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Cheap flights from Valparaiso, Florida to Chicago from $120

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 8/3. 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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0 bags

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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.
Multiple Airlines Logo
1:07 pm - 8:52 pm
VPS
-
ORD
7h 45m
1 stop
Multiple Airlines Logo
9:57 pm - 11:38 pm
ORD
-
VPS
25h 41m
1 stop
$295Multiple Airlines
Thu, Aug 6 - Sat, Aug 15
Multiple Airlines Logo
7:40 am - 7:53 pm
VPS
-
ORD
12h 13m
2 stops
Multiple Airlines Logo
9:57 pm - 11:38 pm
ORD
-
VPS
25h 41m
1 stop
$311Multiple Airlines
Thu, Aug 6 - Sat, Aug 15
Multiple Airlines Logo
1:07 pm - 8:52 pm
VPS
-
ORD
7h 45m
1 stop
Multiple Airlines Logo
8:05 am - 11:17 pm
ORD
-
VPS
15h 12m
2 stops
$336Multiple Airlines
Thu, Aug 6 - Thu, Aug 13
Multiple Airlines Logo
9:06 pm - 5:28 am
VPS
-
ORD
32h 22m
1 stop
Multiple Airlines Logo
6:31 pm - 5:03 pm
ORD
-
VPS
22h 32m
1 stop
$338Multiple Airlines
Mon, Jul 13 - Thu, Jul 16
Multiple Airlines Logo
8:18 pm - 7:53 pm
VPS
-
ORD
23h 35m
2 stops
Multiple Airlines Logo
9:57 pm - 11:38 pm
ORD
-
VPS
25h 41m
1 stop
$339Multiple Airlines
Fri, Aug 7 - Sat, Aug 15
Multiple Airlines Logo
8:39 am - 7:53 am
VPS
-
ORD
23h 14m
2 stops
Multiple Airlines Logo
6:39 pm - 5:03 pm
ORD
-
VPS
22h 24m
1 stop
$344Multiple Airlines
Mon, Jul 13 - Wed, Jul 15
Multiple Airlines Logo
1:07 pm - 8:52 pm
VPS
-
ORD
7h 45m
1 stop
Multiple Airlines Logo
1:50 pm - 3:17 pm
ORD
-
VPS
25h 27m
2 stops
$356Multiple Airlines
Thu, Aug 6 - Tue, Aug 11
Multiple Airlines Logo
1:07 pm - 8:52 pm
VPS
-
ORD
7h 45m
1 stop
Multiple Airlines Logo
9:57 pm - 5:24 pm
ORD
-
VPS
19h 27m
2 stops
$362Multiple Airlines
Thu, Aug 13 - Sun, Aug 16
Multiple Airlines Logo
1:07 pm - 8:52 pm
VPS
-
ORD
7h 45m
1 stop
Multiple Airlines Logo
9:57 pm - 11:38 pm
ORD
-
VPS
25h 41m
1 stop
$364Multiple Airlines
Thu, Aug 6 - Wed, Aug 12
Multiple Airlines Logo
8:39 pm - 7:53 pm
VPS
-
ORD
23h 14m
2 stops
Multiple Airlines Logo
6:31 pm - 5:03 pm
ORD
-
VPS
22h 32m
1 stop
$370Multiple Airlines
Mon, Jul 13 - Thu, Jul 16

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

Our best Southwest deals on Valparaiso, Florida to Chicago O'Hare Intl Airport flight tickets
Southwest
May 28
VPS7:20 amValparaiso Destin-Ft Walton Beach
5h 30m
1 stop
ORD12:50 pmChicago O'Hare Intl
Jun 2
ORD2:40 pmChicago O'Hare Intl
6h 20m
1 stop
VPS9:00 pmValparaiso Destin-Ft Walton Beach
$374
Southwest
May 28
VPS7:20 amValparaiso Destin-Ft Walton Beach
5h 30m
1 stop
ORD12:50 pmChicago O'Hare Intl
Jun 2
ORD11:55 amChicago O'Hare Intl
9h 05m
2 stops
VPS9:00 pmValparaiso Destin-Ft Walton Beach
$380
Southwest
May 28
VPS7:20 amValparaiso Destin-Ft Walton Beach
5h 30m
1 stop
ORD12:50 pmChicago O'Hare Intl
May 31
ORD2:40 pmChicago O'Hare Intl
6h 25m
1 stop
VPS9:05 pmValparaiso Destin-Ft Walton Beach
$408

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
May 28
VPS11:20 amValparaiso Destin-Ft Walton Beach
2h 43m
ORD2:03 pmChicago O'Hare Intl
Jun 2
ORD8:15 amChicago O'Hare Intl
2h 35m
VPS10:50 amValparaiso Destin-Ft Walton Beach
$399
American Airlines
Jul 1
VPS11:16 amValparaiso Destin-Ft Walton Beach
2h 41m
ORD1:57 pmChicago O'Hare Intl
Jul 9
ORD1:17 pmChicago O'Hare Intl
4h 47m
1 stop
VPS6:04 pmValparaiso Destin-Ft Walton Beach
$405
American Airlines
May 28
VPS11:20 amValparaiso Destin-Ft Walton Beach
2h 43m
ORD2:03 pmChicago O'Hare Intl
Jun 2
ORD4:05 pmChicago O'Hare Intl
7h 42m
1 stop
VPS11:47 pmValparaiso Destin-Ft Walton Beach
$409

