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Cheap flights from Valparaiso, Florida to Chicago from $47

This is the cheapest one-way flight price found by a momondo user in the last 72 hours by searching for a flight from Valparaiso, Florida to Chicago departing on 3/12. 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
0 bags

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Find the cheapest flights from Valparaiso, Florida to Chicago

Cheap round-trip flights

Enter your travel dates to find the best prices.
Allegiant Air Logo
5:40 pm - 7:56 pm
VPS
-
MDW
2h 16mnonstop
Allegiant Air Logo
8:46 pm - 10:54 pm
MDW
-
VPS
2h 08mnonstop
$103Allegiant Air
Thu, Mar 5 - Sun, Mar 8
Allegiant Air Logo
12:31 pm - 2:50 pm
VPS
-
MDW
2h 19mnonstop
Allegiant Air Logo
3:40 pm - 5:46 pm
MDW
-
VPS
2h 06mnonstop
$114Allegiant Air
Sun, Feb 15 - Sun, Feb 22
Multiple Airlines Logo
5:40 pm - 7:56 pm
VPS
-
MDW
2h 16mnonstop
Multiple Airlines Logo
7:30 am - 1:52 pm
MDW
-
VPS
6h 22m
1 stop
$231Multiple Airlines
Thu, Mar 5 - Sun, Mar 8
Multiple Airlines Logo
12:31 pm - 2:50 pm
VPS
-
MDW
2h 19mnonstop
Multiple Airlines Logo
6:00 am - 7:58 pm
MDW
-
VPS
13h 58m
2 stops
$240Multiple Airlines
Sun, Feb 15 - Sun, Feb 22
Multiple Airlines Logo
7:00 am - 1:41 pm
VPS
-
MDW
30h 41m
3 stops
Multiple Airlines Logo
8:46 pm - 10:54 pm
MDW
-
VPS
2h 08mnonstop
$242Multiple Airlines
Thu, Mar 5 - Sun, Mar 8
Multiple Airlines Logo
8:48 pm - 11:51 pm
VPS
-
MDW
27h 03m
2 stops
Multiple Airlines Logo
8:46 pm - 10:54 pm
MDW
-
VPS
2h 08mnonstop
$258Multiple Airlines
Thu, Mar 5 - Sun, Mar 8
Southwest Logo
5:15 pm - 11:05 pm
VPS
-
MDW
5h 50m
1 stop
Southwest Logo
10:00 am - 5:15 pm
MDW
-
VPS
7h 15m
1 stop
$307Southwest
Wed, Apr 29 - Sat, May 2
Allegiant Air Logo
5:37 pm - 7:53 pm
VPS
-
MDW
2h 16mnonstop
Allegiant Air Logo
8:43 pm - 10:51 pm
MDW
-
VPS
2h 08mnonstop
$311Allegiant Air
Thu, Mar 26 - Sun, Mar 29
Southwest Logo
12:30 pm - 7:45 pm
VPS
-
MDW
7h 15m
2 stops
Southwest Logo
4:20 pm - 9:00 pm
MDW
-
VPS
4h 40m
1 stop
$312Southwest
Wed, Apr 29 - Sat, May 2
Southwest Logo
12:30 pm - 7:45 pm
VPS
-
MDW
7h 15m
2 stops
Southwest Logo
12:05 pm - 9:00 pm
MDW
-
VPS
8h 55m
2 stops
$317Southwest
Wed, Apr 29 - Sat, May 2

Allegiant Air flights from Valparaiso, Florida to Chicago Midway Airport

Our best Allegiant Air deals on Valparaiso, Florida to Chicago Midway Airport flight tickets
Allegiant Air
Mar 5
VPS5:40 pmValparaiso Destin-Ft Walton Beach
2h 16m
MDW7:56 pmChicago Midway
Mar 8
MDW8:46 pmChicago Midway
2h 08m
VPS10:54 pmValparaiso Destin-Ft Walton Beach
$103
Allegiant Air
Feb 15
VPS12:31 pmValparaiso Destin-Ft Walton Beach
2h 19m
MDW2:50 pmChicago Midway
Feb 22
MDW3:40 pmChicago Midway
2h 06m
VPS5:46 pmValparaiso Destin-Ft Walton Beach
$114
Allegiant Air
Mar 26
VPS5:37 pmValparaiso Destin-Ft Walton Beach
2h 16m
MDW7:53 pmChicago Midway
Mar 29
MDW8:43 pmChicago Midway
2h 08m
VPS10:51 pmValparaiso Destin-Ft Walton Beach
$311

