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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 7/11. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — VPS
Jun 17 — Jun 241
Tue 6/17
Tue 6/24
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 Friday or Monday and return on a Thursday

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 June 12, 2025.

Round-trip from

$129
(Lucky2Go)

One-way from

$54
(Booking.com)

Popular in

March

Cheapest in

January

Average price

$235

Good round-trip deal

$86 or less

Good one-way deal

$54 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. 22% potential increase in price ($86 potential increase over avg. RT price).
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Cheapest flight prices on average. 7% potential price decrease ($22 potential savings vs. average RT price).
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Average for round-trip flights in June 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 June 12, 2025.

This Lucky2Go deal was found by Cheapflights users on 6/10. 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 Lucky2Go is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 8/19:12 amMDW - VPS
Nonstop2h 11mAllegiant Air
Mon 8/46:00 amVPS - MDW
Nonstop2h 22mAllegiant Air
Deal found 6/10$129
This American Airlines deal was found by Cheapflights users on 6/10. 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 7/87:43 amORD - VPS
Nonstop2h 24mAmerican Airlines
Wed 7/1610:53 amVPS - ORD
Nonstop2h 39mAmerican Airlines
Deal found 6/10$168
This Southwest deal was found by Cheapflights users on 6/10. 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.
Tue 7/84:00 pmORD - VPS
1 stop5h 20mSouthwest
Wed 7/167:00 amVPS - ORD
1 stop5h 45mSouthwest
Deal found 6/10$187
This Delta deal was found by Cheapflights users on 6/10. 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 7/85:35 amORD - VPS
1 stop4h 40mDelta
Wed 7/164:59 pmVPS - ORD
1 stop4h 31mDelta
Deal found 6/10$207
This Southwest deal was found by Cheapflights users on 6/9. 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.
Fri 7/48:35 amMDW - VPS
2 stops11h 30mSouthwest
Fri 7/118:00 pmVPS - MDW
1 stop5h 05mSouthwest
Deal found 6/9$235
This Mytrip deal was found by Cheapflights users on 6/11. 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 8/311:11 amORD - VPS
2 stops36h 09mMultiple Airlines
Fri 8/89:08 pmVPS - ORD
1 stop17h 05mMultiple Airlines
Deal found 6/11$243
This Sun Country Air deal was found by Cheapflights users on 6/10. 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 7/176:00 amORD - VPS
1 stop11h 08mSun Country Air
Sun 7/206:14 pmVPS - ORD
1 stop23h 13mSun Country Air
Deal found 6/10$284
This Delta deal was found by Cheapflights users on 6/10. 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.
Wed 7/306:00 amMDW - VPS
1 stop6h 50mDelta
Mon 8/44:59 pmVPS - MDW
1 stop4h 43mDelta
Deal found 6/10$316

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 June 12, 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 8/1