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 May 7, 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 8/6

1:07 pm-8:52 pm

1 stop7h 45m

Chicago O'Hare Intl

Sat 8/15

9:57 pm-11:38 pm

1 stop25h 41m

$295

ValparaisoChicago

VPS - ORD

VPSORD

Valparaiso Destin-Ft Walton Beach

Thu 8/6

7:40 am-7:53 pm

2 stops12h 13m

Chicago O'Hare Intl

Sat 8/15

9:57 pm-11:38 pm

1 stop25h 41m

$311
Quickest round-trip

ValparaisoChicago

VPS - ORD

VPSORD

Valparaiso Destin-Ft Walton Beach

Thu 8/6

1:07 pm-8:52 pm

1 stop7h 45m

Chicago O'Hare Intl

Thu 8/13

8:05 am-11:17 pm

2 stops15h 12m

$336

ValparaisoChicago

VPS - ORD

VPSORD

Valparaiso Destin-Ft Walton Beach

Mon 7/13

9:06 pm-5:28 am

1 stop32h 22m

Chicago O'Hare Intl

Thu 7/16

6:31 pm-5:03 pm

1 stop22h 32m

$338

ValparaisoChicago

VPS - ORD

VPSORD

Valparaiso Destin-Ft Walton Beach

Fri 8/7

8:18 pm-7:53 pm

2 stops23h 35m

Chicago O'Hare Intl

Sat 8/15

9:57 pm-11:38 pm

1 stop25h 41m

$339

ValparaisoChicago

VPS - ORD

VPSORD

Valparaiso Destin-Ft Walton Beach

Mon 7/13

8:39 am-7:53 am

2 stops23h 14m

Chicago O'Hare Intl

Wed 7/15

6:39 pm-5:03 pm

1 stop22h 24m

$344

ValparaisoChicago

VPS - ORD

VPSORD

Valparaiso Destin-Ft Walton Beach

Thu 8/6

1:07 pm-8:52 pm

1 stop7h 45m

Chicago O'Hare Intl

Tue 8/11

1:50 pm-3:17 pm

2 stops25h 27m

$356

ValparaisoChicago

VPS - ORD

VPSORD

Valparaiso Destin-Ft Walton Beach

Thu 8/13

1:07 pm-8:52 pm

1 stop7h 45m

Chicago O'Hare Intl

Sun 8/16

9:57 pm-5:24 pm

2 stops19h 27m

$362

ValparaisoChicago

VPS - ORD

VPSORD

Valparaiso Destin-Ft Walton Beach

Thu 8/6

1:07 pm-8:52 pm

1 stop7h 45m

Chicago O'Hare Intl

Wed 8/12

9:57 pm-11:38 pm

1 stop25h 41m

$364

ValparaisoChicago

VPS - ORD

VPSORD

Valparaiso Destin-Ft Walton Beach

Mon 7/13

8:39 pm-7:53 pm

2 stops23h 14m

Chicago O'Hare Intl

Thu 7/16

6:31 pm-5:03 pm

1 stop22h 32m

$370

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 typical price of a round-trip flight between Valparaiso, Florida and Chicago O'Hare Intl Airport?

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 $370. This is often the case because there is less demand to fly during this day of the week. On the other hand, Monday 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 $582.

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 afternoon because they tend to be around $1,474. 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

Can stopping save me money on Valparaiso, Florida to Chicago O'Hare Intl Airport flights?

You could potentially save up to 41% 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

$292

Fastest flight time

2h 41m

Direct flights

Every day
The best one-way flight to Chicago O'Hare Intl Airport from Valparaiso, Florida in the past 72 hours is $292. The best round-trip flight deal from Valparaiso, Florida to Chicago O'Hare Intl Airport found on momondo in the last 72 hours is $422.
The fastest flight from Valparaiso, Florida to Chicago O'Hare Intl Airport takes 2h 41m
Direct flights go from Valparaiso, Florida to Chicago O'Hare Intl Airport every day.
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 41m, 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 $157Free CancellationRating
7.1
11,668 reviews
Search American Airlines flights
SouthwestPriceFrom $234Free CancellationRating
7.9
4,305 reviews
Search Southwest flights

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

    Across 7 American Airlines flights from Valparaiso, Florida to Chicago O'Hare Intl Airport this week, the average price was $380, with the best American Airlines deals starting from $157 round-trip. 11,668 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
Lake Geneva
Schaumburg
South Haven
Rockford
Merrillville
Gurnee
Rosemont
Naperville
New Buffalo
Orland Park
Oak Brook
Kenosha
Joliet
Aurora
Janesville
Racine
Hammond
Tinley Park
Elgin
Evanston

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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