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$47+ 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 12/21. Fares are subject to change and may not be available on all flights or dates of travel.
VPS — ORD
Nov 28 — Dec 51
Fri 11/28
Fri 12/5
1 adult, Economy
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Cheap flight deals from Valparaiso to Illinois

Keep the following information in mind while searching for Valparaiso to Illinois flight deals. Data was last updated October 29, 2025.

Most accurate provider

eDreams
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$131
(Cheapflightsfares)

One-way from

$47
(Cheapflightsfares)

Popular in

March

Cheapest in

May

Average price

$191

Good round-trip deal

$112 or less

Good one-way deal

$82 or less
Provider with most accurate pricing for Valparaiso Destin-Ft Walton Beach-Chicago (CHI) flight deals.
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Provider most trusted by Cheapflights users for Valparaiso Destin-Ft Walton Beach-Chicago (CHI) flights.
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From Valparaiso Destin-Ft Walton Beach to Illinois
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One-way flight from Valparaiso Destin-Ft Walton Beach to Illinois
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High demand for flights, 7% potential price rise
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Cheapest flight prices on average. 7% potential price decrease ($16 potential savings vs. average RT price).
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Average for round-trip flights in October 2025
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Price to beat on a round-trip flight from Valparaiso Destin-Ft Walton Beach to Illinois.
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Price to beat on a one-way flight from Valparaiso Destin-Ft Walton Beach to Illinois.
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Find 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 October 29, 2025.

This Cheapflightsfares deal was found by Cheapflights users on 10/26. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 11/235:24 pmVPS - MDW
Nonstop2h 19mAllegiant Air
Sat 11/299:09 amMDW - VPS
Nonstop2h 13mAllegiant Air
Deal found 10/26$131
This Booking.com deal was found by Cheapflights users on 10/27. 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 Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 11/99:00 amVPS - MDW
Nonstop2h 17mAllegiant Air
Thu 11/1312:07 pmMDW - VPS
Nonstop2h 05mAllegiant Air
Deal found 10/27$213
This Southwest deal was found by Cheapflights users on 10/28. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/311:20 amVPS - STL
1 stop5h 00mSouthwest
Sun 12/75:15 amSTL - VPS
1 stop8h 30mSouthwest
Deal found 10/28$221
This Kiwi.com deal was found by Cheapflights users on 10/26. 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.
Tue 12/231:01 pmVPS - MDW
Nonstop2h 19mMultiple Airlines
Tue 12/303:10 pmMDW - VPS
2 stops27h 04mMultiple Airlines
Deal found 10/26$248
This Kiwi.com deal was found by Cheapflights users on 10/29. 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.
Sun 11/2312:00 pmVPS - MDW
2 stops34h 43mMultiple Airlines
Sat 11/299:09 amMDW - VPS
Nonstop2h 13mMultiple Airlines
Deal found 10/29$281
This Sun Country Air deal was found by Cheapflights users on 10/27. 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 Sun Country Air is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/186:29 pmVPS - ORD
1 stop24h 09mSun Country Air
Sun 12/217:50 pmORD - VPS
1 stop14h 39mSun Country Air
Deal found 10/27$294
This Kiwi.com deal was found by Cheapflights users on 10/26. 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.
Fri 11/215:52 pmVPS - MDW
2 stops28h 51mMultiple Airlines
Sat 11/299:09 amMDW - VPS
Nonstop2h 13mMultiple Airlines
Deal found 10/26$300
This Kiwi.com deal was found by Cheapflights users on 10/28. 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.
Wed 11/1210:11 amVPS - MDW
2 stops29h 32mAllegiant Air
Sun 11/1612:07 pmMDW - VPS
Nonstop2h 05mAllegiant Air
Deal found 10/28$303
This Kiwi.com deal was found by Cheapflights users on 10/27. 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.
Sun 11/911:40 amVPS - MDW
3 stops47h 58mMultiple Airlines
Thu 11/1312:07 pmMDW - VPS
Nonstop2h 05mMultiple Airlines
Deal found 10/27$313
This Delta deal was found by Cheapflights users on 10/28. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 11/127:00 amVPS - STL
1 stop6h 00mDelta
Sun 11/169:33 amSTL - VPS
1 stop6h 34mDelta
Deal found 10/28$315
This Delta deal was found by Cheapflights users on 10/28. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/286:00 amVPS - STL
1 stop3h 49mDelta
Wed 12/39:30 amSTL - VPS
1 stop6h 42mDelta
Deal found 10/28$331
This Southwest deal was found by Cheapflights users on 10/27. 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.
Wed 12/107:15 amVPS - ORD
1 stop5h 00mSouthwest
Sat 12/131:45 pmORD - VPS
1 stop4h 10mSouthwest
Deal found 10/27$369

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 October 29, 2025.
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

