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$52+ 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 6/11. Fares are subject to change and may not be available on all flights or dates of travel.
VPS — MDW
May 21 — May 281
Wed 5/21
Wed 5/28
1 adult, Economy
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Cheap 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 May 16, 2025.

Most accurate provider

FlightHub
3 stars

Most trusted provider

Expedia
3 stars

Round-trip from

$247
(Delta)

One-way from

$52
(Booking.com)

Popular in

December

Cheapest in

February

Average price

$451

Good round-trip deal

$86 or less
Provider with most accurate pricing for Valparaiso Destin-Ft Walton Beach-Chicago Midway flight deals.
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Provider most trusted by Cheapflights users for Valparaiso Destin-Ft Walton Beach-Chicago Midway flights.
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From Valparaiso Destin-Ft Walton Beach to Chicago Midway
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One-way flight from Valparaiso Destin-Ft Walton Beach to Chicago Midway
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Highest demand for flights based on searches. 23% potential increase in price ($95 potential increase over avg. RT price).
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Cheapest flight prices on average. 7% potential price decrease ($20 potential savings vs. average RT price).
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Average for round-trip flights in May 2025
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Price to beat on a round-trip flight from Valparaiso Destin-Ft Walton Beach to Chicago Midway.
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Find 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 May 16, 2025.

This Delta deal was found by Cheapflights users on 5/15. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/302:59 pmVPS - MDW
1 stop6h 28mDelta
Tue 6/34:15 pmMDW - VPS
1 stop6h 52mDelta
Deal found 5/15$247
This Southwest deal was found by Cheapflights users on 5/15. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/176:30 pmVPS - MDW
1 stop6h 15mSouthwest
Mon 10/205:50 amMDW - VPS
1 stop5h 35mSouthwest
Deal found 5/15$297
This Mytrip deal was found by Cheapflights users on 5/15. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 9/286:30 amVPS - MDW
2 stops29h 30mAllegiant Air
Thu 10/211:07 amMDW - VPS
Nonstop2h 05mAllegiant Air
Deal found 5/15$353
This Mytrip deal was found by Cheapflights users on 5/15. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 9/286:30 amVPS - MDW
2 stops29h 30mMultiple Airlines
Thu 10/24:46 pmMDW - VPS
3 stops41h 13mMultiple Airlines
Deal found 5/15$494

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 May 16, 2025.
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

Fri 5/30

2:59 pm-9:27 pm

1 stop6h 28m

Chicago Midway

Tue 6/3

4:15 pm-11:07 pm

1 stop6h 52m

$247

ValparaisoChicago

VPS - MDW

VPSMDW

Valparaiso Destin-Ft Walton Beach

Fri 10/17

6:30 pm-12:45 am

1 stop6h 15m

Chicago Midway

Mon 10/20

5:50 am-11:25 am

1 stop5h 35m

$297

ValparaisoChicago

VPS - MDW

VPSMDW

Valparaiso Destin-Ft Walton Beach

Sun 9/28

6:30 am-12:00 pm

2 stops29h 30m

Chicago Midway

Thu 10/2

11:07 am-1:12 pm

Nonstop2h 05m

$353

ValparaisoChicago

VPS - MDW

VPSMDW

Valparaiso Destin-Ft Walton Beach

Sun 9/28

6:30 am-12:00 pm

2 stops29h 30m

Chicago Midway

Thu 10/2

4:46 pm-9:59 am

3 stops41h 13m

$494

ValparaisoChicago

VPS - MDW

VPSMDW

Valparaiso Destin-Ft Walton Beach

Wed 6/11

1:15 pm-3:37 pm

Nonstop2h 22m

$52

ValparaisoChicago

VPS - MDW

VPSMDW

Valparaiso Destin-Ft Walton Beach

Tue 7/15

4:00 pm-9:05 pm

1 stop5h 05m

$88

ValparaisoChicago

VPS - MDW

VPSMDW

Valparaiso Destin-Ft Walton Beach

Fri 7/4

9:06 am-3:41 pm

1 stop6h 35m

$152

ValparaisoChicago

VPS - MDW

VPSMDW

Valparaiso Destin-Ft Walton Beach

Thu 10/30

11:09 am-6:26 pm

3 stops31h 17m

$346

Flights are sorted by cheapest round-trip flights first.

Deals found on 5/14

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 May.
ProviderPrice AccuracyTrust Score*
ExpediaPrice Accuracy1 starTrust Score*3 stars
FlightHubPrice Accuracy3 starsTrust Score*2 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 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 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, April is the cheapest month in which you can book a flight from Valparaiso, Florida to Chicago Midway Airport (average of $160). Flying from Valparaiso, Florida to Chicago Midway Airport in November is currently the most expensive (average of $249). 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 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 May 16, 2025.

