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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 12/1. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — VPS
Dec 2 — Dec 91
Tue 12/2
Tue 12/9
1 adult, Economy
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1. Tell us where you want to go

Enter your travel information like dates, passengers, trip type (one-way or round trip), and preferred cabin class then click “Find deals”

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Cheapflights Tip: The best prices from Chicago to Valparaiso Destin-Ft Walton Beach are usually found in January or October, booked 30 days in advance, depart on a Wednesday or Monday and return on a Thursday

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 November 2, 2025.

This Cheapflightsfares deal was found by Cheapflights users on 11/1. 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 12/186:54 pmMDW - VPS
Nonstop2h 13mAllegiant Air
Tue 12/301:01 pmVPS - MDW
Nonstop2h 19mAllegiant Air
Deal found 11/1$116
This Trip.com deal was found by Cheapflights users on 11/1. 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/208:33 pmMDW - VPS
Nonstop2h 13mAllegiant Air
Tue 11/2511:31 amVPS - MDW
Nonstop2h 19mAllegiant Air
Deal found 11/1$166
This Cheapflightsfares deal was found by Cheapflights users on 11/1. 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 11/1312:07 pmMDW - VPS
Nonstop2h 05mAllegiant Air
Sun 11/169:00 amVPS - MDW
Nonstop2h 17mAllegiant Air
Deal found 11/1$189
This Sun Country Air deal was found by Cheapflights users on 11/2. 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 stop5h 44mSun Country Air
Mon 12/2211:26 amVPS - ORD
1 stop23h 00mSun Country Air
Deal found 11/2$264
This Kiwi.com deal was found by Cheapflights users on 11/1. 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 11/169:24 amORD - VPS
2 stops30h 02mMultiple Airlines
Thu 11/206:35 amVPS - ORD
1 stop6h 21mMultiple Airlines
Deal found 11/1$346
This Southwest deal was found by Cheapflights users on 11/1. 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 12/256:35 amMDW - VPS
1 stop3h 45mSouthwest
Mon 12/292:00 pmVPS - MDW
1 stop3h 55mSouthwest
Deal found 11/1$406
This Southwest deal was found by Cheapflights users on 11/1. 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 12/21:45 pmORD - VPS
1 stop7h 25mSouthwest
Sat 12/67:00 amVPS - ORD
1 stop5h 15mSouthwest
Deal found 11/1$412
This American Airlines deal was found by Cheapflights users on 11/1. 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 12/28:29 amORD - VPS
Nonstop2h 28mAmerican Airlines
Sat 12/611:29 amVPS - ORD
Nonstop2h 43mAmerican Airlines
Deal found 11/1$426
This Southwest deal was found by Cheapflights users on 11/1. 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 12/15:25 amMDW - VPS
1 stop7h 55mSouthwest
Fri 12/57:15 amVPS - MDW
1 stop5h 30mSouthwest
Deal found 11/1$435
This Southwest deal was found by Cheapflights users on 11/1. 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 12/21:45 pmORD - VPS
1 stop7h 25mSouthwest
Fri 12/57:15 amVPS - ORD
1 stop5h 00mSouthwest
Deal found 11/1$441
This Delta deal was found by Cheapflights users on 11/1. 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.
Mon 12/19:51 amORD - VPS
1 stop6h 16mDelta
Fri 12/55:00 pmVPS - ORD
1 stop4h 56mDelta
Deal found 11/1$445
This Delta deal was found by Cheapflights users on 11/1. 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.
Mon 12/112:47 pmMDW - VPS
1 stop5h 15mDelta
Fri 12/57:20 pmVPS - MDW
1 stop4h 27mDelta
Deal found 11/1$445

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 November 2, 2025.

Most accurate provider

eDreams
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$116
(Cheapflightsfares)

One-way from

$54
(Cheapflightsfares)

Popular in

March

Cheapest in

January

Average price

$310

Good round-trip deal

$309 or less
Provider with most accurate pricing for Chicago (CHI)-Valparaiso Destin-Ft Walton Beach flight deals.
Search Deals
Provider most trusted by Cheapflights users for Chicago (CHI)-Valparaiso Destin-Ft Walton Beach flights.
Search Deals
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. 25% potential increase in price ($108 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 6% potential price decrease ($20 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in November 2025
Search Deals
Price to beat on a round-trip flight from Chicago (CHI) to Valparaiso Destin-Ft Walton Beach.
Search Deals

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 November 2, 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 11/13

