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Cheap flights from Chicago Midway Airport to Valparaiso from $94

This is the cheapest one-way flight price found by a momondo user in the last 72 hours by searching for a flight from Chicago Midway Airport to Valparaiso departing on 4/4. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.
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0 bags

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Find the cheapest flights from Chicago Midway Airport to Valparaiso

Cheap round-trip flights

Enter your travel dates to find the best prices.
Allegiant Air Logo
3:40 pm - 5:46 pm
MDW
-
VPS
2h 06mnonstop
Allegiant Air Logo
5:40 pm - 7:56 pm
VPS
-
MDW
2h 16mnonstop
$112Allegiant Air
Thu, Feb 26 - Thu, Mar 5
Allegiant Air Logo
3:40 pm - 5:46 pm
MDW
-
VPS
2h 06mnonstop
Allegiant Air Logo
5:40 pm - 7:56 pm
VPS
-
MDW
2h 16mnonstop
$120Allegiant Air
Sun, Feb 22 - Thu, Mar 5
Allegiant Air Logo
3:40 pm - 5:46 pm
MDW
-
VPS
2h 06mnonstop
Allegiant Air Logo
5:37 pm - 7:53 pm
VPS
-
MDW
2h 16mnonstop
$124Allegiant Air
Sun, Mar 1 - Thu, Mar 12
Allegiant Air Logo
9:30 pm - 11:37 pm
MDW
-
VPS
2h 07mnonstop
Allegiant Air Logo
6:21 pm - 8:40 pm
VPS
-
MDW
2h 19mnonstop
$152Allegiant Air
Mon, May 25 - Fri, May 29
Allegiant Air Logo
3:40 pm - 5:46 pm
MDW
-
VPS
2h 06mnonstop
Allegiant Air Logo
5:40 pm - 7:56 pm
VPS
-
MDW
2h 16mnonstop
$164Allegiant Air
Sun, Mar 1 - Sun, Mar 8
Allegiant Air Logo
8:46 pm - 10:54 pm
MDW
-
VPS
2h 08mnonstop
Allegiant Air Logo
5:37 pm - 7:53 pm
VPS
-
MDW
2h 16mnonstop
$166Allegiant Air
Thu, Mar 5 - Thu, Mar 12
Allegiant Air Logo
3:40 pm - 5:46 pm
MDW
-
VPS
2h 06mnonstop
Allegiant Air Logo
12:31 pm - 2:50 pm
VPS
-
MDW
2h 19mnonstop
$193Allegiant Air
Thu, Feb 26 - Sun, Mar 1
Multiple Airlines Logo
7:53 pm - 7:50 pm
MDW
-
VPS
47h 57m
2 stops
Multiple Airlines Logo
5:40 pm - 7:56 pm
VPS
-
MDW
2h 16mnonstop
$200Multiple Airlines
Fri, Feb 27 - Thu, Mar 5
Allegiant Air Logo
8:46 pm - 10:54 pm
MDW
-
VPS
2h 08mnonstop
Allegiant Air Logo
5:40 pm - 7:56 pm
VPS
-
MDW
2h 16mnonstop
$206Allegiant Air
Thu, Mar 5 - Sun, Mar 8
Allegiant Air Logo
3:40 pm - 5:46 pm
MDW
-
VPS
2h 06mnonstop
Allegiant Air Logo
12:31 pm - 2:50 pm
VPS
-
MDW
2h 19mnonstop
$211Allegiant Air
Thu, Feb 26 - Sun, Mar 1

