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$92+ Cheap flights from Valparaiso, FL (VPS) to Illinois

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 2/26. Fares are subject to change and may not be available on all flights or dates of travel.
VPS — ORD
Feb 28 — Mar 71
Sat 2/28
Sat 3/7
1 adult, Economy
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Cheap flight deals from Valparaiso to Illinois

Cheapest flights from Valparaiso to Illinois
Explore the most affordable flight options available from Valparaiso to Illinois. Find the lowest fares from popular airlines and budget airlines, with prices last updated on January 29, 2026.

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.
Mon 6/296:12 pm
VPS
-
MDW
Nonstop2h 21m
Allegiant Air
Fri 7/39:15 pm
MDW
-
VPS
Nonstop2h 14m
Allegiant Air
Deal found 1/28$194
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.
Fri 8/76:14 pm
VPS
-
MDW
Nonstop2h 21m
Allegiant Air
Mon 8/109:25 pm
MDW
-
VPS
Nonstop2h 14m
Allegiant Air
Deal found 1/28$253
This Kiwi.com deal was found by Cheapflights users on 1/26. 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.
Thu 4/232:40 pm
VPS
-
MDW
Nonstop2h 17m
Multiple Airlines
Mon 4/279:14 am
MDW
-
VPS
3 stops23h 34m
Multiple Airlines
Deal found 1/26$299
This American Airlines 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/84:04 pm
VPS
-
ORD
1 stop5h 21m
American Airlines
Tue 8/117:08 am
ORD
-
VPS
Nonstop2h 12m
American Airlines
Deal found 1/28$326
This Southwest deal was found by Cheapflights users on 1/27. 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 2/247:00 am
VPS
-
ORD
1 stop5h 15m
Southwest
Tue 3/31:45 pm
ORD
-
VPS
1 stop5h 10m
Southwest
Deal found 1/27$333
This Southwest deal was found by Cheapflights users on 1/27. 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 2/247:00 am
VPS
-
MDW
1 stop6h 25m
Southwest
Tue 3/38:15 am
MDW
-
VPS
1 stop5h 05m
Southwest
Deal found 1/27$333
This American Airlines 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 7/111:37 am
VPS
-
ORD
Nonstop2h 42m
American Airlines
Thu 7/98:38 am
ORD
-
VPS
Nonstop2h 29m
American Airlines
Deal found 1/28$335
This Southwest deal was found by Cheapflights users on 1/26. 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 3/56:00 pm
VPS
-
STL
1 stop6h 05m
Southwest
Sun 3/85:50 pm
STL
-
VPS
1 stop3h 25m
Southwest
Deal found 1/26$340
This American Airlines deal was found by Cheapflights users on 1/27. 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.
Sat 2/1412:49 pm
VPS
-
STL
1 stop6h 41m
American Airlines
Thu 2/194:13 pm
STL
-
VPS
1 stop7h 05m
American Airlines
Deal found 1/27$341
This Kiwi.com deal was found by Cheapflights users on 1/27. 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 3/1312:11 pm
VPS
-
MDW
3 stops33h 34m
Multiple Airlines
Sun 3/158:43 pm
MDW
-
VPS
Nonstop2h 08m
Multiple Airlines
Deal found 1/27$342
This Delta deal was found by Cheapflights users on 1/27. 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.
Fri 4/174:59 pm
VPS
-
STL
1 stop4h 20m
Delta
Thu 4/236:50 pm
STL
-
VPS
1 stop4h 29m
Delta
Deal found 1/27$342
This American Airlines 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 3/186:00 am
VPS
-
STL
2 stops9h 35m
American Airlines
Thu 3/266:20 pm
STL
-
VPS
1 stop5h 39m
American Airlines
Deal found 1/28$348

Find flight deals from Valparaiso to Illinois

Keep the following information in mind while searching for Valparaiso to Illinois flight deals. Data was last updated January 29, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$194
(Kiwi.com)

One-way from

$92
(Kiwi.com)

Popular in

December

Cheapest in

May

Average price

$376

Good round-trip deal

$102 or less

Good one-way deal

$73 or less
Provider with most accurate pricing for Valparaiso Destin-Ft Walton Beach-Chicago (CHI) flight deals.
Search Deals
Provider most trusted by Cheapflights users for Valparaiso Destin-Ft Walton Beach-Chicago (CHI) flights.
Search Deals
From Valparaiso Destin-Ft Walton Beach to Illinois
Search Deals
One-way flight from Valparaiso Destin-Ft Walton Beach to Illinois
Search Deals
Highest demand for flights based on searches. 27% potential increase in price ($82 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 7% potential price decrease ($16 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 Valparaiso Destin-Ft Walton Beach to Illinois.
Search Deals
Price to beat on a one-way flight from Valparaiso Destin-Ft Walton Beach to Illinois.
Search Deals

Cheapflights Fare Finder

 
Customize your flight search to find flights from Valparaiso to Illinois 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 29, 2026.
Use the filters below to find and compare flights from Valparaiso to Illinois that are best for you.

