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Valparaiso

$92+ Cheap flights from Midway (MDW) to Valparaiso, FL (VPS)

This is the cheapest round-trip flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 3/1. Fares are subject to change and may not be available on all flights or dates of travel.
MDW — VPS
Feb 20 — Feb 271
Fri 2/20
Fri 2/27
1 adult, Economy
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Cheap flight deals from Midway to Valparaiso

Cheapest flights from Midway to Valparaiso
Explore the most affordable flight options available from Midway to Valparaiso. Find the lowest fares from popular airlines and budget airlines, with prices last updated on January 21, 2026.

This Mytrip deal was found by Cheapflights users on 1/21. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 3/13:40 pm
MDW
-
VPS
Nonstop2h 06m
Allegiant Air
Thu 3/125:37 pm
VPS
-
MDW
Nonstop2h 16m
Allegiant Air
Deal found 1/21$92
This Kiwi.com 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 3/88:46 pm
MDW
-
VPS
Nonstop2h 08m
Allegiant Air
Thu 3/125:37 pm
VPS
-
MDW
Nonstop2h 16m
Allegiant Air
Deal found 1/19$106
This Kiwi.com 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 3/13:40 pm
MDW
-
VPS
Nonstop2h 06m
Allegiant Air
Thu 3/55:40 pm
VPS
-
MDW
Nonstop2h 16m
Allegiant Air
Deal found 1/20$138
This Kiwi.com 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 7/39:15 pm
MDW
-
VPS
Nonstop2h 14m
Allegiant Air
Fri 7/106:05 pm
VPS
-
MDW
Nonstop2h 20m
Allegiant Air
Deal found 1/20$187
This Kiwi.com 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 5/35:47 pm
MDW
-
VPS
Nonstop2h 09m
Allegiant Air
Sun 5/102:40 pm
VPS
-
MDW
Nonstop2h 17m
Allegiant Air
Deal found 1/19$194
This Kiwi.com 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 3/128:43 pm
MDW
-
VPS
Nonstop2h 08m
Allegiant Air
Thu 3/265:37 pm
VPS
-
MDW
Nonstop2h 16m
Allegiant Air
Deal found 1/19$197
This Kiwi.com 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 3/87:30 am
MDW
-
VPS
1 stop6h 22m
Multiple Airlines
Thu 3/125:37 pm
VPS
-
MDW
Nonstop2h 16m
Multiple Airlines
Deal found 1/19$211
This Booking.com 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 Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 2/194:10 pm
MDW
-
VPS
Nonstop2h 06m
Allegiant Air
Sun 2/2212:31 pm
VPS
-
MDW
Nonstop2h 19m
Allegiant Air
Deal found 1/19$221
This Kiwi.com 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 3/158:43 pm
MDW
-
VPS
Nonstop2h 08m
Allegiant Air
Thu 3/265:37 pm
VPS
-
MDW
Nonstop2h 16m
Allegiant Air
Deal found 1/19$230

Find flight deals from Midway to Valparaiso

Discover tips and strategies to find the most affordable flight options for your journey from Midway (MDW) to Valparaiso (VPS). 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 January 21, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

Expedia
3 stars

Round-trip from

$92
(Mytrip)

Popular in

November

Cheapest in

July

Average price

$250

Good round-trip deal

$166 or less

Good one-way deal

$146 or less
Provider with most accurate pricing for Chicago Midway-Valparaiso Destin-Ft Walton Beach flight deals.
Search Deals
Provider most trusted by Cheapflights users for Chicago Midway-Valparaiso Destin-Ft Walton Beach flights.
Search Deals
From Chicago Midway to Valparaiso Destin-Ft Walton Beach
Search Deals
Highest demand for flights based on searches. 28% potential increase in price ($95 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 7% potential price decrease ($17 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in January 2026
Search Deals
Price to beat on a round-trip flight from Chicago Midway to Valparaiso Destin-Ft Walton Beach.
Search Deals
Price to beat on a one-way flight from Chicago Midway to Valparaiso Destin-Ft Walton Beach.
Search Deals

Cheapflights Fare Finder

 
Customize your flight search to find flights from Midway to Valparaiso 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 January 21, 2026.
Use the filters below to find and compare flights from Chicago Midway Airport to Valparaiso that are best for you.

