Latest deals
Insights
When to book
FAQs
Reviews
Price Alerts

Cheap flights from Valparaiso, Florida to Chicago from $49

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 12/23. 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.

Save money when you book flights with momondo

Big names and deals

Big names and deals

Search 100s of travel sites to compare prices.

Filter for what you want

Filter for what you want

Free Wi-Fi? Stopover? Instantly customize your results.

Trusted and free

Trusted and free

We’re completely free to use - no hidden charges or fees.

Price Alerts

Price Alerts

Not ready to book? to track prices.
Search flight deals

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
9:00 am - 11:17 amVPS-MDW
2h 17mnonstop
Allegiant Air Logo
12:07 pm - 2:12 pmMDW-VPS
2h 05mnonstop
$106Allegiant Air
Find Deal
Thu, Nov 6 - Sun, Nov 9
Multiple Airlines Logo
6:35 am - 11:55 pmVPS-MDW
17h 20m1 stop
Multiple Airlines Logo
12:07 pm - 2:12 pmMDW-VPS
2h 05mnonstop
$183Multiple Airlines
Find Deal
Thu, Nov 6 - Sun, Nov 9
Multiple Airlines Logo
6:35 am - 11:55 pmVPS-MDW
17h 20m1 stop
Multiple Airlines Logo
12:07 pm - 2:12 pmMDW-VPS
2h 05mnonstop
$217Multiple Airlines
Find Deal
Thu, Nov 6 - Sun, Nov 9
Multiple Airlines Logo
6:35 am - 11:55 pmVPS-MDW
17h 20m1 stop
Multiple Airlines Logo
12:07 pm - 2:12 pmMDW-VPS
2h 05mnonstop
$226Multiple Airlines
Find Deal
Thu, Nov 6 - Sun, Nov 9
Multiple Airlines Logo
11:40 am - 12:37 pmVPS-MDW
48h 57m3 stops
Multiple Airlines Logo
12:07 pm - 2:12 pmMDW-VPS
2h 05mnonstop
$231Multiple Airlines
Find Deal
Thu, Nov 6 - Sun, Nov 9
Allegiant Air Logo
8:00 am - 10:17 amVPS-MDW
2h 17mnonstop
Allegiant Air Logo
12:07 pm - 2:12 pmMDW-VPS
2h 05mnonstop
$259Allegiant Air
Find Deal
Sun, Oct 26 - Thu, Oct 30
Southwest Logo
11:00 am - 7:05 pmVPS-MDW
8h 05m1 stop
Southwest Logo
6:20 am - 1:45 pmMDW-VPS
7h 25m2 stops
$425Southwest
Find Deal
Sat, Nov 15 - Fri, Nov 21
Southwest Logo
7:00 am - 4:20 pmVPS-MDW
9h 20m2 stops
Southwest Logo
6:20 am - 1:45 pmMDW-VPS
7h 25m2 stops
$430Southwest
Find Deal
Sat, Nov 15 - Fri, Nov 21
Delta Logo
9:25 am - 4:25 pmVPS-MDW
7h 00m1 stop
Delta Logo
10:35 am - 3:11 pmMDW-VPS
4h 36m1 stop
$445Delta
Find Deal
Tue, Mar 10 - Wed, Mar 11
Delta Logo
7:45 am - 6:34 pmVPS-MDW
10h 49m2 stops
Delta Logo
1:05 pm - 6:29 pmMDW-VPS
5h 24m1 stop
$459Delta
Find Deal
Tue, Mar 10 - Wed, Mar 11

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
Nov 6
VPS9:00 amValparaiso Destin-Ft Walton Beach
2h 17m
MDW11:17 amChicago Midway
Nov 9
MDW12:07 pmChicago Midway
2h 05m
VPS2:12 pmValparaiso Destin-Ft Walton Beach
$106
Find similar
Allegiant Air
Oct 26
VPS8:00 amValparaiso Destin-Ft Walton Beach
2h 17m
MDW10:17 amChicago Midway
Oct 30
MDW12:07 pmChicago Midway
2h 05m
VPS2:12 pmValparaiso Destin-Ft Walton Beach
$259
Find similar
Allegiant Air
Oct 26
VPS4:32 pmValparaiso Destin-Ft Walton Beach
27h 02m
1 stop
MDW7:34 pmChicago Midway
Oct 30
MDW12:07 pmChicago Midway
2h 05m
VPS2:12 pmValparaiso Destin-Ft Walton Beach
$300
Find similar

