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Cheap flights from Chicago Midway Airport to Valparaiso from $50

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 11/9. 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

Allegiant Air Logo
11:07 am - 1:12 pmMDW-VPS
2h 05mnonstop
Allegiant Air Logo
8:00 am - 10:17 amVPS-MDW
2h 17mnonstop
$179Allegiant Air
Find Deal
dom., oct. 5 - jue., oct. 16
Southwest Logo
7:40 am - 1:15 pmMDW-VPS
5h 35m1 stop
Southwest Logo
4:15 pm - 10:25 pmVPS-MDW
6h 10m1 stop
$207Southwest
Find Deal
mar., oct. 7 - mié., oct. 8
Southwest Logo
5:35 am - 11:20 amMDW-VPS
5h 45m1 stop
Southwest Logo
12:05 pm - 7:10 pmVPS-MDW
7h 05m2 stops
$212Southwest
Find Deal
mar., oct. 7 - mié., oct. 8
Southwest Logo
8:30 am - 1:25 pmMDW-VPS
4h 55m1 stop
Southwest Logo
4:15 pm - 11:15 pmVPS-MDW
7h 00m1 stop
$221Southwest
Find Deal
mar., sep. 30 - lun., oct. 6
Southwest Logo
10:10 am - 3:35 pmMDW-VPS
5h 25m2 stops
Southwest Logo
10:20 am - 5:05 pmVPS-MDW
6h 45m2 stops
$231Southwest
Find Deal
mar., oct. 7 - mié., oct. 8
Southwest Logo
5:55 am - 1:20 pmMDW-VPS
7h 25m1 stop
Southwest Logo
7:00 am - 1:25 pmVPS-MDW
6h 25m1 stop
$235Southwest
Find Deal
mar., feb. 3 - mié., feb. 11
Southwest Logo
5:55 am - 1:20 pmMDW-VPS
7h 25m1 stop
Southwest Logo
2:00 pm - 10:05 pmVPS-MDW
8h 05m2 stops
$240Southwest
Find Deal
mar., feb. 3 - mié., feb. 11
Allegiant Air Logo
12:08 pm - 8:30 pmMDW-VPS
8h 22m1 stop
Allegiant Air Logo
8:00 am - 10:17 amVPS-MDW
2h 17mnonstop
$257Allegiant Air
Find Deal
lun., oct. 6 - jue., oct. 16
Delta Logo
1:00 pm - 11:08 pmMDW-VPS
10h 08m2 stops
Delta Logo
6:00 am - 6:34 pmVPS-MDW
12h 34m2 stops
$290Delta
Find Deal
sáb., ene. 31 - mié., feb. 11
Delta Logo
6:00 am - 9:59 amMDW-VPS
3h 59m1 stop
Delta Logo
6:00 am - 9:51 amVPS-MDW
3h 51m1 stop
$301Delta
Find Deal
mar., oct. 7 - jue., oct. 16

Delta flights from Chicago Midway Airport to Valparaiso, Florida

Our best Delta deals on Chicago Midway Airport to Valparaiso, Florida flight tickets
Delta
Jan 31
MDW1:00 pmChicago Midway
10h 08m
2 stops
VPS11:08 pmValparaiso Destin-Ft Walton Beach
Feb 11
VPS6:00 amValparaiso Destin-Ft Walton Beach
12h 34m
2 stops
MDW6:34 pmChicago Midway
$290
Find similar
Delta
Oct 7
MDW6:00 amChicago Midway
3h 59m
1 stop
VPS9:59 amValparaiso Destin-Ft Walton Beach
Oct 16
VPS6:00 amValparaiso Destin-Ft Walton Beach
3h 51m
1 stop
MDW9:51 amChicago Midway
$301
Find similar
Delta
Feb 6
MDW9:30 amChicago Midway
13h 38m
2 stops
VPS11:08 pmValparaiso Destin-Ft Walton Beach
Feb 11
VPS6:00 amValparaiso Destin-Ft Walton Beach
12h 34m
2 stops
MDW6:34 pmChicago Midway
$320
Find similar

