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Valparaiso

$104+ 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 2/20. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — VPS
Jan 25 — Feb 11
Sat 1/25
Sat 2/1
1 adult, Economy
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The best prices from Chicago to Valparaiso Destin-Ft Walton Beach are usually found in January or February, booked 29 days in advance, depart on a Monday or Thursday and return on a Friday

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 January 20, 2025.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$184
(Kiwi.com)

One-way from

$104
(Cheapflightsfares)

Popular in

March

Cheapest in

January

Average price

$122
Provider with most accurate pricing for Chicago (CHI)-Valparaiso Destin-Ft Walton Beach flight deals.
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Provider most trusted by Cheapflights users for Chicago (CHI)-Valparaiso Destin-Ft Walton Beach flights.
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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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High demand for flights, 9% potential price rise
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Best time to find cheap flights, 5% potential price drop
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Average for round-trip flights in January 2025
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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 January 20, 2025.

This Gotogate deal was found by Cheapflights users on 1/19. 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 Gotogate is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 3/92:22 pmMDW - VPS
Nonstop2h 12mAllegiant Air
Thu 3/1311:15 amVPS - MDW
Nonstop2h 17mAllegiant Air
Deal found 1/19$115
This Delta deal was found by Cheapflights users on 1/20. 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.
Tue 3/49:38 amORD - VPS
1 stop13h 15mDelta
Wed 3/129:20 amVPS - ORD
1 stop14h 36mDelta
Deal found 1/20$324
This American Airlines deal was found by Cheapflights users on 1/19. 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 3/45:00 amORD - VPS
1 stop5h 45mAmerican Airlines
Tue 3/112:50 pmVPS - ORD
Nonstop2h 33mAmerican Airlines
Deal found 1/19$336
This Delta deal was found by Cheapflights users on 1/19. 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 3/55:05 pmMDW - VPS
1 stop5h 48mDelta
Tue 3/115:45 pmVPS - MDW
1 stop4h 38mDelta
Deal found 1/19$345
This Southwest deal was found by Cheapflights users on 1/19. 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 2/117:30 amORD - VPS
2 stops11h 25mSouthwest
Tue 2/1811:35 amVPS - ORD
2 stops11h 00mSouthwest
Deal found 1/19$357
This Mytrip deal was found by Cheapflights users on 1/20. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 3/65:55 amORD - VPS
3 stops16h 14mMultiple Airlines
Wed 3/127:59 amVPS - ORD
2 stops16h 08mMultiple Airlines
Deal found 1/20$372
This Southwest deal was found by Cheapflights users on 1/19. 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.
Wed 2/1910:25 amMDW - VPS
1 stop8h 30mSouthwest
Mon 2/247:20 amVPS - MDW
1 stop6h 50mSouthwest
Deal found 1/19$380
This Sun Country Air deal was found by Cheapflights users on 1/19. 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 5/158:05 pmORD - VPS
1 stop15h 01mSun Country Air
Sun 5/186:10 pmVPS - ORD
1 stop24h 59mSun Country Air
Deal found 1/19$414

Find flights from Chicago to Valparaiso within your budget

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 January 20, 2025.

