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Cheap flights from Valparaiso, Florida to Chicago from $135

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 7/20. 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
1 adult, Economy, 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.
Delta Logo
11:49 am - 6:45 pm
VPS
-
ORD
6h 56m
1 stop
Delta Logo
8:05 am - 2:02 pm
ORD
-
VPS
5h 57m
1 stop
$315Delta
Thu, Sep 24 - Sun, Sep 27
Delta Logo
7:10 pm - 11:59 pm
VPS
-
ORD
4h 49m
1 stop
Delta Logo
5:30 am - 10:58 am
ORD
-
VPS
5h 28m
1 stop
$325Delta
Fri, Sep 25 - Mon, Sep 28
Multiple Airlines Logo
6:25 am - 12:15 pm
VPS
-
ORD
29h 50m
2 stops
Multiple Airlines Logo
7:25 am - 5:03 pm
ORD
-
VPS
9h 38m
1 stop
$330Multiple Airlines
Mon, Jul 20 - Thu, Jul 23
Delta Logo
2:18 pm - 8:30 am
VPS
-
ORD
18h 12m
1 stop
Delta Logo
6:45 pm - 1:13 pm
ORD
-
VPS
18h 28m
1 stop
$333Delta
Tue, Aug 4 - Tue, Aug 11
Multiple Airlines Logo
9:07 pm - 5:37 am
VPS
-
ORD
32h 30m
1 stop
Multiple Airlines Logo
7:15 am - 8:17 pm
ORD
-
VPS
13h 02m
1 stop
$336Multiple Airlines
Mon, Aug 10 - Mon, Aug 17
Delta Logo
2:45 pm - 8:55 pm
VPS
-
ORD
6h 10m
1 stop
Delta Logo
6:45 pm - 1:13 pm
ORD
-
VPS
18h 28m
1 stop
$349Delta
Sat, Aug 8 - Tue, Aug 11
Multiple Airlines Logo
9:07 pm - 8:52 pm
VPS
-
ORD
23h 45m
2 stops
Multiple Airlines Logo
7:15 am - 8:17 pm
ORD
-
VPS
13h 02m
1 stop
$358Multiple Airlines
Mon, Aug 10 - Mon, Aug 17
Multiple Airlines Logo
9:06 pm - 5:37 am
VPS
-
ORD
32h 31m
1 stop
Multiple Airlines Logo
7:25 am - 5:03 pm
ORD
-
VPS
9h 38m
1 stop
$361Multiple Airlines
Mon, Jul 20 - Thu, Jul 23
Multiple Airlines Logo
9:07 pm - 5:37 am
VPS
-
ORD
32h 30m
1 stop
Multiple Airlines Logo
7:15 am - 8:17 pm
ORD
-
VPS
13h 02m
1 stop
$363Multiple Airlines
Mon, Aug 10 - Mon, Aug 17
American Airlines Logo
11:29 am - 1:58 pm
VPS
-
ORD
2h 29mnonstop
American Airlines Logo
8:33 am - 10:59 am
ORD
-
VPS
2h 26mnonstop
$376American Airlines
Tue, Nov 24 - Tue, Dec 1

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American Airlines flights from Valparaiso, Florida to Chicago O'Hare Intl Airport

Our best American Airlines deals on Valparaiso, Florida to Chicago O'Hare Intl Airport flight tickets
American Airlines
Nov 24
VPS11:29 amValparaiso Destin-Ft Walton Beach
2h 29m
ORD1:58 pmChicago O'Hare Intl
Dec 1
ORD8:33 amChicago O'Hare Intl
2h 26m
VPS10:59 amValparaiso Destin-Ft Walton Beach
$376
American Airlines
Nov 24
VPS11:29 amValparaiso Destin-Ft Walton Beach
2h 29m
ORD1:58 pmChicago O'Hare Intl
Dec 1
ORD4:05 pmChicago O'Hare Intl
5h 05m
1 stop
VPS9:10 pmValparaiso Destin-Ft Walton Beach
$386
American Airlines
Aug 26
VPS11:28 amValparaiso Destin-Ft Walton Beach
2h 45m
ORD2:13 pmChicago O'Hare Intl
Aug 30
ORD8:26 amChicago O'Hare Intl
2h 28m
VPS10:54 amValparaiso Destin-Ft Walton Beach
$405

