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Midway

$58+ 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 10/5. Fares are subject to change and may not be available on all flights or dates of travel.
VPS — MDW
Aug 28 — Sep 41
Fri 8/28
Fri 9/4
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 July 29, 2026.

This Cheapflightsfares deal was found by Cheapflights users on 7/29. 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 8/146:14 pm
VPS
-
MDW
Nonstop2h 21m
Allegiant Air
Mon 8/179:25 pm
MDW
-
VPS
Nonstop2h 14m
Allegiant Air
Deal found 7/29$134
This Kiwi.com deal was found by Cheapflights users on 7/26. 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 10/26:16 pm
VPS
-
MDW
Nonstop2h 18m
Allegiant Air
Mon 10/59:02 pm
MDW
-
VPS
Nonstop2h 11m
Allegiant Air
Deal found 7/26$135
This Kiwi.com deal was found by Cheapflights users on 7/26. 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 10/26:16 pm
VPS
-
MDW
Nonstop2h 18m
Allegiant Air
Fri 10/99:25 pm
MDW
-
VPS
Nonstop2h 11m
Allegiant Air
Deal found 7/26$168
This Kiwi.com deal was found by Cheapflights users on 7/26. 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 10/55:54 pm
VPS
-
MDW
Nonstop2h 18m
Allegiant Air
Fri 10/99:25 pm
MDW
-
VPS
Nonstop2h 11m
Allegiant Air
Deal found 7/26$173
This Cheapflightsfares deal was found by Cheapflights users on 7/28. 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 8/76:14 pm
VPS
-
MDW
Nonstop2h 21m
Allegiant Air
Mon 8/109:25 pm
MDW
-
VPS
Nonstop2h 14m
Allegiant Air
Deal found 7/28$192
This Kiwi.com deal was found by Cheapflights users on 7/26. 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 10/26:16 pm
VPS
-
MDW
Nonstop2h 18m
Multiple Airlines
Mon 10/56:25 am
MDW
-
VPS
2 stops13h 52m
Multiple Airlines
Deal found 7/26$232
This Kiwi.com deal was found by Cheapflights users on 7/26. 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 10/44:20 pm
VPS
-
MDW
1 stop19h 46m
Allegiant Air
Mon 10/59:02 pm
MDW
-
VPS
Nonstop2h 11m
Allegiant Air
Deal found 7/26$251
This Kiwi.com deal was found by Cheapflights users on 7/28. 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 10/26:16 pm
VPS
-
MDW
Nonstop2h 18m
Multiple Airlines
Sun 10/46:46 pm
MDW
-
VPS
2 stops25h 31m
Multiple Airlines
Deal found 7/28$261
This Kiwi.com deal was found by Cheapflights users on 7/26. 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 10/26:16 pm
VPS
-
MDW
Nonstop2h 18m
Multiple Airlines
Sat 10/1012:03 pm
MDW
-
VPS
2 stops44h 14m
Multiple Airlines
Deal found 7/26$276

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 July 29, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$134
(Cheapflightsfares)

One-way from

$58
(Kissandfly.com)

Popular in

August

Cheapest in

October

Average price

$491

Good round-trip deal

$200 or less

Good one-way deal

$72 or less
Provider with most accurate pricing for Valparaiso Destin-Ft Walton Beach-Chicago Midway flight deals.
Search Deals
Provider most trusted by Cheapflights users for Valparaiso Destin-Ft Walton Beach-Chicago Midway flights.
Search Deals
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. 32% potential increase in price ($177 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 11% potential price decrease ($39 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in July 2026
Search Deals
Price to beat on a round-trip flight from Valparaiso Destin-Ft Walton Beach to Chicago Midway.
Search Deals
Price to beat on a one-way flight from Valparaiso Destin-Ft Walton Beach to Chicago Midway.
Search Deals

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 29, 2026.
Use the filters below to find and compare flights from Valparaiso to Chicago Midway Airport that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip
Quickest round-trip