Fly from

Any airport

Fly to

Any airport

Route

Depart

Return

Price

ChicagoValparaiso

MDW - VPS

MDWVPS

Chicago Midway

Sun 3/9

2:22 pm-4:34 pm

Nonstop2h 12m

Valparaiso Destin-Ft Walton Beach

Thu 3/13

11:15 am-1:32 pm

Nonstop2h 17m

$115

ChicagoValparaiso

ORD - VPS

ORDVPS

Chicago O'Hare Intl

Tue 3/4

7:05 am-3:57 pm

1 stop8h 52m

Valparaiso Destin-Ft Walton Beach

Tue 3/11

7:00 am-4:20 pm

1 stop9h 20m

$324

ChicagoValparaiso

MDW - VPS

MDWVPS

Chicago Midway

Tue 3/4

6:00 am-3:57 pm

1 stop9h 57m

Valparaiso Destin-Ft Walton Beach

Tue 3/11

7:00 am-4:14 pm

1 stop9h 14m

$324

ChicagoValparaiso

ORD - VPS

ORDVPS

Chicago O'Hare Intl

Tue 3/4

5:00 am-10:45 am

1 stop5h 45m

Valparaiso Destin-Ft Walton Beach

Tue 3/11

2:50 pm-5:23 pm

Nonstop2h 33m

$336

ChicagoValparaiso

ORD - VPS

ORDVPS

Chicago O'Hare Intl

Tue 2/11

7:30 am-6:55 pm

2 stops11h 25m

Valparaiso Destin-Ft Walton Beach

Tue 2/18

11:35 am-10:35 pm

2 stops11h 00m

$357

ChicagoValparaiso

ORD - VPS

ORDVPS

Chicago O'Hare Intl

Thu 3/6

5:55 am-10:09 pm

3 stops16h 14m

Valparaiso Destin-Ft Walton Beach

Wed 3/12

7:59 am-12:07 am

2 stops16h 08m

$372

ChicagoValparaiso

MDW - VPS

MDWVPS

Chicago Midway

Wed 2/19

10:25 am-6:55 pm

1 stop8h 30m

Valparaiso Destin-Ft Walton Beach

Mon 2/24

7:20 am-2:10 pm

1 stop6h 50m

$380

ChicagoValparaiso

ORD - VPS

ORDVPS

Chicago O'Hare Intl

Thu 5/15

8:05 pm-11:06 am

1 stop15h 01m

Valparaiso Destin-Ft Walton Beach

Sun 5/18

6:10 pm-7:09 pm

1 stop24h 59m

$414

ChicagoValparaiso

MDW - VPS

MDWVPS

Chicago Midway

Thu 2/20

11:38 am-1:50 pm

Nonstop2h 12m

$104

ChicagoValparaiso

ORD - VPS

ORDVPS

Chicago O'Hare Intl

Wed 3/26

8:00 am-10:35 am

Nonstop2h 35m

$164

Flights are sorted by cheapest round-trip flights first.

Deals found on 1/20

Showing 1-10 of 16 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 January.
ProviderPrice AccuracyTrust Score*
ExpediaPrice Accuracy1 starTrust Score*3 stars
FlightHubPrice Accuracy3 starsTrust Score*3 stars
eDreamsPrice Accuracy3 starsTrust Score*3 stars
CheapflightsfaresPrice Accuracy3 starsTrust Score*1 star

*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.

Travel insights for flights from Chicago to Valparaiso

Get recent, data-driven insights about flights from Chicago to Valparaiso including ideal travel times, pricing trends, and more.

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 17, 2025.

Booking 29 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 $414). 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 January 20, 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 54% on your trip compared to booking a flight in the afternoon.

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 January 20, 2025.
Get a feel of what it's like to fly with Delta and Southwest 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
8.1
Very good
4,659 reviews

Overall

8.1

Food

7.2

Crew

8.7

Comfort

8.1

Entertainment

7.7

Boarding

8.2

Reviews

1 / 10

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
8.1
Very good
4,659 reviews
Southwest
8.1
Very good
4,659 reviews

Overall

8.1

Food

7.2

Crew

8.7

Comfort

8.1

Entertainment

7.7

Boarding

8.2

Reviews

1 / 10

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
8,521 reviews
Southwest
8.1
Very good
4,659 reviews

Overall

8.1

Food

7.2

Crew

8.7

Comfort

8.1

Entertainment

7.7

Boarding

8.2

Reviews

1 / 10

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
7.4
Good
801 reviews
Southwest
8.1
Very good
4,659 reviews

Overall

8.1

Food

7.2

Crew

8.7

Comfort

8.1

Entertainment

7.7

Boarding

8.2

Reviews

1 / 10

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
8.1
Very good
4,659 reviews

Overall

8.1

Food

7.2

Crew

8.7

Comfort

8.1

Entertainment

7.7

Boarding

8.2

Reviews

1 / 10

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
7.0
Good
384 reviews
Southwest
8.1
Very good
4,659 reviews

Overall

8.1

Food

7.2

Crew

8.7

Comfort

8.1

Entertainment

7.7

Boarding

8.2

Reviews

1 / 10

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 3 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 $184, 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 American Airlines - these airlines can fly you to your destination from $324 and $336, respectively. Allegiant Air is 38% 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 $104. American Airlines flights start at $164 while deals on Delta start at $167 one-way.

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

    The cheapest flight price from Chicago to Valparaiso, Florida is $395. On average you can expect to pay $525. The most popular route, (Chicago O'Hare Intl - Valparaiso Destin-Ft Walton Beach), can usually be booked for $314.

  • 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 $414). 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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Alternative routes for Chicago to Valparaiso

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Top 3 airlines flying from Chicago to Valparaiso

Discover the top 3 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 January 20, 2025.
AirlineCheapestAverageFlexibilityOn-time
Allegiant AirCheapest$82Average$177FlexibilityNo cancel feeOn-time88%
DeltaCheapest$199Average$399FlexibilityNo cancel feeOn-timeN/A
American AirlinesCheapest$233Average$402FlexibilityNo cancel feeOn-time71%
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