Southwest flights from Chicago Midway Airport to Valparaiso, Florida

Our best Southwest deals on Chicago Midway Airport to Valparaiso, Florida flight tickets
Southwest
Feb 26
MDW5:15 amChicago Midway
8h 00m
1 stop
VPS1:15 pmValparaiso Destin-Ft Walton Beach
Mar 2
VPS2:30 pmValparaiso Destin-Ft Walton Beach
5h 40m
1 stop
MDW8:10 pmChicago Midway
$229
Southwest
Mar 16
MDW5:25 amChicago Midway
4h 20m
1 stop
VPS9:45 amValparaiso Destin-Ft Walton Beach
Mar 17
VPS12:35 pmValparaiso Destin-Ft Walton Beach
6h 55m
2 stops
MDW7:30 pmChicago Midway
$231
Southwest
Feb 28
MDW5:40 amChicago Midway
4h 55m
1 stop
VPS10:35 amValparaiso Destin-Ft Walton Beach
Mar 3
VPS7:00 amValparaiso Destin-Ft Walton Beach
6h 25m
1 stop
MDW1:25 pmChicago Midway
$255

Allegiant Air flights from Chicago Midway Airport to Valparaiso, Florida

Our best Allegiant Air deals on Chicago Midway Airport to Valparaiso, Florida flight tickets
Allegiant Air
Feb 26
MDW3:40 pmChicago Midway
2h 06m
VPS5:46 pmValparaiso Destin-Ft Walton Beach
Mar 5
VPS5:40 pmValparaiso Destin-Ft Walton Beach
2h 16m
MDW7:56 pmChicago Midway
$112
Allegiant Air
Feb 22
MDW3:40 pmChicago Midway
2h 06m
VPS5:46 pmValparaiso Destin-Ft Walton Beach
Mar 5
VPS5:40 pmValparaiso Destin-Ft Walton Beach
2h 16m
MDW7:56 pmChicago Midway
$120
Allegiant Air
Mar 1
MDW3:40 pmChicago Midway
2h 06m
VPS5:46 pmValparaiso Destin-Ft Walton Beach
Mar 12
VPS5:37 pmValparaiso Destin-Ft Walton Beach
2h 16m
MDW7:53 pmChicago Midway
$124

momondo Fare Finder

 
Customize your flight search to find flights from Chicago Midway Airport to Valparaiso, Florida 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, momondo users made 832,500 searches. Data last updated February 12, 2026.
Use the filters below to find and compare flights from Chicago Midway Airport to Valparaiso, Florida that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

