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Valparaiso

$50+ Cheap flights from Illinois 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 5/29. Fares are subject to change and may not be available on all flights or dates of travel.
ORD — VPS
Jun 3 — Jun 101
Wed 6/3
Wed 6/10
1 adult, Economy
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Cheap flight deals from Illinois to Valparaiso

Cheapest flights from Illinois to Valparaiso
Explore the most affordable flight options available from Illinois to Valparaiso. Find the lowest fares from popular airlines and budget airlines, with prices last updated on May 4, 2026.

This Kiwi.com deal was found by Cheapflights users on 5/3. 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.
Mon 7/63:27 pm
EVV
-
VPS
Nonstop1h 38m
Allegiant Air
Mon 7/139:15 am
VPS
-
EVV
Nonstop1h 36m
Allegiant Air
Deal found 5/3$70
This Cheapflightsfares deal was found by Cheapflights users on 5/1. 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.
Sun 6/289:18 pm
BLV
-
VPS
Nonstop1h 42m
Allegiant Air
Tue 7/149:00 am
VPS
-
BLV
Nonstop1h 44m
Allegiant Air
Deal found 5/1$84
This Cheapflightsfares deal was found by Cheapflights users on 5/4. 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.
Fri 6/59:35 pm
BLV
-
VPS
Nonstop1h 42m
Allegiant Air
Thu 6/118:00 am
VPS
-
BLV
Nonstop1h 44m
Allegiant Air
Deal found 5/4$89
This Cheapflightsfares deal was found by Cheapflights users on 5/1. 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.
Fri 6/129:34 pm
BLV
-
VPS
Nonstop1h 42m
Allegiant Air
Mon 6/157:10 pm
VPS
-
BLV
Nonstop1h 44m
Allegiant Air
Deal found 5/1$98
This Cheapflightsfares deal was found by Cheapflights users on 5/2. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 6/19:30 pm
MDW
-
VPS
Nonstop2h 07m
Allegiant Air
Mon 6/156:12 pm
VPS
-
MDW
Nonstop2h 21m
Allegiant Air
Deal found 5/2$98
This Kiwi.com deal was found by Cheapflights users on 5/2. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 7/1011:41 am
EVV
-
VPS
Nonstop1h 38m
Allegiant Air
Mon 7/139:15 am
VPS
-
EVV
Nonstop1h 36m
Allegiant Air
Deal found 5/2$102
This Cheapflightsfares deal was found by Cheapflights users on 5/3. 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.
Fri 6/129:23 pm
MDW
-
VPS
Nonstop2h 13m
Allegiant Air
Mon 6/156:12 pm
VPS
-
MDW
Nonstop2h 21m
Allegiant Air
Deal found 5/3$112
This Cheapflightsfares deal was found by Cheapflights users on 4/30. 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.
Mon 6/229:23 pm
MDW
-
VPS
Nonstop2h 13m
Allegiant Air
Mon 6/296:12 pm
VPS
-
MDW
Nonstop2h 21m
Allegiant Air
Deal found 4/30$113
This Kiwi.com deal was found by Cheapflights users on 5/1. 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.
Mon 6/811:46 am
EVV
-
VPS
Nonstop1h 33m
Allegiant Air
Mon 6/159:15 am
VPS
-
EVV
Nonstop1h 41m
Allegiant Air
Deal found 5/1$114
This Cheapflightsfares deal was found by Cheapflights users on 5/4. 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.
Mon 7/209:20 pm
MDW
-
VPS
Nonstop2h 14m
Allegiant Air
Fri 7/246:11 pm
VPS
-
MDW
Nonstop2h 20m
Allegiant Air
Deal found 5/4$115
This Cheapflightsfares deal was found by Cheapflights users on 5/4. 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.
Fri 7/179:21 pm
MDW
-
VPS
Nonstop2h 14m
Allegiant Air
Mon 7/206:10 pm
VPS
-
MDW
Nonstop2h 20m
Allegiant Air
Deal found 5/4$118
This Gotogate deal was found by Cheapflights users on 4/30. 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.
Mon 10/266:44 pm
MDW
-
VPS
Nonstop2h 11m
Allegiant Air
Fri 10/305:50 pm
VPS
-
MDW
Nonstop2h 18m
Allegiant Air
Deal found 4/30$125

