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$62+ 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 2/20. Fares are subject to change and may not be available on all flights or dates of travel.
VPS — CHI
ene. 26 — feb. 21
dom. 1/26
dom. 2/2
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 enero 21, 2025.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$101
(Mytrip)

One-way from

$62
(Mytrip)

Popular in

September

Cheapest in

February

Average price

$233
Provider with most accurate pricing for Valparaiso Destin-Ft Walton Beach-Chicago (CHI) flight deals.
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Provider most trusted by Cheapflights users for Valparaiso Destin-Ft Walton Beach-Chicago (CHI) flights.
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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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High demand for flights, 9% potential price rise
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Best time to find cheap flights, 6% potential price drop
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Average for round-trip flights in January 2025
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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 enero 21, 2025.

This Mytrip deal was found by Cheapflights users on 1/20. 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.
jue. 2/278:30 amVPS - MDW
Nonstop2h 18mAllegiant Air
dom. 3/92:22 pmMDW - VPS
Nonstop2h 12mAllegiant Air
Deal found 1/20$101
This Delta deal was found by Cheapflights users on 1/19. 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.
mar. 2/255:00 pmVPS - ORD
1 stop6h 48mDelta
dom. 3/27:05 amORD - VPS
1 stop7h 05mDelta
Deal found 1/19$353
This Southwest deal was found by Cheapflights users on 1/20. 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.
mar. 2/187:20 amVPS - ORD
1 stop5h 40mSouthwest
jue. 2/207:00 amORD - VPS
1 stop3h 50mSouthwest
Deal found 1/20$358
This Southwest deal was found by Cheapflights users on 1/20. 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.
mar. 2/187:20 amVPS - MDW
1 stop6h 50mSouthwest
jue. 2/205:55 amMDW - VPS
1 stop4h 55mSouthwest
Deal found 1/20$358
This American Airlines deal was found by Cheapflights users on 1/19. 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.
mar. 2/2512:59 pmVPS - ORD
2 stops7h 09mAmerican Airlines
dom. 3/25:10 amORD - VPS
1 stop7h 06mAmerican Airlines
Deal found 1/19$359
This Mytrip deal was found by Cheapflights users on 1/20. 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.
jue. 2/277:35 amVPS - ORD
1 stop13h 58mMultiple Airlines
dom. 3/97:42 pmORD - VPS
3 stops22h 06mMultiple Airlines
Deal found 1/20$420
This Delta deal was found by Cheapflights users on 1/20. 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.
jue. 2/65:00 pmVPS - MDW
1 stop5h 20mDelta
dom. 2/96:00 amMDW - VPS
1 stop3h 59mDelta
Deal found 1/20$455

Find flights from Valparaiso to Chicago within your budget

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 enero 21, 2025.