Southwest flights from Valparaiso, Florida to Chicago Midway Airport

Our best Southwest deals on Valparaiso, Florida to Chicago Midway Airport flight tickets
Southwest
Apr 29
VPS5:15 pmValparaiso Destin-Ft Walton Beach
5h 50m
1 stop
MDW11:05 pmChicago Midway
May 2
MDW10:00 amChicago Midway
7h 15m
1 stop
VPS5:15 pmValparaiso Destin-Ft Walton Beach
$307
Southwest
Apr 29
VPS12:30 pmValparaiso Destin-Ft Walton Beach
7h 15m
2 stops
MDW7:45 pmChicago Midway
May 2
MDW4:20 pmChicago Midway
4h 40m
1 stop
VPS9:00 pmValparaiso Destin-Ft Walton Beach
$312
Southwest
Apr 29
VPS12:30 pmValparaiso Destin-Ft Walton Beach
7h 15m
2 stops
MDW7:45 pmChicago Midway
May 2
MDW12:05 pmChicago Midway
8h 55m
2 stops
VPS9:00 pmValparaiso Destin-Ft Walton Beach
$317

momondo Fare Finder

 
Customize your flight search to find flights from Valparaiso, Florida to Chicago Midway Airport 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 January 26, 2026.
Use the filters below to find and compare flights from Valparaiso, Florida to Chicago Midway Airport that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

ValparaisoChicago

VPS - MDW

VPSMDW

Valparaiso Destin-Ft Walton Beach

Thu 3/5

5:40 pm-7:56 pm

Nonstop2h 16m

Chicago Midway

Sun 3/8

8:46 pm-10:54 pm

Nonstop2h 08m

$103

ValparaisoChicago

VPS - MDW

VPSMDW

Valparaiso Destin-Ft Walton Beach

Sun 2/15

12:31 pm-2:50 pm

Nonstop2h 19m

Chicago Midway

Sun 2/22

3:40 pm-5:46 pm

Nonstop2h 06m

$114

ValparaisoChicago

VPS - MDW

VPSMDW

Valparaiso Destin-Ft Walton Beach

Thu 3/5

5:40 pm-7:56 pm

Nonstop2h 16m

Chicago Midway

Sun 3/8

7:30 am-1:52 pm

1 stop6h 22m

$231

ValparaisoChicago

VPS - MDW

VPSMDW

Valparaiso Destin-Ft Walton Beach

Sun 2/15

12:31 pm-2:50 pm

Nonstop2h 19m

Chicago Midway

Sun 2/22

6:00 am-7:58 pm

2 stops13h 58m

$240

ValparaisoChicago

VPS - MDW

VPSMDW

Valparaiso Destin-Ft Walton Beach

Thu 3/5

7:00 am-1:41 pm

3 stops30h 41m

Chicago Midway

Sun 3/8

8:46 pm-10:54 pm

Nonstop2h 08m

$242

ValparaisoChicago

VPS - MDW

VPSMDW

Valparaiso Destin-Ft Walton Beach

Thu 3/5

8:48 pm-11:51 pm

2 stops27h 03m

Chicago Midway

Sun 3/8

8:46 pm-10:54 pm

Nonstop2h 08m

$258

ValparaisoChicago

VPS - MDW

VPSMDW

Valparaiso Destin-Ft Walton Beach

Wed 4/29

5:15 pm-11:05 pm

1 stop5h 50m

Chicago Midway

Sat 5/2

10:00 am-5:15 pm

1 stop7h 15m

$307

ValparaisoChicago

VPS - MDW

VPSMDW

Valparaiso Destin-Ft Walton Beach

Thu 3/26

5:37 pm-7:53 pm

Nonstop2h 16m

Chicago Midway

Sun 3/29

8:43 pm-10:51 pm

Nonstop2h 08m

$311

ValparaisoChicago

VPS - MDW

VPSMDW

Valparaiso Destin-Ft Walton Beach

Wed 4/29

12:30 pm-7:45 pm

2 stops7h 15m

Chicago Midway

Sat 5/2

4:20 pm-9:00 pm

1 stop4h 40m

$312

ValparaisoChicago

VPS - MDW

VPSMDW

Valparaiso Destin-Ft Walton Beach

Wed 4/29

12:30 pm-7:45 pm

2 stops7h 15m

Chicago Midway

Sat 5/2

12:05 pm-9:00 pm

2 stops8h 55m

$317

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 Chicago from

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

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 Chicago Midway Airport?