Fly from

Midway

Fly to

Valparaiso

Route

Depart

Return

Price

ChicagoValparaiso

MDW - VPS

MDWVPS

Chicago Midway

Tue 4/21

5:31 pm-11:14 pm

1 stop5h 43m

Valparaiso Destin-Ft Walton Beach

Sat 4/25

5:10 pm-10:29 pm

1 stop5h 19m

$336

ChicagoValparaiso

MDW - VPS

MDWVPS

Chicago Midway

Sat 2/21

6:50 am-12:45 pm

1 stop5h 55m

Valparaiso Destin-Ft Walton Beach

Sat 2/28

7:15 am-5:05 pm

1 stop9h 50m

$339

ChicagoValparaiso

MDW - VPS

MDWVPS

Chicago Midway

Mon 4/13

5:30 am-9:20 am

1 stop3h 50m

Valparaiso Destin-Ft Walton Beach

Wed 4/22

12:30 pm-4:45 pm

1 stop4h 15m

$352

ChicagoValparaiso

MDW - VPS

MDWVPS

Chicago Midway

Tue 3/17

10:45 am-4:08 pm

1 stop5h 23m

Valparaiso Destin-Ft Walton Beach

Thu 3/26

7:05 am-12:02 pm

1 stop4h 57m

$355

ChicagoValparaiso

MDW - VPS

MDWVPS

Chicago Midway

Wed 3/18

5:40 pm-11:15 pm

1 stop5h 35m

Valparaiso Destin-Ft Walton Beach

Thu 3/26

7:05 am-12:02 pm

1 stop4h 57m

$355

ChicagoValparaiso

MDW - VPS

MDWVPS

Chicago Midway

Mon 2/23

6:00 am-11:15 am

1 stop5h 15m

Valparaiso Destin-Ft Walton Beach

Sat 2/28

6:00 am-10:21 am

1 stop4h 21m

$355

ChicagoValparaiso

MDW - VPS

MDWVPS

Chicago Midway

Wed 3/4

12:45 pm-6:19 pm

1 stop5h 34m

Valparaiso Destin-Ft Walton Beach

Mon 3/9

5:04 pm-10:31 pm

1 stop5h 27m

$355

ChicagoValparaiso

MDW - VPS

MDWVPS

Chicago Midway

Mon 2/23

5:25 am-10:30 am

1 stop5h 05m

Valparaiso Destin-Ft Walton Beach

Sat 2/28

7:15 am-1:30 pm

2 stops6h 15m

$358

ChicagoValparaiso

MDW - VPS

MDWVPS

Chicago Midway

Sun 3/29

8:43 pm-10:51 pm

Nonstop2h 08m

$138

ChicagoValparaiso

MDW - VPS

MDWVPS

Chicago Midway

Wed 4/8

3:00 pm-9:00 pm

1 stop6h 00m

$168

Flights are sorted by cheapest round-trip flights first.

Deals found on 1/19

Showing 1-10 of 16 results
1
2

Compare providers for flights from Midway to Valparaiso

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 Midway to Valparaiso in January.
ProviderPrice AccuracyTrust Score*
ExpediaPrice Accuracy2 starsTrust Score*3 stars
FlightHubPrice Accuracy3 starsTrust Score*1 star

*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 Chicago Midway Airport-Valparaiso, Florida flights, users find the pricing of FlightHub to be most consistent on Cheapflights vs. FlightHub Users can find the same prices on Chicago Midway Airport-Valparaiso, Florida flight deals on Cheapflights vs. FlightHub >95% of the time. Price accuracy is based on data collected from Chicago Midway Airport-Valparaiso, Florida flight searches over the past month and is updated monthly.
  • Most trusted provider: When it comes to deals on Chicago Midway Airport-Valparaiso, Florida flights, Cheapflights users trust Expedia the most. Expedia 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 Chicago Midway Airport-Valparaiso, Florida 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 Midway to Valparaiso

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

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

Currently, July is the cheapest month in which you can book a flight from Chicago Midway Airport to Valparaiso, Florida (average of $81). Flying from Chicago Midway Airport to Valparaiso, Florida in December is currently the most expensive (average of $242). 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 MDW to VPS?

