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Cheap flights from Chicago Midway Airport to Valparaiso from $164

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 2/7. 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
8:43 pm - 10:51 pm
MDW
-
VPS
2h 08mnonstop
Allegiant Air Logo
5:37 pm - 7:53 pm
VPS
-
MDW
2h 16mnonstop
$171Allegiant Air
Thu, Mar 12 - Sun, Mar 15
Multiple Airlines Logo
7:30 am - 1:50 pm
MDW
-
VPS
6h 20m1 stop
Multiple Airlines Logo
5:37 pm - 7:53 pm
VPS
-
MDW
2h 16mnonstop
$282Multiple Airlines
Thu, Mar 12 - Sun, Mar 15
Allegiant Air Logo
9:13 pm - 11:21 pm
MDW
-
VPS
2h 08mnonstop
Allegiant Air Logo
2:40 pm - 4:57 pm
VPS
-
MDW
2h 17mnonstop
$289Allegiant Air
Thu, Mar 19 - Thu, Apr 2
Delta Logo
6:25 am - 12:09 pm
MDW
-
VPS
5h 44m1 stop
Delta Logo
1:00 pm - 4:55 pm
VPS
-
MDW
3h 55m1 stop
$315Delta
Tue, Mar 17 - Tue, Mar 31
Southwest Logo
8:15 am - 1:20 pm
MDW
-
VPS
5h 05m1 stop
Southwest Logo
7:00 am - 2:55 pm
VPS
-
MDW
7h 55m2 stops
$321Southwest
Wed, Feb 18 - Wed, Feb 25
Southwest Logo
6:00 am - 1:20 pm
MDW
-
VPS
7h 20m2 stops
Southwest Logo
12:15 pm - 9:00 pm
VPS
-
MDW
8h 45m2 stops
$326Southwest
Wed, Feb 18 - Wed, Feb 25
Delta Logo
5:40 pm - 11:06 pm
MDW
-
VPS
5h 26m1 stop
Delta Logo
6:00 am - 9:56 am
VPS
-
MDW
3h 56m1 stop
$334Delta
Mon, Mar 23 - Wed, Apr 1
Delta Logo
4:30 pm - 11:06 pm
MDW
-
VPS
6h 36m1 stop
Delta Logo
5:13 pm - 10:31 pm
VPS
-
MDW
5h 18m1 stop
$336Delta
Sat, Apr 4 - Sat, Apr 11
Southwest Logo
5:25 am - 9:45 am
MDW
-
VPS
4h 20m1 stop
Southwest Logo
12:35 pm - 7:30 pm
VPS
-
MDW
6h 55m2 stops
$340Southwest
Fri, Mar 20 - Tue, Mar 31
Delta Logo
6:25 am - 12:09 pm
MDW
-
VPS
5h 44m1 stop
Delta Logo
6:00 am - 9:56 am
VPS
-
MDW
3h 56m1 stop
$353Delta
Thu, Mar 12 - Sun, Mar 15

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
Mar 12
MDW8:43 pmChicago Midway
2h 08m
VPS10:51 pmValparaiso Destin-Ft Walton Beach
Mar 15
VPS5:37 pmValparaiso Destin-Ft Walton Beach
2h 16m
MDW7:53 pmChicago Midway
$171
Find similar
Allegiant Air
Mar 19
MDW9:13 pmChicago Midway
2h 08m
VPS11:21 pmValparaiso Destin-Ft Walton Beach
Apr 2
VPS2:40 pmValparaiso Destin-Ft Walton Beach
2h 17m
MDW4:57 pmChicago Midway
$289
Find similar
Allegiant Air
May 22
MDW9:30 pmChicago Midway
2h 07m
VPS11:37 pmValparaiso Destin-Ft Walton Beach
May 26
VPS5:11 pmValparaiso Destin-Ft Walton Beach
39h 13m
2 stops
MDW8:24 amChicago Midway
$408
Find similar

