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$37+ 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 5/19. Fares are subject to change and may not be available on all flights or dates of travel.
VPS — CHI
Apr 27 — May 41
Sun 4/27
Sun 5/4
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 April 22, 2025.

Most accurate provider

eDreams
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$87
(Mytrip)

One-way from

$37
(Gotogate)

Popular in

September

Cheapest in

February

Average price

$191

Good round-trip deal

$96 or less

Good one-way deal

$232 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. 13% potential increase in price ($38 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 6% potential price decrease ($16 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in April 2025
Search Deals
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).
Search Deals

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 April 22, 2025.

This Mytrip deal was found by Cheapflights users on 4/22. 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.
Fri 6/136:00 amVPS - MDW
Nonstop2h 22mAllegiant Air
Mon 6/169:12 amMDW - VPS
Nonstop2h 11mAllegiant Air
Deal found 4/22$87
This American Airlines deal was found by Cheapflights users on 4/22. 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 6/411:08 amVPS - ORD
Nonstop2h 29mAmerican Airlines
Wed 6/117:43 amORD - VPS
Nonstop2h 16mAmerican Airlines
Deal found 4/22$158
This Delta deal was found by Cheapflights users on 4/22. 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 6/41:25 pmVPS - ORD
1 stop5h 23mDelta
Wed 6/119:49 amORD - VPS
1 stop6h 25mDelta
Deal found 4/22$177
This Delta deal was found by Cheapflights users on 4/22. 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 6/172:45 pmVPS - MDW
1 stop7h 00mDelta
Tue 6/246:00 amMDW - VPS
1 stop4h 27mDelta
Deal found 4/22$177
This Southwest deal was found by Cheapflights users on 4/21. 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 8/127:00 amVPS - ORD
1 stop5h 45mSouthwest
Tue 8/197:30 amORD - VPS
1 stop5h 55mSouthwest
Deal found 4/21$297
This Sun Country Air deal was found by Cheapflights users on 4/22. 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 7/36:02 pmVPS - ORD
1 stop18h 49mSun Country Air
Sun 7/66:45 amORD - VPS
1 stop10h 17mSun Country Air
Deal found 4/22$304
This Mytrip deal was found by Cheapflights users on 4/22. 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.
Fri 6/139:09 pmVPS - ORD
1 stop13h 41mMultiple Airlines
Mon 6/169:28 pmORD - VPS
1 stop16h 16mMultiple Airlines
Deal found 4/22$307
This Southwest deal was found by Cheapflights users on 4/22. 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 5/66:25 pmVPS - MDW
1 stop4h 45mSouthwest
Wed 5/76:20 amMDW - VPS
1 stop5h 05mSouthwest
Deal found 4/22$347

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 April 22, 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 5/30