ValparaisoChicago

VPS - MDW

VPSMDW

Valparaiso Destin-Ft Walton Beach

Fri 8/14

6:14 pm-8:35 pm

Nonstop2h 21m

Chicago Midway

Mon 8/17

9:25 pm-11:39 pm

Nonstop2h 14m

$134

ValparaisoChicago

VPS - MDW

VPSMDW

Valparaiso Destin-Ft Walton Beach

Sat 9/5

3:00 pm-7:20 pm

1 stop4h 20m

Chicago Midway

Mon 9/7

5:55 am-9:35 am

1 stop3h 40m

$321

ValparaisoChicago

VPS - MDW

VPSMDW

Valparaiso Destin-Ft Walton Beach

Thu 9/24

6:25 pm-10:25 pm

1 stop4h 00m

Chicago Midway

Sat 10/3

11:25 am-5:15 pm

1 stop5h 50m

$321

ValparaisoChicago

VPS - MDW

VPSMDW

Valparaiso Destin-Ft Walton Beach

Fri 10/2

6:16 pm-8:34 pm

Nonstop2h 18m

Chicago Midway

Sun 10/4

6:46 pm-9:22 pm

3 stops26h 36m

$346

ValparaisoChicago

VPS - MDW

VPSMDW

Valparaiso Destin-Ft Walton Beach

Sat 10/3

5:05 pm-10:44 pm

1 stop5h 39m

Chicago Midway

Tue 10/6

12:27 pm-11:19 pm

2 stops10h 52m

$360
Cheapest one-way
Quickest one-way

ValparaisoChicago

VPS - MDW

VPSMDW

Valparaiso Destin-Ft Walton Beach

Fri 8/7

6:14 pm-8:35 pm

Nonstop2h 21m

$89

ValparaisoChicago

VPS - MDW

VPSMDW

Valparaiso Destin-Ft Walton Beach

Mon 9/21

6:25 pm-10:25 pm

1 stop4h 00m

$160

ValparaisoChicago

VPS - MDW

VPSMDW

Valparaiso Destin-Ft Walton Beach

Sun 9/27

7:50 pm-11:44 pm

2 stops27h 54m

$211

ValparaisoChicago

VPS - MDW

VPSMDW

Valparaiso Destin-Ft Walton Beach

Sat 8/1

7:21 pm-1:58 pm

1 stop18h 37m

$229

ValparaisoChicago

VPS - MDW

VPSMDW

Valparaiso Destin-Ft Walton Beach

Sun 8/30

10:55 am-8:40 pm

1 stop9h 45m

$237

Flights are sorted by cheapest round-trip flights first.

Deals found on 7/28

Showing 1-10 of 14 resultsSorted by cheapest first
1
2

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 July.
ProviderPrice AccuracyTrust Score*
FlightHubPrice Accuracy3 starsTrust Score*3 stars
ExpediaPrice Accuracy1 starTrust 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 FlightHub to be most consistent on Cheapflights vs. FlightHub Users can find the same prices on Valparaiso, Florida-Chicago Midway Airport flight deals on Cheapflights vs. FlightHub >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 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 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 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 29, 2026.

When flying from Valparaiso, Florida to Chicago Midway Airport, the time of day you decide to fly out makes little to no difference towards the overall price you’ll pay on tickets.

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 29, 2026.
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
7.3
Good
680 reviews

Crew

8.1

Overall

7.3

Boarding

7.6

Comfort

6.9

Entertainment

5.4

Food

5.8

Reviews

1 / 20
10.0
Excellent

Jeff,Jun 2026

DEN - TYS

Everything about the flight timing was perfect. The plane was clean and comfortable. The only aggravation is no access to phone charging or complementary food/drink on a cross-country trip. There were no entertainment options, so I'm not sure how I'm supposed to evaluate that on a survey. It's a discount carrier, I get it, but other options are flying the same route with better depart/arrival times that offer these options.
Allegiant Air
7.3
Good
680 reviews
Allegiant Air
7.3
Good
680 reviews

Crew

8.1

Overall

7.3

Boarding

7.6

Comfort

6.9

Entertainment

5.4

Food

5.8

Reviews

1 / 20
10.0
Excellent

Jeff,Jun 2026

DEN - TYS

Everything about the flight timing was perfect. The plane was clean and comfortable. The only aggravation is no access to phone charging or complementary food/drink on a cross-country trip. There were no entertainment options, so I'm not sure how I'm supposed to evaluate that on a survey. It's a discount carrier, I get it, but other options are flying the same route with better depart/arrival times that offer these options.

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 2h 21m. Allegiant Air provides one of the quickest options available for as low as $134. 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 is the cheapest airline to fly from Valparaiso, Florida to Chicago Midway Airport round-trip?

    Our cheapest airline available from Valparaiso, Florida to Chicago Midway Airport is Allegiant Air. Our recent data shows that you can find tickets from as low as $86 on this airline.

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

    On average you can expect to pay $139 for a flight from Valparaiso, Florida to Chicago Midway Airport. The cheapest flight overall is $62 while the most popular route, (Valparaiso Destin-Ft Walton Beach - Chicago Midway) is currently priced at $148.

  • 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.

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
Benton Harbor
Lansing
Merrillville
Valparaiso
Hammond
Saint Joseph
Porter

Browse thousands of different options on Cheapflights for your next trip

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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 July 29, 2026.
AirlineCheapestAverageFlexibilityOn-time
Allegiant AirCheapest$86Average$188FlexibilityNo cancel feeOn-time88%

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