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$75+ 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 3/12. Fares are subject to change and may not be available on all flights or dates of travel.
VPS — CHI
Jan 15 — Jan 221
Thu 1/15
Thu 1/22
1 adult, Economy
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Cheap 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 December 16, 2025.

This Booking.com deal was found by Cheapflights users on 12/15. 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 12/213:45 pmVPS - MDW
Nonstop2h 19mAllegiant Air
Tue 12/234:10 pmMDW - VPS
Nonstop2h 13mAllegiant Air
Deal found 12/15$215
This American Airlines deal was found by Cheapflights users on 12/15. 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 12/2311:41 amVPS - ORD
Nonstop2h 41mAmerican Airlines
Tue 12/304:05 pmORD - VPS
1 stop5h 27mAmerican Airlines
Deal found 12/15$372
This American Airlines deal was found by Cheapflights users on 12/15. 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.
Fri 12/1912:11 pmVPS - ORD
Nonstop2h 41mAmerican Airlines
Sat 1/38:39 amORD - VPS
Nonstop2h 39mAmerican Airlines
Deal found 12/15$377
This American Airlines deal was found by Cheapflights users on 12/15. 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 12/303:46 pmVPS - ORD
1 stop7h 29mAmerican Airlines
Mon 1/58:32 amORD - VPS
Nonstop2h 39mAmerican Airlines
Deal found 12/15$387
This American Airlines deal was found by Cheapflights users on 12/15. 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.
Thu 12/1812:08 pmVPS - ORD
Nonstop2h 41mAmerican Airlines
Mon 12/228:32 amORD - VPS
Nonstop2h 39mAmerican Airlines
Deal found 12/15$392
This American Airlines deal was found by Cheapflights users on 12/15. 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 12/307:39 amVPS - ORD
1 stop5h 01mAmerican Airlines
Sun 1/48:03 amORD - VPS
1 stop7h 50mAmerican Airlines
Deal found 12/15$396
This Delta deal was found by Cheapflights users on 12/15. 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 12/196:00 amVPS - MDW
1 stop5h 55mDelta
Sat 1/36:00 amMDW - VPS
1 stop4h 34mDelta
Deal found 12/15$396
This Southwest deal was found by Cheapflights users on 12/15. 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 12/306:10 pmVPS - MDW
1 stop7h 00mSouthwest
Mon 1/52:55 pmMDW - VPS
1 stop6h 20mSouthwest
Deal found 12/15$411
This American Airlines deal was found by Cheapflights users on 12/15. 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 12/307:39 amVPS - ORD
1 stop6h 33mAmerican Airlines
Sat 1/37:36 amORD - VPS
1 stop7h 30mAmerican Airlines
Deal found 12/15$416
This Southwest deal was found by Cheapflights users on 12/15. 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 12/306:10 pmVPS - MDW
1 stop7h 00mSouthwest
Sun 1/45:25 amMDW - VPS
2 stops7h 55mSouthwest
Deal found 12/15$417
This Southwest deal was found by Cheapflights users on 12/15. 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 12/186:05 pmVPS - MDW
1 stop6h 05mSouthwest
Mon 12/225:25 amMDW - VPS
1 stop5h 50mSouthwest
Deal found 12/15$452
This Kiwi.com deal was found by Cheapflights users on 12/15. 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 12/217:58 pmVPS - MDW
2 stops26h 00mMultiple Airlines
Tue 12/234:10 pmMDW - VPS
Nonstop2h 13mMultiple Airlines
Deal found 12/15$453

Find 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 December 16, 2025.

Most accurate provider

eDreams
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$269
(Kiwi.com)

One-way from

$75
(Booking.com)

Popular in

March

Cheapest in

May

Average price

$194

Good round-trip deal

$370 or less

Good one-way deal

$136 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 Chicago (CHI)
Search Deals
One-way flight from Valparaiso Destin-Ft Walton Beach to Chicago (CHI)
Search Deals
Highest demand for flights based on searches. 2% potential increase in price ($4 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 9% potential price decrease ($19 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in December 2025
Search Deals
Price to beat on a round-trip flight from Valparaiso Destin-Ft Walton Beach to Chicago (CHI).
Search Deals
Price to beat on a one-way flight from Valparaiso Destin-Ft Walton Beach to Chicago (CHI).
Search Deals

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 December 16, 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

