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Midway

$75+ Cheap flights from Valparaiso, FL (VPS) to Midway (MDW)

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 3/12. Fares are subject to change and may not be available on all flights or dates of travel.
VPS — MDW
Jan 15 — Jan 221
Thu 1/15
Thu 1/22
1 adult, Economy
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Cheap flight deals from Valparaiso to Midway

Cheapest flights from Valparaiso to Midway
Explore the most affordable flight options available from Valparaiso to Midway. Find the lowest fares from popular airlines and budget airlines, with prices last updated on December 16, 2025.

This Booking.com deal was found by Cheapflights users on 12/15. 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.
Sun 12/213:45 pmVPS - MDW
Nonstop2h 19mAllegiant Air
Tue 12/234:10 pmMDW - VPS
Nonstop2h 13mAllegiant Air
Deal found 12/15$215
This Delta deal was found by Cheapflights users on 12/15. 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.
Fri 12/196:00 amVPS - MDW
1 stop5h 55mDelta
Sat 1/36:00 amMDW - VPS
1 stop4h 34mDelta
Deal found 12/15$396
This Southwest deal was found by Cheapflights users on 12/15. 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 12/306:10 pmVPS - MDW
1 stop7h 00mSouthwest
Mon 1/52:55 pmMDW - VPS
1 stop6h 20mSouthwest
Deal found 12/15$411
This Southwest deal was found by Cheapflights users on 12/15. 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 12/306:10 pmVPS - MDW
1 stop7h 00mSouthwest
Sun 1/45:25 amMDW - VPS
2 stops7h 55mSouthwest
Deal found 12/15$417
This Southwest deal was found by Cheapflights users on 12/15. 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 12/186:05 pmVPS - MDW
1 stop6h 05mSouthwest
Mon 12/225:25 amMDW - VPS
1 stop5h 50mSouthwest
Deal found 12/15$452
This Kiwi.com deal was found by Cheapflights users on 12/15. 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 12/217:58 pmVPS - MDW
2 stops26h 00mMultiple Airlines
Tue 12/234:10 pmMDW - VPS
Nonstop2h 13mMultiple Airlines
Deal found 12/15$453
This Southwest deal was found by Cheapflights users on 12/14. 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.
Fri 12/196:10 pmVPS - MDW
1 stop7h 00mSouthwest
Sat 1/312:25 pmMDW - VPS
2 stops9h 25mSouthwest
Deal found 12/14$458
This Southwest deal was found by Cheapflights users on 12/15. 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 12/172:00 pmVPS - MDW
1 stop7h 00mSouthwest
Fri 12/1912:00 pmMDW - VPS
1 stop5h 25mSouthwest
Deal found 12/15$469
This Southwest deal was found by Cheapflights users on 12/15. 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 12/172:00 pmVPS - MDW
1 stop7h 00mSouthwest
Thu 12/187:40 amMDW - VPS
1 stop6h 05mSouthwest
Deal found 12/15$490

Find flight deals from Valparaiso to Midway

Discover tips and strategies to find the most affordable flight options for your journey from Valparaiso (VPS) to Midway (MDW). 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 December 16, 2025.

Most accurate provider

eDreams
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$269
(Kiwi.com)

One-way from

$75
(Booking.com)

Popular in

March

Cheapest in

May

Average price

$194

Good one-way deal

$136 or less
Provider with most accurate pricing for Valparaiso Destin-Ft Walton Beach-Chicago Midway flight deals.
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Provider most trusted by Cheapflights users for Valparaiso Destin-Ft Walton Beach-Chicago Midway flights.
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From Valparaiso Destin-Ft Walton Beach to Chicago Midway
Search Deals
One-way flight from Valparaiso Destin-Ft Walton Beach to Chicago Midway
Search Deals
Highest demand for flights based on searches. 2% potential increase in price ($4 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 9% potential price decrease ($19 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in December 2025
Search Deals
Price to beat on a one-way flight from Valparaiso Destin-Ft Walton Beach to Chicago Midway.
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Cheapflights Fare Finder

 
Customize your flight search to find flights from Valparaiso to Midway 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 December 16, 2025.
Use the filters below to find and compare flights from Valparaiso to Chicago Midway Airport that are best for you.