Fly from

Valparaiso

Fly to

Illinois

Route

Depart

Return

Price

ValparaisoChicago

VPS - MDW

VPSMDW

Valparaiso Destin-Ft Walton Beach

Mon 6/29

6:12 pm-8:33 pm

Nonstop2h 21m

Chicago Midway

Fri 7/3

9:15 pm-11:29 pm

Nonstop2h 14m

$194

ValparaisoChicago

VPS - MDW

VPSMDW

Valparaiso Destin-Ft Walton Beach

Thu 4/23

2:40 pm-4:57 pm

Nonstop2h 17m

Chicago Midway

Mon 4/27

9:14 am-8:48 am

3 stops23h 34m

$299

ValparaisoChicago

VPS - MDW

VPSMDW

Valparaiso Destin-Ft Walton Beach

Tue 2/24

7:00 am-1:25 pm

1 stop6h 25m

Chicago Midway

Tue 3/3

8:15 am-1:20 pm

1 stop5h 05m

$333

ValparaisoChicago

VPS - ORD

VPSORD

Valparaiso Destin-Ft Walton Beach

Wed 7/1

11:37 am-2:19 pm

Nonstop2h 42m

Chicago O'Hare Intl

Thu 7/9

8:38 am-11:07 am

Nonstop2h 29m

$335

ValparaisoChicago

VPS - ORD

VPSORD

Valparaiso Destin-Ft Walton Beach

Tue 2/24

12:15 pm-9:50 pm

2 stops9h 35m

Chicago O'Hare Intl

Tue 3/3

1:45 pm-6:55 pm

1 stop5h 10m

$339

ValparaisoSt. Louis

VPS - STL

VPSSTL

Valparaiso Destin-Ft Walton Beach

Thu 3/5

6:00 pm-12:05 am

1 stop6h 05m

Lambert-St Louis

Sun 3/8

5:50 pm-9:15 pm

1 stop3h 25m

$340

ValparaisoSt. Louis

VPS - STL

VPSSTL

Valparaiso Destin-Ft Walton Beach

Sat 2/14

12:49 pm-7:30 pm

1 stop6h 41m

Lambert-St Louis

Thu 2/19

4:13 pm-11:18 pm

1 stop7h 05m

$341

ValparaisoSt. Louis

VPS - STL

VPSSTL

Valparaiso Destin-Ft Walton Beach

Fri 3/13

5:04 pm-11:58 pm

1 stop6h 54m

Lambert-St Louis

Mon 3/16

6:59 pm-11:15 pm

1 stop4h 16m

$342

ValparaisoSt. Louis

VPS - STL

VPSSTL

Valparaiso Destin-Ft Walton Beach

Fri 4/17

4:59 pm-9:19 pm

1 stop4h 20m

Lambert-St Louis

Thu 4/23

6:50 pm-11:19 pm

1 stop4h 29m

$342

ValparaisoSt. Louis

VPS - STL

VPSSTL

Valparaiso Destin-Ft Walton Beach

Wed 5/13

9:25 am-3:58 pm

1 stop6h 33m

Lambert-St Louis

Sun 5/17

6:30 am-1:29 pm

1 stop6h 59m

$342

Flights are sorted by cheapest round-trip flights first.

Deals found on 1/27

Showing 1-10 of 54 results
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Best time to book a flight from Valparaiso to Illinois

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

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

Currently, June is the cheapest month in which you can book a flight from Valparaiso, Florida to Illinois (average of $78). Flying from Valparaiso, Florida to Illinois in December is currently the most expensive (average of $228). 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 VPS to IL?

Find hourly flight availability from Valparaiso to Illinois. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated January 29, 2026.

It’s typically best to fly out from Valparaiso, Florida to Illinois in the evening. Doing so could potentially save you 70% on the flight price compared to flying in the afternoon, which is usually more expensive.

Reviews of airlines servicing Illinois

Get insights into the airlines that provide service to Illinois. 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 Illinois. Reviews last updated January 29, 2026.
Get a feel of what it's like to fly with Southwest, Delta, and American Airlines from Valparaiso to Illinois by reading reviews from past customers. You can also see how each airline compares in terms of entertainment options, comfort, food, crew/service, and boarding process.
Southwest
8.0
Very good
4,267 reviews

Entertainment

7.5

Crew

8.6

Comfort

8.0

Overall

8.0

Boarding

8.1

Food

7.0

Reviews

1 / 20
2.0
Mediocre

Anonymous,Feb 2025

MCO - STL

Cancelled at last minute, SWA unable to assist in formulating alternate plans. Wound up renting a car and driving 13 hours to beat bad weather forecast at home. Not SWA’s fault that there was significant bad weather across the country.
Southwest
8.0
Very good
4,267 reviews
Southwest
8.0
Very good
4,267 reviews

