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Cheap flights from Valparaiso, Florida to Chicago from $65

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 6/22. 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

Discover deals from 900+ travel sites with momondo.

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
4:05 pm - 6:22 pm
VPS
-
MDW
2h 17mnonstop
Allegiant Air Logo
7:08 pm - 9:17 pm
MDW
-
VPS
2h 09mnonstop
$111Allegiant Air
Thu, Apr 30 - Thu, May 7
Allegiant Air Logo
4:05 pm - 6:22 pm
VPS
-
MDW
2h 17mnonstop
Allegiant Air Logo
7:08 pm - 9:17 pm
MDW
-
VPS
2h 09mnonstop
$112Allegiant Air
Thu, Apr 30 - Thu, May 7
Allegiant Air Logo
4:05 pm - 6:22 pm
VPS
-
MDW
2h 17mnonstop
Allegiant Air Logo
7:08 pm - 9:17 pm
MDW
-
VPS
2h 09mnonstop
$118Allegiant Air
Thu, Apr 30 - Thu, May 7
Allegiant Air Logo
6:12 pm - 8:33 pm
VPS
-
MDW
2h 21mnonstop
Allegiant Air Logo
9:23 pm - 11:36 pm
MDW
-
VPS
2h 13mnonstop
$130Allegiant Air
Fri, Jun 5 - Mon, Jun 8
Multiple Airlines Logo
7:30 am - 1:00 pm
VPS
-
MDW
29h 30m
1 stop
Multiple Airlines Logo
7:08 pm - 9:17 pm
MDW
-
VPS
2h 09mnonstop
$216Multiple Airlines
Thu, Apr 30 - Thu, May 7
Multiple Airlines Logo
4:05 pm - 6:22 pm
VPS
-
MDW
2h 17mnonstop
Multiple Airlines Logo
6:00 am - 8:48 am
MDW
-
VPS
26h 48m
2 stops
$217Multiple Airlines
Thu, Apr 30 - Mon, May 4
Allegiant Air Logo
8:30 pm - 2:38 pm
VPS
-
MDW
18h 08m
1 stop
Allegiant Air Logo
9:20 pm - 11:34 pm
MDW
-
VPS
2h 14mnonstop
$226Allegiant Air
Thu, Jul 23 - Mon, Jul 27
Multiple Airlines Logo
4:05 pm - 6:22 pm
VPS
-
MDW
2h 17mnonstop
Multiple Airlines Logo
6:00 am - 2:58 pm
MDW
-
VPS
32h 58m
2 stops
$249Multiple Airlines
Thu, Apr 30 - Thu, May 7
Multiple Airlines Logo
4:05 pm - 6:22 pm
VPS
-
MDW
2h 17mnonstop
Multiple Airlines Logo
6:00 am - 2:58 pm
MDW
-
VPS
32h 58m
2 stops
$256Multiple Airlines
Thu, Apr 30 - Thu, May 7
Multiple Airlines Logo
6:12 pm - 8:33 pm
VPS
-
MDW
2h 21mnonstop
Multiple Airlines Logo
6:00 am - 5:02 pm
MDW
-
VPS
35h 02m
2 stops
$259Multiple Airlines
Fri, Jun 5 - Mon, Jun 8

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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
May 7
VPS4:01 pmValparaiso Destin-Ft Walton Beach
2h 17m
MDW6:18 pmChicago Midway
May 10
MDW5:47 pmChicago Midway
2h 09m
VPS7:56 pmValparaiso Destin-Ft Walton Beach
$82
Allegiant Air
Apr 30
VPS4:05 pmValparaiso Destin-Ft Walton Beach
2h 17m
MDW6:22 pmChicago Midway
May 7
MDW7:08 pmChicago Midway
2h 09m
VPS9:17 pmValparaiso Destin-Ft Walton Beach
$111
Allegiant Air
Apr 30
VPS4:05 pmValparaiso Destin-Ft Walton Beach
2h 17m
MDW6:22 pmChicago Midway
May 7
MDW7:08 pmChicago Midway
2h 09m
VPS9:17 pmValparaiso Destin-Ft Walton Beach
$112

Southwest flights from Valparaiso, Florida to Chicago Midway Airport

Our best Southwest deals on Valparaiso, Florida to Chicago Midway Airport flight tickets
Southwest
Jun 2
VPS7:15 amValparaiso Destin-Ft Walton Beach
6h 15m
1 stop
MDW1:30 pmChicago Midway
Jun 4
MDW2:45 pmChicago Midway
4h 30m
1 stop
VPS7:15 pmValparaiso Destin-Ft Walton Beach
$388
Southwest
Jun 5
VPS6:05 pmValparaiso Destin-Ft Walton Beach
3h 50m
1 stop
MDW9:55 pmChicago Midway
Jun 9
MDW6:30 amChicago Midway
4h 55m
1 stop
VPS11:25 amValparaiso Destin-Ft Walton Beach
$389
Southwest
Jul 23
VPS6:05 pmValparaiso Destin-Ft Walton Beach
6h 10m
1 stop
MDW12:15 amChicago Midway
Jul 28
MDW6:30 amChicago Midway
4h 55m
1 stop
VPS11:25 amValparaiso Destin-Ft Walton Beach
$390