Fly from

Any airport

Fly to

Any airport

Route

Depart

Return

Price

ValparaisoChicago

VPS - MDW

VPSMDW

Valparaiso Destin-Ft Walton Beach

jue. 2/27

8:30 am-10:48 am

Nonstop2h 18m

Chicago Midway

dom. 3/9

2:22 pm-4:34 pm

Nonstop2h 12m

$101

ValparaisoChicago

VPS - ORD

VPSORD

Valparaiso Destin-Ft Walton Beach

mar. 2/25

5:00 pm-11:48 pm

1 stop6h 48m

Chicago O'Hare Intl

dom. 3/2

7:05 am-2:10 pm

1 stop7h 05m

$353

ValparaisoChicago

VPS - ORD

VPSORD

Valparaiso Destin-Ft Walton Beach

mar. 2/18

7:20 am-1:00 pm

1 stop5h 40m

Chicago O'Hare Intl

jue. 2/20

7:00 am-10:50 am

1 stop3h 50m

$358

ValparaisoChicago

VPS - MDW

VPSMDW

Valparaiso Destin-Ft Walton Beach

mar. 2/18

7:20 am-2:10 pm

1 stop6h 50m

Chicago Midway

jue. 2/20

5:55 am-10:50 am

1 stop4h 55m

$358

ValparaisoChicago

VPS - ORD

VPSORD

Valparaiso Destin-Ft Walton Beach

mar. 2/25

12:59 pm-8:08 pm

2 stops7h 09m

Chicago O'Hare Intl

dom. 3/2

5:10 am-12:16 pm

1 stop7h 06m

$359

ValparaisoChicago

VPS - ORD

VPSORD

Valparaiso Destin-Ft Walton Beach

jue. 2/27

7:35 am-9:33 pm

1 stop13h 58m

Chicago O'Hare Intl

dom. 3/9

7:42 pm-5:48 pm

3 stops22h 06m

$420

ValparaisoChicago

VPS - MDW

VPSMDW

Valparaiso Destin-Ft Walton Beach

jue. 2/6

5:00 pm-10:20 pm

1 stop5h 20m

Chicago Midway

dom. 2/9

6:00 am-9:59 am

1 stop3h 59m

$455

ValparaisoChicago

VPS - MDW

VPSMDW

Valparaiso Destin-Ft Walton Beach

jue. 2/20

8:30 am-10:48 am

Nonstop2h 18m

$62

ValparaisoChicago

VPS - ORD

VPSORD

Valparaiso Destin-Ft Walton Beach

jue. 4/17

6:10 pm-10:46 am

1 stop16h 36m

$137

ValparaisoChicago

VPS - ORD

VPSORD

Valparaiso Destin-Ft Walton Beach

mar. 2/18

7:20 am-1:00 pm

1 stop5h 40m

$151

Flights are sorted by cheapest round-trip flights first.

Deals found on 1/18

Showing 1-10 of 15 results
1
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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*
ExpediaPrice Accuracy1 starTrust Score*3 stars
FlightHubPrice Accuracy3 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 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.

Travel insights for flights from Valparaiso to Chicago

Get recent, data-driven insights about flights from Valparaiso to Chicago including ideal travel times, pricing trends, and more.

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 $320). 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 enero 21, 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 38% 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 enero 21, 2025.
Southwest
8.1
Very good
4,659 reviews

Crew

8.7

Comfort

8.1

Entertainment

7.7

Overall

8.1

Boarding

8.2

Food

7.2

Reviews

1 / 10

No tray tables for food or drink not convenient nor comfortable

Southwest
8.1
Very good
4,659 reviews
Southwest
8.1
Very good
4,659 reviews

Crew

8.7

Comfort

8.1

Entertainment

7.7

Overall

8.1

Boarding

8.2

Food

7.2

Reviews

1 / 10

No tray tables for food or drink not convenient nor comfortable

Delta
8.0
Very good
8,521 reviews
Southwest
8.1
Very good
4,659 reviews

Crew

8.7

Comfort

8.1

Entertainment

7.7

Overall

8.1

Boarding

8.2

Food

7.2

Reviews

1 / 10

No tray tables for food or drink not convenient nor comfortable

Allegiant Air
7.4
Good
801 reviews
Southwest
8.1
Very good
4,659 reviews

Crew

8.7

Comfort

8.1

Entertainment

7.7

Overall

8.1

Boarding

8.2

Food

7.2

Reviews

1 / 10

No tray tables for food or drink not convenient nor comfortable

American Airlines
7.2
Good
10,000 reviews
Southwest
8.1
Very good
4,659 reviews

Crew

8.7

Comfort

8.1

Entertainment

7.7

Overall

8.1

Boarding

8.2

Food

7.2

Reviews

1 / 10

No tray tables for food or drink not convenient nor comfortable

Sun Country Air
7.0
Good
386 reviews
Southwest
8.1
Very good
4,659 reviews

Crew

8.7

Comfort

8.1

Entertainment

7.7

Overall

8.1

Boarding

8.2

Food

7.2

Reviews

1 / 10

No tray tables for food or drink not convenient nor comfortable

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.

  • 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 $101. Other airlines that can offer you cheap pricing are Delta, from $353, and Southwest, from $358. Users have found that Allegiant Air is 61% 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 $62. Sun Country Air flights start at $137 while deals on Southwest start at $151 one-way.

  • 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 $320). 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
New Buffalo
Hammond
Benton Harbor
Porter
Lansing
Valparaiso
Chesterton

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Alternative routes for Valparaiso to 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 enero 21, 2025.
AirlineCheapestAverageFlexibilityOn-time
Allegiant AirCheapest$78Average$134FlexibilityNo cancel feeOn-time88%
DeltaCheapest$196Average$419FlexibilityNo cancel feeOn-timeN/A
American AirlinesCheapest$239Average$332FlexibilityNo cancel feeOn-time71%
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