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Midway

$69+ 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 3/26. Fares are subject to change and may not be available on all flights or dates of travel.
VPS — MDW
Apr 15 — Apr 221
Wed 4/15
Wed 4/22
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 March 16, 2026.

This Cheapflightsfares deal was found by Cheapflights users on 3/12. 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 5/72:40 pm
VPS
-
MDW
Nonstop2h 17m
Allegiant Air
Sun 5/105:47 pm
MDW
-
VPS
Nonstop2h 09m
Allegiant Air
Deal found 3/12$101
This Cheapflightsfares deal was found by Cheapflights users on 3/13. 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 4/304:05 pm
VPS
-
MDW
Nonstop2h 17m
Allegiant Air
Thu 5/75:47 pm
MDW
-
VPS
Nonstop2h 09m
Allegiant Air
Deal found 3/13$111
This Booking.com deal was found by Cheapflights users on 3/14. 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.
Sun 3/295:37 pm
VPS
-
MDW
Nonstop2h 16m
Allegiant Air
Thu 4/25:47 pm
MDW
-
VPS
Nonstop2h 09m
Allegiant Air
Deal found 3/14$212
This Cheapflightsfares deal was found by Cheapflights users on 3/12. 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 4/92:40 pm
VPS
-
MDW
Nonstop2h 17m
Allegiant Air
Thu 4/167:12 pm
MDW
-
VPS
Nonstop2h 09m
Allegiant Air
Deal found 3/12$226
This Kiwi.com deal was found by Cheapflights users on 3/12. 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 5/221:19 pm
VPS
-
MDW
Nonstop2h 19m
Allegiant Air
Sun 5/249:14 am
MDW
-
VPS
2 stops34h 32m
Allegiant Air
Deal found 3/12$309
This Kiwi.com deal was found by Cheapflights users on 3/12. 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 3/265:37 pm
VPS
-
MDW
Nonstop2h 16m
Multiple Airlines
Mon 3/309:51 pm
MDW
-
VPS
2 stops17h 21m
Multiple Airlines
Deal found 3/12$329
This Kiwi.com deal was found by Cheapflights users on 3/15. 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 7/246:05 pm
VPS
-
MDW
Nonstop2h 20m
Multiple Airlines
Tue 8/49:11 pm
MDW
-
VPS
3 stops46h 37m
Multiple Airlines
Deal found 3/15$349
This Kiwi.com deal was found by Cheapflights users on 3/14. 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 3/298:19 pm
VPS
-
MDW
2 stops23h 28m
Multiple Airlines
Thu 4/25:47 pm
MDW
-
VPS
Nonstop2h 09m
Multiple Airlines
Deal found 3/14$354
This Kiwi.com deal was found by Cheapflights users on 3/16. 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 3/308:42 pm
VPS
-
MDW
2 stops18h 51m
Multiple Airlines
Thu 4/25:47 pm
MDW
-
VPS
Nonstop2h 09m
Multiple Airlines
Deal found 3/16$355
This Kiwi.com deal was found by Cheapflights users on 3/12. 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 5/221:19 pm
VPS
-
MDW
Nonstop2h 19m
Multiple Airlines
Sun 5/2412:27 pm
MDW
-
VPS
3 stops29h 37m
Multiple Airlines
Deal found 3/12$372

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 March 16, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$101
(Cheapflightsfares)

One-way from

$69
(Trip.com)

Popular in

December

Cheapest in

May

Average price

$345

Good round-trip deal

$232 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. 18% potential increase in price ($57 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 5% potential price decrease ($13 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in March 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 March 16, 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