Entertainment

7.5

Crew

8.6

Comfort

8.0

Overall

8.0

Boarding

8.1

Food

7.0

Reviews

1 / 20
2.0
Mediocre

Anonymous,Feb 2025

MCO - STL

Cancelled at last minute, SWA unable to assist in formulating alternate plans. Wound up renting a car and driving 13 hours to beat bad weather forecast at home. Not SWA’s fault that there was significant bad weather across the country.
Delta
7.9
Good
8,127 reviews
Southwest
8.0
Very good
4,267 reviews

Entertainment

7.5

Crew

8.6

Comfort

8.0

Overall

8.0

Boarding

8.1

Food

7.0

Reviews

1 / 20
2.0
Mediocre

Anonymous,Feb 2025

MCO - STL

Cancelled at last minute, SWA unable to assist in formulating alternate plans. Wound up renting a car and driving 13 hours to beat bad weather forecast at home. Not SWA’s fault that there was significant bad weather across the country.
American Airlines
7.2
Good
11,206 reviews
Southwest
8.0
Very good
4,267 reviews

Entertainment

7.5

Crew

8.6

Comfort

8.0

Overall

8.0

Boarding

8.1

Food

7.0

Reviews

1 / 20
2.0
Mediocre

Anonymous,Feb 2025

MCO - STL

Cancelled at last minute, SWA unable to assist in formulating alternate plans. Wound up renting a car and driving 13 hours to beat bad weather forecast at home. Not SWA’s fault that there was significant bad weather across the country.
Allegiant Air
7.2
Good
706 reviews
Southwest
8.0
Very good
4,267 reviews

Entertainment

7.5

Crew

8.6

Comfort

8.0

Overall

8.0

Boarding

8.1

Food

7.0

Reviews

1 / 20
2.0
Mediocre

Anonymous,Feb 2025

MCO - STL

Cancelled at last minute, SWA unable to assist in formulating alternate plans. Wound up renting a car and driving 13 hours to beat bad weather forecast at home. Not SWA’s fault that there was significant bad weather across the country.

Related info for your journey

Find useful and relevant information for your journey from Valparaiso to Illinois. 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 from for flights from Valparaiso to Illinois?

    If you book a flight to Illinois from Valparaiso, you will be flying from Destin-Ft Walton Beach, which is the city’s only airport. Valparaiso Destin-Ft Walton Beach (VPS) is located 3.1 mi from the center of Valparaiso.

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

    Airlines like Allegiant Air, Southwest, and American Airlines fly from Valparaiso, Florida to Illinois in about 2h 21m. The time it takes to get you to your destination can typically vary by up to 4h 04m. There are 783 mi between Valparaiso, Florida and Illinois. Both multi-stop and nonstop flights can be found to your destination and back.

  • What are the cheapest airlines to fly from Valparaiso, Florida to Illinois one-way?

    For one-way options, check prices for Allegiant Air. According to our data, you can fly for as low as $37. Users have also found prices from $88 and $112 on American Airlines and Southwest, respectively.

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

    While some choose either Valparaiso Destin-Ft Walton Beach - Chicago Midway or Valparaiso Destin-Ft Walton Beach - Lambert-St Louis, Valparaiso Destin-Ft Walton Beach - Chicago O'Hare Intl is the most popular route from Valparaiso, Florida to Illinois.

  • What are the most reliable airlines from Valparaiso, Florida to Illinois?

    The top 3 most reliable airlines when flying from Valparaiso, Florida to Illinois are Qatar Airways (68%), American Airlines (65%) and Envoy Air (65%).

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

    On average you can expect to pay $345 for a flight from Valparaiso, Florida to Illinois. The cheapest flight overall is $147 while the most popular route, (Valparaiso Destin-Ft Walton Beach - Chicago O'Hare Intl) is currently priced at $351.

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

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

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

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

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

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

    Currently, June is the cheapest month in which you can book a flight from Valparaiso, Florida to Illinois (average of $78). Flying from Valparaiso, Florida to Illinois in December is currently the most expensive (average of $228). 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

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Alternative routes for Valparaiso to Illinois

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Top 3 airlines flying from Valparaiso to Illinois

Discover the top 3 airlines that operate flights from Valparaiso to Illinois. 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 29, 2026.
AirlineCheapestAverageFlexibilityOn-time
Allegiant AirCheapest$78Average$143FlexibilityNo cancel feeOn-time88%
American AirlinesCheapest$157Average$376FlexibilityNo cancel feeOn-time71%
DeltaCheapest$323Average$425FlexibilityNo cancel feeOn-timeN/A

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