Southwest flights from Chicago Midway Airport to Valparaiso, Florida

Our best Southwest deals on Chicago Midway Airport to Valparaiso, Florida flight tickets
Southwest
Oct 7
MDW7:40 amChicago Midway
5h 35m
1 stop
VPS1:15 pmValparaiso Destin-Ft Walton Beach
Oct 8
VPS4:15 pmValparaiso Destin-Ft Walton Beach
6h 10m
1 stop
MDW10:25 pmChicago Midway
$207
Find similar
Southwest
Oct 7
MDW5:35 amChicago Midway
5h 45m
1 stop
VPS11:20 amValparaiso Destin-Ft Walton Beach
Oct 8
VPS12:05 pmValparaiso Destin-Ft Walton Beach
7h 05m
2 stops
MDW7:10 pmChicago Midway
$212
Find similar
Southwest
Sep 30
MDW8:30 amChicago Midway
4h 55m
1 stop
VPS1:25 pmValparaiso Destin-Ft Walton Beach
Oct 6
VPS4:15 pmValparaiso Destin-Ft Walton Beach
7h 00m
1 stop
MDW11:15 pmChicago Midway
$221
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 agosto 14, 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

dom. 10/5

11:07 am-1:12 pm

Nonstop2h 05m

Valparaiso Destin-Ft Walton Beach

jue. 10/16

8:00 am-10:17 am

Nonstop2h 17m

$179

ChicagoValparaiso

MDW - VPS

MDWVPS

Chicago Midway

mar. 10/7

7:40 am-1:15 pm

1 stop5h 35m

Valparaiso Destin-Ft Walton Beach

mié. 10/8

4:15 pm-10:25 pm

1 stop6h 10m

$207

ChicagoValparaiso

MDW - VPS

MDWVPS

Chicago Midway

mar. 10/7

5:35 am-11:20 am

1 stop5h 45m

Valparaiso Destin-Ft Walton Beach

mié. 10/8

12:05 pm-7:10 pm

2 stops7h 05m

$212

ChicagoValparaiso

MDW - VPS

MDWVPS

Chicago Midway

mar. 9/30

8:30 am-1:25 pm

1 stop4h 55m

Valparaiso Destin-Ft Walton Beach

lun. 10/6

4:15 pm-11:15 pm

1 stop7h 00m

$221

ChicagoValparaiso

MDW - VPS

MDWVPS

Chicago Midway

mar. 10/7

10:10 am-3:35 pm

2 stops5h 25m

Valparaiso Destin-Ft Walton Beach

mié. 10/8

10:20 am-5:05 pm

2 stops6h 45m

$231

ChicagoValparaiso

MDW - VPS

MDWVPS

Chicago Midway

mar. 2/3

5:55 am-1:20 pm

1 stop7h 25m

Valparaiso Destin-Ft Walton Beach

mié. 2/11

7:00 am-1:25 pm

1 stop6h 25m

$235

ChicagoValparaiso

MDW - VPS

MDWVPS

Chicago Midway

mar. 2/3

5:55 am-1:20 pm

1 stop7h 25m

Valparaiso Destin-Ft Walton Beach

mié. 2/11

2:00 pm-10:05 pm

2 stops8h 05m

$240

ChicagoValparaiso

MDW - VPS

MDWVPS

Chicago Midway

lun. 10/6

12:08 pm-8:30 pm

1 stop8h 22m

Valparaiso Destin-Ft Walton Beach

jue. 10/16

8:00 am-10:17 am

Nonstop2h 17m

$257

ChicagoValparaiso

MDW - VPS

MDWVPS

Chicago Midway

sáb. 1/31

1:00 pm-11:08 pm

2 stops10h 08m

Valparaiso Destin-Ft Walton Beach

mié. 2/11

6:00 am-6:34 pm

2 stops12h 34m

$290

ChicagoValparaiso

MDW - VPS

MDWVPS

Chicago Midway

mar. 10/7

6:00 am-9:59 am

1 stop3h 59m

Valparaiso Destin-Ft Walton Beach

jue. 10/16

6:00 am-9:51 am

1 stop3h 51m

$301

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 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 $192. This is often the case because there is less demand to fly during this day of the week. On the other hand, Saturday 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 $121. In contrast, the most expensive time of day to depart to Valparaiso, Florida is in the morning when prices are around $379.

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 are 1 cabin classes 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.

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 05m

Direct flights

Mon, Wed, Fri and Sun

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 $179.
The fastest flight from Chicago Midway Airport to Valparaiso, Florida takes 2h 05m
Direct flights go from Chicago Midway Airport to Valparaiso, Florida on Monday, Wednesday, Friday and Sunday. The only airline offering direct flights is Allegiant Air.
There is 1 airport near Valparaiso, Florida: 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 05m 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 $85Free CancellationRating
7.2
701 reviews
Search Allegiant Air flights
SouthwestPriceFrom $212Free CancellationRating
8.0
4,244 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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