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Valparaiso

$54+ Cheap flights from Midway (MDW) to Valparaiso, FL (VPS)

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 11/16. Fares are subject to change and may not be available on all flights or dates of travel.
MDW — VPS
Oct 11 — Oct 181
Sat 10/11
Sat 10/18
1 adult, Economy
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Cheap 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 September 11, 2025.

Round-trip from

$137
(Kiwi.com)

One-way from

$54
(Cheapflightsfares)

Popular in

March

Cheapest in

July

Average price

$325

Good round-trip deal

$180 or less

Good one-way deal

$64 or less
From Chicago Midway to Valparaiso Destin-Ft Walton Beach
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One-way flight from Chicago Midway to Valparaiso Destin-Ft Walton Beach
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High demand for flights, 3% potential price rise
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Cheapest flight prices on average. 7% potential price decrease ($16 potential savings vs. average RT price).
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Average for round-trip flights in September 2025
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Price to beat on a round-trip flight from Chicago Midway to Valparaiso Destin-Ft Walton Beach.
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Price to beat on a one-way flight from Chicago Midway to Valparaiso Destin-Ft Walton Beach.
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Find 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 September 11, 2025.

This Kiwi.com deal was found by Cheapflights users on 9/9. 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 10/1911:07 amMDW - VPS
Nonstop2h 05mAllegiant Air
Thu 10/309:00 amVPS - MDW
Nonstop2h 17mAllegiant Air
Deal found 9/9$137
This Gotogate deal was found by Cheapflights users on 9/11. 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 Gotogate is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 10/2611:07 amMDW - VPS
Nonstop2h 05mAllegiant Air
Sun 11/29:00 amVPS - MDW
Nonstop2h 17mAllegiant Air
Deal found 9/11$175
This Cheapflightsfares deal was found by Cheapflights users on 9/9. 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.
Thu 10/2311:07 amMDW - VPS
Nonstop2h 05mAllegiant Air
Sun 10/268:00 amVPS - MDW
Nonstop2h 17mAllegiant Air
Deal found 9/9$183
This Kiwi.com deal was found by Cheapflights users on 9/10. 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 10/912:30 pmMDW - VPS
1 stop10h 12mMultiple Airlines
Thu 10/168:00 amVPS - MDW
Nonstop2h 17mMultiple Airlines
Deal found 9/10$186
This Cheapflightsfares deal was found by Cheapflights users on 9/10. 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.
Thu 10/911:07 amMDW - VPS
Nonstop2h 05mAllegiant Air
Thu 10/168:00 amVPS - MDW
Nonstop2h 17mAllegiant Air
Deal found 9/10$205
This Cheapflightsfares deal was found by Cheapflights users on 9/9. 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.
Thu 11/208:33 pmMDW - VPS
Nonstop2h 13mAllegiant Air
Sun 11/235:24 pmVPS - MDW
Nonstop2h 19mAllegiant Air
Deal found 9/9$222
This Kiwi.com deal was found by Cheapflights users on 9/9. 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 10/1911:07 amMDW - VPS
Nonstop2h 05mMultiple Airlines
Thu 10/306:30 amVPS - MDW
1 stop16h 55mMultiple Airlines
Deal found 9/9$245
This Cheapflightsfares deal was found by Cheapflights users on 9/9. 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.
Tue 12/234:10 pmMDW - VPS
Nonstop2h 13mAllegiant Air
Tue 12/301:01 pmVPS - MDW
Nonstop2h 19mAllegiant Air
Deal found 9/9$247
This Kiwi.com deal was found by Cheapflights users on 9/10. 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.
Mon 9/293:16 pmMDW - VPS
1 stop7h 34mMultiple Airlines
Mon 10/611:33 amVPS - MDW
2 stops35h 47mMultiple Airlines
Deal found 9/10$260

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 September 11, 2025.
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

