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Cheap flights from Valparaiso, Florida to Chicago from $48

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 10/30. 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

Allegiant Air Logo
9:00 am - 11:17 amVPS-MDW
2h 17mnonstop
Allegiant Air Logo
12:07 pm - 2:12 pmMDW-VPS
2h 05mnonstop
$103Allegiant Air
Find Deal
Thu, Nov 6 - Sun, Nov 9
Allegiant Air Logo
8:00 am - 10:17 amVPS-MDW
2h 17mnonstop
Allegiant Air Logo
11:07 am - 1:12 pmMDW-VPS
2h 05mnonstop
$121Allegiant Air
Find Deal
Thu, Oct 2 - Sun, Oct 5
Allegiant Air Logo
8:00 am - 10:17 amVPS-MDW
2h 17mnonstop
Allegiant Air Logo
11:07 am - 1:12 pmMDW-VPS
2h 05mnonstop
$147Allegiant Air
Find Deal
Thu, Oct 2 - Sun, Oct 5
Allegiant Air Logo
8:00 am - 10:17 amVPS-MDW
2h 17mnonstop
Allegiant Air Logo
11:07 am - 1:12 pmMDW-VPS
2h 05mnonstop
$217Allegiant Air
Find Deal
Thu, Oct 2 - Thu, Oct 9
Southwest Logo
10:30 am - 3:05 pmVPS-MDW
4h 35m1 stop
Southwest Logo
8:40 am - 3:35 pmMDW-VPS
6h 55m1 stop
$221Southwest
Find Deal
Sat, Oct 4 - Tue, Oct 7
Southwest Logo
10:35 am - 4:25 pmVPS-MDW
5h 50m1 stop
Southwest Logo
12:00 pm - 9:05 pmMDW-VPS
9h 05m1 stop
$227Southwest
Find Deal
Tue, Sep 9 - Thu, Sep 11
Logo
8:00 am - 10:17 amVPS-MDW
2h 17mnonstop
Logo
5:15 pm - 12:48 pmMDW-VPS
19h 33m2 stops
$255
Find Deal
Thu, Oct 2 - Mon, Oct 6
Logo
11:00 am - 10:21 amVPS-MDW
23h 21m2 stops
Logo
11:07 am - 1:12 pmMDW-VPS
2h 05mnonstop
$259
Find Deal
Fri, Oct 24 - Sun, Oct 26
Delta Logo
2:55 pm - 9:36 pmVPS-MDW
6h 41m1 stop
Delta Logo
6:00 am - 10:36 amMDW-VPS
4h 36m1 stop
$301Delta
Find Deal
Wed, Sep 17 - Sun, Sep 21
Delta Logo
6:00 am - 6:35 pmVPS-MDW
12h 35m2 stops
Delta Logo
9:35 am - 9:58 pmMDW-VPS
12h 23m2 stops
$327Delta
Find Deal
Sat, Oct 4 - Tue, Oct 7

Southwest flights from Valparaiso, Florida to Chicago Midway Airport

Our best Southwest deals on Valparaiso, Florida to Chicago Midway Airport flight tickets
Southwest
Oct 4
VPS10:30 amValparaiso Destin-Ft Walton Beach
4h 35m
1 stop
MDW3:05 pmChicago Midway
Oct 7
MDW8:40 amChicago Midway
6h 55m
1 stop
VPS3:35 pmValparaiso Destin-Ft Walton Beach
$221
Find similar
Southwest
Sep 9
VPS10:35 amValparaiso Destin-Ft Walton Beach
5h 50m
1 stop
MDW4:25 pmChicago Midway
Sep 11
MDW12:00 pmChicago Midway
9h 05m
1 stop
VPS9:05 pmValparaiso Destin-Ft Walton Beach
$227
Find similar
Southwest
Sep 9
VPS10:35 amValparaiso Destin-Ft Walton Beach
8h 35m
2 stops
MDW7:10 pmChicago Midway
Sep 11
MDW12:00 pmChicago Midway
9h 05m
1 stop
VPS9:05 pmValparaiso Destin-Ft Walton Beach
$232
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
Sep 17
VPS2:55 pmValparaiso Destin-Ft Walton Beach
6h 41m
1 stop
MDW9:36 pmChicago Midway
Sep 21
MDW6:00 amChicago Midway
4h 36m
1 stop
VPS10:36 amValparaiso Destin-Ft Walton Beach
$301
Find similar
Delta
Oct 4
VPS6:00 amValparaiso Destin-Ft Walton Beach
12h 35m
2 stops
MDW6:35 pmChicago Midway
Oct 7
MDW9:35 amChicago Midway
12h 23m
2 stops
VPS9:58 pmValparaiso Destin-Ft Walton Beach
$327
Find similar
Delta
Oct 4
VPS6:00 amValparaiso Destin-Ft Walton Beach
12h 35m
2 stops
MDW6:35 pmChicago Midway
Oct 6
MDW5:04 pmChicago Midway
6h 01m
1 stop
VPS11:05 pmValparaiso Destin-Ft Walton Beach
$357
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 August 14, 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