Wed 1/21

1:31 pm-4:11 pm

Nonstop2h 40m

Chicago O'Hare Intl

Wed 1/28

10:30 am-1:01 pm

Nonstop2h 31m

$296

ValparaisoChicago

VPS - ORD

VPSORD

Valparaiso Destin-Ft Walton Beach

Sat 2/14

12:15 pm-2:59 pm

Nonstop2h 44m

Chicago O'Hare Intl

Wed 2/18

9:15 am-11:45 am

Nonstop2h 30m

$301

ValparaisoChicago

VPS - ORD

VPSORD

Valparaiso Destin-Ft Walton Beach

Sat 2/14

4:36 pm-12:10 am

1 stop7h 34m

Chicago O'Hare Intl

Tue 2/17

9:15 am-11:45 am

Nonstop2h 30m

$311

ValparaisoChicago

VPS - ORD

VPSORD

Valparaiso Destin-Ft Walton Beach

Wed 1/21

7:00 am-12:15 pm

1 stop5h 15m

Chicago O'Hare Intl

Wed 1/28

1:45 pm-6:55 pm

1 stop5h 10m

$315

ValparaisoChicago

VPS - ORD

VPSORD

Valparaiso Destin-Ft Walton Beach

Sat 1/24

6:00 am-10:13 am

1 stop4h 13m

Chicago O'Hare Intl

Wed 1/28

9:55 am-4:40 pm

1 stop6h 45m

$315

ValparaisoChicago

VPS - ORD

VPSORD

Valparaiso Destin-Ft Walton Beach

Sat 2/14

3:00 pm-7:19 pm

1 stop4h 19m

Chicago O'Hare Intl

Wed 2/18

9:52 am-4:03 pm

1 stop6h 11m

$315

ValparaisoChicago

VPS - ORD

VPSORD

Valparaiso Destin-Ft Walton Beach

Sat 2/14

3:00 pm-7:19 pm

1 stop4h 19m

Chicago O'Hare Intl

Tue 2/17

9:52 am-4:03 pm

1 stop6h 11m

$315

ValparaisoChicago

VPS - MDW

VPSMDW

Valparaiso Destin-Ft Walton Beach

Wed 4/1

7:05 am-12:02 pm

1 stop4h 57m

Chicago Midway

Tue 4/7

10:49 am-4:08 pm

1 stop5h 19m

$315

ValparaisoChicago

VPS - MDW

VPSMDW

Valparaiso Destin-Ft Walton Beach

Tue 3/31

6:00 am-12:02 pm

1 stop6h 02m

Chicago Midway

Sat 4/4

4:30 pm-11:02 pm

1 stop6h 32m

$315

ValparaisoChicago

VPS - MDW

VPSMDW

Valparaiso Destin-Ft Walton Beach

Tue 3/31

7:15 am-5:05 pm

1 stop9h 50m

Chicago Midway

Sat 4/4

5:30 am-3:55 pm

2 stops10h 25m

$326

Flights are sorted by cheapest round-trip flights first.

Deals found on 12/15

Showing 1-10 of 36 results
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Compare providers for flights from Valparaiso to Chicago

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 Valparaiso to Chicago in December.
ProviderPrice AccuracyTrust Score*
FlightHubPrice Accuracy3 starsTrust Score*1 star
eDreamsPrice Accuracy3 starsTrust Score*3 stars
ExpediaPrice Accuracy2 starsTrust Score*3 stars

*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 Valparaiso, Florida-Chicago flights, users find the pricing of eDreams to be most consistent on Cheapflights vs. eDreams Users can find the same prices on Valparaiso, Florida-Chicago flight deals on Cheapflights vs. eDreams >95% of the time. Price accuracy is based on data collected from Valparaiso, Florida-Chicago flight searches over the past month and is updated monthly.
  • Most trusted provider: When it comes to deals on Valparaiso, Florida-Chicago flights, Cheapflights users trust eDreams the most. eDreams 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 Valparaiso, Florida-Chicago 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 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, June is the cheapest month in which you can book a flight from Valparaiso, Florida to Chicago (average of $99). Flying from Valparaiso, Florida to Chicago 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 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 December 16, 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 afternoon tend to be the most expensive. A flight at noon could potentially save you up to 64% on airfare.

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

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 December 16, 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
7.9
Good
4,250 reviews

Entertainment

7.5

Crew

8.6

Food

7.0

Boarding

8.1

Overall

7.9

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
7.9
Good
4,250 reviews
Southwest
7.9
Good
4,250 reviews

Entertainment

7.5

Crew

8.6

Food

7.0

Boarding

8.1

Overall

7.9

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
11,049 reviews
Southwest
7.9
Good
4,250 reviews

Entertainment

7.5

Crew

8.6

Food

7.0

Boarding

8.1

Overall

7.9

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
700 reviews
Southwest
7.9
Good
4,250 reviews

Entertainment

7.5

Crew

8.6

Food

7.0

Boarding

8.1

Overall

7.9

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 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. 3 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 2h 40m. American Airlines provides one of the quickest options available for as low as $296. 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 $84. Other airlines that can offer you cheap pricing are American Airlines, from $157, and Delta, from $323. Users have found that Allegiant Air is 57% cheaper than the other options available to this destination.

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

    To fly one-way, consider booking your trip with Allegiant Air, which is currently one of the cheapest options available, starting at $47. American Airlines flights start at $169 while deals on Delta start at $217 one-way.

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

    No one likes to see their flight delayed. When booking a flight from Valparaiso, Florida to Chicago consider choosing Qatar Airways (70%), American Airlines (68%) or Envoy Air (68%) as they are the most reliable in getting you off to your destination on time.

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

    While on average a flight from Valparaiso, Florida to Chicago is generally $399, our data shows the cheapest flight currently is $114. When looking at the most popular route, (Valparaiso Destin-Ft Walton Beach - Chicago O'Hare Intl), you can expect to pay $315 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, June is the cheapest month in which you can book a flight from Valparaiso, Florida to Chicago (average of $99). Flying from Valparaiso, Florida to Chicago 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

Traveling to a place near Chicago?

Book flights to Chicago if you plan to visit one of these locations
Lansing
Merrillville
Hammond
Porter
Benton Harbor

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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 3 airlines flying from Valparaiso to Chicago

Discover the top 3 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 December 16, 2025.
AirlineCheapestAverageFlexibilityOn-time
Allegiant AirCheapest$84Average$144FlexibilityNo cancel feeOn-time88%
American AirlinesCheapest$157Average$376FlexibilityNo cancel feeOn-time71%
DeltaCheapest$323Average$425FlexibilityNo cancel feeOn-timeN/A

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