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Valparaiso

$85+ 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 3/4. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — VPS
מרץ 1 — מרץ 81
א' 3/1
א' 3/8
1 adult, Economy
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Find cheap flights from Chicago to Valparaiso with Cheapflights

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”

2. Select your favorite providers

We find the providers serving your travel needs. Choose up to four travel providers to compare side-by-side for flights, hotels, or car rentals.

3. Compare prices and book

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Cheapflights Tip: The best prices from Chicago to Valparaiso Destin-Ft Walton Beach are usually found in October or June, booked 17 days in advance, depart on a Monday or Wednesday and return on a Wednesday

Cheap 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 ינואר 30, 2026.

This Kiwi.com deal was found by Cheapflights users on 1/29. 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.
א' 3/88:46 pm
MDW
-
VPS
Nonstop2h 08m
Allegiant Air
ה' 3/125:37 pm
VPS
-
MDW
Nonstop2h 16m
Allegiant Air
Deal found 1/29$105
This Kiwi.com deal was found by Cheapflights users on 1/29. 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.
א' 2/153:40 pm
MDW
-
VPS
Nonstop2h 06m
Allegiant Air
ה' 2/191:01 pm
VPS
-
MDW
Nonstop2h 19m
Allegiant Air
Deal found 1/29$146
This Booking.com 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 Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
ה' 3/128:43 pm
MDW
-
VPS
Nonstop2h 08m
Allegiant Air
א' 3/155:37 pm
VPS
-
MDW
Nonstop2h 16m
Allegiant Air
Deal found 1/28$168
This Kiwi.com 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
ב' 6/299:23 pm
MDW
-
VPS
Nonstop2h 13m
Allegiant Air
ו' 7/36:05 pm
VPS
-
MDW
Nonstop2h 20m
Allegiant Air
Deal found 1/28$170
This Mytrip 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
ה' 2/124:10 pm
MDW
-
VPS
Nonstop2h 06m
Allegiant Air
א' 2/1512:31 pm
VPS
-
MDW
Nonstop2h 19m
Allegiant Air
Deal found 1/28$193
This Kiwi.com deal was found by Cheapflights users on 1/29. 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.
א' 3/87:30 am
MDW
-
VPS
1 stop6h 22m
Multiple Airlines
ה' 3/125:37 pm
VPS
-
MDW
Nonstop2h 16m
Multiple Airlines
Deal found 1/29$202
This Kiwi.com deal was found by Cheapflights users on 1/29. 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.
א' 2/153:40 pm
MDW
-
VPS
Nonstop2h 06m
Allegiant Air
א' 2/2212:31 pm
VPS
-
MDW
Nonstop2h 19m
Allegiant Air
Deal found 1/29$219
This Kiwi.com 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
ד' 3/47:15 am
MDW
-
VPS
3 stops30h 37m
Multiple Airlines
ה' 3/55:40 pm
VPS
-
MDW
Nonstop2h 16m
Multiple Airlines
Deal found 1/28$225
This Booking.com 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 Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
ה' 2/194:10 pm
MDW
-
VPS
Nonstop2h 06m
Allegiant Air
א' 2/2212:31 pm
VPS
-
MDW
Nonstop2h 19m
Allegiant Air
Deal found 1/28$231
This Kiwi.com deal was found by Cheapflights users on 1/29. 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.
א' 2/153:40 pm
MDW
-
VPS
Nonstop2h 06m
Multiple Airlines
ה' 2/198:48 pm
VPS
-
MDW
2 stops25h 37m
Multiple Airlines
Deal found 1/29$243
This Kiwi.com 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
ה' 3/127:30 am
MDW
-
VPS
1 stop6h 20m
Multiple Airlines
א' 3/155:37 pm
VPS
-
MDW
Nonstop2h 16m
Multiple Airlines
Deal found 1/28$250
This Kiwi.com 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
ב' 2/166:00 am
MDW
-
VPS
2 stops33h 17m
Multiple Airlines
ה' 2/191:01 pm
VPS
-
MDW
Nonstop2h 19m
Multiple Airlines
Deal found 1/28$261

Find 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 ינואר 30, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$105
(Kiwi.com)

One-way from

$85
(Kiwi.com)

Popular in

March

Cheapest in

October

Average price

$382

Good round-trip deal

$164 or less

Good one-way deal

$138 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. 15% potential increase in price ($62 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 6% potential price decrease ($19 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in January 2026
Search Deals
Price to beat on a round-trip flight from Chicago (CHI) to Valparaiso Destin-Ft Walton Beach.
Search Deals
Price to beat on a one-way 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 ינואר 30, 2026.
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

