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Cheap flights from Valparaiso, Florida to Chicago from $209

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 12/31. 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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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
1:01 pm - 3:20 pmVPS-MDW
2h 19mnonstop
Allegiant Air Logo
4:10 pm - 6:23 pmMDW-VPS
2h 13mnonstop
$220Allegiant Air
Find Deal
mar., dic. 23 - mar., dic. 30
Allegiant Air Logo
1:01 pm - 3:20 pmVPS-MDW
2h 19mnonstop
Allegiant Air Logo
4:10 pm - 6:23 pmMDW-VPS
2h 13mnonstop
$227Allegiant Air
Find Deal
mar., dic. 23 - mar., dic. 30
Delta Logo
7:13 pm - 5:55 pmVPS-MDW
22h 42m2 stops
Delta Logo
6:35 pm - 1:00 pmMDW-VPS
18h 25m2 stops
$272Delta
Find Deal
jue., ene. 29 - lun., feb. 2
Delta Logo
1:02 pm - 9:08 amVPS-MDW
20h 06m1 stop
Delta Logo
1:26 pm - 10:59 amMDW-VPS
21h 33m2 stops
$298Delta
Find Deal
jue., ene. 29 - lun., feb. 2
Multiple Airlines Logo
10:00 am - 11:25 pmVPS-MDW
13h 25m3 stops
Multiple Airlines Logo
3:40 pm - 5:46 pmMDW-VPS
2h 06mnonstop
$316Multiple Airlines
Find Deal
lun., feb. 23 - jue., feb. 26
Multiple Airlines Logo
1:01 pm - 3:20 pmVPS-MDW
2h 19mnonstop
Multiple Airlines Logo
6:14 am - 6:14 pmMDW-VPS
36h 00m2 stops
$318Multiple Airlines
Find Deal
mar., dic. 23 - mar., dic. 30
Multiple Airlines Logo
1:01 pm - 3:20 pmVPS-MDW
2h 19mnonstop
Multiple Airlines Logo
8:00 am - 6:14 pmMDW-VPS
34h 14m3 stops
$319Multiple Airlines
Find Deal
mar., dic. 23 - mar., dic. 30
Multiple Airlines Logo
3:45 pm - 6:04 pmVPS-MDW
2h 19mnonstop
Multiple Airlines Logo
6:12 am - 11:56 amMDW-VPS
29h 44m3 stops
$324Multiple Airlines
Find Deal
jue., dic. 18 - lun., dic. 22
Southwest Logo
7:15 am - 12:45 pmVPS-MDW
5h 30m1 stop
Southwest Logo
5:35 am - 10:20 amMDW-VPS
4h 45m1 stop
$348Southwest
Find Deal
mié., dic. 17 - mié., dic. 31
Delta Logo
1:02 pm - 6:36 pmVPS-MDW
5h 34m1 stop
Delta Logo
6:00 am - 11:15 amMDW-VPS
5h 15m1 stop
$353Delta
Find Deal
jue., ene. 29 - lun., feb. 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
Dec 23
VPS1:01 pmValparaiso Destin-Ft Walton Beach
2h 19m
MDW3:20 pmChicago Midway
Dec 30
MDW4:10 pmChicago Midway
2h 13m
VPS6:23 pmValparaiso Destin-Ft Walton Beach
$220
Find similar
Allegiant Air
Dec 23
VPS1:01 pmValparaiso Destin-Ft Walton Beach
2h 19m
MDW3:20 pmChicago Midway
Dec 30
MDW4:10 pmChicago Midway
2h 13m
VPS6:23 pmValparaiso Destin-Ft Walton Beach
$227
Find similar

Delta flights from Valparaiso, Florida to Chicago Midway Airport

Our best Delta deals on Valparaiso, Florida to Chicago Midway Airport flight tickets
Delta
Jan 29
VPS7:13 pmValparaiso Destin-Ft Walton Beach
22h 42m
2 stops
MDW5:55 pmChicago Midway
Feb 2
MDW6:35 pmChicago Midway
18h 25m
2 stops
VPS1:00 pmValparaiso Destin-Ft Walton Beach
$272
Find similar
Delta
Jan 29
VPS1:02 pmValparaiso Destin-Ft Walton Beach
20h 06m
1 stop
MDW9:08 amChicago Midway
Feb 2
MDW1:26 pmChicago Midway
21h 33m
2 stops
VPS10:59 amValparaiso Destin-Ft Walton Beach
$298
Find similar
Delta
Jan 29
VPS1:02 pmValparaiso Destin-Ft Walton Beach
5h 34m
1 stop
MDW6:36 pmChicago Midway
Feb 2
MDW6:00 amChicago Midway
5h 15m
1 stop
VPS11:15 amValparaiso Destin-Ft Walton Beach
$353
Find similar