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 April 16, 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

Cheapest round-trip
Quickest round-trip

ValparaisoChicago

VPS - MDW

VPSMDW

Valparaiso Destin-Ft Walton Beach

Thu 4/30

4:05 pm-6:22 pm

Nonstop2h 17m

Chicago Midway

Thu 5/7

7:08 pm-9:17 pm

Nonstop2h 09m

$111

ValparaisoChicago

VPS - MDW

VPSMDW

Valparaiso Destin-Ft Walton Beach

Thu 4/30

4:05 pm-6:22 pm

Nonstop2h 17m

Chicago Midway

Thu 5/7

7:08 pm-9:17 pm

Nonstop2h 09m

$112

ValparaisoChicago

VPS - MDW

VPSMDW

Valparaiso Destin-Ft Walton Beach

Thu 4/30

4:05 pm-6:22 pm

Nonstop2h 17m

Chicago Midway

Thu 5/7

7:08 pm-9:17 pm

Nonstop2h 09m

$118

ValparaisoChicago

VPS - MDW

VPSMDW

Valparaiso Destin-Ft Walton Beach

Fri 6/5

6:12 pm-8:33 pm

Nonstop2h 21m

Chicago Midway

Mon 6/8

9:23 pm-11:36 pm

Nonstop2h 13m

$130

ValparaisoChicago

VPS - MDW

VPSMDW

Valparaiso Destin-Ft Walton Beach

Thu 4/30

7:30 am-1:00 pm

1 stop29h 30m

Chicago Midway

Thu 5/7

7:08 pm-9:17 pm

Nonstop2h 09m

$216

ValparaisoChicago

VPS - MDW

VPSMDW

Valparaiso Destin-Ft Walton Beach

Thu 4/30

4:05 pm-6:22 pm

Nonstop2h 17m

Chicago Midway

Mon 5/4

6:00 am-8:48 am

2 stops26h 48m

$217

ValparaisoChicago

VPS - MDW

VPSMDW

Valparaiso Destin-Ft Walton Beach

Thu 7/23

8:30 pm-2:38 pm

1 stop18h 08m

Chicago Midway

Mon 7/27

9:20 pm-11:34 pm

Nonstop2h 14m

$226

ValparaisoChicago

VPS - MDW

VPSMDW

Valparaiso Destin-Ft Walton Beach

Thu 4/30

4:05 pm-6:22 pm

Nonstop2h 17m

Chicago Midway

Thu 5/7

6:00 am-2:58 pm

2 stops32h 58m

$249

ValparaisoChicago

VPS - MDW

VPSMDW

Valparaiso Destin-Ft Walton Beach

Thu 4/30

4:05 pm-6:22 pm

Nonstop2h 17m

Chicago Midway

Thu 5/7

6:00 am-2:58 pm

2 stops32h 58m

$256

ValparaisoChicago

VPS - MDW

VPSMDW

Valparaiso Destin-Ft Walton Beach

Fri 6/5

6:12 pm-8:33 pm

Nonstop2h 21m

Chicago Midway

Mon 6/8

6:00 am-5:02 pm

2 stops35h 02m

$259

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, Wednesday is the cheapest day to fly to Chicago Midway Airport from Valparaiso, Florida. The lowest ticket price found for a Wednesday departure recently was $102. 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, Friday 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 $182.

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

Flying to Chicago Midway Airport from Valparaiso, Florida in the morning is the least expensive time of day to depart. momondo users have found prices as low as $132 when looking at flights departing in the morning. Try not to purchase tickets at noon because they tend to be around $190. 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

Fastest flight time

2h 17m

Direct flights

Mon, Tue, Fri and Sat
The fastest flight from Valparaiso, Florida to Chicago Midway Airport takes 2h 17m
Direct flights go from Valparaiso, Florida to Chicago Midway Airport on Monday, Tuesday, Friday and Saturday. The only airline offering direct flights is Allegiant Air.
Search flight deals

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

  • 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 17m 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
7.3
707 reviews
Search Allegiant Air flights

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

    Allegiant Air operates around 1 flight from Valparaiso, Florida to Chicago Midway Airport every week. The average price of these flights found in the last 72 hours has been $188, but momondo users have found Allegiant Air deals from Valparaiso, Florida to Chicago Midway Airport from as low as $86 round-trip. Allegiant Air has been scored 7.3/10 in 707 reviews.

Traveling to a place near Chicago?

Book flights to Chicago if you plan to visit one of these locations
Merrillville
New Buffalo
Hammond
Saint Joseph
Benton Harbor
Portage
Lansing
Valparaiso
Munster
Schererville
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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