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Cheap flights from Chicago Midway Airport to Valparaiso from $49

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 8/14. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.
1 adult
1 adult, Economy, 0 bags

Discover deals from 900+ travel sites with momondo.

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
9:24 pm - 11:35 pm
MDW
-
VPS
2h 11mnonstop
Allegiant Air Logo
5:54 pm - 8:12 pm
VPS
-
MDW
2h 18mnonstop
$96Allegiant Air
Fri, Oct 2 - Mon, Oct 5
Allegiant Air Logo
9:21 pm - 11:35 pm
MDW
-
VPS
2h 14mnonstop
Allegiant Air Logo
6:10 pm - 8:30 pm
VPS
-
MDW
2h 20mnonstop
$97Allegiant Air
Fri, Jul 24 - Mon, Jul 27
Allegiant Air Logo
9:21 pm - 11:35 pm
MDW
-
VPS
2h 14mnonstop
Allegiant Air Logo
6:11 pm - 8:31 pm
VPS
-
MDW
2h 20mnonstop
$101Allegiant Air
Fri, Jul 24 - Fri, Jul 31
Allegiant Air Logo
1:08 pm - 3:19 pm
MDW
-
VPS
2h 11mnonstop
Allegiant Air Logo
6:30 am - 8:54 am
VPS
-
MDW
2h 24mnonstop
$111Allegiant Air
Mon, Nov 16 - Thu, Nov 19
Allegiant Air Logo
9:21 pm - 11:35 pm
MDW
-
VPS
2h 14mnonstop
Allegiant Air Logo
6:11 pm - 8:31 pm
VPS
-
MDW
2h 20mnonstop
$112Allegiant Air
Fri, Jul 24 - Fri, Jul 31
Allegiant Air Logo
9:21 pm - 11:35 pm
MDW
-
VPS
2h 14mnonstop
Allegiant Air Logo
6:11 pm - 8:31 pm
VPS
-
MDW
2h 20mnonstop
$117Allegiant Air
Fri, Jul 24 - Fri, Jul 31
Allegiant Air Logo
9:21 pm - 11:35 pm
MDW
-
VPS
2h 14mnonstop
Allegiant Air Logo
6:11 pm - 8:31 pm
VPS
-
MDW
2h 20mnonstop
$118Allegiant Air
Fri, Jul 24 - Fri, Jul 31
Allegiant Air Logo
9:21 pm - 11:35 pm
MDW
-
VPS
2h 14mnonstop
Allegiant Air Logo
6:10 pm - 8:30 pm
VPS
-
MDW
2h 20mnonstop
$123Allegiant Air
Fri, Jul 24 - Mon, Jul 27
Allegiant Air Logo
9:25 pm - 11:39 pm
MDW
-
VPS
2h 14mnonstop
Allegiant Air Logo
6:14 pm - 8:35 pm
VPS
-
MDW
2h 21mnonstop
$138Allegiant Air
Fri, Aug 14 - Mon, Aug 17
Allegiant Air Logo
9:20 pm - 11:34 pm
MDW
-
VPS
2h 14mnonstop
Allegiant Air Logo
6:14 pm - 8:35 pm
VPS
-
MDW
2h 21mnonstop
$144Allegiant Air
Mon, Aug 3 - Fri, Aug 7

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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
Oct 2
MDW9:24 pmChicago Midway
2h 11m
VPS11:35 pmValparaiso Destin-Ft Walton Beach
Oct 5
VPS5:54 pmValparaiso Destin-Ft Walton Beach
2h 18m
MDW8:12 pmChicago Midway
$96
Allegiant Air
Jul 24
MDW9:21 pmChicago Midway
2h 14m
VPS11:35 pmValparaiso Destin-Ft Walton Beach
Jul 27
VPS6:10 pmValparaiso Destin-Ft Walton Beach
2h 20m
MDW8:30 pmChicago Midway
$97
Allegiant Air
Jul 24
MDW9:21 pmChicago Midway
2h 14m
VPS11:35 pmValparaiso Destin-Ft Walton Beach
Jul 31
VPS6:11 pmValparaiso Destin-Ft Walton Beach
2h 20m
MDW8:31 pmChicago Midway
$101

Delta flights from Chicago Midway Airport to Valparaiso, Florida

Our best Delta deals on Chicago Midway Airport to Valparaiso, Florida flight tickets
Delta
Jul 11
MDW6:00 amChicago Midway
6h 29m
1 stop
VPS12:29 pmValparaiso Destin-Ft Walton Beach
Jul 18
VPS2:56 pmValparaiso Destin-Ft Walton Beach
7h 19m
1 stop
MDW10:15 pmChicago Midway
$395
Delta
Jul 11
MDW6:00 amChicago Midway
6h 29m
1 stop
VPS12:29 pmValparaiso Destin-Ft Walton Beach
Jul 18
VPS2:56 pmValparaiso Destin-Ft Walton Beach
7h 19m
1 stop
MDW10:15 pmChicago Midway
$405
Delta
Jul 11
MDW6:00 amChicago Midway
4h 29m
1 stop
VPS10:29 amValparaiso Destin-Ft Walton Beach
Jul 18
VPS2:56 pmValparaiso Destin-Ft Walton Beach
7h 19m
1 stop
MDW10:15 pmChicago Midway
$471

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 July 3, 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