6:00 am-8:22 am

Nonstop2h 22m

Chicago Midway

Mon 6/2

9:12 am-11:23 am

Nonstop2h 11m

$87

ValparaisoChicago

VPS - ORD

VPSORD

Valparaiso Destin-Ft Walton Beach

Wed 6/4

11:08 am-1:37 pm

Nonstop2h 29m

Chicago O'Hare Intl

Wed 6/11

7:43 am-9:59 am

Nonstop2h 16m

$158

ValparaisoChicago

VPS - ORD

VPSORD

Valparaiso Destin-Ft Walton Beach

Wed 6/4

1:25 pm-6:48 pm

1 stop5h 23m

Chicago O'Hare Intl

Wed 6/11

9:49 am-4:14 pm

1 stop6h 25m

$177

ValparaisoChicago

VPS - MDW

VPSMDW

Valparaiso Destin-Ft Walton Beach

Tue 6/17

2:45 pm-9:45 pm

1 stop7h 00m

Chicago Midway

Tue 6/24

6:00 am-10:27 am

1 stop4h 27m

$177

ValparaisoChicago

VPS - ORD

VPSORD

Valparaiso Destin-Ft Walton Beach

Tue 8/12

7:00 am-12:45 pm

1 stop5h 45m

Chicago O'Hare Intl

Tue 8/19

7:30 am-1:25 pm

1 stop5h 55m

$297

ValparaisoChicago

VPS - ORD

VPSORD

Valparaiso Destin-Ft Walton Beach

Thu 7/3

6:02 pm-12:51 pm

1 stop18h 49m

Chicago O'Hare Intl

Sun 7/6

6:45 am-5:02 pm

1 stop10h 17m

$304

ValparaisoChicago

VPS - ORD

VPSORD

Valparaiso Destin-Ft Walton Beach

Fri 6/13

9:09 pm-10:50 am

1 stop13h 41m

Chicago O'Hare Intl

Mon 6/16

9:28 pm-1:44 pm

1 stop16h 16m

$307

ValparaisoChicago

VPS - MDW

VPSMDW

Valparaiso Destin-Ft Walton Beach

Mon 6/16

8:00 pm-1:05 am

1 stop5h 05m

Chicago Midway

Sun 6/22

5:45 am-9:55 am

1 stop4h 10m

$388

ValparaisoChicago

VPS - MDW

VPSMDW

Valparaiso Destin-Ft Walton Beach

Mon 5/19

6:30 am-8:52 am

Nonstop2h 22m

$37

ValparaisoChicago

VPS - ORD

VPSORD

Valparaiso Destin-Ft Walton Beach

Tue 7/8

7:00 am-12:45 pm

1 stop5h 45m

$88

Flights are sorted by cheapest round-trip flights first.

Deals found on 4/22

Showing 1-10 of 17 results
1
2

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 April.
ProviderPrice AccuracyTrust Score*
ExpediaPrice Accuracy1 starTrust Score*3 stars
eDreamsPrice Accuracy3 starsTrust Score*3 stars
FlightHubPrice Accuracy3 starsTrust Score*2 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, 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 April 22, 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.

Weekly flight availability from Valparaiso, Florida to Chicago

Explore weekly flight availability from Valparaiso to Chicago. Discover flights operating on different days of the week, giving you the flexibility to choose a travel day that best fits your plans. Compare info to find the most convenient option for your journey. Data last updated April 22, 2025.

The most flights from VPS to CHI are scheduled on a Monday (2 on average). You will have fewer flight options on Monday, which is when the least amount of flights are scheduled (2 on average).

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 April 22, 2025.
Southwest
8.0
Very good
4,286 reviews

Entertainment

7.6

Food

7.1

Boarding

8.2

Overall

8.0

Crew

8.6

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
8.0
Very good
4,286 reviews
Southwest
8.0
Very good
4,286 reviews

Entertainment

7.6

Food

7.1

Boarding

8.2

Overall

8.0

Crew

8.6

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.
Delta
8.0
Very good
7,920 reviews
Southwest
8.0
Very good
4,286 reviews

Entertainment

7.6

Food

7.1

Boarding

8.2

Overall

8.0

Crew

8.6

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.
Avelo Airlines
7.5
Good
Southwest
8.0
Very good
4,286 reviews

Entertainment

7.6

Food

7.1

Boarding

8.2

Overall

8.0

Crew

8.6

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
7.3
Good
734 reviews
Southwest
8.0
Very good
4,286 reviews

Entertainment

7.6

Food

7.1

Boarding

8.2

Overall

8.0

Crew

8.6

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
10,000 reviews
Southwest
8.0
Very good
4,286 reviews

Entertainment

7.6

Food

7.1

Boarding

8.2

Overall

8.0

Crew

8.6

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. 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 2 outbound flights 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 $87. Other airlines that can offer you cheap pricing are American Airlines, from $158, and Delta, from $177. Users have found that Allegiant Air is 65% 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 $37. Southwest flights start at $88 while deals on Avelo Airlines start at $135 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 (92%), American Airlines (80%) or Qatar Airways (78%) 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 $356, our data shows the cheapest flight currently is $134. When looking at the most popular route, (Valparaiso Destin-Ft Walton Beach - Chicago O'Hare Intl), you can expect to pay $177 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
Hammond
Benton Harbor
Porter
Lansing
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 April 22, 2025.
AirlineCheapestAverageFlexibilityOn-time
DeltaCheapest$196Average$397FlexibilityNo cancel feeOn-timeN/A
American AirlinesCheapest$239Average$353FlexibilityNo cancel feeOn-time71%

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