Find flight deals from Illinois to Valparaiso

Keep the following information in mind while searching for Illinois to Valparaiso flight deals. Data was last updated May 4, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$70
(Kiwi.com)

One-way from

$50
(Kiwi.com)

Popular in

September

Cheapest in

October

Average price

$348

Good round-trip deal

$114 or less

Good one-way deal

$89 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 Illinois to Valparaiso Destin-Ft Walton Beach
Search Deals
One-way flight from Illinois to Valparaiso Destin-Ft Walton Beach
Search Deals
High demand for flights, 6% potential price rise
Search Deals
Cheapest flight prices on average. 1% potential price decrease ($5 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in May 2026
Search Deals
Price to beat on a round-trip flight from Illinois to Valparaiso Destin-Ft Walton Beach.
Search Deals
Price to beat on a one-way flight from Illinois to Valparaiso Destin-Ft Walton Beach.
Search Deals

Cheapflights Fare Finder

 
Customize your flight search to find flights from Illinois 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 May 4, 2026.
Use the filters below to find and compare flights from Illinois to Valparaiso that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip

BellevilleValparaiso

BLV - VPS

BLVVPS

Belleville

Fri 6/5

9:35 pm-11:17 pm

Nonstop1h 42m

Valparaiso Destin-Ft Walton Beach

Thu 6/11

8:00 am-9:44 am

Nonstop1h 44m

$89

BellevilleValparaiso

BLV - VPS

BLVVPS

Belleville

Fri 6/12

9:34 pm-11:16 pm

Nonstop1h 42m

Valparaiso Destin-Ft Walton Beach

Mon 6/15

7:10 pm-8:54 pm

Nonstop1h 44m

$98
Quickest round-trip

EvansvilleValparaiso

EVV - VPS

EVVVPS

Evansville Dress Regional

Fri 7/10

11:41 am-1:19 pm

Nonstop1h 38m

Valparaiso Destin-Ft Walton Beach

Mon 7/13

9:15 am-10:51 am

Nonstop1h 36m

$102

PeoriaValparaiso

PIA - VPS

PIAVPS

Greater Peoria

Thu 5/28

8:20 pm-10:19 pm

Nonstop1h 59m

Valparaiso Destin-Ft Walton Beach

Sun 5/31

8:15 am-10:19 am

Nonstop2h 04m

$115

BellevilleValparaiso

BLV - VPS

BLVVPS

Belleville

Fri 9/11

2:19 pm-4:00 pm

Nonstop1h 41m

Valparaiso Destin-Ft Walton Beach

Mon 9/14

6:10 pm-7:56 pm

Nonstop1h 46m

$196

BellevilleValparaiso

BLV - VPS

BLVVPS

Belleville

Thu 10/22

8:02 pm-9:42 pm

Nonstop1h 40m

Valparaiso Destin-Ft Walton Beach

Tue 10/27

10:00 am-11:46 am

Nonstop1h 46m

$202

EvansvilleValparaiso

EVV - VPS

EVVVPS

Evansville Dress Regional

Thu 8/6

6:39 pm-11:15 pm

2 stops28h 36m

Valparaiso Destin-Ft Walton Beach

Mon 8/10

6:15 am-7:56 am

Nonstop1h 41m

$227

EvansvilleValparaiso

EVV - VPS

EVVVPS

Evansville Dress Regional

Thu 5/28

8:08 am-6:04 pm

2 stops33h 56m

Valparaiso Destin-Ft Walton Beach

Fri 6/5

9:15 am-10:56 am

Nonstop1h 41m

$273

EvansvilleValparaiso

EVV - VPS

EVVVPS

Evansville Dress Regional

Mon 7/6

8:33 am-6:04 pm

2 stops33h 31m

Valparaiso Destin-Ft Walton Beach

Mon 7/13

9:15 am-10:51 am

Nonstop1h 36m

$281

PeoriaValparaiso

PIA - VPS

PIAVPS

Greater Peoria

Sat 7/4

8:11 pm-1:23 pm

2 stops41h 12m

Valparaiso Destin-Ft Walton Beach

Sat 7/11

1:11 pm-3:13 pm

Nonstop2h 02m

$287

Flights are sorted by cheapest round-trip flights first.

