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$91+ 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 8/10. Fares are subject to change and may not be available on all flights or dates of travel.
VPS — CHI
Sep 2 — Sep 91
Wed 9/2
Wed 9/9
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 August 3, 2026.

This Cheapflightsfares deal was found by Cheapflights users on 7/29. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 8/146:14 pm
VPS
-
MDW
Nonstop2h 21m
Allegiant Air
Mon 8/179:25 pm
MDW
-
VPS
Nonstop2h 14m
Allegiant Air
Deal found 7/29$134
This Kiwi.com deal was found by Cheapflights users on 7/30. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/138:37 pm
VPS
-
MDW
1 stop18h 22m
Allegiant Air
Mon 8/179:25 pm
MDW
-
VPS
Nonstop2h 14m
Allegiant Air
Deal found 7/30$207
This Kiwi.com deal was found by Cheapflights users on 8/1. 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 8/36:10 pm
VPS
-
MDW
Nonstop2h 20m
Allegiant Air
Fri 8/79:25 pm
MDW
-
VPS
Nonstop2h 14m
Allegiant Air
Deal found 8/1$254
This Kiwi.com deal was found by Cheapflights users on 7/29. 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.
Fri 8/146:14 pm
VPS
-
MDW
Nonstop2h 21m
Multiple Airlines
Mon 8/1711:06 am
MDW
-
VPS
2 stops46h 42m
Multiple Airlines
Deal found 7/29$293
This Kiwi.com deal was found by Cheapflights users on 8/2. 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.
Thu 9/1010:56 am
VPS
-
ORD
1 stop13h 27m
Multiple Airlines
Sun 9/136:30 am
ORD
-
VPS
1 stop9h 50m
Multiple Airlines
Deal found 8/2$316
This Southwest deal was found by Cheapflights users on 7/30. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/77:15 am
VPS
-
MDW
1 stop3h 40m
Southwest
Sat 10/1011:25 am
MDW
-
VPS
1 stop5h 50m
Southwest
Deal found 7/30$317
This Kiwi.com deal was found by Cheapflights users on 7/30. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/139:05 pm
VPS
-
MDW
3 stops24h 58m
Multiple Airlines
Mon 8/179:25 pm
MDW
-
VPS
Nonstop2h 14m
Multiple Airlines
Deal found 7/30$319
This Southwest deal was found by Cheapflights users on 7/30. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/276:25 pm
VPS
-
MDW
1 stop3h 55m
Southwest
Mon 8/315:30 am
MDW
-
VPS
1 stop6h 25m
Southwest
Deal found 7/30$321
This Kiwi.com deal was found by Cheapflights users on 8/2. 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.
Thu 9/1010:56 am
VPS
-
ORD
1 stop13h 27m
Multiple Airlines
Thu 9/177:28 pm
ORD
-
VPS
2 stops21h 35m
Multiple Airlines
Deal found 8/2$333
This Southwest deal was found by Cheapflights users on 7/30. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/292:00 pm
VPS
-
MDW
1 stop5h 05m
Southwest
Sat 9/56:35 am
MDW
-
VPS
1 stop6h 35m
Southwest
Deal found 7/30$344
This Kiwi.com deal was found by Cheapflights users on 7/31. 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 10/157:00 am
VPS
-
ORD
1 stop27h 01m
Multiple Airlines
Sat 10/171:52 pm
ORD
-
VPS
2 stops33h 45m
Multiple Airlines
Deal found 7/31$345
This Kiwi.com deal was found by Cheapflights users on 7/30. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/1210:35 am
VPS
-
ORD
1 stop8h 00m
Multiple Airlines
Sun 11/152:03 pm
ORD
-
VPS
2 stops29h 03m
Multiple Airlines
Deal found 7/30$368

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 August 3, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$134
(Cheapflightsfares)

One-way from

$91
(Super.com)

Popular in

August

Cheapest in

October

Average price

$801

Good round-trip deal

$200 or less

Good one-way deal

$72 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. 32% potential increase in price ($177 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 11% potential price decrease ($39 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in August 2026
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 August 3, 2026.
Use the filters below to find and compare flights from Valparaiso to Chicago that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip
Quickest round-trip