א' 2/15

3:40 pm-5:46 pm

Nonstop2h 06m

Valparaiso Destin-Ft Walton Beach

א' 2/22

12:31 pm-2:50 pm

Nonstop2h 19m

$219

ChicagoValparaiso

MDW - VPS

MDWVPS

Chicago Midway

א' 2/15

3:40 pm-5:46 pm

Nonstop2h 06m

Valparaiso Destin-Ft Walton Beach

ה' 2/19

8:48 pm-10:25 pm

2 stops25h 37m

$243

ChicagoValparaiso

MDW - VPS

MDWVPS

Chicago Midway

א' 2/15

3:40 pm-5:46 pm

Nonstop2h 06m

Valparaiso Destin-Ft Walton Beach

ו' 2/20

10:00 am-2:55 pm

2 stops28h 55m

$332

ChicagoValparaiso

MDW - VPS

MDWVPS

Chicago Midway

ד' 3/11

6:00 am-11:50 am

1 stop5h 50m

Valparaiso Destin-Ft Walton Beach

ג' 3/17

12:35 pm-5:05 pm

1 stop4h 30m

$333

ChicagoValparaiso

MDW - VPS

MDWVPS

Chicago Midway

ד' 3/4

6:00 am-11:40 am

1 stop5h 40m

Valparaiso Destin-Ft Walton Beach

ה' 3/5

7:20 am-11:55 am

1 stop4h 35m

$350

ChicagoValparaiso

MDW - VPS

MDWVPS

Chicago Midway

ב' 3/2

5:25 am-10:30 am

1 stop5h 05m

Valparaiso Destin-Ft Walton Beach

ש' 3/7

12:45 pm-8:10 pm

1 stop7h 25m

$351

ChicagoValparaiso

MDW - VPS

MDWVPS

Chicago Midway

ד' 3/11

6:00 am-11:50 am

1 stop5h 50m

Valparaiso Destin-Ft Walton Beach

א' 3/15

4:00 pm-10:40 pm

1 stop6h 40m

$353

ChicagoValparaiso

ORD - VPS

ORDVPS

Chicago O'Hare Intl

ד' 4/29

9:50 am-2:13 pm

1 stop4h 23m

Valparaiso Destin-Ft Walton Beach

ב' 5/4

1:53 pm-6:48 pm

1 stop4h 55m

$355

ChicagoValparaiso

MDW - VPS

MDWVPS

Chicago Midway

ש' 5/16

4:30 pm-11:08 pm

1 stop6h 38m

Valparaiso Destin-Ft Walton Beach

ה' 5/21

6:00 am-9:51 am

1 stop3h 51m

$355

ChicagoValparaiso

ORD - VPS

ORDVPS

Chicago O'Hare Intl

ד' 3/4

6:05 am-6:55 pm

2 stops12h 50m

Valparaiso Destin-Ft Walton Beach

ה' 3/5

7:20 am-12:50 pm

1 stop5h 30m

$361

Flights are sorted by cheapest round-trip flights first.

Deals found on 1/29

Showing 1-10 of 38 results
1
2
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4

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 January.
ProviderPrice AccuracyTrust Score*
ExpediaPrice Accuracy1 starTrust Score*3 stars
FlightHubPrice Accuracy3 starsTrust Score*3 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 January 23, 2026.

Booking 17 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 $209). 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 ינואר 30, 2026.

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 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 ינואר 30, 2026.
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
4,267 reviews

Comfort

8.0

Boarding

8.1

Entertainment

7.5

Crew

8.6

Food

7.0

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
4,267 reviews
Southwest
8.0
Very good
4,267 reviews

Comfort

8.0

Boarding

8.1

Entertainment

7.5

Crew

8.6

Food

7.0

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
7.9
Good
8,124 reviews
Southwest
8.0
Very good
4,267 reviews

Comfort

8.0

Boarding

8.1

Entertainment

7.5

Crew

8.6

Food

7.0

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
11,207 reviews
Southwest
8.0
Very good
4,267 reviews

Comfort

8.0

Boarding

8.1

Entertainment

7.5

Crew

8.6

Food

7.0

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
706 reviews
Southwest
8.0
Very good
4,267 reviews

Comfort

8.0

Boarding

8.1

Entertainment

7.5

Crew

8.6

Food

7.0

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.

  • 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 06m. The time it takes to get you to your destination can typically vary by up to 5h 23m. 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 $82, 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 Southwest and Delta - these airlines can fly you to your destination from $212 and $236, respectively. Allegiant Air is 75% cheaper than the average price of flights available within the next 90 days to this destination.

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

    The cheapest flight price from Chicago to Valparaiso, Florida is $295. On average you can expect to pay $433. The most popular route, (Chicago O'Hare Intl - Valparaiso Destin-Ft Walton Beach), can usually be booked for $301.

  • 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 $209). 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 ינואר 30, 2026.
AirlineCheapestAverageFlexibilityOn-time
Allegiant AirCheapest$82Average$168FlexibilityNo cancel feeOn-time88%
SouthwestCheapest$212Average$381FlexibilityNo cancel feeOn-time63%
DeltaCheapest$236Average$437FlexibilityNo cancel feeOn-timeN/A
American AirlinesCheapest$239Average$406FlexibilityNo cancel feeOn-time71%

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