HomeSearch by dateVacation packagesHotelsFlight dealsCar rentalTravel tips & news
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 5/26. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — VPS
abr. 27 — may. 41
dom. 4/27
dom. 5/4
1 adult, Economy
We work with more than 300 partners to bring you better travel deals

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

Review each provider’s pricing and select the best option for you! Book through your favorite provider’s website for a seamless experience.

Cheapflights Tip: The best prices from Chicago to Valparaiso Destin-Ft Walton Beach are usually found in January or May, booked 85 days in advance, depart on a Monday or Friday 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 abril 22, 2025.

Most accurate provider

FlightHub
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$115
(Booking.com)

One-way from

$54
(Booking.com)

Popular in

March

Cheapest in

January

Average price

$389

Good round-trip deal

$94 or less

Good one-way deal

$59 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. 21% potential increase in price ($83 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 7% potential price decrease ($23 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in April 2025
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

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 abril 22, 2025.

This Booking.com deal was found by Cheapflights users on 4/21. 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.
vie. 6/69:12 amMDW - VPS
Nonstop2h 11mAllegiant Air
vie. 6/136:00 amVPS - MDW
Nonstop2h 22mAllegiant Air
Deal found 4/21$115
This American Airlines deal was found by Cheapflights users on 4/22. 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.
mié. 6/48:00 amORD - VPS
Nonstop2h 18mAmerican Airlines
mié. 6/1110:41 amVPS - ORD
Nonstop2h 36mAmerican Airlines
Deal found 4/22$158
This Delta deal was found by Cheapflights users on 4/22. 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.
mié. 6/41:30 pmORD - VPS
1 stop5h 03mDelta
mar. 6/102:45 pmVPS - ORD
1 stop6h 39mDelta
Deal found 4/22$177
This Delta deal was found by Cheapflights users on 4/20. 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.
mar. 5/206:00 amMDW - VPS
1 stop6h 30mDelta
mié. 5/289:18 amVPS - MDW
1 stop6h 02mDelta
Deal found 4/20$192
This Southwest deal was found by Cheapflights users on 4/21. 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.
jue. 7/175:15 amMDW - VPS
1 stop4h 40mSouthwest
mar. 7/224:00 pmVPS - MDW
1 stop5h 05mSouthwest
Deal found 4/21$259
This Southwest deal was found by Cheapflights users on 4/22. 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.
mié. 7/212:40 pmORD - VPS
2 stops8h 40mSouthwest
mié. 7/97:00 amVPS - ORD
1 stop5h 45mSouthwest
Deal found 4/22$265
This Mytrip deal was found by Cheapflights users on 4/22. 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.
mié. 6/49:08 pmORD - VPS
1 stop17h 37mMultiple Airlines
mié. 6/116:15 amVPS - ORD
2 stops16h 49mMultiple Airlines
Deal found 4/22$282
This Sun Country Air deal was found by Cheapflights users on 4/20. 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.
dom. 10/198:00 amORD - VPS
1 stop8h 17mSun Country Air
jue. 10/3011:09 amVPS - ORD
1 stop7h 17mSun Country Air
Deal found 4/20$391

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 abril 22, 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

vie. 6/6

9:12 am-11:23 am

Nonstop2h 11m

Valparaiso Destin-Ft Walton Beach

vie. 6/13

6:00 am-8:22 am

Nonstop2h 22m

$115

ChicagoValparaiso

ORD - VPS

ORDVPS

Chicago O'Hare Intl

mié. 6/4

8:00 am-10:18 am

Nonstop2h 18m

Valparaiso Destin-Ft Walton Beach

mié. 6/11

10:41 am-1:17 pm

Nonstop2h 36m

$158

ChicagoValparaiso

ORD - VPS

ORDVPS

Chicago O'Hare Intl

mié. 6/4

1:30 pm-6:33 pm

1 stop5h 03m

Valparaiso Destin-Ft Walton Beach

mar. 6/10

2:45 pm-9:24 pm

1 stop6h 39m

$177

ChicagoValparaiso

MDW - VPS

MDWVPS

Chicago Midway

mar. 5/20

6:00 am-12:30 pm

1 stop6h 30m

Valparaiso Destin-Ft Walton Beach

mié. 5/28

9:18 am-3:20 pm

1 stop6h 02m

$192

ChicagoValparaiso

MDW - VPS

MDWVPS

Chicago Midway

jue. 7/17

5:15 am-9:55 am

1 stop4h 40m

Valparaiso Destin-Ft Walton Beach

mar. 7/22

4:00 pm-9:05 pm

1 stop5h 05m

$259

ChicagoValparaiso

ORD - VPS

ORDVPS

Chicago O'Hare Intl

mié. 7/2

12:40 pm-9:20 pm

2 stops8h 40m

Valparaiso Destin-Ft Walton Beach

mié. 7/9

7:00 am-12:45 pm

1 stop5h 45m

$265

ChicagoValparaiso

ORD - VPS

ORDVPS

Chicago O'Hare Intl

mié. 6/4

9:08 pm-2:45 pm

1 stop17h 37m

Valparaiso Destin-Ft Walton Beach

mié. 6/11

6:15 am-11:04 pm

2 stops16h 49m

$282

ChicagoValparaiso

ORD - VPS

ORDVPS

Chicago O'Hare Intl

jue. 5/8

8:05 pm-11:06 am

1 stop15h 01m

Valparaiso Destin-Ft Walton Beach

lun. 5/12

12:11 pm-7:09 pm

1 stop6h 58m

$414

ChicagoValparaiso

MDW - VPS

MDWVPS

Chicago Midway

lun. 6/2

9:12 am-11:23 am

Nonstop2h 11m

$54

ChicagoValparaiso

ORD - VPS

ORDVPS

Chicago O'Hare Intl

mié. 6/18

4:00 pm-9:20 pm

1 stop5h 20m

$90

Flights are sorted by cheapest round-trip flights first.

