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$49+ Cheap flights from Valparaiso, FL (VPS) to Chicago (CHI)

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 10/30. Fares are subject to change and may not be available on all flights or dates of travel.
VPS — CHI
Oct 14 — Oct 211
Tue 10/14
Tue 10/21
1 adult, Economy
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Cheap flight deals from Valparaiso to Chicago

Discover tips and strategies to find the most affordable flight options for your journey from Valparaiso (VPS) to Chicago (CHI). 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 September 14, 2025.

Round-trip from

$198
(Cheapflightsfares)

One-way from

$49
(Cheapflightsfares)

Popular in

March

Cheapest in

May

Average price

$287

Good round-trip deal

$478 or less
From Valparaiso Destin-Ft Walton Beach to Chicago (CHI)
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One-way flight from Valparaiso Destin-Ft Walton Beach to Chicago (CHI)
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High demand for flights, 12% potential price rise
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Cheapest flight prices on average. 7% potential price decrease ($15 potential savings vs. average RT price).
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Average for round-trip flights in September 2025
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Price to beat on a round-trip flight from Valparaiso Destin-Ft Walton Beach to Chicago (CHI).
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Find flight deals from Valparaiso to Chicago

Cheapest flights from Valparaiso to Chicago
Explore the most affordable flight options available from Valparaiso to Chicago. Find the lowest fares from popular airlines and budget airlines, with prices last updated on September 14, 2025.

This Cheapflightsfares deal was found by Cheapflights users on 9/13. 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.
Tue 11/2511:31 amVPS - MDW
Nonstop2h 19mAllegiant Air
Sat 11/299:09 amMDW - VPS
Nonstop2h 13mAllegiant Air
Deal found 9/13$198
This Kiwi.com deal was found by Cheapflights users on 9/12. 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 10/105:31 pmVPS - ORD
2 stops37h 43mMultiple Airlines
Mon 10/206:40 amORD - VPS
1 stop30h 08mMultiple Airlines
Deal found 9/12$293
This Kiwi.com deal was found by Cheapflights users on 9/13. 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.
Sat 10/186:30 amVPS - MDW
2 stops16h 17mMultiple Airlines
Mon 10/2012:08 pmMDW - VPS
1 stop4h 54mMultiple Airlines
Deal found 9/13$298
This Kiwi.com deal was found by Cheapflights users on 9/13. 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.
Sat 10/186:30 amVPS - ORD
1 stop10h 35mMultiple Airlines
Mon 10/207:43 pmORD - VPS
2 stops17h 05mMultiple Airlines
Deal found 9/13$307
This Sun Country Air deal was found by Cheapflights users on 9/13. 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.
Wed 11/266:27 pmVPS - ORD
1 stop13h 53mSun Country Air
Sat 11/298:22 pmORD - VPS
1 stop12h 46mSun Country Air
Deal found 9/13$311
This Kiwi.com deal was found by Cheapflights users on 9/13. 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.
Sat 10/116:30 amVPS - ORD
1 stop10h 35mMultiple Airlines
Sat 10/117:43 pmORD - VPS
2 stops17h 07mMultiple Airlines
Deal found 9/13$312
This American Airlines deal was found by Cheapflights users on 9/12. 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 10/117:00 amVPS - ORD
1 stop10h 10mAmerican Airlines
Sat 10/186:45 amORD - VPS
1 stop12h 08mAmerican Airlines
Deal found 9/12$316
This Southwest deal was found by Cheapflights users on 9/12. 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.
Fri 10/102:30 pmVPS - ORD
1 stop7h 00mSouthwest
Mon 10/202:50 pmORD - VPS
1 stop7h 05mSouthwest
Deal found 9/12$321
This Kiwi.com deal was found by Cheapflights users on 9/13. 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 10/173:46 pmVPS - ORD
2 stops18h 28mMultiple Airlines
Mon 10/2011:13 amORD - VPS
1 stop25h 35mMultiple Airlines
Deal found 9/13$326
This Kiwi.com deal was found by Cheapflights users on 9/13. 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 10/173:46 pmVPS - MDW
2 stops18h 35mMultiple Airlines
Mon 10/2012:08 pmMDW - VPS
1 stop4h 54mMultiple Airlines
Deal found 9/13$333
This Southwest deal was found by Cheapflights users on 9/13. 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.
Sat 10/185:30 pmVPS - MDW
1 stop4h 55mSouthwest
Mon 10/2012:55 pmMDW - VPS
1 stop5h 00mSouthwest
Deal found 9/13$349
This Southwest deal was found by Cheapflights users on 9/12. 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.
Mon 10/277:05 amVPS - ORD
1 stop9h 20mSouthwest
Mon 11/31:45 pmORD - VPS
1 stop7h 25mSouthwest
Deal found 9/12$354

