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$55+ 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 12/21. Fares are subject to change and may not be available on all flights or dates of travel.
VPS — CHI
Dec 2 — Dec 91
Tue 12/2
Tue 12/9
1 adult, Economy
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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 November 2, 2025.

This Booking.com deal was found by Cheapflights users on 10/31. 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 Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/231:01 pmVPS - MDW
Nonstop2h 19mAllegiant Air
Tue 12/304:10 pmMDW - VPS
Nonstop2h 13mAllegiant Air
Deal found 10/31$122
This Cheapflightsfares deal was found by Cheapflights users on 11/1. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/69:00 amVPS - MDW
Nonstop2h 17mAllegiant Air
Sun 11/912:07 pmMDW - VPS
Nonstop2h 05mAllegiant Air
Deal found 11/1$139
This Cheapflightsfares deal was found by Cheapflights users on 11/1. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/183:45 pmVPS - MDW
Nonstop2h 19mAllegiant Air
Tue 12/234:10 pmMDW - VPS
Nonstop2h 13mAllegiant Air
Deal found 11/1$142
This Mytrip deal was found by Cheapflights users on 10/31. 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 Mytrip 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 10/31$144
This Kiwi.com deal was found by Cheapflights users on 10/31. 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.
Tue 12/231:01 pmVPS - MDW
Nonstop2h 19mMultiple Airlines
Tue 12/306:14 amMDW - VPS
2 stops36h 00mMultiple Airlines
Deal found 10/31$233
This Cheapflightsfares deal was found by Cheapflights users on 11/1. 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 Cheapflightsfares 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 11/1$236
This Kiwi.com deal was found by Cheapflights users on 10/31. 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.
Sun 11/2312:00 pmVPS - MDW
2 stops28h 52mMultiple Airlines
Sat 11/299:09 amMDW - VPS
Nonstop2h 13mMultiple Airlines
Deal found 10/31$280
This Kiwi.com deal was found by Cheapflights users on 11/1. 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.
Thu 11/66:35 amVPS - MDW
1 stop17h 20mMultiple Airlines
Sun 11/912:07 pmMDW - VPS
Nonstop2h 05mMultiple Airlines
Deal found 11/1$339
This Kiwi.com deal was found by Cheapflights users on 10/31. 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.
Sat 11/157:53 pmVPS - ORD
2 stops16h 33mMultiple Airlines
Wed 11/192:31 pmORD - VPS
1 stop22h 24mMultiple Airlines
Deal found 10/31$371
This Kiwi.com deal was found by Cheapflights users on 11/1. 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.
Thu 12/186:29 pmVPS - ORD
1 stop22h 13mMultiple Airlines
Tue 12/237:57 pmORD - VPS
2 stops45h 14mMultiple Airlines
Deal found 11/1$384
This Sun Country Air deal was found by Cheapflights users on 10/31. 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 Sun Country Air is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 11/234:56 pmVPS - ORD
1 stop17h 43mSun Country Air
Sat 11/2910:00 amORD - VPS
1 stop23h 08mSun Country Air
Deal found 10/31$404
This Southwest deal was found by Cheapflights users on 11/1. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 12/157:15 amVPS - ORD
1 stop5h 00mSouthwest
Fri 12/195:15 pmORD - VPS
1 stop3h 55mSouthwest
Deal found 11/1$406

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 November 2, 2025.