Deals found on 4/21

Showing 1-10 of 17 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 April.
ProviderPrice AccuracyTrust Score*
ExpediaPrice Accuracy1 starTrust Score*3 stars
FlightHubPrice Accuracy3 starsTrust Score*2 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 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 April 18, 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 $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 abril 22, 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 61% on your trip compared to booking a flight in the morning.

Weekly flight availability from Chicago to Valparaiso, Florida

Explore weekly flight availability from Chicago to Valparaiso. Discover flights operating on different days of the week, giving you the flexibility to choose a travel day that best fits your plans. Compare info to find the most convenient option for your journey. Data last updated abril 22, 2025.

The most flights from CHI to VPS are scheduled on a Monday (1 on average). You will have fewer flight options on Monday, which is when the least amount of flights are scheduled (1 on average).

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 abril 22, 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
8.0
Very good
4,287 reviews

Comfort

8.0

Food

7.1

Boarding

8.2

Overall

8.0

Crew

8.6

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

Comfort

8.0

Food

7.1

Boarding

8.2

Overall

8.0

Crew

8.6

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
7,920 reviews
Southwest
8.0
Very good
4,287 reviews

Comfort

8.0

Food

7.1

Boarding

8.2

Overall

8.0

Crew

8.6

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
734 reviews
Southwest
8.0
Very good
4,287 reviews

Comfort

8.0

Food

7.1

Boarding

8.2

Overall

8.0

Crew

8.6

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
8.0
Very good
4,287 reviews

Comfort

8.0

Food

7.1

Boarding

8.2

Overall

8.0

Crew

8.6

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
349 reviews
Southwest
8.0
Very good
4,287 reviews

Comfort

8.0

Food

7.1

Boarding

8.2

Overall

8.0

Crew

8.6

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 1 inbound flight 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 $115, 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 $158 and $177, respectively. Allegiant Air is 61% 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 $143 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 (92%), American Airlines (84%) or Republic Airways (82%) 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 $108. On average you can expect to pay $428. The most popular route, (Chicago O'Hare Intl - Valparaiso Destin-Ft Walton Beach), can usually be booked for $256.

  • 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.

See more FAQs

Traveling to a place near Chicago?

Book flights to Chicago if you plan to visit one of these locations
Crestview
Andalusia

Browse thousands of different options on Cheapflights for your next trip

Toggle through the tabs below to find thousands of options on Cheapflights for your next trip.

Alternative routes for Chicago to Valparaiso

See prices for flight routes from nearby airports that may be better suited for you.
O'Hare Intl to Miami flights
O'Hare Intl to Orlando flights
O'Hare Intl to Fort Lauderdale flights
O'Hare Intl to Tampa flights
O'Hare Intl to Fort Myers flights
Midway to Orlando flights
O'Hare Intl to Jacksonville flights
O'Hare Intl to Sarasota flights
Midway to Tampa flights
St. Louis to Miami flights
Midway to Miami flights
O'Hare Intl to Pensacola flights
O'Hare Intl to West Palm Beach flights
St. Louis to Orlando flights
O'Hare Intl to Panama City flights
Midway to Fort Lauderdale flights
O'Hare Intl to Key West flights
Midway to Fort Myers flights
Midway to West Palm Beach flights
Midway to Jacksonville flights
O'Hare Intl to Valparaiso flights
Peoria to Orlando flights
Moline to Orlando flights
St. Louis to Tampa flights
Midway to Panama City flights
St. Louis to Jacksonville flights
St. Louis to Fort Lauderdale flights
St. Louis to Pensacola flights
Midway to Sarasota flights
Midway to Pensacola flights
Midway to Key West flights
St. Louis to Sarasota flights
St. Louis to Key West flights
Moline to Tampa flights
O'Hare Intl to Daytona Beach flights
Moline to Fort Myers flights
St. Louis to Panama City flights
St. Louis to West Palm Beach flights
Moline to Pensacola flights
Rockford to Orlando Sanford Intl flights
Rockford to St Petersburg flights
Midway to Daytona Beach flights
O'Hare Intl to St Petersburg flights
Peoria to Fort Lauderdale flights
Peoria to Pensacola flights
Peoria to Miami flights
Springfield to Orlando flights
Peoria to Tampa flights
Bloomington to Orlando flights
St. Louis to Valparaiso flights

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 abril 22, 2025.
AirlineCheapestAverageFlexibilityOn-time
Allegiant AirCheapest$92Average$168FlexibilityNo cancel feeOn-time88%
DeltaCheapest$199Average$320FlexibilityNo cancel feeOn-timeN/A
American AirlinesCheapest$233Average$401FlexibilityNo cancel feeOn-time71%
SouthwestCheapest$366Average$388FlexibilityNo cancel feeOn-time63%

100% Free

Cheapflights is completely free to use, so you can start saving the moment you arrive.

Book with Flexibility

Our users can plan ahead with confidence and find flights with no change fees

Travel Smart

Millions of people come to us for their flight needs every year. We help make travel planning easy by providing useful insights and data-driven graphs that can inform your decisions.