Cheapflights Fare Finder

 
Customize your flight search to find flights from Valparaiso to Chicago 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 September 14, 2025.
Use the filters below to find and compare flights from Valparaiso to Chicago that are best for you.

Fly from

Valparaiso

Fly to

Chicago

Route

Depart

Return

Price

ValparaisoChicago

VPS - ORD

VPSORD

Valparaiso Destin-Ft Walton Beach

Fri 10/10

5:31 pm-7:14 am

2 stops37h 43m

Chicago O'Hare Intl

Mon 10/20

6:40 am-12:48 pm

1 stop30h 08m

$293

ValparaisoChicago

VPS - MDW

VPSMDW

Valparaiso Destin-Ft Walton Beach

Sat 10/18

6:30 am-10:47 pm

2 stops16h 17m

Chicago Midway

Mon 10/20

12:08 pm-5:02 pm

1 stop4h 54m

$298

ValparaisoChicago

VPS - ORD

VPSORD

Valparaiso Destin-Ft Walton Beach

Wed 11/26

6:27 pm-8:20 am

1 stop13h 53m

Chicago O'Hare Intl

Sat 11/29

8:22 pm-9:08 am

1 stop12h 46m

$311

ValparaisoChicago

VPS - ORD

VPSORD

Valparaiso Destin-Ft Walton Beach

Sat 10/11

6:30 am-5:05 pm

1 stop10h 35m

Chicago O'Hare Intl

Sat 10/11

7:43 pm-12:50 pm

2 stops17h 07m

$312

ValparaisoChicago

VPS - ORD

VPSORD

Valparaiso Destin-Ft Walton Beach

Fri 10/17

3:46 pm-10:14 am

2 stops18h 28m

Chicago O'Hare Intl

Mon 10/20

11:13 am-12:48 pm

1 stop25h 35m

$326

ValparaisoChicago

VPS - ORD

VPSORD

Valparaiso Destin-Ft Walton Beach

Tue 2/17

7:10 am-12:15 pm

1 stop5h 05m

Chicago O'Hare Intl

Fri 2/20

5:15 pm-9:10 pm

1 stop3h 55m

$339

ValparaisoChicago

VPS - MDW

VPSMDW

Valparaiso Destin-Ft Walton Beach

Sat 10/18

5:30 pm-10:25 pm

1 stop4h 55m

Chicago Midway

Mon 10/20

12:55 pm-5:55 pm

1 stop5h 00m

$349

ValparaisoChicago

VPS - ORD

VPSORD

Valparaiso Destin-Ft Walton Beach

Mon 10/27

7:05 am-4:25 pm

1 stop9h 20m

Chicago O'Hare Intl

Mon 11/3

1:45 pm-9:10 pm

1 stop7h 25m

$361

ValparaisoChicago

VPS - ORD

VPSORD

Valparaiso Destin-Ft Walton Beach

Wed 2/18

12:30 pm-2:59 pm

Nonstop2h 29m

Chicago O'Hare Intl

Fri 2/20

9:34 am-12:00 pm

Nonstop2h 26m

$364

ValparaisoChicago

VPS - MDW

VPSMDW

Valparaiso Destin-Ft Walton Beach

Fri 12/5

11:20 am-4:00 pm

1 stop4h 40m

Chicago Midway

Mon 12/8

5:00 am-1:15 pm

1 stop8h 15m

$369

Flights are sorted by cheapest round-trip flights first.

