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Cheap flights from Valparaiso, Florida to Chicago from $103

This is the cheapest round-trip flight price found by a momondo user in the last 72 hours by searching for a flight from Valparaiso, Florida to Chicago departing on 3/5. 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
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
1:01 pm - 3:20 pm
VPS
-
MDW
2h 19mnonstop
Allegiant Air Logo
3:40 pm - 5:46 pm
MDW
-
VPS
2h 06mnonstop
$108Allegiant Air
Thu, Feb 19 - Sun, Feb 22
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
$145Allegiant Air
Thu, Mar 12 - Sun, Mar 15
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
$159Allegiant Air
Thu, Mar 12 - Sun, Mar 15
Multiple Airlines Logo
7:00 am - 9:12 pm
VPS
-
MDW
14h 12m
2 stops
Multiple Airlines Logo
3:40 pm - 5:46 pm
MDW
-
VPS
2h 06mnonstop
$224Multiple Airlines
Thu, Feb 19 - 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
American Airlines Logo
1:00 pm - 3:44 pm
VPS
-
ORD
2h 44mnonstop
American Airlines Logo
3:16 pm - 10:24 pm
ORD
-
VPS
7h 08m
1 stop
$345American Airlines
Fri, Mar 13 - Sat, Mar 14
Southwest Logo
7:10 am - 12:15 pm
VPS
-
ORD
5h 05m
1 stop
Southwest Logo
1:45 pm - 6:55 pm
ORD
-
VPS
5h 10m
1 stop
$352Southwest
Mon, Mar 2 - Wed, Mar 4
American Airlines Logo
4:40 pm - 12:16 am
VPS
-
ORD
7h 36m
1 stop
American Airlines Logo
3:16 pm - 10:24 pm
ORD
-
VPS
7h 08m
1 stop
$355American Airlines
Fri, Mar 13 - Sat, Mar 14
Delta Logo
1:34 pm - 6:49 pm
VPS
-
ORD
5h 15m
1 stop
Delta Logo
5:20 am - 10:47 am
ORD
-
VPS
5h 27m
1 stop
$374Delta
Fri, Apr 17 - Sun, Apr 19

Delta flights from Valparaiso, Florida to Chicago

Our best Delta deals on Valparaiso, Florida to Chicago flight tickets
Delta
Apr 17
VPS1:34 pmValparaiso Destin-Ft Walton Beach
5h 15m
1 stop
ORD6:49 pmChicago O'Hare Intl
Apr 19
ORD5:20 amChicago O'Hare Intl
5h 27m
1 stop
VPS10:47 amValparaiso Destin-Ft Walton Beach
$374
Delta
Apr 12
VPS6:00 amValparaiso Destin-Ft Walton Beach
3h 59m
1 stop
ORD9:59 amChicago O'Hare Intl
Apr 19
ORD8:15 amChicago O'Hare Intl
5h 54m
1 stop
VPS2:09 pmValparaiso Destin-Ft Walton Beach
$396
Delta
Feb 14
VPS7:05 amValparaiso Destin-Ft Walton Beach
7h 05m
1 stop
ORD2:10 pmChicago O'Hare Intl
Feb 17
ORD9:52 amChicago O'Hare Intl
4h 10m
1 stop
VPS2:02 pmValparaiso Destin-Ft Walton Beach
$402

American Airlines flights from Valparaiso, Florida to Chicago

Our best American Airlines deals on Valparaiso, Florida to Chicago flight tickets
American Airlines
Mar 13
VPS1:00 pmValparaiso Destin-Ft Walton Beach
2h 44m
ORD3:44 pmChicago O'Hare Intl
Mar 14
ORD3:16 pmChicago O'Hare Intl
7h 08m
1 stop
VPS10:24 pmValparaiso Destin-Ft Walton Beach
$345
American Airlines
Mar 13
VPS4:40 pmValparaiso Destin-Ft Walton Beach
7h 36m
1 stop
ORD12:16 amChicago O'Hare Intl
Mar 14
ORD3:16 pmChicago O'Hare Intl
7h 08m
1 stop
VPS10:24 pmValparaiso Destin-Ft Walton Beach
$355
American Airlines
Feb 17
VPS4:00 pmValparaiso Destin-Ft Walton Beach
6h 00m
1 stop
ORD10:00 pmChicago O'Hare Intl
Feb 21
ORD9:05 amChicago O'Hare Intl
2h 29m
VPS11:34 amValparaiso Destin-Ft Walton Beach
$359

momondo Fare Finder

 
Customize your flight search to find flights from Valparaiso, Florida to Chicago 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 24, 2026.
Use the filters below to find and compare flights from Valparaiso, Florida to Chicago 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

