HomeSearch by dateVacation packagesHotelsFlight dealsCar rentalTravel tips & news
Midway

$53+ 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 10/30. Fares are subject to change and may not be available on all flights or dates of travel.
VPS — MDW
oct. 16 — oct. 231
jue. 10/16
jue. 10/23
1 adult, Economy
We work with more than 300 partners to bring you better travel deals

Find cheap flights from Valparaiso to Midway with Cheapflights

1. Tell us where you want to go

Enter your travel information like dates, passengers, trip type (one-way or round trip), and preferred cabin class then click “Find deals”

2. Select your favorite providers

We find the providers serving your travel needs. Choose up to four travel providers to compare side-by-side for flights, hotels, or car rentals.

3. Compare prices and book

Review each provider’s pricing and select the best option for you! Book through your favorite provider’s website for a seamless experience.

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 septiembre 16, 2025.

Round-trip from

$155
(Cheapflightsfares)

One-way from

$53
(Cheapflightsfares)

Popular in

November

Cheapest in

May

Average price

$272
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. 25% potential increase in price ($85 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 8% potential price decrease ($19 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in September 2025
Search Deals

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 septiembre 16, 2025.

This Cheapflightsfares deal was found by Cheapflights users on 9/15. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
jue. 10/238:00 amVPS - MDW
Nonstop2h 17mAllegiant Air
dom. 10/2611:07 amMDW - VPS
Nonstop2h 05mAllegiant Air
Deal found 9/15$155
This Kiwi.com deal was found by Cheapflights users on 9/14. 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.
jue. 11/205:24 pmVPS - MDW
Nonstop2h 19mAllegiant Air
lun. 12/19:24 amMDW - VPS
Nonstop2h 13mAllegiant Air
Deal found 9/14$158
This Kiwi.com deal was found by Cheapflights users on 9/14. 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.
jue. 11/205:24 pmVPS - MDW
Nonstop2h 19mAllegiant Air
sáb. 11/299:09 amMDW - VPS
Nonstop2h 13mAllegiant Air
Deal found 9/14$167
This Kiwi.com deal was found by Cheapflights users on 9/14. 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.
mar. 11/2511:31 amVPS - MDW
Nonstop2h 19mAllegiant Air
lun. 12/19:24 amMDW - VPS
Nonstop2h 13mAllegiant Air
Deal found 9/14$191
This Kiwi.com deal was found by Cheapflights users on 9/14. 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.
mar. 11/2511:31 amVPS - MDW
Nonstop2h 19mAllegiant Air
sáb. 11/299:09 amMDW - VPS
Nonstop2h 13mAllegiant Air
Deal found 9/14$200
This Kiwi.com deal was found by Cheapflights users on 9/14. 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.
dom. 11/235:24 pmVPS - MDW
Nonstop2h 19mAllegiant Air
lun. 12/19:24 amMDW - VPS
Nonstop2h 13mAllegiant Air
Deal found 9/14$230
This Kiwi.com deal was found by Cheapflights users on 9/14. 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.
dom. 11/235:24 pmVPS - MDW
Nonstop2h 19mAllegiant Air
sáb. 11/299:09 amMDW - VPS
Nonstop2h 13mAllegiant Air
Deal found 9/14$240
This Kiwi.com deal was found by Cheapflights users on 9/15. 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.
jue. 10/236:30 amVPS - MDW
1 stop16h 55mMultiple Airlines
dom. 10/2611:07 amMDW - VPS
Nonstop2h 05mMultiple Airlines
Deal found 9/15$241
This Kiwi.com deal was found by Cheapflights users on 9/14. 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.
vie. 10/173:46 pmVPS - MDW
2 stops18h 35mMultiple Airlines
dom. 10/1911:07 amMDW - VPS
Nonstop2h 05mMultiple Airlines
Deal found 9/14$273
This Kiwi.com deal was found by Cheapflights users on 9/14. 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.
jue. 11/206:35 amVPS - MDW
2 stops16h 08mMultiple Airlines
lun. 12/19:24 amMDW - VPS
Nonstop2h 13mMultiple Airlines
Deal found 9/14$284
This Kiwi.com deal was found by Cheapflights users on 9/14. 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.
jue. 11/206:35 amVPS - MDW
2 stops16h 08mMultiple Airlines
sáb. 11/299:09 amMDW - VPS
Nonstop2h 13mMultiple Airlines
Deal found 9/14$295