Deals found on 4/30

Showing 1-10 of 60 resultsSorted by cheapest first
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Best time to book a flight from Illinois to Valparaiso

Have a flexible travel schedule? Discover the best time to fly to Valparaiso from Illinois 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 Illinois to Valparaiso

How far ahead should I book a flight from Illinois to Valparaiso, Florida?

The best time to book flights from Illinois to Valparaiso, Florida is 42 days before your desired departure date. The cost of your flight will likely increase significantly if you book two weeks in advance of your flight.

What is the cheapest month to book a flight from Illinois to Valparaiso, Florida?

Currently, October is the cheapest month in which you can book a flight from Illinois to Valparaiso, Florida (average of $52). Flying from Illinois to Valparaiso, Florida in January is currently the most expensive (average of $250). 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 IL to VPS?

Find hourly flight availability from Illinois 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 May 4, 2026.

When flying from Illinois to Valparaiso, Florida, the time of day you fly usually plays a role in the price. Save by searching for a flight in the evening, which can drop the price by up to 37% versus a flight at noon.

What is the cheapest day to fly from Illinois to Valparaiso, Florida?

Use this chart to determine the cheapest time to fly round-trip from Illinois to Valparaiso. Price data was last updated on May 2, 2026.

Travelers seeking maximum savings on their Illinois to Valparaiso, Florida flight should consider departing on Wednesday afternoons when fares are most often at their lowest. Tuesday mornings flights should be avoided if possible as fares are typically the most expensive at this time.

Weekly flight availability from Illinois to Valparaiso, Florida

Explore weekly flight availability from Illinois 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 May 4, 2026.

The most flights from USIL 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).

How much does it cost to fly round-trip from Illinois to Valparaiso, Florida?

Related info for your journey

Find useful and relevant information for your journey from Illinois 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 Illinois?

    Valparaiso Destin-Ft Walton Beach (VPS) is the airport you will fly into if you book a flight from Illinois to Valparaiso. It is only a 3.1 mi journey from Destin-Ft Walton Beach (VPS) to Valparaiso’s city center.

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

    A quick flight from Illinois to Valparaiso, Florida can take about 1h 42m. Allegiant Air provides one of the quickest options available for as low as $84. The distance from Illinois to Valparaiso, Florida is about 589 mi. All flights are typically nonstop.

  • What are the most popular routes from Illinois to Valparaiso, Florida?

    Most travelers choose Chicago O'Hare Intl - Valparaiso Destin-Ft Walton Beach, Lambert-St Louis - Valparaiso Destin-Ft Walton Beach or Chicago Midway - Valparaiso Destin-Ft Walton Beach when deciding on the best route from Illinois to Valparaiso, Florida.

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

    Looking at all options, your cheapest flight can be booked for $355. While the most popular route (Chicago O'Hare Intl - Valparaiso Destin-Ft Walton Beach) can be booked for $328 on average, our data indicates $678 when flying from Illinois to Valparaiso, Florida.

  • Can I find deals for flights from Illinois to Valparaiso that include hotel bookings?

    Yes. In addition to deals on Illinois to Valparaiso flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from Illinois to Valparaiso?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Illinois to Valparaiso.

  • Can I find deals for business class flights from Illinois to Valparaiso?

    Yes. Cheapflights offers flight deals from Illinois 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 Illinois to Valparaiso, Florida?

    Currently, October is the cheapest month in which you can book a flight from Illinois to Valparaiso, Florida (average of $52). Flying from Illinois to Valparaiso, Florida in January is currently the most expensive (average of $250). 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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Top 4 airlines flying from Illinois to Valparaiso

Discover the top 4 airlines that operate flights from Illinois 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 May 4, 2026.
AirlineCheapestAverageFlexibilityOn-time
Allegiant AirCheapest$82Average$195FlexibilityNo cancel feeOn-time88%
SouthwestCheapest$212Average$413FlexibilityNo cancel feeOn-time63%
American AirlinesCheapest$235Average$472FlexibilityNo cancel feeOn-time71%
DeltaCheapest$236Average$453FlexibilityNo cancel feeOn-timeN/A

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