Fly from

Valparaiso

Fly to

Midway

Route

Depart

Return

Price

ValparaisoChicago

VPS - MDW

VPSMDW

Valparaiso Destin-Ft Walton Beach

Wed 4/1

7:05 am-12:02 pm

1 stop4h 57m

Chicago Midway

Tue 4/7

10:49 am-4:08 pm

1 stop5h 19m

$315

ValparaisoChicago

VPS - MDW

VPSMDW

Valparaiso Destin-Ft Walton Beach

Tue 3/31

6:00 am-12:02 pm

1 stop6h 02m

Chicago Midway

Sat 4/4

4:30 pm-11:02 pm

1 stop6h 32m

$315

ValparaisoChicago

VPS - MDW

VPSMDW

Valparaiso Destin-Ft Walton Beach

Tue 3/31

7:15 am-5:05 pm

1 stop9h 50m

Chicago Midway

Sat 4/4

5:30 am-3:55 pm

2 stops10h 25m

$326

ValparaisoChicago

VPS - MDW

VPSMDW

Valparaiso Destin-Ft Walton Beach

Wed 4/1

6:00 am-12:02 pm

1 stop6h 02m

Chicago Midway

Mon 4/6

10:49 am-4:08 pm

1 stop5h 19m

$334

ValparaisoChicago

VPS - MDW

VPSMDW

Valparaiso Destin-Ft Walton Beach

Tue 2/3

6:00 am-9:53 am

1 stop3h 53m

Chicago Midway

Mon 2/9

6:00 am-12:59 pm

1 stop6h 59m

$334

ValparaisoChicago

VPS - MDW

VPSMDW

Valparaiso Destin-Ft Walton Beach

Mon 3/30

5:10 pm-10:29 pm

1 stop5h 19m

Chicago Midway

Sat 4/4

4:30 pm-11:02 pm

1 stop6h 32m

$334

ValparaisoChicago

VPS - MDW

VPSMDW

Valparaiso Destin-Ft Walton Beach

Tue 3/31

5:10 pm-10:29 pm

1 stop5h 19m

Chicago Midway

Mon 4/6

6:30 am-11:40 am

1 stop5h 10m

$334

ValparaisoChicago

VPS - MDW

VPSMDW

Valparaiso Destin-Ft Walton Beach

Mon 3/30

5:10 pm-10:29 pm

1 stop5h 19m

Chicago Midway

Tue 4/7

10:49 am-4:08 pm

1 stop5h 19m

$334

ValparaisoChicago

VPS - MDW

VPSMDW

Valparaiso Destin-Ft Walton Beach

Tue 1/27

7:00 am-1:20 pm

1 stop6h 20m

Chicago Midway

Fri 1/30

8:55 am-6:55 pm

2 stops10h 00m

$340

ValparaisoChicago

VPS - MDW

VPSMDW

Valparaiso Destin-Ft Walton Beach

Fri 1/16

11:31 am-4:29 pm

1 stop4h 58m

Chicago Midway

Sun 1/18

11:21 am-4:05 pm

1 stop4h 44m

$353

Flights are sorted by cheapest round-trip flights first.

Deals found on 12/15

Showing 1-10 of 21 results
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Compare providers for flights from Valparaiso to Midway

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 Midway in December.
ProviderPrice AccuracyTrust Score*
ExpediaPrice Accuracy2 starsTrust Score*3 stars
FlightHubPrice Accuracy3 starsTrust Score*1 star
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 Midway Airport 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 Midway Airport flight deals on Cheapflights vs. eDreams >95% of the time. Price accuracy is based on data collected from Valparaiso, Florida-Chicago Midway Airport flight searches over the past month and is updated monthly.
  • Most trusted provider: When it comes to deals on Valparaiso, Florida-Chicago Midway Airport 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 Midway Airport 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 Midway

Have a flexible travel schedule? Discover the best time to fly to Midway 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 Midway Airport

What is the cheapest month to book a flight from Valparaiso, Florida to Chicago Midway Airport?

