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Cheap flights from Chicago Midway Airport to Valparaiso from $59

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

Enter your travel dates to find the best prices.
Allegiant Air Logo
12:07 pm - 2:12 pmMDW-VPS
2h 05mnonstop
Allegiant Air Logo
9:00 am - 11:17 amVPS-MDW
2h 17mnonstop
$130Allegiant Air
Find Deal
jue., oct. 30 - jue., nov. 6
Allegiant Air Logo
12:07 pm - 2:12 pmMDW-VPS
2h 05mnonstop
Allegiant Air Logo
9:00 am - 11:17 amVPS-MDW
2h 17mnonstop
$142Allegiant Air
Find Deal
dom., nov. 2 - jue., nov. 6
Allegiant Air Logo
12:07 pm - 2:12 pmMDW-VPS
2h 05mnonstop
Allegiant Air Logo
9:00 am - 11:17 amVPS-MDW
2h 17mnonstop
$149Allegiant Air
Find Deal
jue., oct. 30 - jue., nov. 6
Allegiant Air Logo
12:07 pm - 2:12 pmMDW-VPS
2h 05mnonstop
Allegiant Air Logo
9:00 am - 11:17 amVPS-MDW
2h 17mnonstop
$178Allegiant Air
Find Deal
jue., oct. 30 - dom., nov. 2
Multiple Airlines Logo
1:37 pm - 7:03 pmMDW-VPS
29h 26m2 stops
Multiple Airlines Logo
9:00 am - 11:17 amVPS-MDW
2h 17mnonstop
$197Multiple Airlines
Find Deal
vie., oct. 31 - jue., nov. 6
Multiple Airlines Logo
12:30 pm - 6:16 pmMDW-VPS
29h 46m2 stops
Multiple Airlines Logo
9:00 am - 11:17 amVPS-MDW
2h 17mnonstop
$223Multiple Airlines
Find Deal
jue., oct. 30 - jue., nov. 6
Southwest Logo
7:40 am - 1:15 pmMDW-VPS
5h 35m1 stop
Southwest Logo
7:15 am - 12:45 pmVPS-MDW
5h 30m1 stop
$279Southwest
Find Deal
mié., oct. 29 - mié., nov. 5
Southwest Logo
1:15 pm - 9:10 pmMDW-VPS
7h 55m2 stops
Southwest Logo
2:00 pm - 7:20 pmVPS-MDW
5h 20m1 stop
$284Southwest
Find Deal
mié., oct. 29 - mié., nov. 5
Delta Logo
5:04 pm - 8:59 pmMDW-VPS
3h 55m1 stop
Delta Logo
3:45 pm - 10:14 pmVPS-MDW
6h 29m1 stop
$355Delta
Find Deal
lun., oct. 27 - vie., oct. 31
Delta Logo
9:35 am - 9:58 pmMDW-VPS
12h 23m2 stops
Delta Logo
6:00 am - 6:25 pmVPS-MDW
12h 25m2 stops
$366Delta
Find Deal
mar., nov. 4 - sáb., nov. 8

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 30
MDW12:07 pmChicago Midway
2h 05m
VPS2:12 pmValparaiso Destin-Ft Walton Beach
Nov 6
VPS9:00 amValparaiso Destin-Ft Walton Beach
2h 17m
MDW11:17 amChicago Midway
$130
Find similar
Allegiant Air
Nov 2
MDW12:07 pmChicago Midway
2h 05m
VPS2:12 pmValparaiso Destin-Ft Walton Beach
Nov 6
VPS9:00 amValparaiso Destin-Ft Walton Beach
2h 17m
MDW11:17 amChicago Midway
$142
Find similar
Allegiant Air
Oct 30
MDW12:07 pmChicago Midway
2h 05m
VPS2:12 pmValparaiso Destin-Ft Walton Beach
Nov 6
VPS9:00 amValparaiso Destin-Ft Walton Beach
2h 17m
MDW11:17 amChicago Midway
$149
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
Oct 27
MDW5:04 pmChicago Midway
3h 55m
1 stop
VPS8:59 pmValparaiso Destin-Ft Walton Beach
Oct 31
VPS3:45 pmValparaiso Destin-Ft Walton Beach
6h 29m
1 stop
MDW10:14 pmChicago Midway
$355
Find similar
Delta
Nov 4
MDW9:35 amChicago Midway
12h 23m
2 stops
VPS9:58 pmValparaiso Destin-Ft Walton Beach
Nov 8
VPS6:00 amValparaiso Destin-Ft Walton Beach
12h 25m
2 stops
MDW6:25 pmChicago Midway
$366
Find similar
Delta
Oct 27
MDW5:04 pmChicago Midway
3h 55m
1 stop
VPS8:59 pmValparaiso Destin-Ft Walton Beach
Oct 31
VPS5:00 pmValparaiso Destin-Ft Walton Beach
15h 40m
2 stops
MDW8:40 amChicago Midway
$367
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 octubre 2, 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

