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Valparaiso

$55+ 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 12/1. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — VPS
Aug 6 — Aug 131
Wed 8/6
Wed 8/13
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 Wednesday or Monday and return on a Wednesday

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 August 1, 2025.

Round-trip from

$167
(Mytrip)

One-way from

$55
(Cheapflightsfares)

Popular in

March

Cheapest in

January

Average price

$311

Good round-trip deal

$86 or less

Good one-way deal

$64 or less
From Chicago (CHI) to Valparaiso Destin-Ft Walton Beach
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One-way flight from Chicago (CHI) to Valparaiso Destin-Ft Walton Beach
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Highest demand for flights based on searches. 21% potential increase in price ($86 potential increase over avg. RT price).
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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 August 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 August 1, 2025.

This Mytrip deal was found by Cheapflights users on 7/31. 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.
Fri 9/267:50 pmMDW - VPS
1 stop14h 17mAllegiant Air
Thu 10/28:00 amVPS - MDW
Nonstop2h 17mAllegiant Air
Deal found 7/31$167
This Delta deal was found by Cheapflights users on 7/31. 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 8/306:10 amORD - VPS
1 stop5h 50mDelta
Sat 9/66:00 amVPS - ORD
1 stop4h 04mDelta
Deal found 7/31$225
This Delta deal was found by Cheapflights users on 7/31. 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 8/304:25 pmMDW - VPS
1 stop5h 29mDelta
Sat 9/611:40 amVPS - MDW
1 stop3h 48mDelta
Deal found 7/31$225
This Southwest 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/232:55 pmORD - VPS
1 stop3h 50mSouthwest
Wed 8/277:00 amVPS - ORD
1 stop5h 45mSouthwest
Deal found 7/30$235
This Southwest deal was found by Cheapflights users on 7/31. 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 8/215:10 amMDW - VPS
1 stop6h 05mSouthwest
Tue 8/262:00 pmVPS - MDW
1 stop5h 45mSouthwest
Deal found 7/31$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 7/31. 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.
Fri 9/266:30 amORD - VPS
2 stops16h 22mMultiple Airlines
Thu 10/25:02 pmVPS - ORD
2 stops23h 16mMultiple Airlines
Deal found 7/31$264
This American Airlines deal was found by Cheapflights users on 7/31. 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 8/211:20 pmORD - VPS
1 stop8h 08mAmerican Airlines
Tue 8/2612:01 pmVPS - ORD
1 stop6h 28mAmerican Airlines
Deal found 7/31$281

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 August 1, 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