ChicagoValparaiso

MDW - VPS

MDWVPS

Chicago Midway

Thu 2/26

3:40 pm-5:46 pm

Nonstop2h 06m

Valparaiso Destin-Ft Walton Beach

Thu 3/5

5:40 pm-7:56 pm

Nonstop2h 16m

$112

ChicagoValparaiso

MDW - VPS

MDWVPS

Chicago Midway

Sun 2/22

3:40 pm-5:46 pm

Nonstop2h 06m

Valparaiso Destin-Ft Walton Beach

Thu 3/5

5:40 pm-7:56 pm

Nonstop2h 16m

$120

ChicagoValparaiso

MDW - VPS

MDWVPS

Chicago Midway

Sun 3/1

3:40 pm-5:46 pm

Nonstop2h 06m

Valparaiso Destin-Ft Walton Beach

Thu 3/12

5:37 pm-7:53 pm

Nonstop2h 16m

$124

ChicagoValparaiso

MDW - VPS

MDWVPS

Chicago Midway

Mon 5/25

9:30 pm-11:37 pm

Nonstop2h 07m

Valparaiso Destin-Ft Walton Beach

Fri 5/29

6:21 pm-8:40 pm

Nonstop2h 19m

$152

ChicagoValparaiso

MDW - VPS

MDWVPS

Chicago Midway

Sun 3/1

3:40 pm-5:46 pm

Nonstop2h 06m

Valparaiso Destin-Ft Walton Beach

Sun 3/8

5:40 pm-7:56 pm

Nonstop2h 16m

$164

ChicagoValparaiso

MDW - VPS

MDWVPS

Chicago Midway

Thu 3/5

8:46 pm-10:54 pm

Nonstop2h 08m

Valparaiso Destin-Ft Walton Beach

Thu 3/12

5:37 pm-7:53 pm

Nonstop2h 16m

$166

ChicagoValparaiso

MDW - VPS

MDWVPS

Chicago Midway

Thu 2/26

3:40 pm-5:46 pm

Nonstop2h 06m

Valparaiso Destin-Ft Walton Beach

Sun 3/1

12:31 pm-2:50 pm

Nonstop2h 19m

$193

ChicagoValparaiso

MDW - VPS

MDWVPS

Chicago Midway

Fri 2/27

7:53 pm-7:50 pm

2 stops47h 57m

Valparaiso Destin-Ft Walton Beach

Thu 3/5

5:40 pm-7:56 pm

Nonstop2h 16m

$200

ChicagoValparaiso

MDW - VPS

MDWVPS

Chicago Midway

Thu 3/5

8:46 pm-10:54 pm

Nonstop2h 08m

Valparaiso Destin-Ft Walton Beach

Sun 3/8

5:40 pm-7:56 pm

Nonstop2h 16m

$206

ChicagoValparaiso

MDW - VPS

MDWVPS

Chicago Midway

Thu 2/26

3:40 pm-5:46 pm

Nonstop2h 06m

Valparaiso Destin-Ft Walton Beach

Sun 3/1

12:31 pm-2:50 pm

Nonstop2h 19m

$211

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 20 resultsSorted by cheapest first
1
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See travel insights to Valparaiso from

How to get the cheapest flight ticket from Chicago Midway Airport to Valparaiso, Florida

Look no further. We've gone through all the searches for this route on momondo so you have the important information and insights to find the cheapest flight ticket for your trip

What is the cheapest day to depart on your flight to Valparaiso, Florida?

The cheapest day to depart on your flight to Valparaiso, Florida is on a Monday when prices can be found for as low as $276. This is often the case because there is less demand to fly during this day of the week. On the other hand, Sunday is the most expensive day to depart from Chicago Midway Airport because it is more convenient for both business and leisure travelers. As a result, prices tend to be around $395.

What is the cheapest time of day to depart on your flight to Valparaiso, Florida?

Our data shows that the cheapest Chicago Midway Airport to Valparaiso, Florida flights are usually those with departure times in the afternoon. Our users have found flights to Valparaiso, Florida in the afternoon for as low as $151. In contrast, the most expensive time of day to depart to Valparaiso, Florida is in the morning when prices are around $391.

What is the cheapest Chicago Midway to Valparaiso Destin-Ft Walton Beach flight route?

Fly from Chicago Midway to Valparaiso Destin-Ft Walton Beach for the best Chicago Midway - Valparaiso Destin-Ft Walton Beach flight prices

What cabin class options are available on Chicago Midway to Valparaiso Destin-Ft Walton Beach flights?

There is only 1 cabin class available to choose from on Chicago Midway to Valparaiso Destin-Ft Walton Beach flights. Cabin price and availability will vary by airline so perform a search above to find the right deals for you.

Can stopping save me money on Chicago Midway Airport to Valparaiso, Florida flights?

No. A direct flight is the cheapest option for a flight between Chicago Midway Airport to Valparaiso, Florida.

When to book flights from Chicago Midway Airport to Valparaiso, Florida

Are you open to changing your travel dates? Check out the ideal times to fly from Chicago Midway Airport to Valparaiso, Florida according to our flight data. Find out which month and days have the cheapest flights.
Estimated round-trip price

Cheap Chicago Midway Airport to Valparaiso, Florida (MDW to VPS) flight deals and tips

Find info about flight duration, direct flights, and airports for your flight from Chicago Midway Airport to Valparaiso, Florida

