 March 28, 2025.
AirlineCheapestAverageFlexibilityOn-time
Allegiant AirCheapest$114Average$176FlexibilityNo cancel feeOn-time88%
DeltaCheapest$199Average$336FlexibilityNo cancel feeOn-timeN/A
American AirlinesCheapest$233Average$406FlexibilityNo cancel feeOn-time71%
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