ValparaisoChicago

VPS - MDW

VPSMDW

Valparaiso Destin-Ft Walton Beach

Fri 8/14

6:14 pm-8:35 pm

Nonstop2h 21m

Chicago Midway

Mon 8/17

9:25 pm-11:39 pm

Nonstop2h 14m

$134

ValparaisoChicago

VPS - MDW

VPSMDW

Valparaiso Destin-Ft Walton Beach

Fri 8/14

6:14 pm-8:35 pm

Nonstop2h 21m

Chicago Midway

Mon 8/17

11:06 am-9:48 am

2 stops46h 42m

$293

ValparaisoChicago

VPS - MDW

VPSMDW

Valparaiso Destin-Ft Walton Beach

Wed 10/7

12:15 pm-9:20 pm

2 stops9h 05m

Chicago Midway

Sat 10/10

11:25 am-5:15 pm

1 stop5h 50m

$327

ValparaisoChicago

VPS - MDW

VPSMDW

Valparaiso Destin-Ft Walton Beach

Sat 9/5

7:25 am-1:20 pm

2 stops5h 55m

Chicago Midway

Mon 9/7

5:55 am-9:35 am

1 stop3h 40m

$327

ValparaisoChicago

VPS - MDW

VPSMDW

Valparaiso Destin-Ft Walton Beach

Sat 8/29

10:55 am-8:30 pm

2 stops9h 35m

Chicago Midway

Sat 9/5

6:45 am-4:35 pm

2 stops9h 50m

$355

ValparaisoChicago

VPS - MDW

VPSMDW

Valparaiso Destin-Ft Walton Beach

Mon 9/14

12:40 pm-7:20 pm

1 stop6h 40m

Chicago Midway

Mon 9/21

5:30 pm-9:00 pm

1 stop3h 30m

$363

ValparaisoChicago

VPS - MDW

VPSMDW

Valparaiso Destin-Ft Walton Beach

Tue 9/22

2:15 pm-8:50 pm

1 stop6h 35m

Chicago Midway

Fri 9/25

5:30 pm-9:00 pm

1 stop3h 30m

$365

ValparaisoChicago

VPS - ORD

VPSORD

Valparaiso Destin-Ft Walton Beach

Tue 11/24

11:44 am-2:39 pm

Nonstop2h 55m

Chicago O'Hare Intl

Wed 12/2

8:33 am-10:59 am

Nonstop2h 26m

$386

ValparaisoChicago

VPS - ORD

VPSORD

Valparaiso Destin-Ft Walton Beach

Tue 11/24

5:00 pm-11:59 pm

1 stop6h 59m

Chicago O'Hare Intl

Tue 12/1

6:19 pm-11:20 pm

1 stop5h 01m

$405

ValparaisoChicago

VPS - ORD

VPSORD

Valparaiso Destin-Ft Walton Beach

Thu 10/15

2:46 pm-8:52 pm

1 stop6h 06m

Chicago O'Hare Intl

Sat 10/17

1:23 pm-6:42 pm

1 stop5h 19m

$434

Flights are sorted by cheapest round-trip flights first.

Deals found on 7/30

Showing 1-10 of 34 resultsSorted by cheapest first
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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 August.
ProviderPrice AccuracyTrust Score*
FlightHubPrice Accuracy3 starsTrust Score*3 stars
ExpediaPrice Accuracy1 starTrust Score*3 stars
Kiwi.comPrice Accuracy3 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 FlightHub to be most consistent on Cheapflights vs. FlightHub Users can find the same prices on Valparaiso, Florida-Chicago flight deals on Cheapflights vs. FlightHub >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 FlightHub the most. FlightHub 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, February is the cheapest month in which you can book a flight from Valparaiso, Florida to Chicago (average of $295). Flying from Valparaiso, Florida to Chicago in August is currently the most expensive (average of $517). 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 August 3, 2026.

Regardless of the time of day you decide to fly, the ticket price will remain around the same. Book flights from Valparaiso, Florida to Chicago as you normally would.

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 August 3, 2026.
Get a feel of what it's like to fly with Allegiant Air and American Airlines 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.
Allegiant Air
7.3
Good
680 reviews

