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Midway

$167+ 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 6/17. Fares are subject to change and may not be available on all flights or dates of travel.
VPS — MDW
Feb 28 — Mar 71
Sat 2/28
Sat 3/7
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 January 29, 2026.

This Kiwi.com deal was found by Cheapflights users on 1/28. 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.
Mon 6/296:12 pm
VPS
-
MDW
Nonstop2h 21m
Allegiant Air
Fri 7/39:15 pm
MDW
-
VPS
Nonstop2h 14m
Allegiant Air
Deal found 1/28$194
This Kiwi.com deal was found by Cheapflights users on 1/28. 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 8/76:14 pm
VPS
-
MDW
Nonstop2h 21m
Allegiant Air
Mon 8/109:25 pm
MDW
-
VPS
Nonstop2h 14m
Allegiant Air
Deal found 1/28$253
This Kiwi.com deal was found by Cheapflights users on 1/26. 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.
Thu 4/232:40 pm
VPS
-
MDW
Nonstop2h 17m
Multiple Airlines
Mon 4/279:14 am
MDW
-
VPS
3 stops23h 34m
Multiple Airlines
Deal found 1/26$299
This Southwest deal was found by Cheapflights users on 1/27. 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 2/247:00 am
VPS
-
MDW
1 stop6h 25m
Southwest
Tue 3/38:15 am
MDW
-
VPS
1 stop5h 05m
Southwest
Deal found 1/27$333
This Kiwi.com deal was found by Cheapflights users on 1/27. 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 3/1312:11 pm
VPS
-
MDW
3 stops33h 34m
Multiple Airlines
Sun 3/158:43 pm
MDW
-
VPS
Nonstop2h 08m
Multiple Airlines
Deal found 1/27$342
This Kiwi.com deal was found by Cheapflights users on 1/28. 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 4/178:00 am
VPS
-
MDW
2 stops35h 31m
Multiple Airlines
Sun 4/195:47 pm
MDW
-
VPS
Nonstop2h 09m
Multiple Airlines
Deal found 1/28$351
This Delta deal was found by Cheapflights users on 1/26. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 4/236:00 am
VPS
-
MDW
1 stop6h 07m
Delta
Tue 4/285:21 pm
MDW
-
VPS
1 stop5h 58m
Delta
Deal found 1/26$355
This Southwest deal was found by Cheapflights users on 1/28. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/812:15 pm
VPS
-
MDW
1 stop8h 05m
Southwest
Tue 8/116:30 am
MDW
-
VPS
1 stop7h 00m
Southwest
Deal found 1/28$368

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 January 29, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$194
(Kiwi.com)

One-way from

$167
(Southwest)

Popular in

December

Cheapest in

May

Average price

$376

Good round-trip deal

$102 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. 27% potential increase in price ($82 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 7% potential price decrease ($16 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 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 January 29, 2026.
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

Mon 6/29

6:12 pm-8:33 pm

Nonstop2h 21m

Chicago Midway

Fri 7/3

9:15 pm-11:29 pm

Nonstop2h 14m

$194

ValparaisoChicago

VPS - MDW

VPSMDW

Valparaiso Destin-Ft Walton Beach

Thu 4/23

2:40 pm-4:57 pm

Nonstop2h 17m

Chicago Midway

Mon 4/27

9:14 am-8:48 am

3 stops23h 34m

$299

ValparaisoChicago

VPS - MDW

VPSMDW

Valparaiso Destin-Ft Walton Beach

Tue 2/24

7:00 am-1:25 pm

1 stop6h 25m

Chicago Midway

Tue 3/3

8:15 am-1:20 pm

1 stop5h 05m

$333

ValparaisoChicago

VPS - MDW

VPSMDW

Valparaiso Destin-Ft Walton Beach

Fri 3/13

8:42 pm-8:21 pm

2 stops23h 39m

Chicago Midway

Sun 3/15

8:43 pm-10:51 pm

Nonstop2h 08m

$354

ValparaisoChicago

VPS - MDW

VPSMDW

Valparaiso Destin-Ft Walton Beach

Fri 3/13

7:20 am-11:55 am

1 stop4h 35m

Chicago Midway

Mon 3/16

4:05 pm-9:05 pm

1 stop5h 00m

$370

ValparaisoChicago

VPS - MDW

VPSMDW

Valparaiso Destin-Ft Walton Beach

Fri 4/17

4:59 pm-10:28 pm

1 stop5h 29m

Chicago Midway

Sun 4/19

6:00 am-12:48 pm

1 stop6h 48m

$374

ValparaisoChicago

VPS - MDW

VPSMDW

Valparaiso Destin-Ft Walton Beach

Wed 7/1

6:00 am-9:51 am

1 stop3h 51m

Chicago Midway

Thu 7/9

6:00 am-10:11 am

1 stop4h 11m

$377

ValparaisoChicago

VPS - MDW

VPSMDW

Valparaiso Destin-Ft Walton Beach

Wed 6/17

4:00 pm-12:05 am

1 stop8h 05m

$167

ValparaisoChicago

VPS - MDW

VPSMDW

Valparaiso Destin-Ft Walton Beach

Mon 4/6

4:00 pm-9:20 pm

1 stop5h 20m

$183

ValparaisoChicago

VPS - MDW

VPSMDW

Valparaiso Destin-Ft Walton Beach

Fri 3/13

6:00 pm-12:05 am

1 stop6h 05m

$186

Flights are sorted by cheapest round-trip flights first.

Deals found on 1/27

Showing 1-10 of 15 results
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 January.
ProviderPrice AccuracyTrust Score*
ExpediaPrice Accuracy1 starTrust Score*3 stars
FlightHubPrice 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 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 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 $108). 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 January 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
7.2
Good
706 reviews

Boarding

7.6

Food

5.9

Overall

7.2

Crew

8.1

Entertainment

5.5

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
706 reviews
Allegiant Air
7.2
Good
706 reviews

Boarding

7.6

Food

5.9

Overall

7.2

Crew

8.1

Entertainment

5.5

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 2h 21m. Allegiant Air provides one of the quickest options available for as low as $194. 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 $104 for a flight from Valparaiso, Florida to Chicago Midway Airport. The cheapest flight overall is $68 while the most popular route, (Valparaiso Destin-Ft Walton Beach - Chicago Midway) is currently priced at $194.

  • 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 $108). 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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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 January 29, 2026.
AirlineCheapestAverageFlexibilityOn-time
Allegiant AirCheapest$86Average$144FlexibilityNo cancel feeOn-time88%

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