It’s typically best to fly out from Valparaiso, Florida to Chicago Midway Airport at noon. Doing so could potentially save you 38% on the flight price compared to flying in the afternoon, which is usually more expensive.

Rainfall in Midway by month

Plan your trip to Midway by taking into account the average rainfall totals by month.

In terms of precipitation, rainfall in Chicago Midway Airport ranges from 1.7 - 4.9 inches per month. August is typically the wettest month, when rainfall can reach 4.9 in. January is typically the driest time to visit Chicago Midway Airport when rainfall is around 1.7 in.

Temperature in Midway by month

Plan your trip to Midway by taking into account the average temperature totals by month.

If weather is an important factor for your trip to Chicago Midway Airport, use this chart to help with planning. For those seeking warmer temperatures, July is the ideal time of year to visit, when temperatures reach an average of 73.4 F. Travelers looking to avoid the cold should look outside of January, when temperatures are typically at their lowest (around 23.0 F).

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 May 16, 2025.
Southwest
8.0
Very good
4,289 reviews

Boarding

8.2

Entertainment

7.6

Comfort

8.0

Food

7.1

Crew

8.6

Overall

8.0

Reviews

1 / 20
2.0
Mediocre

Anonymous,Feb 2025

MCO - STL

Cancelled at last minute, SWA unable to assist in formulating alternate plans. Wound up renting a car and driving 13 hours to beat bad weather forecast at home. Not SWA’s fault that there was significant bad weather across the country.
Southwest
8.0
Very good
4,289 reviews
Southwest
8.0
Very good
4,289 reviews

Boarding

8.2

Entertainment

7.6

Comfort

8.0

Food

7.1

Crew

8.6

Overall

8.0

Reviews

1 / 20
2.0
Mediocre

Anonymous,Feb 2025

MCO - STL

Cancelled at last minute, SWA unable to assist in formulating alternate plans. Wound up renting a car and driving 13 hours to beat bad weather forecast at home. Not SWA’s fault that there was significant bad weather across the country.
Delta
8.0
Very good
7,946 reviews
Southwest
8.0
Very good
4,289 reviews

Boarding

8.2

Entertainment

7.6

Comfort

8.0

Food

7.1

Crew

8.6

Overall

8.0

Reviews

1 / 20
2.0
Mediocre

Anonymous,Feb 2025

MCO - STL

Cancelled at last minute, SWA unable to assist in formulating alternate plans. Wound up renting a car and driving 13 hours to beat bad weather forecast at home. Not SWA’s fault that there was significant bad weather across the country.
Allegiant Air
7.3
Good
732 reviews
Southwest
8.0
Very good
4,289 reviews

Boarding

8.2

Entertainment

7.6

Comfort

8.0

Food

7.1

Crew

8.6

Overall

8.0

Reviews

1 / 20
2.0
Mediocre

Anonymous,Feb 2025

MCO - STL

Cancelled at last minute, SWA unable to assist in formulating alternate plans. Wound up renting a car and driving 13 hours to beat bad weather forecast at home. Not SWA’s fault that there was significant bad weather across the country.

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.

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

    Our cheapest airline available from Valparaiso, Florida to Chicago Midway Airport is Delta. Our recent data shows that you can find tickets from as low as $247 on this airline. Additional options worth looking into are Southwest and Allegiant Air, starting at $297 and $353 round-trip. You may be able to fly from Valparaiso, Florida to Chicago Midway Airport for 18% less than the average price by searching for these airlines.

  • What are the cheapest airlines to fly from Valparaiso, Florida to Chicago Midway Airport one-way?

    One-way options have recently been found by users for as low as $52 on Allegiant Air. Other airlines that offer cheap prices include Southwest from $88 and Delta from $152 one-way.

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

    On average you can expect to pay $89 for a flight from Valparaiso, Florida to Chicago Midway Airport. The cheapest flight overall is $86 while the most popular route, (Valparaiso Destin-Ft Walton Beach - Chicago Midway) is currently priced at $133.

  • 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, April is the cheapest month in which you can book a flight from Valparaiso, Florida to Chicago Midway Airport (average of $160). Flying from Valparaiso, Florida to Chicago Midway Airport in November is currently the most expensive (average of $249). 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
Merrillville
Hammond
Benton Harbor
Porter
Lansing
Valparaiso
Chesterton

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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 May 16, 2025.
AirlineCheapestAverageFlexibilityOn-time
DeltaCheapest$242Average$424FlexibilityNo cancel feeOn-timeN/A

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