Thu 11/6

9:00 am-11:17 am

Nonstop2h 17m

Chicago Midway

Sun 11/9

12:07 pm-2:12 pm

Nonstop2h 05m

$103

ValparaisoChicago

VPS - MDW

VPSMDW

Valparaiso Destin-Ft Walton Beach

Thu 10/2

8:00 am-10:17 am

Nonstop2h 17m

Chicago Midway

Sun 10/5

11:07 am-1:12 pm

Nonstop2h 05m

$121

ValparaisoChicago

VPS - MDW

VPSMDW

Valparaiso Destin-Ft Walton Beach

Thu 10/2

8:00 am-10:17 am

Nonstop2h 17m

Chicago Midway

Sun 10/5

11:07 am-1:12 pm

Nonstop2h 05m

$147

ValparaisoChicago

VPS - MDW

VPSMDW

Valparaiso Destin-Ft Walton Beach

Thu 10/2

8:00 am-10:17 am

Nonstop2h 17m

Chicago Midway

Thu 10/9

11:07 am-1:12 pm

Nonstop2h 05m

$217

ValparaisoChicago

VPS - MDW

VPSMDW

Valparaiso Destin-Ft Walton Beach

Sat 10/4

10:30 am-3:05 pm

1 stop4h 35m

Chicago Midway

Tue 10/7

8:40 am-3:35 pm

1 stop6h 55m

$221

ValparaisoChicago

VPS - MDW

VPSMDW

Valparaiso Destin-Ft Walton Beach

Tue 9/9

10:35 am-4:25 pm

1 stop5h 50m

Chicago Midway

Thu 9/11

12:00 pm-9:05 pm

1 stop9h 05m

$227

ValparaisoChicago

VPS - MDW

VPSMDW

Valparaiso Destin-Ft Walton Beach

Thu 10/2

8:00 am-10:17 am

Nonstop2h 17m

Chicago Midway

Mon 10/6

5:15 pm-12:48 pm

2 stops19h 33m

$255

ValparaisoChicago

VPS - MDW

VPSMDW

Valparaiso Destin-Ft Walton Beach

Fri 10/24

11:00 am-10:21 am

2 stops23h 21m

Chicago Midway

Sun 10/26

11:07 am-1:12 pm

Nonstop2h 05m

$259

ValparaisoChicago

VPS - MDW

VPSMDW

Valparaiso Destin-Ft Walton Beach

Wed 9/17

2:55 pm-9:36 pm

1 stop6h 41m

Chicago Midway

Sun 9/21

6:00 am-10:36 am

1 stop4h 36m

$301

ValparaisoChicago

VPS - MDW

VPSMDW

Valparaiso Destin-Ft Walton Beach

Sat 10/4

6:00 am-6:35 pm

2 stops12h 35m

Chicago Midway

Tue 10/7

9:35 am-9:58 pm

2 stops12h 23m

$327

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 $112 when looking at flights departing at noon. Try not to purchase tickets in the afternoon because they tend to be around $180. 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 are 1 cabin classes 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

$48

Fastest flight time

2h 17m

Direct flights

Mon, Tue, Wed, Fri and Sun
The best one-way flight to Chicago Midway Airport from Valparaiso, Florida in the past 72 hours is $48. The best round-trip flight deal from Valparaiso, Florida to Chicago Midway Airport found on momondo in the last 72 hours is $103.
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, Wednesday, Friday and Sunday. The only airline offering direct flights is Allegiant Air.
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 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 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?

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
Lansing
Portage
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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