Sun 10/26

11:07 am-1:12 pm

Nonstop2h 05m

Valparaiso Destin-Ft Walton Beach

Sun 11/2

9:00 am-11:17 am

Nonstop2h 17m

$175

ChicagoValparaiso

MDW - VPS

MDWVPS

Chicago Midway

Thu 10/9

11:07 am-1:12 pm

Nonstop2h 05m

Valparaiso Destin-Ft Walton Beach

Thu 10/16

8:00 am-10:17 am

Nonstop2h 17m

$205

ChicagoValparaiso

MDW - VPS

MDWVPS

Chicago Midway

Thu 11/20

8:33 pm-10:46 pm

Nonstop2h 13m

Valparaiso Destin-Ft Walton Beach

Sun 11/23

5:24 pm-7:43 pm

Nonstop2h 19m

$222

ChicagoValparaiso

MDW - VPS

MDWVPS

Chicago Midway

Tue 12/23

4:10 pm-6:23 pm

Nonstop2h 13m

Valparaiso Destin-Ft Walton Beach

Tue 12/30

1:01 pm-3:20 pm

Nonstop2h 19m

$247

ChicagoValparaiso

MDW - VPS

MDWVPS

Chicago Midway

Thu 10/9

12:30 pm-10:42 pm

1 stop10h 12m

Valparaiso Destin-Ft Walton Beach

Thu 10/16

5:02 pm-11:46 pm

2 stops30h 44m

$272

ChicagoValparaiso

MDW - VPS

MDWVPS

Chicago Midway

Sun 10/26

11:07 am-1:12 pm

Nonstop2h 05m

Valparaiso Destin-Ft Walton Beach

Sun 11/2

11:40 am-11:38 am

2 stops47h 58m

$282

ChicagoValparaiso

MDW - VPS

MDWVPS

Chicago Midway

Fri 11/7

12:14 pm-7:03 pm

3 stops30h 49m

Valparaiso Destin-Ft Walton Beach

Sun 11/9

9:00 am-11:17 am

Nonstop2h 17m

$289

ChicagoValparaiso

MDW - VPS

MDWVPS

Chicago Midway

Thu 10/23

11:07 am-1:12 pm

Nonstop2h 05m

Valparaiso Destin-Ft Walton Beach

Mon 10/27

9:00 am-11:25 pm

2 stops38h 25m

$324

ChicagoValparaiso

MDW - VPS

MDWVPS

Chicago Midway

Thu 10/2

11:07 am-1:12 pm

Nonstop2h 05m

Valparaiso Destin-Ft Walton Beach

Mon 10/6

3:46 pm-11:25 pm

3 stops31h 39m

$329

ChicagoValparaiso

MDW - VPS

MDWVPS

Chicago Midway

Mon 10/20

6:23 pm-3:08 pm

2 stops20h 45m

Valparaiso Destin-Ft Walton Beach

Mon 10/27

7:10 pm-6:25 pm

2 stops23h 15m

$348

Flights are sorted by cheapest round-trip flights first.

Deals found on 9/9

Showing 1-10 of 20 results
1
2

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, September is the cheapest month in which you can book a flight from Chicago Midway Airport to Valparaiso, Florida (average of $274). Flying from Chicago Midway Airport to Valparaiso, Florida in March is currently the most expensive (average of $386). 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 September 11, 2025.

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 61% 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 September 11, 2025.
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
4,248 reviews

Food

7.0

Boarding

8.1

Overall

8.0

Entertainment

7.5

Crew

8.6

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
4,248 reviews
Southwest
8.0
Very good
4,248 reviews

Food

7.0

Boarding

8.1

Overall

8.0

Entertainment

7.5

Crew

8.6

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
702 reviews
Southwest
8.0
Very good
4,248 reviews

Food

7.0

Boarding

8.1

Overall

8.0

Entertainment

7.5

Crew

8.6

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 2h 05m. Chicago Midway Airport and Valparaiso, Florida are separated by a distance of 783 mi. Generally, flights for this route are nonstop.

  • 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 61% 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 $59. On average you can expect to pay $192. The most popular route, (Chicago Midway - Valparaiso Destin-Ft Walton Beach), can usually be booked for $179.

  • 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, September is the cheapest month in which you can book a flight from Chicago Midway Airport to Valparaiso, Florida (average of $274). Flying from Chicago Midway Airport to Valparaiso, Florida in March is currently the most expensive (average of $386). 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

See prices for flight routes from nearby airports that may be better suited for you.
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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 September 11, 2025.
AirlineCheapestAverageFlexibilityOn-time
Allegiant AirCheapest$82Average$139FlexibilityNo cancel feeOn-time88%
SouthwestCheapest$212Average$388FlexibilityNo cancel feeOn-time63%

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