9:12 am-11:23 am

Nonstop2h 11m

Valparaiso Destin-Ft Walton Beach

Mon 8/4

6:00 am-8:22 am

Nonstop2h 22m

$129

ChicagoValparaiso

ORD - VPS

ORDVPS

Chicago O'Hare Intl

Tue 7/8

7:43 am-10:07 am

Nonstop2h 24m

Valparaiso Destin-Ft Walton Beach

Wed 7/16

10:53 am-1:32 pm

Nonstop2h 39m

$168

ChicagoValparaiso

ORD - VPS

ORDVPS

Chicago O'Hare Intl

Tue 7/8

4:00 pm-9:20 pm

1 stop5h 20m

Valparaiso Destin-Ft Walton Beach

Wed 7/16

7:00 am-12:45 pm

1 stop5h 45m

$187

ChicagoValparaiso

ORD - VPS

ORDVPS

Chicago O'Hare Intl

Tue 7/8

5:35 am-10:15 am

1 stop4h 40m

Valparaiso Destin-Ft Walton Beach

Wed 7/16

4:59 pm-9:30 pm

1 stop4h 31m

$207

ChicagoValparaiso

MDW - VPS

MDWVPS

Chicago Midway

Fri 7/4

8:35 am-8:05 pm

2 stops11h 30m

Valparaiso Destin-Ft Walton Beach

Fri 7/11

8:00 pm-1:05 am

1 stop5h 05m

$235

ChicagoValparaiso

ORD - VPS

ORDVPS

Chicago O'Hare Intl

Sun 8/3

11:11 am-11:20 pm

2 stops36h 09m

Valparaiso Destin-Ft Walton Beach

Fri 8/8

9:08 pm-2:13 pm

1 stop17h 05m

$243

ChicagoValparaiso

ORD - VPS

ORDVPS

Chicago O'Hare Intl

Thu 7/17

6:00 am-5:08 pm

1 stop11h 08m

Valparaiso Destin-Ft Walton Beach

Sun 7/20

6:14 pm-5:27 pm

1 stop23h 13m

$284

ChicagoValparaiso

MDW - VPS

MDWVPS

Chicago Midway

Wed 7/30

6:00 am-12:50 pm

1 stop6h 50m

Valparaiso Destin-Ft Walton Beach

Mon 8/4

4:59 pm-9:42 pm

1 stop4h 43m

$316

ChicagoValparaiso

MDW - VPS

MDWVPS

Chicago Midway

Fri 7/11

9:12 am-11:23 am

Nonstop2h 11m

$54

ChicagoValparaiso

ORD - VPS

ORDVPS

Chicago O'Hare Intl

Mon 7/14

1:30 pm-7:10 pm

1 stop5h 40m

$74

Flights are sorted by cheapest round-trip flights first.

Deals found on 6/11

Showing 1-10 of 18 results
1
2

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 June 9, 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, 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 $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 June 12, 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 62% 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 June 12, 2025.
Get a feel of what it's like to fly with Southwest, Delta and Qatar Airways 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
4,287 reviews

Food

7.1

Entertainment

7.6

Boarding

8.2

Overall

8.0

Comfort

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
4,287 reviews
Southwest
8.0
Very good
4,287 reviews

Food

7.1

Entertainment

7.6

Boarding

8.2

Overall

8.0

Comfort

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
7,946 reviews
Southwest
8.0
Very good
4,287 reviews

Food

7.1

Entertainment

7.6

Boarding

8.2

Overall

8.0

Comfort

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.
Qatar Airways
7.4
Good
3,584 reviews
Southwest
8.0
Very good
4,287 reviews

Food

7.1

Entertainment

7.6

Boarding

8.2

Overall

8.0

Comfort

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.
Allegiant Air
7.3
Good
725 reviews
Southwest
8.0
Very good
4,287 reviews

Food

7.1

Entertainment

7.6

Boarding

8.2

Overall

8.0

Comfort

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
4,287 reviews

Food

7.1

Entertainment

7.6

Boarding

8.2

Overall

8.0

Comfort

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 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 $129, 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 Southwest - these airlines can fly you to your destination from $168 and $187, respectively. Allegiant Air is 57% 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 $74 while deals on Sun Country Air start at $138 one-way.

  • What are the most reliable airlines from Chicago to Valparaiso, Florida?

    No one likes to see their flight delayed. When booking a flight from Chicago to Valparaiso, Florida consider choosing Envoy Air (84%), American Airlines (72%) or Republic Airways (0%) as they are the most reliable in getting you off to your destination on time.

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

    The cheapest flight price from Chicago to Valparaiso, Florida is $157. On average you can expect to pay $406. The most popular route, (Chicago O'Hare Intl - Valparaiso Destin-Ft Walton Beach), can usually be booked for $187.

  • 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 $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.

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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 June 12, 2025.
AirlineCheapestAverageFlexibilityOn-time
Allegiant AirCheapest$92Average$180FlexibilityNo cancel feeOn-time88%
DeltaCheapest$199Average$339FlexibilityNo cancel feeOn-timeN/A
SouthwestCheapest$212Average$394FlexibilityNo cancel feeOn-time63%
American AirlinesCheapest$222Average$398FlexibilityNo cancel feeOn-time71%

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