12:07 pm-2:12 pm

Nonstop2h 05m

Valparaiso Destin-Ft Walton Beach

Sun 11/16

9:00 am-11:17 am

Nonstop2h 17m

$189

ChicagoValparaiso

MDW - VPS

MDWVPS

Chicago Midway

Thu 4/9

5:47 pm-7:56 pm

Nonstop2h 09m

Valparaiso Destin-Ft Walton Beach

Sun 4/12

2:40 pm-4:57 pm

Nonstop2h 17m

$258

ChicagoValparaiso

MDW - VPS

MDWVPS

Chicago Midway

Sat 1/24

6:40 am-5:20 pm

2 stops10h 40m

Valparaiso Destin-Ft Walton Beach

Thu 1/29

2:00 pm-10:55 pm

2 stops8h 55m

$388

ChicagoValparaiso

ORD - VPS

ORDVPS

Chicago O'Hare Intl

Tue 1/27

10:35 am-11:05 pm

2 stops12h 30m

Valparaiso Destin-Ft Walton Beach

Wed 1/28

12:05 pm-4:54 pm

1 stop4h 49m

$390

ChicagoValparaiso

MDW - VPS

MDWVPS

Chicago Midway

Tue 3/3

1:00 pm-3:42 pm

2 stops26h 42m

Valparaiso Destin-Ft Walton Beach

Thu 3/5

4:20 pm-9:46 pm

1 stop5h 26m

$390

ChicagoValparaiso

MDW - VPS

MDWVPS

Chicago Midway

Tue 1/27

9:34 am-11:05 pm

2 stops13h 31m

Valparaiso Destin-Ft Walton Beach

Fri 1/30

1:02 pm-6:36 pm

1 stop5h 34m

$390

ChicagoValparaiso

MDW - VPS

MDWVPS

Chicago Midway

Tue 1/27

9:34 am-11:05 pm

2 stops13h 31m

Valparaiso Destin-Ft Walton Beach

Thu 1/29

6:00 am-12:01 pm

1 stop6h 01m

$390

ChicagoValparaiso

ORD - VPS

ORDVPS

Chicago O'Hare Intl

Wed 2/25

6:05 am-1:59 pm

3 stops31h 54m

Valparaiso Destin-Ft Walton Beach

Sun 3/1

7:40 am-3:55 pm

1 stop8h 15m

$410

ChicagoValparaiso

ORD - VPS

ORDVPS

Chicago O'Hare Intl

Tue 12/2

1:45 pm-9:10 pm

1 stop7h 25m

Valparaiso Destin-Ft Walton Beach

Sat 12/6

7:00 am-12:15 pm

1 stop5h 15m

$412

ChicagoValparaiso

MDW - VPS

MDWVPS

Chicago Midway

Thu 12/25

11:15 am-9:10 pm

2 stops9h 55m

Valparaiso Destin-Ft Walton Beach

Mon 12/29

6:10 pm-1:10 am

1 stop7h 00m

$412

Flights are sorted by cheapest round-trip flights first.

Deals found on 11/2

Showing 1-10 of 39 results
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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 November.
ProviderPrice AccuracyTrust Score*
ExpediaPrice Accuracy2 starsTrust Score*3 stars
FlightHubPrice Accuracy3 starsTrust Score*1 star
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 eDreams to be most consistent on Cheapflights vs. eDreams Users can find the same prices on Chicago-Valparaiso, Florida flight deals on Cheapflights vs. eDreams >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 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-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 October 31, 2025.

Booking 30 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 $81). Flying from Chicago to Valparaiso, Florida in December is currently the most expensive (average of $200). 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 November 2, 2025.

A simple way to save on the total cost of your ticket is to fly from Chicago to Valparaiso, Florida in the evening. If you’re flexible enough to do this you can expect to save up to 49% on your trip compared to booking a flight at noon.

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 November 2, 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
4,238 reviews

Crew

8.6

Food

7.0

Boarding

8.1

Comfort

8.0

Entertainment

7.5

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
4,238 reviews
Southwest
8.0
Very good
4,238 reviews

Crew

8.6

Food

7.0

Boarding

8.1

Comfort

8.0

Entertainment

7.5

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
7.9
Good
8,001 reviews
Southwest
8.0
Very good
4,238 reviews

Crew

8.6

Food

7.0

Boarding

8.1

Comfort

8.0

Entertainment

7.5

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
11,036 reviews
Southwest
8.0
Very good
4,238 reviews

Crew

8.6

Food

7.0

Boarding

8.1

Comfort

8.0

Entertainment

7.5

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
694 reviews
Southwest
8.0
Very good
4,238 reviews

Crew

8.6

Food

7.0

Boarding

8.1

Comfort

8.0

Entertainment

7.5

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.

  • How long is the flight from Chicago to Valparaiso, Florida?

    Airlines like Allegiant Air, Southwest, and Delta fly from Chicago to Valparaiso, Florida in about 2h 05m. The time it takes to get you to your destination can typically vary by up to 10h 25m. Chicago and Valparaiso, Florida are separated by a distance of 783 mi. 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 to Valparaiso, Florida round-trip?

    Currently priced at $85, 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 $207 and $212, respectively. Allegiant Air is 73% 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. Delta flights start at $174 while deals on Southwest start at $180 one-way.

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

    The cheapest flight price from Chicago to Valparaiso, Florida is $425. On average you can expect to pay $624. The most popular route, (Chicago O'Hare Intl - Valparaiso Destin-Ft Walton Beach), can usually be booked for $264.

  • 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 $81). Flying from Chicago to Valparaiso, Florida in December is currently the most expensive (average of $200). 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

See prices for flight routes from nearby airports that may be better suited for you.
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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 November 2, 2025.
AirlineCheapestAverageFlexibilityOn-time
Allegiant AirCheapest$85Average$168FlexibilityNo cancel feeOn-time88%
DeltaCheapest$207Average$495FlexibilityNo cancel feeOn-timeN/A
SouthwestCheapest$212Average$381FlexibilityNo cancel feeOn-time63%
American AirlinesCheapest$238Average$420FlexibilityNo cancel feeOn-time71%

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