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 septiembre 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

jue. 10/23

8:00 am-10:17 am

Nonstop2h 17m

Chicago Midway

dom. 10/26

11:07 am-1:12 pm

Nonstop2h 05m

$155

ValparaisoChicago

VPS - MDW

VPSMDW

Valparaiso Destin-Ft Walton Beach

mar. 11/25

11:31 am-1:50 pm

Nonstop2h 19m

Chicago Midway

lun. 12/1

9:24 am-11:37 am

Nonstop2h 13m

$191

ValparaisoChicago

VPS - MDW

VPSMDW

Valparaiso Destin-Ft Walton Beach

dom. 11/23

5:24 pm-7:43 pm

Nonstop2h 19m

Chicago Midway

sáb. 11/29

9:09 am-11:22 am

Nonstop2h 13m

$240

ValparaisoChicago

VPS - MDW

VPSMDW

Valparaiso Destin-Ft Walton Beach

jue. 10/23

8:00 am-10:17 am

Nonstop2h 17m

Chicago Midway

dom. 10/26

11:57 am-1:32 pm

2 stops25h 35m

$244

ValparaisoChicago

VPS - MDW

VPSMDW

Valparaiso Destin-Ft Walton Beach

vie. 10/17

10:15 am-10:47 pm

2 stops36h 32m

Chicago Midway

dom. 10/19

11:07 am-1:12 pm

Nonstop2h 05m

$273

ValparaisoChicago

VPS - MDW

VPSMDW

Valparaiso Destin-Ft Walton Beach

lun. 11/24

6:00 am-11:52 am

1 stop5h 52m

Chicago Midway

jue. 11/27

6:00 am-11:06 am

1 stop5h 06m

$375

ValparaisoChicago

VPS - MDW

VPSMDW

Valparaiso Destin-Ft Walton Beach

jue. 11/20

5:24 pm-7:43 pm

Nonstop2h 19m

Chicago Midway

mié. 11/26

2:11 pm-5:21 pm

3 stops27h 10m

$390

ValparaisoChicago

VPS - MDW

VPSMDW

Valparaiso Destin-Ft Walton Beach

vie. 10/17

12:00 pm-5:40 pm

1 stop5h 40m

Chicago Midway

dom. 10/19

6:15 am-11:55 am

1 stop5h 40m

$402

ValparaisoChicago

VPS - MDW

VPSMDW

Valparaiso Destin-Ft Walton Beach

mié. 10/22

12:05 pm-6:30 pm

1 stop6h 25m

$157

ValparaisoChicago

VPS - MDW

VPSMDW

Valparaiso Destin-Ft Walton Beach

mar. 12/16

11:20 am-4:00 pm

1 stop4h 40m

$157

Flights are sorted by cheapest round-trip flights first.

Deals found on 9/14

Showing 1-10 of 15 results
1
2

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.

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 0 different airlines.

  • 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 17m. Allegiant Air provides one of the quickest options available for as low as $155. The distance from Valparaiso, Florida to Chicago Midway Airport is about 783 mi. Most flights are nonstop.

  • 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 Chicago Midway Airport?

Book flights to Chicago Midway Airport if you plan to visit one of these locations
Merrillville
Lansing
Hammond
Benton Harbor
Porter
Chesterton

Browse thousands of different options on Cheapflights for your next trip

Toggle through the tabs below to find thousands of options on Cheapflights for your next trip.

Alternative routes for Valparaiso to Midway

See prices for flight routes from nearby airports that may be better suited for you.
Miami to O'Hare Intl flights
Fort Lauderdale to O'Hare Intl flights
Orlando to O'Hare Intl flights
Tampa to O'Hare Intl flights
Orlando to Midway flights
Miami to Midway flights
Jacksonville to O'Hare Intl flights
Tampa to Midway flights
West Palm Beach to O'Hare Intl flights
Fort Lauderdale to Midway flights
Fort Myers to O'Hare Intl flights
Pensacola to O'Hare Intl flights
Jacksonville to Midway flights
West Palm Beach to Midway flights
Sarasota to O'Hare Intl flights
Fort Myers to Midway flights
Pensacola to Midway flights
Daytona Beach to O'Hare Intl flights
Tallahassee to O'Hare Intl flights
Melbourne to O'Hare Intl flights
Gainesville to O'Hare Intl flights
Panama City to O'Hare Intl flights
Tallahassee to Midway flights
Valparaiso to O'Hare Intl flights
Gainesville to Midway flights
Sarasota to Midway flights
Orlando Sanford Intl to Rockford flights
Key West to O'Hare Intl flights
Panama City to Midway flights
St Petersburg to Rockford flights
Orlando to Rockford flights
Valdosta to O'Hare Intl flights
Key West to Midway flights
Daytona Beach to Midway flights
Melbourne to Midway flights
Fort Lauderdale to Rockford flights
Punta Gorda to Rockford flights
Fort Myers to Rockford flights
Tampa to Rockford flights
Pensacola to Rockford flights

100% Free

Cheapflights is completely free to use, so you can start saving the moment you arrive.

Book with Flexibility

Our users can plan ahead with confidence and find flights with no change fees

Travel Smart

Millions of people come to us for their flight needs every year. We help make travel planning easy by providing useful insights and data-driven graphs that can inform your decisions.