Crew

8.1

Overall

7.3

Comfort

6.9

Entertainment

5.5

Boarding

7.6

Food

5.8

Reviews

1 / 20
2.0
Mediocre

Nic,Aug 2026

SRQ - ALB

Worker at gate refused to let me measure my personal item and insisted it needed to be a carryon and to pay 75$. I understand if it’s too big but she wouldn’t even let me go measure it. She eventually let me measure my own luggage after back n forth. It is a few inches too big and she comes over and attempts to grab my suitcase out my hands and I pull it away from her. She then shuts the door of the gate and says to call the police. I then just offer to pay for the carryon and she says ok. Then refuses to use let me use my tap to pay, luckily I had my physical card on me. As soon as I walked out the door I respectfully asked for her name. She began screaming at me and threatening me. This worker was just so hostile I understand if my stuffs too big I will pay the difference I’m not trying to get over on the rules. I was confused because I was allowed to board my destination flight with this item as a personal item. So I was confused by this whole situation from the go. It also caused a massive scene at the airport and I was extremely embarrassed. It genuinely seemed like this worker was out to get me for some reason. I had literally just arrived to the gate as it was already boarding so I hadn’t done anything prior. Super weird situation and it really spooked me.
Allegiant Air
7.3
Good
680 reviews
Allegiant Air
7.3
Good
680 reviews

Crew

8.1

Overall

7.3

Comfort

6.9

Entertainment

5.5

Boarding

7.6

Food

5.8

Reviews

1 / 20
2.0
Mediocre

Nic,Aug 2026

SRQ - ALB

Worker at gate refused to let me measure my personal item and insisted it needed to be a carryon and to pay 75$. I understand if it’s too big but she wouldn’t even let me go measure it. She eventually let me measure my own luggage after back n forth. It is a few inches too big and she comes over and attempts to grab my suitcase out my hands and I pull it away from her. She then shuts the door of the gate and says to call the police. I then just offer to pay for the carryon and she says ok. Then refuses to use let me use my tap to pay, luckily I had my physical card on me. As soon as I walked out the door I respectfully asked for her name. She began screaming at me and threatening me. This worker was just so hostile I understand if my stuffs too big I will pay the difference I’m not trying to get over on the rules. I was confused because I was allowed to board my destination flight with this item as a personal item. So I was confused by this whole situation from the go. It also caused a massive scene at the airport and I was extremely embarrassed. It genuinely seemed like this worker was out to get me for some reason. I had literally just arrived to the gate as it was already boarding so I hadn’t done anything prior. Super weird situation and it really spooked me.
American Airlines
7.1
Good
11,842 reviews
Allegiant Air
7.3
Good
680 reviews

Crew

8.1

Overall

7.3

Comfort

6.9

Entertainment

5.5

Boarding

7.6

Food

5.8

Reviews

1 / 20
2.0
Mediocre

Nic,Aug 2026

SRQ - ALB

Worker at gate refused to let me measure my personal item and insisted it needed to be a carryon and to pay 75$. I understand if it’s too big but she wouldn’t even let me go measure it. She eventually let me measure my own luggage after back n forth. It is a few inches too big and she comes over and attempts to grab my suitcase out my hands and I pull it away from her. She then shuts the door of the gate and says to call the police. I then just offer to pay for the carryon and she says ok. Then refuses to use let me use my tap to pay, luckily I had my physical card on me. As soon as I walked out the door I respectfully asked for her name. She began screaming at me and threatening me. This worker was just so hostile I understand if my stuffs too big I will pay the difference I’m not trying to get over on the rules. I was confused because I was allowed to board my destination flight with this item as a personal item. So I was confused by this whole situation from the go. It also caused a massive scene at the airport and I was extremely embarrassed. It genuinely seemed like this worker was out to get me for some reason. I had literally just arrived to the gate as it was already boarding so I hadn’t done anything prior. Super weird situation and it really spooked me.

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 21m. Allegiant Air provides one of the quickest options available for as low as $134. The distance between Valparaiso, Florida and Chicago is about 783 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 $86. Other airlines that can offer you cheap pricing are Southwest, from $234, and American Airlines, from $295. Users have found that Allegiant Air is 76% cheaper than the other options available to this destination.

  • 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 (93%), American Airlines (89%) or Envoy Air (89%) 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 $573, our data shows the cheapest flight currently is $433. When looking at the most popular route, (Valparaiso Destin-Ft Walton Beach - Chicago O'Hare Intl), you can expect to pay $316 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, February is the cheapest month in which you can book a flight from Valparaiso, Florida to Chicago (average of $295). Flying from Valparaiso, Florida to Chicago in August is currently the most expensive (average of $517). 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
Benton Harbor
Lansing
Merrillville
Valparaiso
Hammond
Saint Joseph
Porter

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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 August 3, 2026.
AirlineCheapestAverageFlexibilityOn-time
Allegiant AirCheapest$86Average$188FlexibilityNo cancel feeOn-time88%
SouthwestCheapest$234Average$400FlexibilityNo cancel feeOn-time63%
American AirlinesCheapest$295Average$477FlexibilityNo cancel feeOn-time71%

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