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$48+ 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 10/30. Fares are subject to change and may not be available on all flights or dates of travel.
VPS — MDW
Aug 5 — Aug 121
Tue 8/5
Tue 8/12
1 adult, Economy
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Cheap 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 July 31, 2025.

Round-trip from

$258
(Southwest)

One-way from

$48
(Booking.com)

Popular in

May

Cheapest in

February

Average price

$212

Good one-way deal

$86 or less
From Valparaiso Destin-Ft Walton Beach to Chicago Midway
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One-way flight from Valparaiso Destin-Ft Walton Beach to Chicago Midway
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Highest demand for flights based on searches. 17% potential increase in price ($66 potential increase over avg. RT price).
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Cheapest flight prices on average. 12% potential price decrease ($36 potential savings vs. average RT price).
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Average for round-trip flights in July 2025
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Price to beat on a one-way flight from Valparaiso Destin-Ft Walton Beach to Chicago Midway.
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Find 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 July 31, 2025.

This Cheapflightsfares deal was found by Cheapflights users on 7/30. 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.
Fri 8/16:00 amVPS - MDW
Nonstop2h 22mAllegiant Air
Fri 8/89:12 amMDW - VPS
Nonstop2h 11mAllegiant Air
Deal found 7/30$145
This Southwest deal was found by Cheapflights users on 7/30. 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 9/112:00 pmVPS - MDW
1 stop6h 50mSouthwest
Sat 9/132:50 pmMDW - VPS
1 stop3h 55mSouthwest
Deal found 7/30$258
This Delta deal was found by Cheapflights users on 7/30. 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 9/52:58 pmVPS - MDW
1 stop6h 28mDelta
Sun 9/76:00 amMDW - VPS
1 stop6h 59mDelta
Deal found 7/30$425

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 July 31, 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

Thu 9/11

2:00 pm-8:50 pm

1 stop6h 50m

Chicago Midway

Sat 9/13

2:50 pm-6:45 pm

1 stop3h 55m

$258

ValparaisoChicago

VPS - MDW

VPSMDW

Valparaiso Destin-Ft Walton Beach

Fri 9/5

2:58 pm-9:26 pm

1 stop6h 28m

Chicago Midway

Sun 9/7

6:00 am-12:59 pm

1 stop6h 59m

$425

ValparaisoChicago

VPS - MDW

VPSMDW

Valparaiso Destin-Ft Walton Beach

Thu 10/30

9:00 am-11:17 am

Nonstop2h 17m

$48

ValparaisoChicago

VPS - MDW

VPSMDW

Valparaiso Destin-Ft Walton Beach

Sat 8/30

10:30 am-2:50 pm

1 stop4h 20m

$117

ValparaisoChicago

VPS - MDW

VPSMDW

Valparaiso Destin-Ft Walton Beach

Sat 8/30

2:58 pm-9:12 pm

1 stop6h 14m

$177

ValparaisoChicago

VPS - MDW

VPSMDW

Valparaiso Destin-Ft Walton Beach

Thu 9/25

1:40 pm-8:52 pm

3 stops31h 12m

$193

Flights are sorted by cheapest round-trip flights first.

Deals found on 7/30

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, April is the cheapest month in which you can book a flight from Valparaiso, Florida to Chicago Midway Airport (average of $160). Flying from Valparaiso, Florida to Chicago Midway Airport in November is currently the most expensive (average of $249). 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 MDW?

Find hourly flight availability from Valparaiso to Midway. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated July 31, 2025.

It’s typically best to fly out from Valparaiso, Florida to Chicago Midway Airport at noon. Doing so could potentially save you 38% on the flight price compared to flying in the afternoon, which is usually more expensive.

How much does it cost to fly round-trip from Valparaiso, Florida to Chicago Midway Airport?

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 July 31, 2025.
Get a feel of what it's like to fly with Southwest, Delta, and 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.
Southwest
8.0
Very good
4,246 reviews

Entertainment

7.5

Boarding

8.1

Food

7.0

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
4,246 reviews
Southwest
8.0
Very good
4,246 reviews

Entertainment

7.5

Boarding

8.1

Food

7.0

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
7,981 reviews
Southwest
8.0
Very good
4,246 reviews

Entertainment

7.5

Boarding

8.1

Food

7.0

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
7.2
Good
702 reviews
Southwest
8.0
Very good
4,246 reviews

Entertainment

7.5

Boarding

8.1

Food

7.0

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 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 0 different airlines.

  • What are the cheapest airlines flying from Valparaiso, Florida to Chicago Midway Airport round-trip?

    Our cheapest airline available from Valparaiso, Florida to Chicago Midway Airport is Southwest. Our recent data shows that you can find tickets from as low as $258 on this airline. An additional option worth looking into is Delta, starting at $425. You may be able to fly from Valparaiso, Florida to Chicago Midway Airport for 19% less than the average price by searching for these airlines.

  • What are the cheapest airlines to fly from Valparaiso, Florida to Chicago Midway Airport one-way?

    One-way options have recently been found by users for as low as $48 on Allegiant Air. Other airlines that offer cheap prices include Southwest from $117 and Delta from $177 one-way.

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

    On average you can expect to pay $104 for a flight from Valparaiso, Florida to Chicago Midway Airport. The cheapest flight overall is $52 while the most popular route, (Valparaiso Destin-Ft Walton Beach - Chicago Midway) is currently priced at $145.

  • 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, April is the cheapest month in which you can book a flight from Valparaiso, Florida to Chicago Midway Airport (average of $160). Flying from Valparaiso, Florida to Chicago Midway Airport in November is currently the most expensive (average of $249). 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
Merrillville
Lansing
Hammond
Benton Harbor
Porter
Valparaiso
Chesterton

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