Sun 11/23

5:24 pm-7:43 pm

Nonstop2h 19m

Chicago Midway

Sat 11/29

9:09 am-11:22 am

Nonstop2h 13m

$131

ValparaisoChicago

VPS - MDW

VPSMDW

Valparaiso Destin-Ft Walton Beach

Tue 12/23

1:01 pm-3:20 pm

Nonstop2h 19m

Chicago Midway

Tue 12/30

4:10 pm-6:23 pm

Nonstop2h 13m

$131

ValparaisoSt. Louis

VPS - STL

VPSSTL

Valparaiso Destin-Ft Walton Beach

Wed 12/3

11:20 am-4:20 pm

1 stop5h 00m

Lambert-St Louis

Sun 12/7

5:15 am-1:45 pm

1 stop8h 30m

$221

ValparaisoChicago

VPS - MDW

VPSMDW

Valparaiso Destin-Ft Walton Beach

Sun 11/23

12:00 pm-10:43 pm

2 stops34h 43m

Chicago Midway

Sat 11/29

9:09 am-11:22 am

Nonstop2h 13m

$281

ValparaisoChicago

VPS - ORD

VPSORD

Valparaiso Destin-Ft Walton Beach

Thu 12/18

6:29 pm-6:38 pm

1 stop24h 09m

Chicago O'Hare Intl

Sun 12/21

7:50 pm-10:29 am

1 stop14h 39m

$294

ValparaisoChicago

VPS - MDW

VPSMDW

Valparaiso Destin-Ft Walton Beach

Fri 11/21

5:52 pm-10:43 pm

2 stops28h 51m

Chicago Midway

Sat 11/29

9:09 am-11:22 am

Nonstop2h 13m

$300

ValparaisoChicago

VPS - MDW

VPSMDW

Valparaiso Destin-Ft Walton Beach

Wed 11/12

10:11 am-3:43 pm

2 stops29h 32m

Chicago Midway

Sun 11/16

12:07 pm-2:12 pm

Nonstop2h 05m

$303

ValparaisoSt. Louis

VPS - STL

VPSSTL

Valparaiso Destin-Ft Walton Beach

Wed 11/12

7:00 am-1:00 pm

1 stop6h 00m

Lambert-St Louis

Sun 11/16

9:33 am-4:07 pm

1 stop6h 34m

$315

ValparaisoChicago

VPS - MDW

VPSMDW

Valparaiso Destin-Ft Walton Beach

Tue 12/23

7:13 pm-5:38 pm

3 stops46h 25m

Chicago Midway

Tue 12/30

4:10 pm-6:23 pm

Nonstop2h 13m

$330

ValparaisoSt. Louis

VPS - STL

VPSSTL

Valparaiso Destin-Ft Walton Beach

Fri 11/28

6:00 am-9:49 am

1 stop3h 49m

Lambert-St Louis

Wed 12/3

9:30 am-4:12 pm

1 stop6h 42m

$331

Flights are sorted by cheapest round-trip flights first.

Deals found on 10/28

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 April is currently the most expensive (average of $202). 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 October 29, 2025.

It’s typically best to fly out from Valparaiso, Florida to Illinois in the evening. Doing so could potentially save you 59% on the flight price compared to flying at noon, which is usually more expensive.

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

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 October 29, 2025.
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
4,240 reviews

Crew

8.6

Entertainment

7.5

Food

7.0

Overall

8.0

Boarding

8.1

Comfort

8.0

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
4,240 reviews
Southwest
8.0
Very good
4,240 reviews

Crew

8.6

Entertainment

7.5

Food

7.0

Overall

8.0

Boarding

8.1

Comfort

8.0

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
7,994 reviews
Southwest
8.0
Very good
4,240 reviews

Crew

8.6

Entertainment

7.5

Food

7.0

Overall

8.0

Boarding

8.1

Comfort

8.0

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
11,032 reviews
Southwest
8.0
Very good
4,240 reviews

Crew

8.6

Entertainment

7.5

Food

7.0

Overall

8.0

Boarding

8.1

Comfort

8.0

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
695 reviews
Southwest
8.0
Very good
4,240 reviews

Crew

8.6

Entertainment

7.5

Food

7.0

Overall

8.0

Boarding

8.1

Comfort

8.0

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 Sun Country Air fly from Valparaiso, Florida to Illinois in about 2h 19m. The time it takes to get you to your destination can typically vary by up to 21h 50m. 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 $60. Users have also found prices from $102 and $127 on Delta and Sun Country Air, 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 - Bloomington-Normal, 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 Envoy Air (100%), Qatar Airways (60%) and American Airlines (59%).

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

    On average you can expect to pay $340 for a flight from Valparaiso, Florida to Illinois. The cheapest flight overall is $170 while the most popular route, (Valparaiso Destin-Ft Walton Beach - Chicago O'Hare Intl) is currently priced at $364.

  • 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 April is currently the most expensive (average of $202). 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

See prices for flight routes from nearby airports that may be better suited for you.
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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 October 29, 2025.
AirlineCheapestAverageFlexibilityOn-time
Allegiant AirCheapest$78Average$159FlexibilityNo cancel feeOn-time88%
American AirlinesCheapest$157Average$380FlexibilityNo cancel feeOn-time71%
DeltaCheapest$323Average$446FlexibilityNo cancel feeOn-timeN/A

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