Delta flights from Valparaiso, Florida to Chicago O'Hare Intl Airport

Our best Delta deals on Valparaiso, Florida to Chicago O'Hare Intl Airport flight tickets
Delta
Sep 24
VPS11:49 amValparaiso Destin-Ft Walton Beach
6h 56m
1 stop
ORD6:45 pmChicago O'Hare Intl
Sep 27
ORD8:05 amChicago O'Hare Intl
5h 57m
1 stop
VPS2:02 pmValparaiso Destin-Ft Walton Beach
$315
Delta
Sep 25
VPS7:10 pmValparaiso Destin-Ft Walton Beach
4h 49m
1 stop
ORD11:59 pmChicago O'Hare Intl
Sep 28
ORD5:30 amChicago O'Hare Intl
5h 28m
1 stop
VPS10:58 amValparaiso Destin-Ft Walton Beach
$325
Delta
Aug 4
VPS2:18 pmValparaiso Destin-Ft Walton Beach
18h 12m
1 stop
ORD8:30 amChicago O'Hare Intl
Aug 11
ORD6:45 pmChicago O'Hare Intl
18h 28m
1 stop
VPS1:13 pmValparaiso Destin-Ft Walton Beach
$333

momondo Fare Finder

 
Customize your flight search to find flights from Valparaiso, Florida to Chicago O'Hare Intl 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 June 25, 2026.
Use the filters below to find and compare flights from Valparaiso, Florida to Chicago O'Hare Intl Airport that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip

ValparaisoChicago

VPS - ORD

VPSORD

Valparaiso Destin-Ft Walton Beach

Thu 9/24

11:49 am-6:45 pm

1 stop6h 56m

Chicago O'Hare Intl

Sun 9/27

8:05 am-2:02 pm

1 stop5h 57m

$315

ValparaisoChicago

VPS - ORD

VPSORD

Valparaiso Destin-Ft Walton Beach

Fri 9/25

7:10 pm-11:59 pm

1 stop4h 49m

Chicago O'Hare Intl

Mon 9/28

5:30 am-10:58 am

1 stop5h 28m

$325

ValparaisoChicago

VPS - ORD

VPSORD

Valparaiso Destin-Ft Walton Beach

Mon 7/20

6:25 am-12:15 pm

2 stops29h 50m

Chicago O'Hare Intl

Thu 7/23

7:25 am-5:03 pm

1 stop9h 38m

$330

ValparaisoChicago

VPS - ORD

VPSORD

Valparaiso Destin-Ft Walton Beach

Tue 8/4

2:18 pm-8:30 am

1 stop18h 12m

Chicago O'Hare Intl

Tue 8/11

6:45 pm-1:13 pm

1 stop18h 28m

$333

ValparaisoChicago

VPS - ORD

VPSORD

Valparaiso Destin-Ft Walton Beach

Mon 8/10

9:07 pm-5:37 am

1 stop32h 30m

Chicago O'Hare Intl

Mon 8/17

7:15 am-8:17 pm

1 stop13h 02m

$336

ValparaisoChicago

VPS - ORD

VPSORD

Valparaiso Destin-Ft Walton Beach

Sat 8/8

2:45 pm-8:55 pm

1 stop6h 10m

Chicago O'Hare Intl

Tue 8/11

6:45 pm-1:13 pm

1 stop18h 28m

$349

ValparaisoChicago

VPS - ORD

VPSORD

Valparaiso Destin-Ft Walton Beach

Mon 8/10

9:07 pm-8:52 pm

2 stops23h 45m

Chicago O'Hare Intl

Mon 8/17

7:15 am-8:17 pm

1 stop13h 02m

$358

ValparaisoChicago

VPS - ORD

VPSORD

Valparaiso Destin-Ft Walton Beach

Mon 7/20

9:06 pm-5:37 am

1 stop32h 31m

Chicago O'Hare Intl

Thu 7/23

7:25 am-5:03 pm

1 stop9h 38m

$361

ValparaisoChicago

VPS - ORD

VPSORD

Valparaiso Destin-Ft Walton Beach

Mon 8/10

9:07 pm-5:37 am

1 stop32h 30m

Chicago O'Hare Intl

Mon 8/17

7:15 am-8:17 pm

1 stop13h 02m

$363
Quickest round-trip

ValparaisoChicago

VPS - ORD

VPSORD

Valparaiso Destin-Ft Walton Beach

Tue 11/24

11:29 am-1:58 pm

Nonstop2h 29m

Chicago O'Hare Intl

Tue 12/1

8:33 am-10:59 am

Nonstop2h 26m

$376

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 O'Hare Intl 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 month to fly to Chicago O'Hare Intl Airport?

The month of September is another great option to travel to Chicago O'Hare Intl Airport, with average flight prices from Valparaiso, Florida averaging around $309.

What is the cheapest day to depart on your flight to Chicago O'Hare Intl Airport?

The cheapest day to depart on your flight to Chicago O'Hare Intl Airport is on a Wednesday when prices can be found for as low as $408. This is often the case because there is less demand to fly during this day of the week. On the other hand, Thursday 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 $609.