jue. 10/30

12:07 pm-2:12 pm

Nonstop2h 05m

Valparaiso Destin-Ft Walton Beach

jue. 11/6

9:00 am-11:17 am

Nonstop2h 17m

$130

ChicagoValparaiso

MDW - VPS

MDWVPS

Chicago Midway

dom. 11/2

12:07 pm-2:12 pm

Nonstop2h 05m

Valparaiso Destin-Ft Walton Beach

jue. 11/6

9:00 am-11:17 am

Nonstop2h 17m

$142

ChicagoValparaiso

MDW - VPS

MDWVPS

Chicago Midway

jue. 10/30

12:07 pm-2:12 pm

Nonstop2h 05m

Valparaiso Destin-Ft Walton Beach

jue. 11/6

9:00 am-11:17 am

Nonstop2h 17m

$149

ChicagoValparaiso

MDW - VPS

MDWVPS

Chicago Midway

jue. 10/30

12:07 pm-2:12 pm

Nonstop2h 05m

Valparaiso Destin-Ft Walton Beach

dom. 11/2

9:00 am-11:17 am

Nonstop2h 17m

$178

ChicagoValparaiso

MDW - VPS

MDWVPS

Chicago Midway

vie. 10/31

1:37 pm-7:03 pm

2 stops29h 26m

Valparaiso Destin-Ft Walton Beach

jue. 11/6

9:00 am-11:17 am

Nonstop2h 17m

$197

ChicagoValparaiso

MDW - VPS

MDWVPS

Chicago Midway

jue. 10/30

12:30 pm-6:16 pm

2 stops29h 46m

Valparaiso Destin-Ft Walton Beach

jue. 11/6

9:00 am-11:17 am

Nonstop2h 17m

$223

ChicagoValparaiso

MDW - VPS

MDWVPS

Chicago Midway

mié. 10/29

7:40 am-1:15 pm

1 stop5h 35m

Valparaiso Destin-Ft Walton Beach

mié. 11/5

7:15 am-12:45 pm

1 stop5h 30m

$279

ChicagoValparaiso

MDW - VPS

MDWVPS

Chicago Midway

mié. 10/29

1:15 pm-9:10 pm

2 stops7h 55m

Valparaiso Destin-Ft Walton Beach

mié. 11/5

2:00 pm-7:20 pm

1 stop5h 20m

$284

ChicagoValparaiso

MDW - VPS

MDWVPS

Chicago Midway

lun. 10/27

5:04 pm-8:59 pm

1 stop3h 55m

Valparaiso Destin-Ft Walton Beach

vie. 10/31

3:45 pm-10:14 pm

1 stop6h 29m

$355

ChicagoValparaiso

MDW - VPS

MDWVPS

Chicago Midway

mar. 11/4

9:35 am-9:58 pm

2 stops12h 23m

Valparaiso Destin-Ft Walton Beach

sáb. 11/8

6:00 am-6:25 pm

2 stops12h 25m

$366

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 $112. In contrast, the most expensive time of day to depart to Valparaiso, Florida is in the morning when prices are around $389.

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

$64

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 $64. The best round-trip flight deal from Chicago Midway Airport to Valparaiso, Florida found on momondo in the last 72 hours is $180.
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 $82Free CancellationRating
7.2
699 reviews
Search Allegiant Air flights
SouthwestPriceFrom $212Free CancellationRating
8.0
4,248 reviews
Search Southwest flights

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

    Allegiant Air operates around 1 flight from Chicago Midway Airport to Valparaiso, Florida every week. The average price of these flights found in the last 72 hours has been $138, but momondo users have found Allegiant Air deals from Chicago Midway Airport to Valparaiso, Florida from as low as $82 round-trip. Allegiant Air has been scored 7.2/10 in 699 reviews.

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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