According to our data, Thursday is the cheapest day to fly to Chicago Midway Airport from Valparaiso, Florida. The lowest ticket price found for a Thursday departure recently was $126. Keep in mind that prices can always vary depending on your route and whether or not you are flying domestic or international. On the other hand, Wednesday is the most expensive day to depart from Valparaiso, Florida because it is more convenient for both business and leisure travelers. As a result, prices tend to be around $180.

What is the cheapest time of day to depart on your flight to Chicago Midway Airport?

Flying to Chicago Midway Airport from Valparaiso, Florida at noon is the least expensive time of day to depart. momondo users have found prices as low as $108 when looking at flights departing at noon. Try not to purchase tickets in the afternoon because they tend to be around $158. Of course, these prices can vary depending on the time of year and what airport you fly to.

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

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

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

There is only 1 cabin class available to choose from on Valparaiso Destin-Ft Walton Beach to Chicago Midway 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 Valparaiso, Florida to Chicago Midway Airport flights?

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

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

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

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

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

Best Price Found

$102

Fastest flight time

2h 16m

Direct flights

Mon, Tue and Fri
The best flight deal from Valparaiso, Florida to Chicago Midway Airport found on momondo in the last 72 hours is $102
The fastest flight from Valparaiso, Florida to Chicago Midway Airport takes 2h 16m
Direct flights go from Valparaiso, Florida to Chicago Midway Airport on Monday, Tuesday and Friday. There are no airlines offering direct flights.
Search flight deals

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

    Chicago Midway is 781.8 mi away from Valparaiso Destin-Ft Walton Beach. 2h 16m is a normal flight duration for this route.

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

    Prices for flights from Valparaiso Destin-Ft Walton Beach Airport to Chicago Midway Airport refresh daily.

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

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

    Although the minimum age for a child to fly alone is five, airlines that offer an unaccompanied minor (UMNR) service may have their own age limits, which could be impacted by factors such as flight length, timing, and layovers. It is recommended that you verify with the airline you are booking with for travel from Valparaiso Destin-Ft Walton Beach Airport to Chicago Midway Airport.

  • What documentation or ID do you need to fly to Chicago Midway Airport?

    The necessary travel and health documents for your Chicago Midway Airport trip may vary depending on your travel plans and individual circumstances. Generally, you should have various documents, such as a national ID card or driver's license and a passport that is valid for six months beyond your scheduled arrival date. We recommend seeking advice from your airline or a trusted third party, such as IATA.

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

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

Best airlines flying from Valparaiso, Florida to Chicago Midway Airport

Compare and see reviews for airlines that fly from Valparaiso, Florida to Chicago Midway Airport with momondo
Airline
Rating
Free Cancellation
Price
Allegiant AirPriceFrom $86Free CancellationRating
7.2
706 reviews
Search Allegiant Air flights

Traveling to a place near Chicago?

Book flights to Chicago if you plan to visit one of these locations
Merrillville
New Buffalo
Hammond
Benton Harbor
Saint Joseph
Portage
Lansing
Schererville
Valparaiso
Munster
Crown Point
Chesterton
Monticello
Porter
Griffith
Saint John

Why use momondo?

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

It is quick and easy to find Valparaiso to Chicago flights on momondo. We search and return numerous flight options from various airlines and agents. You can then use our filters to narrow your search until you have found the most convenient flight to Chicago that suits you.

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

All flight searches from Valparaiso to Chicago on momondo can be filtered to show those which offer flexible booking policies.

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

Once you have performed a search for Valparaiso to Chicago flights, momondo helps you find the right one by offering useful filters to narrow down your flight selection. Flights can be filtered by multiple factors such as airline, airport and price; but also by other criteria like aircraft type and payment method.

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

Price alerts on flights to Chicago from Valparaiso are quick and easy to set up on momondo. Simply perform a search and select the price alert feature. It is as simple as that.

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