Fri 9/26

7:50 pm-10:07 am

1 stop14h 17m

Valparaiso Destin-Ft Walton Beach

Thu 10/2

8:00 am-10:17 am

Nonstop2h 17m

$167

ChicagoValparaiso

ORD - VPS

ORDVPS

Chicago O'Hare Intl

Sat 8/30

6:10 am-12:00 pm

1 stop5h 50m

Valparaiso Destin-Ft Walton Beach

Sat 9/6

6:00 am-10:04 am

1 stop4h 04m

$225

ChicagoValparaiso

MDW - VPS

MDWVPS

Chicago Midway

Sat 8/30

4:25 pm-9:54 pm

1 stop5h 29m

Valparaiso Destin-Ft Walton Beach

Sat 9/6

11:40 am-3:28 pm

1 stop3h 48m

$225

ChicagoValparaiso

ORD - VPS

ORDVPS

Chicago O'Hare Intl

Sat 8/23

2:55 pm-6:45 pm

1 stop3h 50m

Valparaiso Destin-Ft Walton Beach

Wed 8/27

7:00 am-12:45 pm

1 stop5h 45m

$235

ChicagoValparaiso

MDW - VPS

MDWVPS

Chicago Midway

Thu 8/21

5:10 am-11:15 am

1 stop6h 05m

Valparaiso Destin-Ft Walton Beach

Tue 8/26

2:00 pm-7:45 pm

1 stop5h 45m

$235

ChicagoValparaiso

ORD - VPS

ORDVPS

Chicago O'Hare Intl

Wed 11/26

10:54 am-5:26 pm

1 stop6h 32m

Valparaiso Destin-Ft Walton Beach

Fri 11/28

10:11 am-9:02 am

1 stop22h 51m

$248

ChicagoValparaiso

ORD - VPS

ORDVPS

Chicago O'Hare Intl

Fri 9/26

6:30 am-10:52 pm

2 stops16h 22m

Valparaiso Destin-Ft Walton Beach

Thu 10/2

5:02 pm-4:18 pm

2 stops23h 16m

$264

ChicagoValparaiso

ORD - VPS

ORDVPS

Chicago O'Hare Intl

Thu 8/21

1:20 pm-9:28 pm

1 stop8h 08m

Valparaiso Destin-Ft Walton Beach

Tue 8/26

12:01 pm-6:29 pm

1 stop6h 28m

$281

ChicagoValparaiso

MDW - VPS

MDWVPS

Chicago Midway

Mon 12/1

9:24 am-11:37 am

Nonstop2h 13m

$55

ChicagoValparaiso

ORD - VPS

ORDVPS

Chicago O'Hare Intl

Sun 9/14

6:10 am-7:56 pm

1 stop13h 46m

$92

Flights are sorted by cheapest round-trip flights first.

Deals found on 7/30

Showing 1-10 of 16 results
1
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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 July 25, 2025.

Booking 61 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, July is the cheapest month in which you can book a flight from Chicago to Valparaiso, Florida (average of $294). Flying from Chicago 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 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 August 1, 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 67% on your trip compared to booking a flight in the morning.

How much does it cost to fly round-trip from Chicago to Valparaiso, Florida?

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 August 1, 2025.
Get a feel of what it's like to fly with Southwest, Delta, and American Airlines 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
8.0
Very good
4,246 reviews

Boarding

8.1

Crew

8.6

Entertainment

7.5

Food

7.0

Comfort

8.0

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
4,246 reviews
Southwest
8.0
Very good
4,246 reviews

Boarding

8.1

Crew

8.6

Entertainment

7.5

Food

7.0

Comfort

8.0

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
7,981 reviews
Southwest
8.0
Very good
4,246 reviews

Boarding

8.1

Crew

8.6

Entertainment

7.5

Food

7.0

Comfort

8.0

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
4,246 reviews

Boarding

8.1

Crew

8.6

Entertainment

7.5

Food

7.0

Comfort

8.0

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
7.2
Good
702 reviews
Southwest
8.0
Very good
4,246 reviews

Boarding

8.1

Crew

8.6

Entertainment

7.5

Food

7.0

Comfort

8.0

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
334 reviews
Southwest
8.0
Very good
4,246 reviews

Boarding

8.1

Crew

8.6

Entertainment

7.5

Food

7.0

Comfort

8.0

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 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 4 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 $167, 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 Delta and Southwest - these airlines can fly you to your destination from $225 and $235, respectively. Allegiant Air is 45% 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 $55. American Airlines flights start at $109 while deals on Delta start at $114 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 $476. The most popular route, (Chicago O'Hare Intl - Valparaiso Destin-Ft Walton Beach), can usually be booked for $235.

  • 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, July is the cheapest month in which you can book a flight from Chicago to Valparaiso, Florida (average of $294). Flying from Chicago 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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Alternative routes for Chicago to Valparaiso

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Top 4 airlines flying from Chicago to Valparaiso

Discover the top 4 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 August 1, 2025.
AirlineCheapestAverageFlexibilityOn-time
Allegiant AirCheapest$85Average$162FlexibilityNo cancel feeOn-time88%
SouthwestCheapest$212Average$384FlexibilityNo cancel feeOn-time63%
American AirlinesCheapest$235Average$413FlexibilityNo cancel feeOn-time71%
DeltaCheapest$236Average$437FlexibilityNo cancel feeOn-timeN/A

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