Deals found on 9/12

Showing 1-10 of 40 results
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Best time to book a flight from Valparaiso to Chicago

Have a flexible travel schedule? Discover the best time to fly to Chicago 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 Chicago

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

Currently, August is the cheapest month in which you can book a flight from Valparaiso, Florida to Chicago (average of $245). Flying from Valparaiso, Florida to Chicago in March is currently the most expensive (average of $321). 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 CHI?

Find hourly flight availability from Valparaiso to Chicago. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated September 14, 2025.

One of the essential ways to save on airfare from Valparaiso, Florida to Chicago is to remain as flexible as possible. Flights that are in the evening tend to be the most expensive. A flight at noon could potentially save you up to 70% on airfare.

Reviews of airlines servicing Chicago

Get insights into the airlines that provide service to Chicago. 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 Chicago. Reviews last updated September 14, 2025.
Get a feel of what it's like to fly with Southwest, American Airlines, and Allegiant Air from Valparaiso to Chicago 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
4,245 reviews

Boarding

8.1

Comfort

8.0

Food

7.0

Crew

8.6

Entertainment

7.5

Overall

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
4,245 reviews
Southwest
8.0
Very good
4,245 reviews

Boarding

8.1

Comfort

8.0

Food

7.0

Crew

8.6

Entertainment

7.5

Overall

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
10,000 reviews
Southwest
8.0
Very good
4,245 reviews

Boarding

8.1

Comfort

8.0

Food

7.0

Crew

8.6

Entertainment

7.5

Overall

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
699 reviews
Southwest
8.0
Very good
4,245 reviews

Boarding

8.1

Comfort

8.0

Food

7.0

Crew

8.6

Entertainment

7.5

Overall

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 Chicago. 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 Chicago?

    Valparaiso Destin-Ft Walton Beach (VPS), located 3.1 mi from the city center, is the airport you fly out of when you book flights from Valparaiso to Chicago. 2 airlines have flights from Destin-Ft Walton Beach to Chicago on a regular basis. Booking flights from Valparaiso Destin-Ft Walton Beach to Chicago should not be difficult; the airport handles an average of 0 outbound flights to Chicago per day.

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

    A quick flight from Valparaiso, Florida to Chicago can take about 5h 05m. Sun Country Air provides one of the quickest options available for as low as $339. The distance between Valparaiso, Florida and Chicago is about 797 mi. Both multi-stop and nonstop flights can be found to your destination and back.

  • What are the cheapest airlines flying from Valparaiso, Florida to Chicago round-trip?

    Cheapflights users have booked flights from Valparaiso, Florida to Chicago round-trip from $157. Another airline that can offer you cheap pricing is Delta. Users have found that American Airlines is 31% cheaper than the other options available to this destination.

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

    While on average a flight from Valparaiso, Florida to Chicago is generally $798, our data shows the cheapest flight currently is $365. When looking at the most popular route, (Valparaiso Destin-Ft Walton Beach - Chicago O'Hare Intl), you can expect to pay $293 for that flight.

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

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

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

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

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

    Yes. Cheapflights offers flight deals from Valparaiso to Chicago 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 Chicago?

    Currently, August is the cheapest month in which you can book a flight from Valparaiso, Florida to Chicago (average of $245). Flying from Valparaiso, Florida to Chicago in March is currently the most expensive (average of $321). 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
Merrillville
Lansing
Hammond
Benton Harbor
Porter
Chesterton

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Alternative routes for Valparaiso to Chicago

See prices for flight routes from nearby airports that may be better suited for you.
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Top 2 airlines flying from Valparaiso to Chicago

Discover the top 2 airlines that operate flights from Valparaiso to Chicago. 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 September 14, 2025.
AirlineCheapestAverageFlexibilityOn-time
American AirlinesCheapest$157Average$376FlexibilityNo cancel feeOn-time71%
DeltaCheapest$294Average$425FlexibilityNo cancel feeOn-timeN/A

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