Currently, June is the cheapest month in which you can book a flight from Valparaiso, Florida to Chicago Midway Airport (average of $99). Flying from Valparaiso, Florida to Chicago Midway Airport in July is currently the most expensive (average of $284). 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.

Reviews of airlines servicing Midway

Get insights into the airlines that provide service to Midway. 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 Midway. Reviews last updated December 16, 2025.
Get a feel of what it's like to fly with Allegiant Air from Valparaiso to Chicago Midway Airport by reading reviews from past customers. Users have also rated airlines in terms of entertainment options, comfort, food, crew/service, and boarding process.
Allegiant Air
7.2
Good
700 reviews

Food

5.9

Entertainment

5.5

Boarding

7.6

Crew

8.1

Overall

7.2

Comfort

6.8

Reviews

1 / 20
4.0
Okay

Sara,Nov 2025

PSC - AZA

We were delayed and then couldn’t get off due to lightening.
Allegiant Air
7.2
Good
700 reviews
Allegiant Air
7.2
Good
700 reviews

Food

5.9

Entertainment

5.5

Boarding

7.6

Crew

8.1

Overall

7.2

Comfort

6.8

Reviews

1 / 20
4.0
Okay

Sara,Nov 2025

PSC - AZA

We were delayed and then couldn’t get off due to lightening.

Related info for your journey

Find useful and relevant information for your journey from Valparaiso to Midway. 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 Midway?

    If you book a flight to Chicago Midway from Valparaiso, you will be flying from Destin-Ft Walton Beach, which is the city’s only airport. Valparaiso Destin-Ft Walton Beach (VPS) is located 3.1 mi from the center of Valparaiso. There are 0 flights from Destin-Ft Walton Beach to Chicago Midway per day from 1 airline.

  • How long is the flight from Valparaiso, Florida to Chicago Midway Airport?

    A quick flight from Valparaiso, Florida to Chicago Midway Airport can take about 4h 57m. Delta provides one of the quickest options available for as low as $315. The distance from Valparaiso, Florida to Chicago Midway Airport is about 783 mi. When browsing for deals, the options you’ll see will be for both nonstop flights and flights with stops.

  • What are the cheapest flights from Valparaiso, Florida to Chicago Midway Airport?

    On average you can expect to pay $148 for a flight from Valparaiso, Florida to Chicago Midway Airport. The cheapest flight overall is $136 while the most popular route, (Valparaiso Destin-Ft Walton Beach - Chicago Midway) is currently priced at $215.

  • Can I find deals for flights from Valparaiso to Midway that include hotel bookings?

    Yes. In addition to deals on Valparaiso to Midway flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from Valparaiso to Midway?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Valparaiso to Midway.

  • Can I find deals for business class flights from Valparaiso to Midway?

    Yes. Cheapflights offers flight deals from Valparaiso to Midway 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 Midway Airport?

    Currently, June is the cheapest month in which you can book a flight from Valparaiso, Florida to Chicago Midway Airport (average of $99). Flying from Valparaiso, Florida to Chicago Midway Airport in July is currently the most expensive (average of $284). 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 Midway Airport?

Book flights to Chicago Midway Airport if you plan to visit one of these locations
Lansing
Merrillville
Hammond
Porter
Benton Harbor

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Alternative routes for Valparaiso to Midway

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Top airline flying from Valparaiso to Midway

Discover the top airline that operate flights from Valparaiso to Midway. 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 December 16, 2025.
AirlineCheapestAverageFlexibilityOn-time
Allegiant AirCheapest$84Average$144FlexibilityNo cancel feeOn-time88%

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