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 diciembre 2, 2025.
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

mar. 12/23

1:01 pm-3:20 pm

Nonstop2h 19m

Chicago Midway

mar. 12/30

4:10 pm-6:23 pm

Nonstop2h 13m

$220

ValparaisoChicago

VPS - MDW

VPSMDW

Valparaiso Destin-Ft Walton Beach

mar. 12/23

1:01 pm-3:20 pm

Nonstop2h 19m

Chicago Midway

mar. 12/30

4:10 pm-6:23 pm

Nonstop2h 13m

$227

ValparaisoChicago

VPS - MDW

VPSMDW

Valparaiso Destin-Ft Walton Beach

jue. 1/29

7:13 pm-5:55 pm

2 stops22h 42m

Chicago Midway

lun. 2/2

6:35 pm-1:00 pm

2 stops18h 25m

$272

ValparaisoChicago

VPS - MDW

VPSMDW

Valparaiso Destin-Ft Walton Beach

jue. 1/29

1:02 pm-9:08 am

1 stop20h 06m

Chicago Midway

lun. 2/2

1:26 pm-10:59 am

2 stops21h 33m

$298

ValparaisoChicago

VPS - MDW

VPSMDW

Valparaiso Destin-Ft Walton Beach

lun. 2/23

10:00 am-11:25 pm

3 stops13h 25m

Chicago Midway

jue. 2/26

3:40 pm-5:46 pm

Nonstop2h 06m

$316

ValparaisoChicago

VPS - MDW

VPSMDW

Valparaiso Destin-Ft Walton Beach

mar. 12/23

1:01 pm-3:20 pm

Nonstop2h 19m

Chicago Midway

mar. 12/30

6:14 am-6:14 pm

2 stops36h 00m

$318

ValparaisoChicago

VPS - MDW

VPSMDW

Valparaiso Destin-Ft Walton Beach

mar. 12/23

1:01 pm-3:20 pm

Nonstop2h 19m

Chicago Midway

mar. 12/30

8:00 am-6:14 pm

3 stops34h 14m

$319

ValparaisoChicago

VPS - MDW

VPSMDW

Valparaiso Destin-Ft Walton Beach

jue. 12/18

3:45 pm-6:04 pm

Nonstop2h 19m

Chicago Midway

lun. 12/22

6:12 am-11:56 am

3 stops29h 44m

$324

ValparaisoChicago

VPS - MDW

VPSMDW

Valparaiso Destin-Ft Walton Beach

mié. 12/17

7:15 am-12:45 pm

1 stop5h 30m

Chicago Midway

mié. 12/31

5:35 am-10:20 am

1 stop4h 45m

$348

ValparaisoChicago

VPS - MDW

VPSMDW

Valparaiso Destin-Ft Walton Beach

jue. 1/29

1:02 pm-6:36 pm

1 stop5h 34m

Chicago Midway

lun. 2/2

6:00 am-11:15 am

1 stop5h 15m

$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 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, Friday is the cheapest day to fly to Chicago Midway Airport from Valparaiso, Florida. The lowest ticket price found for a Friday departure recently was $129. 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 $105 when looking at flights departing at noon. Try not to purchase tickets in the afternoon because they tend to be around $175. 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

$144

Fastest flight time

2h 19m

Direct flights

Wed and Sun
The best flight deal from Valparaiso, Florida to Chicago Midway Airport found on momondo in the last 72 hours is $144
The fastest flight from Valparaiso, Florida to Chicago Midway Airport takes 2h 19m
Direct flights go from Valparaiso, Florida to Chicago Midway Airport on Wednesday and Sunday. 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 19m 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 $84Free CancellationRating
7.2
698 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 $144, but momondo users have found Allegiant Air deals from Valparaiso, Florida to Chicago Midway Airport from as low as $84 round-trip. Allegiant Air has been scored 7.2/10 in 698 reviews.

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
Crown Point
Munster
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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