Southwest flights from Valparaiso, Florida to Chicago Midway Airport

Our best Southwest deals on Valparaiso, Florida to Chicago Midway Airport flight tickets
Southwest
Nov 15
VPS11:00 amValparaiso Destin-Ft Walton Beach
8h 05m
1 stop
MDW7:05 pmChicago Midway
Nov 21
MDW6:20 amChicago Midway
7h 25m
2 stops
VPS1:45 pmValparaiso Destin-Ft Walton Beach
$425
Find similar
Southwest
Nov 15
VPS7:00 amValparaiso Destin-Ft Walton Beach
9h 20m
2 stops
MDW4:20 pmChicago Midway
Nov 21
MDW6:20 amChicago Midway
7h 25m
2 stops
VPS1:45 pmValparaiso Destin-Ft Walton Beach
$430
Find similar
Southwest
Nov 15
VPS1:25 pmValparaiso Destin-Ft Walton Beach
5h 40m
1 stop
MDW7:05 pmChicago Midway
Nov 21
MDW7:50 amChicago Midway
5h 55m
1 stop
VPS1:45 pmValparaiso Destin-Ft Walton Beach
$438
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 October 13, 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

$106

ValparaisoChicago

VPS - MDW

VPSMDW

Valparaiso Destin-Ft Walton Beach

Thu 11/6

6:35 am-11:55 pm

1 stop17h 20m

Chicago Midway

Sun 11/9

12:07 pm-2:12 pm

Nonstop2h 05m

$183

ValparaisoChicago

VPS - MDW

VPSMDW

Valparaiso Destin-Ft Walton Beach

Thu 11/6

6:35 am-11:55 pm

1 stop17h 20m

Chicago Midway

Sun 11/9

12:07 pm-2:12 pm

Nonstop2h 05m

$217

ValparaisoChicago

VPS - MDW

VPSMDW

Valparaiso Destin-Ft Walton Beach

Thu 11/6

6:35 am-11:55 pm

1 stop17h 20m

Chicago Midway

Sun 11/9

12:07 pm-2:12 pm

Nonstop2h 05m

$226

ValparaisoChicago

VPS - MDW

VPSMDW

Valparaiso Destin-Ft Walton Beach

Thu 11/6

11:40 am-12:37 pm

3 stops48h 57m

Chicago Midway

Sun 11/9

12:07 pm-2:12 pm

Nonstop2h 05m

$231

ValparaisoChicago

VPS - MDW

VPSMDW

Valparaiso Destin-Ft Walton Beach

Sun 10/26

8:00 am-10:17 am

Nonstop2h 17m

Chicago Midway

Thu 10/30

12:07 pm-2:12 pm

Nonstop2h 05m

$259

ValparaisoChicago

VPS - MDW

VPSMDW

Valparaiso Destin-Ft Walton Beach

Sat 11/15

11:00 am-7:05 pm

1 stop8h 05m

Chicago Midway

Fri 11/21

6:20 am-1:45 pm

2 stops7h 25m

$425

ValparaisoChicago

VPS - MDW

VPSMDW

Valparaiso Destin-Ft Walton Beach

Sat 11/15

7:00 am-4:20 pm

2 stops9h 20m

Chicago Midway

Fri 11/21

6:20 am-1:45 pm

2 stops7h 25m

$430

ValparaisoChicago

VPS - MDW

VPSMDW

Valparaiso Destin-Ft Walton Beach

Tue 3/10

9:25 am-4:25 pm

1 stop7h 00m

Chicago Midway

Wed 3/11

10:35 am-3:11 pm

1 stop4h 36m

$445

ValparaisoChicago

VPS - MDW

VPSMDW

Valparaiso Destin-Ft Walton Beach

Tue 3/10

7:45 am-6:34 pm

2 stops10h 49m

Chicago Midway

Wed 3/11

1:05 pm-6:29 pm

1 stop5h 24m

$459

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 20 resultsSorted by cheapest first
1
2

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 $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 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

$112

Fastest flight time

2h 16m

Direct flights

Mon, Tue, Wed, Fri and Sun
The best flight deal from Valparaiso, Florida to Chicago Midway Airport found on momondo in the last 72 hours is $112
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, Wednesday, Friday 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 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 $84Free CancellationRating
7.2
694 reviews
Search Allegiant Air flights

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

    Allegiant Air operates around 2 flights from Valparaiso, Florida to Chicago Midway Airport every week. The average price of these flights found in the last 72 hours has been $178, 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 694 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.

An easier way to manage your Chicago Midway Airport trip

We make it super easy to schedule, organize and travel with friends or family. Trips is free — and available to use no matter where you book.
Start using Trips
Find my bookings

Get notified when prices go down

Daily price changes in your inbox - only with Price Alerts.
1 adult
Wed 11/12
Wed 11/19
By creating a price alert you accept our terms of use and privacy policy.

Find better results for your trip to Chicago