Most accurate provider

eDreams
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$122
(Booking.com)

One-way from

$55
(Cheapflightsfares)

Popular in

March

Cheapest in

May

Average price

$328

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.
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
High demand for flights, 8% potential price rise
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 November 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 November 2, 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 - 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

$122

ValparaisoChicago

VPS - MDW

VPSMDW

Valparaiso Destin-Ft Walton Beach

Thu 12/18

3:45 pm-6:04 pm

Nonstop2h 19m

Chicago Midway

Tue 12/23

4:10 pm-6:23 pm

Nonstop2h 13m

$142

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

$144

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

6:14 am-6:14 pm

2 stops36h 00m

$233

ValparaisoChicago

VPS - MDW

VPSMDW

Valparaiso Destin-Ft Walton Beach

Sun 11/23

12:00 pm-4:52 pm

2 stops28h 52m

Chicago Midway

Sat 11/29

9:09 am-11:22 am

Nonstop2h 13m

$280

ValparaisoChicago

VPS - MDW

VPSMDW

Valparaiso Destin-Ft Walton Beach

Wed 1/14

2:00 pm-7:00 pm

1 stop5h 00m

Chicago Midway

Wed 1/21

6:00 am-11:40 am

1 stop5h 40m

$349

ValparaisoChicago

VPS - ORD

VPSORD

Valparaiso Destin-Ft Walton Beach

Thu 12/18

6:29 pm-4:42 pm

1 stop22h 13m

Chicago O'Hare Intl

Tue 12/23

7:57 pm-5:11 pm

2 stops45h 14m

$384

ValparaisoChicago

VPS - ORD

VPSORD

Valparaiso Destin-Ft Walton Beach

Sat 2/14

7:00 am-10:26 pm

1 stop15h 26m

Chicago O'Hare Intl

Wed 2/18

9:51 am-11:55 pm

1 stop14h 04m

$403

ValparaisoChicago

VPS - ORD

VPSORD

Valparaiso Destin-Ft Walton Beach

Mon 12/15

7:15 am-12:15 pm

1 stop5h 00m

Chicago O'Hare Intl

Fri 12/19

5:15 pm-9:10 pm

1 stop3h 55m

$406

ValparaisoChicago

VPS - MDW

VPSMDW

Valparaiso Destin-Ft Walton Beach

Mon 12/15

11:20 am-4:00 pm

1 stop4h 40m

Chicago Midway

Fri 12/19

5:20 am-1:20 pm

1 stop8h 00m

$406

Flights are sorted by cheapest round-trip flights first.

Deals found on 10/31

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 November.
ProviderPrice AccuracyTrust Score*
FlightHubPrice Accuracy3 starsTrust Score*1 star
ExpediaPrice Accuracy2 starsTrust Score*3 stars
eDreamsPrice 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 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 April is currently the most expensive (average of $221). 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 November 2, 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 in the morning could potentially save you up to 64% 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 November 2, 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
4,241 reviews

Food

7.0

Boarding

8.1

Overall

8.0

Crew

8.6

Comfort

8.0

Entertainment

7.5

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
4,241 reviews
Southwest
8.0
Very good
4,241 reviews

Food

7.0

Boarding

8.1

Overall

8.0

Crew

8.6

Comfort

8.0

Entertainment

7.5

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
11,033 reviews
Southwest
8.0
Very good
4,241 reviews

Food

7.0

Boarding

8.1

Overall

8.0

Crew

8.6

Comfort

8.0

Entertainment

7.5

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
694 reviews
Southwest
8.0
Very good
4,241 reviews

Food

7.0

Boarding

8.1

Overall

8.0

Crew

8.6

Comfort

8.0

Entertainment

7.5

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 1 outbound flight 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 19m. Allegiant Air provides one of the quickest options available for as low as $122. 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 $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 61% 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 Envoy Air (67%), American Airlines (42%) or Qatar Airways (42%) 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 $340, our data shows the cheapest flight currently is $170. When looking at the most popular route, (Valparaiso Destin-Ft Walton Beach - Chicago O'Hare Intl), you can expect to pay $371 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 April is currently the most expensive (average of $221). 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
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Porter
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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 November 2, 2025.
AirlineCheapestAverageFlexibilityOn-time
Allegiant AirCheapest$84Average$178FlexibilityNo cancel feeOn-time88%
American AirlinesCheapest$157Average$380FlexibilityNo cancel feeOn-time71%
DeltaCheapest$323Average$446FlexibilityNo cancel feeOn-timeN/A

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