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$113+ 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 5/25. Fares are subject to change and may not be available on all flights or dates of travel.
VPS — CHI
Feb 27 — Mar 61
Fri 2/27
Fri 3/6
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 January 28, 2026.

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 1/26. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 2/251:00 pm
VPS
-
ORD
Nonstop2h 44m
American Airlines
Wed 3/49:31 am
ORD
-
VPS
Nonstop2h 29m
American Airlines
Deal found 1/26$316
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 Delta 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 3/253:00 pm
VPS
-
ORD
1 stop6h 10m
Delta
Tue 3/312:32 pm
ORD
-
VPS
1 stop6h 20m
Delta
Deal found 1/26$336
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.
Wed 2/2512:15 pm
VPS
-
ORD
2 stops9h 35m
Southwest
Wed 3/41:45 pm
ORD
-
VPS
1 stop5h 10m
Southwest
Deal found 1/26$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 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 5/216:15 pm
VPS
-
MDW
1 stop5h 15m
Southwest
Wed 6/106:30 am
MDW
-
VPS
1 stop4h 55m
Southwest
Deal found 1/26$350
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.
Wed 3/257:15 am
VPS
-
ORD
1 stop5h 35m
Southwest
Mon 3/302:40 pm
ORD
-
VPS
1 stop6h 25m
Southwest
Deal found 1/26$351
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.
Thu 4/2312:05 pm
VPS
-
ORD
Nonstop2h 48m
American Airlines
Mon 4/279:43 am
ORD
-
VPS
Nonstop2h 32m
American Airlines
Deal found 1/27$354
This Delta 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 4/236:00 am
VPS
-
MDW
1 stop6h 07m
Delta
Tue 4/285:21 pm
MDW
-
VPS
1 stop5h 58m
Delta
Deal found 1/26$355

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 January 28, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$299
(Kiwi.com)

One-way from

$113
(Kiwi.com)

Popular in

December

Cheapest in

May

Average price

$376

Good round-trip deal

$102 or less

Good one-way deal

$207 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. 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 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 January 28, 2026.
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 - 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 - ORD

VPSORD

Valparaiso Destin-Ft Walton Beach

Wed 2/25

1:00 pm-3:44 pm

Nonstop2h 44m

Chicago O'Hare Intl

Wed 3/4

9:29 am-3:15 pm

1 stop5h 46m

$326

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

Wed 2/25

7:00 am-12:15 pm

1 stop5h 15m

Chicago O'Hare Intl

Wed 3/4

1:45 pm-6:55 pm

1 stop5h 10m

$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

ValparaisoChicago

VPS - MDW

VPSMDW

Valparaiso Destin-Ft Walton Beach

Fri 3/13

8:42 pm-8:21 pm

2 stops23h 39m

Chicago Midway

Sun 3/15

8:43 pm-10:51 pm

Nonstop2h 08m

$354

ValparaisoChicago

VPS - ORD

VPSORD

Valparaiso Destin-Ft Walton Beach

Thu 6/4

11:37 am-2:19 pm

Nonstop2h 42m

Chicago O'Hare Intl

Mon 6/8

8:38 am-11:07 am

Nonstop2h 29m

$354

ValparaisoChicago

VPS - ORD

VPSORD

Valparaiso Destin-Ft Walton Beach

Thu 4/23

12:05 pm-2:53 pm

Nonstop2h 48m

Chicago O'Hare Intl

Mon 4/27

9:43 am-12:15 pm

Nonstop2h 32m

$354

ValparaisoChicago

VPS - ORD

VPSORD

Valparaiso Destin-Ft Walton Beach

Fri 3/13

4:40 pm-12:16 am

1 stop7h 36m

Chicago O'Hare Intl

Sat 3/14

3:16 pm-10:24 pm

1 stop7h 08m

$354

Flights are sorted by cheapest round-trip flights first.

Deals found on 1/25

Showing 1-10 of 32 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 January.
ProviderPrice AccuracyTrust Score*
FlightHubPrice Accuracy3 starsTrust Score*3 stars
ExpediaPrice Accuracy1 starTrust 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, June is the cheapest month in which you can book a flight from Valparaiso, Florida to Chicago (average of $108). 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 January 28, 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 January 28, 2026.
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
4,267 reviews

Comfort

8.0

Entertainment

7.5

Overall

8.0

Crew

8.6

Food

7.0

Boarding

8.1

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

Comfort

8.0

Entertainment

7.5

Overall

8.0

Crew

8.6

Food

7.0

Boarding

8.1

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
11,199 reviews
Southwest
8.0
Very good
4,267 reviews

Comfort

8.0

Entertainment

7.5

Overall

8.0

Crew

8.6

Food

7.0

Boarding

8.1

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

Comfort

8.0

Entertainment

7.5

Overall

8.0

Crew

8.6

Food

7.0

Boarding

8.1

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 44m. American Airlines provides one of the quickest options available for as low as $326. 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 $86. Other airlines that can offer you cheap pricing are American Airlines, from $157, and Delta, from $323. Users have found that Allegiant Air is 60% 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 (68%), American Airlines (65%) or Envoy Air (65%) 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 $345, our data shows the cheapest flight currently is $147. When looking at the most popular route, (Valparaiso Destin-Ft Walton Beach - Chicago O'Hare Intl), you can expect to pay $333 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 $108). 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?

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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 January 28, 2026.
AirlineCheapestAverageFlexibilityOn-time
Allegiant AirCheapest$86Average$144FlexibilityNo cancel feeOn-time88%
American AirlinesCheapest$157Average$376FlexibilityNo cancel feeOn-time71%
DeltaCheapest$323Average$425FlexibilityNo cancel feeOn-timeN/A

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