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$52+ 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 7/16. Fares are subject to change and may not be available on all flights or dates of travel.
VPS — CHI
Jun 17 — Jun 241
Tue 6/17
Tue 6/24
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 June 12, 2025.

Round-trip from

$86
(Booking.com)

One-way from

$52
(Mytrip)

Popular in

September

Cheapest in

May

Average price

$262

Good round-trip deal

$86 or less

Good one-way deal

$197 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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Highest demand for flights based on searches. 14% potential increase in price ($43 potential increase over avg. RT price).
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Cheapest flight prices on average. 7% potential price decrease ($17 potential savings vs. average RT price).
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Average for round-trip flights in June 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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Price to beat on a one-way 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 June 12, 2025.

This Booking.com deal was found by Cheapflights users on 6/10. 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.
Fri 7/116:00 amVPS - MDW
Nonstop2h 22mAllegiant Air
Wed 7/164:27 pmMDW - VPS
Nonstop2h 11mAllegiant Air
Deal found 6/10$86
This American Airlines deal was found by Cheapflights users on 6/10. 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 7/1010:53 amVPS - ORD
Nonstop2h 39mAmerican Airlines
Mon 7/147:33 amORD - VPS
Nonstop2h 26mAmerican Airlines
Deal found 6/10$158
This Southwest deal was found by Cheapflights users on 6/11. 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 7/246:00 pmVPS - MDW
1 stop6h 55mSouthwest
Mon 7/285:05 amMDW - VPS
1 stop6h 50mSouthwest
Deal found 6/11$176
This Delta deal was found by Cheapflights users on 6/10. 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 7/104:59 pmVPS - ORD
1 stop4h 31mDelta
Mon 7/146:00 amORD - VPS
1 stop6h 05mDelta
Deal found 6/10$177
This Delta deal was found by Cheapflights users on 6/12. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 7/152:45 pmVPS - MDW
1 stop6h 57mDelta
Wed 7/306:00 amMDW - VPS
1 stop4h 15mDelta
Deal found 6/12$177
This Sun Country Air deal was found by Cheapflights users on 6/11. 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.
Thu 7/106:05 pmVPS - ORD
1 stop23h 16mSun Country Air
Thu 7/176:00 amORD - VPS
1 stop11h 08mSun Country Air
Deal found 6/11$284
This Mytrip deal was found by Cheapflights users on 6/11. 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.
Thu 7/248:30 amVPS - ORD
2 stops37h 00mMultiple Airlines
Mon 7/287:08 amORD - VPS
1 stop13h 10mMultiple Airlines
Deal found 6/11$285
This Southwest deal was found by Cheapflights users on 6/11. 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 7/87:00 amVPS - ORD
2 stops9h 45mSouthwest
Wed 7/234:00 pmORD - VPS
1 stop5h 20mSouthwest
Deal found 6/11$310

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 June 12, 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