Delta flights from Chicago Midway Airport to Valparaiso, Florida

Our best Delta deals on Chicago Midway Airport to Valparaiso, Florida flight tickets
Delta
Mar 17
MDW6:25 amChicago Midway
5h 44m
1 stop
VPS12:09 pmValparaiso Destin-Ft Walton Beach
Mar 31
VPS1:00 pmValparaiso Destin-Ft Walton Beach
3h 55m
1 stop
MDW4:55 pmChicago Midway
$315
Find similar
Delta
Mar 23
MDW5:40 pmChicago Midway
5h 26m
1 stop
VPS11:06 pmValparaiso Destin-Ft Walton Beach
Apr 1
VPS6:00 amValparaiso Destin-Ft Walton Beach
3h 56m
1 stop
MDW9:56 amChicago Midway
$334
Find similar
Delta
Apr 4
MDW4:30 pmChicago Midway
6h 36m
1 stop
VPS11:06 pmValparaiso Destin-Ft Walton Beach
Apr 11
VPS5:13 pmValparaiso Destin-Ft Walton Beach
5h 18m
1 stop
MDW10:31 pmChicago Midway
$336
Find similar

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 December 23, 2025.
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 3/12

8:43 pm-10:51 pm

Nonstop2h 08m

Valparaiso Destin-Ft Walton Beach

Sun 3/15

5:37 pm-7:53 pm

Nonstop2h 16m

$171

ChicagoValparaiso

MDW - VPS

MDWVPS

Chicago Midway

Thu 3/12

7:30 am-1:50 pm

1 stop6h 20m

Valparaiso Destin-Ft Walton Beach

Sun 3/15

5:37 pm-7:53 pm

Nonstop2h 16m

$282

ChicagoValparaiso

MDW - VPS

MDWVPS

Chicago Midway

Thu 3/19

9:13 pm-11:21 pm

Nonstop2h 08m

Valparaiso Destin-Ft Walton Beach

Thu 4/2

2:40 pm-4:57 pm

Nonstop2h 17m

$289

ChicagoValparaiso

MDW - VPS

MDWVPS

Chicago Midway

Tue 3/17

6:25 am-12:09 pm

1 stop5h 44m

Valparaiso Destin-Ft Walton Beach

Tue 3/31

1:00 pm-4:55 pm

1 stop3h 55m

$315

ChicagoValparaiso

MDW - VPS

MDWVPS

Chicago Midway

Wed 2/18

8:15 am-1:20 pm

1 stop5h 05m

Valparaiso Destin-Ft Walton Beach

Wed 2/25

7:00 am-2:55 pm

2 stops7h 55m

$321

ChicagoValparaiso

MDW - VPS

MDWVPS

Chicago Midway

Wed 2/18

6:00 am-1:20 pm

2 stops7h 20m

Valparaiso Destin-Ft Walton Beach

Wed 2/25

12:15 pm-9:00 pm

2 stops8h 45m

$326

ChicagoValparaiso

MDW - VPS

MDWVPS

Chicago Midway

Mon 3/23

5:40 pm-11:06 pm

1 stop5h 26m

Valparaiso Destin-Ft Walton Beach

Wed 4/1

6:00 am-9:56 am

1 stop3h 56m

$334

ChicagoValparaiso

MDW - VPS

MDWVPS

Chicago Midway

Sat 4/4

4:30 pm-11:06 pm

1 stop6h 36m

Valparaiso Destin-Ft Walton Beach

Sat 4/11

5:13 pm-10:31 pm

1 stop5h 18m

$336

ChicagoValparaiso

MDW - VPS

MDWVPS

Chicago Midway

Fri 3/20

5:25 am-9:45 am

1 stop4h 20m

Valparaiso Destin-Ft Walton Beach

Tue 3/31

12:35 pm-7:30 pm

2 stops6h 55m

$340

ChicagoValparaiso

MDW - VPS

MDWVPS

Chicago Midway

Thu 3/12

6:25 am-12:09 pm

1 stop5h 44m

Valparaiso Destin-Ft Walton Beach

Sun 3/15

6:00 am-9:56 am

1 stop3h 56m

$353

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 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 April instead. Flights to Valparaiso, Florida in April, while not as cheap as those in July, still average around $117.

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 Wednesday when prices can be found for as low as $224. 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 $123. 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

$110

Fastest flight time

2h 06m

Direct flights

Fri

Airports in Valparaiso, Florida

1 airport
The best one-way flight to Valparaiso, Florida from Chicago Midway Airport in the past 72 hours is $110. The best round-trip flight deal from Chicago Midway Airport to Valparaiso, Florida found on momondo in the last 72 hours is $187.
The fastest flight from Chicago Midway Airport to Valparaiso, Florida takes 2h 06m
Direct flights go from Chicago Midway Airport to Valparaiso, Florida on Friday. 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 06m 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
701 reviews
Search Allegiant Air flights
SouthwestPriceFrom $212Free CancellationRating
8.0
4,253 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
DeFuniak Springs
Andalusia

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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