Best Price Found

$138

Fastest flight time

2h 08m

Direct flights

Mon, Tue, Fri and Sat

Airports in Valparaiso, Florida

1 airport
The best one-way flight to Valparaiso, Florida from Chicago Midway Airport in the past 72 hours is $138. The best round-trip flight deal from Chicago Midway Airport to Valparaiso, Florida found on momondo in the last 72 hours is $164.
The fastest flight from Chicago Midway Airport to Valparaiso, Florida takes 2h 08m
Direct flights go from Chicago Midway Airport to Valparaiso, Florida on Monday, Tuesday, Friday and Saturday. The only airline offering direct flights is Allegiant Air.
There is 1 airport in Valparaiso, Florida. From Chicago Midway Airport there are direct flights to Valparaiso Destin-Ft Walton Beach (VPS).
Search flight deals

  • How far is Chicago Midway to Valparaiso Destin-Ft Walton Beach by plane?

    The distance between Chicago Midway and Valparaiso Destin-Ft Walton Beach is about 781.8 mi. 2h 08m is a normal flight duration for this route.

  • When did momondo last update prices for flights from Chicago Midway Airport to Valparaiso Destin-Ft Walton Beach Airport?

    Prices for flights from Chicago Midway Airport to Valparaiso Destin-Ft Walton Beach Airport are refreshed on a daily basis.

  • How many operators does momondo search for flights from Chicago Midway Airport to Valparaiso Destin-Ft Walton Beach Airport?

  • How old do you have to be to fly from Chicago Midway Airport to Valparaiso Destin-Ft Walton Beach Airport?

    The minimum age a child must be to fly alone is five but airlines that offer an unaccompanied minor (UNMR) service will have their own age restrictions, including rules around flight length, timings, and stopovers. We always recommend checking with the individual airline you are booking with to travel from Chicago Midway Airport to Valparaiso Destin-Ft Walton Beach Airport.

  • What documentation or ID do you need to fly to Valparaiso Destin-Ft Walton Beach Airport?

    The travel and health documents you'll need for your trip to Valparaiso Destin-Ft Walton Beach Airport may differ based on your itinerary and personal situation. Typically, you should have several documents on hand, such as a national ID card or driver's license and a passport that is valid for six months after your intended arrival at Valparaiso Destin-Ft Walton Beach Airport. It is always advisable to seek advice from your airline or a trusted third party, such as IATA.

  • What is the most popular plane model from Chicago Midway Airport to Valparaiso, Florida?

  • What is the most popular airline from Chicago Midway Airport to Valparaiso, Florida?

Best airlines flying from Chicago Midway Airport to Valparaiso, Florida

Compare and see reviews for airlines that fly from Chicago Midway Airport to Valparaiso, Florida with momondo
Airline
Rating
Free Cancellation
Price
Allegiant AirPriceFrom $82Free CancellationRating
7.2
711 reviews
Search Allegiant Air flights
SouthwestPriceFrom $212Free CancellationRating
8.0
4,283 reviews
Search Southwest flights

Traveling to a place near Valparaiso?

Book flights to Valparaiso if you plan to visit one of these locations
Fort Walton Beach
Crestview
Niceville
Andalusia
DeFuniak Springs

Why use momondo?

Why should I use momondo to find a flight deal from Chicago to Valparaiso?

momondo compares prices from hundreds of airlines and agents so you can find and book the best deal on flights from Chicago to Valparaiso. Millions of users trust and use momondo every year so you are in good hands.

Can I find flights from Chicago to Valparaiso with flexible booking policies on momondo?

momondo does allow users to show only those flights to Valparaiso from Chicago which offer a flexible booking policy as well as other useful filters and features.

How can momondo help me find flights from Chicago to Valparaiso?

Once all potential Chicago to Valparaiso flight options are in front of you, momondo lets you sort and filter flights based on preferences such as airline, price and flight times amongst many other options.

I’m not ready to book a flight from Chicago to Valparaiso right now. Can momondo alert me if prices change?

Yes momondo offers price alerts on flights to Valparaiso from Chicago. After performing a search on this page you should be able to see the price alert set up feature. Simply provide a valid email address and momondo will instantly alert you when prices change.

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