Fri 7/11

6:00 am-8:22 am

Nonstop2h 22m

Chicago Midway

Wed 7/16

4:27 pm-6:38 pm

Nonstop2h 11m

$86

ValparaisoChicago

VPS - ORD

VPSORD

Valparaiso Destin-Ft Walton Beach

Thu 7/10

10:53 am-1:32 pm

Nonstop2h 39m

Chicago O'Hare Intl

Mon 7/14

7:33 am-9:59 am

Nonstop2h 26m

$158

ValparaisoChicago

VPS - MDW

VPSMDW

Valparaiso Destin-Ft Walton Beach

Thu 7/24

6:00 pm-12:55 am

1 stop6h 55m

Chicago Midway

Mon 7/28

5:05 am-11:55 am

1 stop6h 50m

$176

ValparaisoChicago

VPS - ORD

VPSORD

Valparaiso Destin-Ft Walton Beach

Thu 7/10

4:59 pm-9:30 pm

1 stop4h 31m

Chicago O'Hare Intl

Mon 7/14

6:00 am-12:05 pm

1 stop6h 05m

$177

ValparaisoChicago

VPS - MDW

VPSMDW

Valparaiso Destin-Ft Walton Beach

Tue 7/15

2:45 pm-9:42 pm

1 stop6h 57m

Chicago Midway

Wed 7/30

6:00 am-10:15 am

1 stop4h 15m

$177

ValparaisoChicago

VPS - ORD

VPSORD

Valparaiso Destin-Ft Walton Beach

Wed 7/2

7:00 am-12:45 pm

1 stop5h 45m

Chicago O'Hare Intl

Wed 7/9

4:00 pm-9:20 pm

1 stop5h 20m

$268

ValparaisoChicago

VPS - ORD

VPSORD

Valparaiso Destin-Ft Walton Beach

Thu 7/10

6:05 pm-5:21 pm

1 stop23h 16m

Chicago O'Hare Intl

Thu 7/17

6:00 am-5:08 pm

1 stop11h 08m

$284

ValparaisoChicago

VPS - ORD

VPSORD

Valparaiso Destin-Ft Walton Beach

Thu 7/24

8:30 am-9:30 pm

2 stops37h 00m

Chicago O'Hare Intl

Mon 7/28

7:08 am-8:18 pm

1 stop13h 10m

$285

ValparaisoChicago

VPS - MDW

VPSMDW

Valparaiso Destin-Ft Walton Beach

Wed 7/16

1:15 pm-3:37 pm

Nonstop2h 22m

$52

ValparaisoChicago

VPS - ORD

VPSORD

Valparaiso Destin-Ft Walton Beach

Tue 8/5

7:00 am-12:45 pm

1 stop5h 45m

$72

Flights are sorted by cheapest round-trip flights first.

Deals found on 6/11

Showing 1-10 of 17 results
1
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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 June 12, 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.

Rainfall in Chicago by month

Plan your trip to Chicago by taking into account the average rainfall totals by month.

In terms of precipitation, rainfall in Chicago ranges from 1.7 - 4.9 inches per month. August is typically the wettest month, when rainfall can reach 4.9 in. January is typically the driest time to visit Chicago when rainfall is around 1.7 in.

Temperature in Chicago by month

Plan your trip to Chicago by taking into account the average temperature totals by month.

If weather is an important factor for your trip to Chicago, use this chart to help with planning. For those seeking warmer temperatures, July is the ideal time of year to visit, when temperatures reach an average of 73.4 F. Travelers looking to avoid the cold should look outside of January, when temperatures are typically at their lowest (around 23.0 F).

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 June 12, 2025.
See what other customers who have flown with Southwest, Delta and Allegiant Air from Valparaiso to Chicago have to say. Users have also rated airlines in terms of entertainment options, comfort, food, crew/service, and boarding process.
Southwest
8.0
Very good
4,287 reviews

Overall

8.0

Entertainment

7.6

Food

7.1

Boarding

8.2

Comfort

8.0

Crew

8.6

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
4,287 reviews
Southwest
8.0
Very good
4,287 reviews

Overall

8.0

Entertainment

7.6

Food

7.1

Boarding

8.2

Comfort

8.0

Crew

8.6

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.
Delta
8.0
Very good
7,950 reviews
Southwest
8.0
Very good
4,287 reviews

Overall

8.0

Entertainment

7.6

Food

7.1

Boarding

8.2

Comfort

8.0

Crew

8.6

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
7.3
Good
725 reviews
Southwest
8.0
Very good
4,287 reviews

Overall

8.0

Entertainment

7.6

Food

7.1

Boarding

8.2

Comfort

8.0

Crew

8.6

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
4,287 reviews

Overall

8.0

Entertainment

7.6

Food

7.1

Boarding

8.2

Comfort

8.0

Crew

8.6

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.
Sun Country Air
6.9
Okay
345 reviews
Southwest
8.0
Very good
4,287 reviews

Overall

8.0

Entertainment

7.6

Food

7.1

Boarding

8.2

Comfort

8.0

Crew

8.6

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 1 outbound flight to Chicago per day.

  • 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 $158, and Southwest, from $176. Users have found that Allegiant Air is 64% 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 $52. Southwest flights start at $72 while deals on Sun Country Air start at $141 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 Envoy Air (75%), Qatar Airways (62%) or American Airlines (61%) 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 $327, our data shows the cheapest flight currently is $157. When looking at the most popular route, (Valparaiso Destin-Ft Walton Beach - Chicago O'Hare Intl), you can expect to pay $187 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 Valparaiso?

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

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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 June 12, 2025.
AirlineCheapestAverageFlexibilityOn-time
DeltaCheapest$202Average$411FlexibilityNo cancel feeOn-timeN/A
American AirlinesCheapest$242Average$355FlexibilityNo cancel feeOn-time71%

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