What is the cheapest time of day to depart on your flight to Chicago O'Hare Intl Airport?

Flying to Chicago O'Hare Intl Airport from Valparaiso, Florida at noon is the least expensive time of day to depart. momondo users have found prices as low as $415 when looking at flights departing at noon. Try not to purchase tickets in the morning because they tend to be around $539. 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 O'Hare Intl flight route?

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

What cabin class options are available on Valparaiso, Florida to Chicago O'Hare Intl Airport flights?

There are 2 cabin classes available to choose from on Valparaiso, Florida to Chicago O'Hare Intl Airport 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 O'Hare Intl Airport flights?

You could potentially save up to 35% on your flight if you consider stops on a Valparaiso, Florida to Chicago O'Hare Intl Airport flight.

How have Valparaiso, Florida to Chicago O'Hare Intl Airport flight prices changed over time?

When to book flights from Valparaiso, Florida to Chicago O'Hare Intl Airport

Are you open to changing your travel dates? Check out the ideal times to fly from Valparaiso, Florida to Chicago O'Hare Intl 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 O'Hare Intl Airport (VPS to ORD) flight deals and tips

Find info about flight duration, direct flights, and airports for your flight from Valparaiso, Florida to Chicago O'Hare Intl Airport

Best Price Found

$754

Fastest flight time

2h 42m

Direct flights

Mon, Tue, Wed, Thu, Fri and Sun
The best one-way flight to Chicago O'Hare Intl Airport from Valparaiso, Florida in the past 72 hours is $754. The best round-trip flight deal from Valparaiso, Florida to Chicago O'Hare Intl Airport found on momondo in the last 72 hours is $465.
The fastest flight from Valparaiso, Florida to Chicago O'Hare Intl Airport takes 2h 42m
Direct flights go from Valparaiso, Florida to Chicago O'Hare Intl Airport on Monday, Tuesday, Wednesday, Thursday, Friday and Sunday. There are no airlines offering direct flights.
Search flight deals

Frequently asked questions about flying from Valparaiso, Florida to Chicago O'Hare Intl Airport

  • How far is Valparaiso Destin-Ft Walton Beach to Chicago O'Hare Intl by plane?

    There are 795.8 mi between Valparaiso Destin-Ft Walton Beach and Chicago O'Hare Intl. Flights usually cover this in 2h 42m, 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 O'Hare Intl Airport?

    Prices for flights from Valparaiso Destin-Ft Walton Beach Airport to Chicago O'Hare Intl Airport refresh daily.

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

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

    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 O'Hare Intl Airport.

  • What documentation or ID do you need to fly to Chicago O'Hare Intl Airport?

    The required travel and health documents for your Chicago O'Hare Intl Airport trip may vary depending on your itinerary and personal circumstances. As a general rule, you should carry multiple documents, including a national ID card or driver's license and a passport valid for six months after your intended arrival at Chicago O'Hare Intl Airport. We recommend that you seek guidance from your airline or a reliable third party such as IATA.

  • What is the most popular plane model from Valparaiso, Florida to Chicago O'Hare Intl Airport?

  • What is the most popular airline from Valparaiso, Florida to Chicago O'Hare Intl Airport?

Best airlines flying from Valparaiso, Florida to Chicago O'Hare Intl Airport

Compare and see reviews for airlines that fly from Valparaiso, Florida to Chicago O'Hare Intl Airport with momondo
Airline
Rating
Free Cancellation
Price
American AirlinesPriceFrom $152Free CancellationRating
7.1
11,757 reviews
Search American Airlines flights
SouthwestPriceFrom $234Free CancellationRating
7.9
4,242 reviews
Search Southwest flights

  • American Airlines Flights From Valparaiso, Florida to Chicago O'Hare Intl Airport

    Across 6 American Airlines flights from Valparaiso, Florida to Chicago O'Hare Intl Airport this week, the average price was $431, with the best American Airlines deals starting from $152 round-trip. 11,757 users have rated American Airlines on momondo, with an average score of 7.1/10.

Traveling to a place near Chicago?

Book flights to Chicago if you plan to visit one of these locations
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Orland Park
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New Buffalo
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Hammond
Aurora
Racine
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South Holland

Why use momondo?

Why should I use momondo to find a flight deal from Valparaiso to Chicago?

momondo collates all your flight options in one place and lets you filter them to find the perfect flight from Valparaiso to Chicago. momondo saves you time and could save you money on your trip.

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

momondo does allow users to show only those flights to Chicago from Valparaiso which offer a flexible booking policy as well as other useful filters and features.

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

Once all potential Valparaiso to Chicago flight options are in front of you, momondo lets you sort and filter flights based on preferences such as airline, price and flight times amongst many other options.

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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