Find hourly flight availability from Midway to Valparaiso. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated January 21, 2026.

When flying from Chicago Midway Airport to Valparaiso, Florida, the time of day you fly usually plays a role in the price. Save by searching for a flight in the afternoon, which can drop the price by up to 62% versus a flight at noon.

Reviews of airlines servicing Valparaiso

Get insights into the airlines that provide service to Valparaiso. 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 Valparaiso. Reviews last updated January 21, 2026.
Get a feel of what it's like to fly with Southwest and Allegiant Air from Chicago Midway Airport to Valparaiso 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
4,266 reviews

Boarding

8.1

Overall

8.0

Crew

8.6

Entertainment

7.5

Food

7.0

Comfort

8.0

Reviews

1 / 20
10.0
Excellent

Sarah,Aug 2024

MDW - AUS

My first time, surprisingly good! It was a good ride overall. Coming from Singapore, this budget flight is better than the budget airline for our national carrier Singapore Airlines.
Southwest
8.0
Very good
4,266 reviews
Southwest
8.0
Very good
4,266 reviews

Boarding

8.1

Overall

8.0

Crew

8.6

Entertainment

7.5

Food

7.0

Comfort

8.0

Reviews

1 / 20
10.0
Excellent

Sarah,Aug 2024

MDW - AUS

My first time, surprisingly good! It was a good ride overall. Coming from Singapore, this budget flight is better than the budget airline for our national carrier Singapore Airlines.
Allegiant Air
7.2
Good
705 reviews
Southwest
8.0
Very good
4,266 reviews

Boarding

8.1

Overall

8.0

Crew

8.6

Entertainment

7.5

Food

7.0

Comfort

8.0

Reviews

1 / 20
10.0
Excellent

Sarah,Aug 2024

MDW - AUS

My first time, surprisingly good! It was a good ride overall. Coming from Singapore, this budget flight is better than the budget airline for our national carrier Singapore Airlines.

Related info for your journey

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

    Located just 3.1 mi from the city center, Valparaiso Destin-Ft Walton Beach is the airport most travelers will use when flying to Valparaiso from Chicago Midway. Booking flights from Chicago Midway to Destin-Ft Walton Beach (VPS) should be relatively easy as there are 0 daily inbound flights from Chicago Midway from 2 different airlines.

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

    Departing from Chicago Midway Airport to Valparaiso, Florida will take you 5h 43m. Chicago Midway Airport and Valparaiso, Florida are separated by a distance of 783 mi. Both multi-stop and nonstop flights can be found to your destination and back.

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

    Allegiant Air, at $82, was found to be the cheapest airline from Chicago Midway Airport to Valparaiso, Florida. An alternate airline flying to your destination would be Southwest. Allegiant Air is 66% cheaper than the average price of flights available within the next 90 days to this destination.

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

    The cheapest flight price from Chicago Midway Airport to Valparaiso, Florida is $106. On average you can expect to pay $172. The most popular route, (Chicago Midway - Valparaiso Destin-Ft Walton Beach), can usually be booked for $97.

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

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

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

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

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

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

    Currently, July is the cheapest month in which you can book a flight from Chicago Midway Airport to Valparaiso, Florida (average of $81). Flying from Chicago Midway Airport to Valparaiso, Florida in December is currently the most expensive (average of $242). 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
Crestview
Andalusia
Niceville

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Alternative routes for Midway to Valparaiso

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Top 2 airlines flying from Midway to Valparaiso

Discover the top 2 airlines that operate flights from Midway to Valparaiso. 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 January 21, 2026.
AirlineCheapestAverageFlexibilityOn-time
Allegiant AirCheapest$82Average$142FlexibilityNo cancel feeOn-time88%
SouthwestCheapest$212Average$381FlexibilityNo cancel feeOn-time63%

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