Cheapest round-trip
Quickest round-trip

ChicagoValparaiso

MDW - VPS

MDWVPS

Chicago Midway

Fri 10/2

9:24 pm-11:35 pm

Nonstop2h 11m

Valparaiso Destin-Ft Walton Beach

Mon 10/5

5:54 pm-8:12 pm

Nonstop2h 18m

$96

ChicagoValparaiso

MDW - VPS

MDWVPS

Chicago Midway

Fri 7/24

9:21 pm-11:35 pm

Nonstop2h 14m

Valparaiso Destin-Ft Walton Beach

Mon 7/27

6:10 pm-8:30 pm

Nonstop2h 20m

$97

ChicagoValparaiso

MDW - VPS

MDWVPS

Chicago Midway

Fri 7/24

9:21 pm-11:35 pm

Nonstop2h 14m

Valparaiso Destin-Ft Walton Beach

Fri 7/31

6:11 pm-8:31 pm

Nonstop2h 20m

$101

ChicagoValparaiso

MDW - VPS

MDWVPS

Chicago Midway

Mon 11/16

1:08 pm-3:19 pm

Nonstop2h 11m

Valparaiso Destin-Ft Walton Beach

Thu 11/19

6:30 am-8:54 am

Nonstop2h 24m

$111

ChicagoValparaiso

MDW - VPS

MDWVPS

Chicago Midway

Fri 7/24

9:21 pm-11:35 pm

Nonstop2h 14m

Valparaiso Destin-Ft Walton Beach

Fri 7/31

6:11 pm-8:31 pm

Nonstop2h 20m

$112

ChicagoValparaiso

MDW - VPS

MDWVPS

Chicago Midway

Fri 7/24

9:21 pm-11:35 pm

Nonstop2h 14m

Valparaiso Destin-Ft Walton Beach

Fri 7/31

6:11 pm-8:31 pm

Nonstop2h 20m

$117

ChicagoValparaiso

MDW - VPS

MDWVPS

Chicago Midway

Fri 7/24

9:21 pm-11:35 pm

Nonstop2h 14m

Valparaiso Destin-Ft Walton Beach

Fri 7/31

6:11 pm-8:31 pm

Nonstop2h 20m

$118

ChicagoValparaiso

MDW - VPS

MDWVPS

Chicago Midway

Fri 7/24

9:21 pm-11:35 pm

Nonstop2h 14m

Valparaiso Destin-Ft Walton Beach

Mon 7/27

6:10 pm-8:30 pm

Nonstop2h 20m

$123

ChicagoValparaiso

MDW - VPS

MDWVPS

Chicago Midway

Fri 8/14

9:25 pm-11:39 pm

Nonstop2h 14m

Valparaiso Destin-Ft Walton Beach

Mon 8/17

6:14 pm-8:35 pm

Nonstop2h 21m

$138

ChicagoValparaiso

MDW - VPS

MDWVPS

Chicago Midway

Mon 8/3

9:20 pm-11:34 pm

Nonstop2h 14m

Valparaiso Destin-Ft Walton Beach

Fri 8/7

6:14 pm-8:35 pm

Nonstop2h 21m

$144

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 20 resultsSorted by cheapest first
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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 typical price of a round-trip flight between Chicago Midway Airport and Valparaiso, Florida?

What is the cheapest month to fly to Valparaiso, Florida?

If you aren’t able to travel during the month of July, then book flights to Valparaiso, Florida from Chicago Midway Airport during November instead. Flights to Valparaiso, Florida in November, while not as cheap as those in July, still average around $133.

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 $199. This is often the case because there is less demand to fly during this day of the week. On the other hand, Friday 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 $448.

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 $174. In contrast, the most expensive time of day to depart to Valparaiso, Florida is in the morning when prices are around $426.

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 Airport to Valparaiso, Florida flights?

There is only 1 cabin class available to choose from on Chicago Midway Airport to Valparaiso, Florida 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

$50

Fastest flight time

2h 11m

Direct flights

Mon, Tue 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 $50. The best round-trip flight deal from Chicago Midway Airport to Valparaiso, Florida found on momondo in the last 72 hours is $280.
The fastest flight from Chicago Midway Airport to Valparaiso, Florida takes 2h 11m
Direct flights go from Chicago Midway Airport to Valparaiso, Florida on Monday, Tuesday 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

Frequently asked questions about flying from Chicago Midway Airport to Valparaiso, Florida

  • 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 11m 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 $96Free CancellationRating
7.3
689 reviews
Search Allegiant Air flights
SouthwestPriceFrom $234Free CancellationRating
7.9
4,250 reviews
Search Southwest flights

  • Southwest Flights From Chicago Midway Airport to Valparaiso, Florida

    Southwest operates around 2 flights from Chicago Midway Airport to Valparaiso, Florida every week. The average price of these flights found in the last 72 hours has been $413, but momondo users have found Southwest deals from Chicago Midway Airport to Valparaiso, Florida from as low as $234 round-trip. Southwest has been scored 7.9/10 in 4,250 reviews.

  • Allegiant Air Flights From Chicago Midway Airport to Valparaiso, Florida

    $96 is the best Allegiant Air flight deal from Chicago Midway Airport to Valparaiso, Florida found on momondo over the last 72 hours. The average Allegiant Air ticket price found was closer to $344, however, with flight time and availability significantly affecting the price. Allegiant Air (7.3/10 from 689 user reviews) flies into Valparaiso, Florida from Chicago Midway Airport 1 time in an average week so prices can vary.

Traveling to a place near Valparaiso?

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