Thu 2/19

1:01 pm-3:20 pm

Nonstop2h 19m

Chicago Midway

Sun 2/22

3:40 pm-5:46 pm

Nonstop2h 06m

$108

ValparaisoChicago

VPS - MDW

VPSMDW

Valparaiso Destin-Ft Walton Beach

Thu 3/12

5:37 pm-7:53 pm

Nonstop2h 16m

Chicago Midway

Sun 3/15

8:43 pm-10:51 pm

Nonstop2h 08m

$145

ValparaisoChicago

VPS - MDW

VPSMDW

Valparaiso Destin-Ft Walton Beach

Thu 3/12

5:37 pm-7:53 pm

Nonstop2h 16m

Chicago Midway

Sun 3/15

8:43 pm-10:51 pm

Nonstop2h 08m

$159

ValparaisoChicago

VPS - MDW

VPSMDW

Valparaiso Destin-Ft Walton Beach

Thu 2/19

7:00 am-9:12 pm

2 stops14h 12m

Chicago Midway

Sun 2/22

3:40 pm-5:46 pm

Nonstop2h 06m

$224

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 - ORD

VPSORD

Valparaiso Destin-Ft Walton Beach

Fri 3/13

1:00 pm-3:44 pm

Nonstop2h 44m

Chicago O'Hare Intl

Sat 3/14

3:16 pm-10:24 pm

1 stop7h 08m

$345

ValparaisoChicago

VPS - ORD

VPSORD

Valparaiso Destin-Ft Walton Beach

Mon 3/2

7:10 am-12:15 pm

1 stop5h 05m

Chicago O'Hare Intl

Wed 3/4

1:45 pm-6:55 pm

1 stop5h 10m

$352

ValparaisoChicago

VPS - ORD

VPSORD

Valparaiso Destin-Ft Walton Beach

Fri 3/13

4:40 pm-12:16 am

1 stop7h 36m

Chicago O'Hare Intl

Sat 3/14

3:16 pm-10:24 pm

1 stop7h 08m

$355

ValparaisoChicago

VPS - ORD

VPSORD

Valparaiso Destin-Ft Walton Beach

Fri 4/17

1:34 pm-6:49 pm

1 stop5h 15m

Chicago O'Hare Intl

Sun 4/19

5:20 am-10:47 am

1 stop5h 27m

$374

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

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 typical price of a round-trip flight between Valparaiso, Florida and Chicago?

What is the cheapest month to fly to Chicago?

The month of May is, on average, the cheapest month to fly to Chicago from Valparaiso, Florida, with most prices found around $103. If you’re not able to fly to Chicago in May, then April is your next best option. Flight prices from Valparaiso, Florida to Chicago during April average around $112.

What is the cheapest day to depart on your flight to Chicago?

The cheapest day to depart on your flight to Chicago is on a Wednesday when prices can be found for as low as $302. This is often the case because there is less demand to fly during this day of the week. When flying out on a Monday, the most expensive travel day of the week, you can expect to see flight prices from Valparaiso, Florida to Chicago for around $582.

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

Our most recent data shows that the best time of day to fly to Chicago is at noon. Flights from Valparaiso, Florida to Chicago during this time can be as low as $295. In contrast, the most expensive time of day to depart to Chicago is in the morning when prices are around $412.

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

Fly from Valparaiso Destin-Ft Walton Beach to Chicago O'Hare Intl for the best Valparaiso Destin-Ft Walton Beach - Chicago flight prices

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

There are 2 cabin classes available to choose from on Valparaiso Destin-Ft Walton Beach to Chicago 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 flights?

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

How have Valparaiso, Florida to Chicago flight prices changed over time?

As of January 2026, prices for Valparaiso, Florida to Chicago flights are approximately 44% more expensive when compared to flights at the same time last year.

When to book flights from Valparaiso, Florida to Chicago

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

Cheap Valparaiso, Florida to Chicago (VPS to CHI) flight deals and tips

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

Best Price Found

$207

Fastest flight time

2h 16m

Direct flights

Every day

Airports in Chicago

3 airports
The best one-way flight to Chicago from Valparaiso, Florida in the past 72 hours is $207. The best round-trip flight deal from Valparaiso, Florida to Chicago found on momondo in the last 72 hours is $102.
The fastest flight from Valparaiso, Florida to Chicago takes 2h 16m
Direct flights go from Valparaiso, Florida to Chicago every day.
There are 3 airports in Chicago. From Valparaiso, Florida there are direct flights to Chicago O'Hare Intl (ORD), Chicago Midway (MDW).
Search flight deals

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

    Valparaiso Destin-Ft Walton Beach and Chicago are 787.3 mi apart from one another. Flights usually cover this in 2h 16m, depending on flying conditions and air traffic around both airports.

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

    Prices for flights from Valparaiso Destin-Ft Walton Beach Airport to Chicago are updated daily.

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

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

    The minimum age for a child to fly alone is five, but airlines offering an unaccompanied minor (UNMR) service may have their age restrictions, such as regulations concerning flight duration, 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.

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

    The necessary travel and health documents for your Chicago 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?

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

Best airlines flying from Valparaiso, Florida to Chicago

Compare and see reviews for airlines that fly from Valparaiso, Florida to Chicago with momondo
Airline
Rating
Free Cancellation
Price
Allegiant AirPriceFrom $86Free CancellationRating
7.2
705 reviews
Search Allegiant Air flights
American AirlinesPriceFrom $157Free CancellationRating
7.2
11,193 reviews
Search American Airlines flights
DeltaPriceFrom $323Free CancellationRating
7.9
8,112 reviews
Search Delta flights

  • American Airlines Flights From Valparaiso, Florida to Chicago

    The lowest priced American Airlines flight from Valparaiso, Florida to Chicago from the last 72 hours was $157. Generally, American Airlines has 4 flights on this route every week with an average price of $376. American Airlines is rated 7.2/10 by our users.

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?

Finding the right flight to Chicago from Valparaiso is quick and easy when you have a range of options in front of you, from reputable agents and recognisable airlines. Options that can then be filtered down to find the best fit. That is what momondo does. We make finding flights to Chicago quick and easy, saving you time and money.

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

Yes. momondo enables you to select and highlight flights to Chicago from Valparaiso with this policy.

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

momondo provides multiple filters to help you find the best flight to Chicago from Valparaiso. Filter by price, airline, airports, cabin, aircraft, payment method, number of stops and more.

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

Yes momondo offers price alerts on flights to Chicago from Valparaiso. After performing a search on this page you should be able to see the price alert set up feature. Simply provide a valid email address and momondo will instantly alert you when prices change.

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Find better results for your trip to the United States

Fly into one of these airports located in Chicago

Airports listed have a maximum distance of 78.5 mi from Chicago
Chicago Midway Airport
Chicago O'Hare Intl Airport
Chicago Greater Rockford Airport