ValparaisoChicago

VPS - MDW

VPSMDW

Valparaiso Destin-Ft Walton Beach

Sun 3/29

8:19 pm-7:47 pm

2 stops23h 28m

Chicago Midway

Thu 4/2

5:47 pm-7:56 pm

Nonstop2h 09m

$354

ValparaisoChicago

VPS - MDW

VPSMDW

Valparaiso Destin-Ft Walton Beach

Mon 3/30

8:42 pm-8:54 pm

3 stops24h 12m

Chicago Midway

Thu 4/2

5:47 pm-7:56 pm

Nonstop2h 09m

$359

ValparaisoChicago

VPS - MDW

VPSMDW

Valparaiso Destin-Ft Walton Beach

Wed 7/1

7:45 am-11:56 am

1 stop4h 11m

Chicago Midway

Thu 7/9

6:00 am-12:25 pm

1 stop6h 25m

$414

ValparaisoChicago

VPS - MDW

VPSMDW

Valparaiso Destin-Ft Walton Beach

Thu 4/23

6:00 am-9:56 am

1 stop3h 56m

Chicago Midway

Mon 4/27

6:00 am-12:47 pm

1 stop6h 47m

$433

ValparaisoChicago

VPS - MDW

VPSMDW

Valparaiso Destin-Ft Walton Beach

Fri 4/24

5:05 pm-10:28 pm

1 stop5h 23m

Chicago Midway

Mon 4/27

5:21 pm-11:19 pm

1 stop5h 58m

$433
Quickest round-trip

ValparaisoChicago

VPS - MDW

VPSMDW

Valparaiso Destin-Ft Walton Beach

Fri 4/17

5:05 pm-10:28 pm

1 stop5h 23m

Chicago Midway

Sun 4/19

6:00 am-10:59 am

1 stop4h 59m

$433

ValparaisoChicago

VPS - MDW

VPSMDW

Valparaiso Destin-Ft Walton Beach

Tue 3/31

12:35 pm-7:30 pm

2 stops6h 55m

Chicago Midway

Sat 4/4

9:20 am-9:05 pm

2 stops11h 45m

$452
Cheapest one-way
Quickest one-way

ValparaisoChicago

VPS - MDW

VPSMDW

Valparaiso Destin-Ft Walton Beach

Thu 4/9

2:40 pm-4:57 pm

Nonstop2h 17m

$148

ValparaisoChicago

VPS - MDW

VPSMDW

Valparaiso Destin-Ft Walton Beach

Sat 4/18

6:00 pm-10:35 pm

1 stop4h 35m

$187

ValparaisoChicago

VPS - MDW

VPSMDW

Valparaiso Destin-Ft Walton Beach

Mon 5/18

6:15 pm-11:30 pm

1 stop5h 15m

$201

Flights are sorted by cheapest round-trip flights first.

Deals found on 3/16

Showing 1-10 of 16 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 March.
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 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 March 16, 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 March 16, 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
712 reviews

Comfort

6.9

Food

5.9

Crew

8.1

Entertainment

5.5

Overall

7.3

Boarding

7.6

Reviews

1 / 20
4.0
Okay

Michael,Feb 2026

PIE - IND

I appreciate the low cost but the seating is ridiculous. So packed it feels dangerous. Actually it was so bad today, I'm going to look for another airline next time I fly.
Allegiant Air
7.3
Good
712 reviews
Allegiant Air
7.3
Good
712 reviews

Comfort

6.9

Food

5.9

Crew

8.1

Entertainment

5.5

Overall

7.3

Boarding

7.6

Reviews

1 / 20
4.0
Okay

Michael,Feb 2026

PIE - IND

I appreciate the low cost but the seating is ridiculous. So packed it feels dangerous. Actually it was so bad today, I'm going to look for another airline next time I fly.

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 4h 11m. Delta provides one of the quickest options available for as low as $414. The distance from Valparaiso, Florida to Chicago Midway Airport is about 783 mi.

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

    On average you can expect to pay $232 for a flight from Valparaiso, Florida to Chicago Midway Airport. The cheapest flight overall is $230 while the most popular route, (Valparaiso Destin-Ft Walton Beach - Chicago Midway) is currently priced at $101.

  • 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
Lansing
Merrillville
Hammond
Porter
Benton Harbor

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 March 16, 2026.
AirlineCheapestAverageFlexibilityOn-time
Allegiant AirCheapest$86Average$188FlexibilityNo cancel feeOn-time88%

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