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Cheap flights from Valparaiso, Florida to Chicago from $122

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 2/26. 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.
Southwest Logo
7:15 am - 12:15 pm
VPS
-
ORD
5h 00m
1 stop
Southwest Logo
2:40 pm - 9:05 pm
ORD
-
VPS
6h 25m
1 stop
$291Southwest
Sa, Feb 28 - Sa, Mrz 7
Southwest Logo
7:15 am - 12:15 pm
VPS
-
ORD
5h 00m
1 stop
Southwest Logo
7:20 pm - 8:45 am
ORD
-
VPS
13h 25m
2 stops
$309Southwest
Sa, Feb 28 - Sa, Mrz 7
American Airlines Logo
1:00 pm - 3:44 pm
VPS
-
ORD
2h 44mnonstop
American Airlines Logo
9:40 am - 12:09 pm
ORD
-
VPS
2h 29mnonstop
$316American Airlines
Di, Mrz 17 - Di, Mrz 24
Multiple Airlines Logo
7:40 am - 6:29 pm
VPS
-
ORD
10h 49m
1 stop
Multiple Airlines Logo
8:16 pm - 2:34 pm
ORD
-
VPS
18h 18m
2 stops
$319Multiple Airlines
Do, Feb 26 - So, Mrz 1
American Airlines Logo
1:00 pm - 3:44 pm
VPS
-
ORD
2h 44mnonstop
American Airlines Logo
2:57 pm - 11:59 pm
ORD
-
VPS
9h 02m
1 stop
$326American Airlines
Mi, Mrz 25 - Mi, Apr 1
Multiple Airlines Logo
7:40 am - 12:40 am
VPS
-
ORD
17h 00m
1 stop
Multiple Airlines Logo
4:44 pm - 12:54 pm
ORD
-
VPS
44h 10m
2 stops
$330Multiple Airlines
Do, Mrz 5 - Mo, Mrz 9
Southwest Logo
7:15 am - 12:50 pm
VPS
-
ORD
5h 35m
1 stop
Southwest Logo
2:40 pm - 9:15 pm
ORD
-
VPS
6h 35m
1 stop
$333Southwest
Mi, Mrz 25 - Mi, Apr 1
Southwest Logo
7:15 am - 9:50 pm
VPS
-
ORD
14h 35m
2 stops
Southwest Logo
7:20 pm - 8:45 am
ORD
-
VPS
13h 25m
2 stops
$334Southwest
Sa, Feb 28 - Sa, Mrz 7
Delta Logo
7:24 pm - 11:54 pm
VPS
-
ORD
4h 30m
1 stop
Delta Logo
9:50 am - 4:08 pm
ORD
-
VPS
6h 18m
1 stop
$335Delta
Di, Mrz 17 - Di, Mrz 24
Southwest Logo
12:35 pm - 9:55 pm
VPS
-
ORD
9h 20m
2 stops
Southwest Logo
2:40 pm - 9:15 pm
ORD
-
VPS
6h 35m
1 stop
$339Southwest
Mi, Mrz 25 - Mi, Apr 1

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
Mar 17
VPS1:00 pmValparaiso Destin-Ft Walton Beach
2h 44m
ORD3:44 pmChicago O'Hare Intl
Mar 24
ORD9:40 amChicago O'Hare Intl
2h 29m
VPS12:09 pmValparaiso Destin-Ft Walton Beach
$316
American Airlines
Mar 25
VPS1:00 pmValparaiso Destin-Ft Walton Beach
2h 44m
ORD3:44 pmChicago O'Hare Intl
Apr 1
ORD2:57 pmChicago O'Hare Intl
9h 02m
1 stop
VPS11:59 pmValparaiso Destin-Ft Walton Beach
$326
American Airlines
Jul 1
VPS6:39 pmValparaiso Destin-Ft Walton Beach
5h 20m
1 stop
ORD11:59 pmChicago O'Hare Intl
Jul 9
ORD8:38 amChicago O'Hare Intl
2h 29m
VPS11:07 amValparaiso Destin-Ft Walton Beach
$345

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
Feb 28
VPS7:15 amValparaiso Destin-Ft Walton Beach
5h 00m
1 stop
ORD12:15 pmChicago O'Hare Intl
Mar 7
ORD2:40 pmChicago O'Hare Intl
6h 25m
1 stop
VPS9:05 pmValparaiso Destin-Ft Walton Beach
$291
Southwest
Feb 28
VPS7:15 amValparaiso Destin-Ft Walton Beach
5h 00m
1 stop
ORD12:15 pmChicago O'Hare Intl
Mar 7
ORD7:20 pmChicago O'Hare Intl
13h 25m
2 stops
VPS8:45 amValparaiso Destin-Ft Walton Beach
$309
Southwest
Mar 25
VPS7:15 amValparaiso Destin-Ft Walton Beach
5h 35m
1 stop
ORD12:50 pmChicago O'Hare Intl
Apr 1
ORD2:40 pmChicago O'Hare Intl
6h 35m
1 stop
VPS9:15 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 Februar 1, 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

ValparaisoChicago

VPS - ORD

VPSORD

Valparaiso Destin-Ft Walton Beach

Sa 2/28

7:15 am-12:15 pm

1 stop5h 00m

Chicago O'Hare Intl

Sa 3/7

2:40 pm-9:05 pm

1 stop6h 25m

$291

ValparaisoChicago

VPS - ORD

VPSORD

Valparaiso Destin-Ft Walton Beach

Sa 2/28

7:15 am-12:15 pm

1 stop5h 00m

Chicago O'Hare Intl

Sa 3/7

7:20 pm-8:45 am

2 stops13h 25m

$309

ValparaisoChicago

VPS - ORD

VPSORD

Valparaiso Destin-Ft Walton Beach

Di 3/17

1:00 pm-3:44 pm

Nonstop2h 44m

Chicago O'Hare Intl

Di 3/24

9:40 am-12:09 pm

Nonstop2h 29m

$316

ValparaisoChicago

VPS - ORD

VPSORD

Valparaiso Destin-Ft Walton Beach

Do 2/26

7:40 am-6:29 pm

1 stop10h 49m

Chicago O'Hare Intl

So 3/1

8:16 pm-2:34 pm

2 stops18h 18m

$319

ValparaisoChicago

VPS - ORD

VPSORD

Valparaiso Destin-Ft Walton Beach

Mi 3/25

1:00 pm-3:44 pm

Nonstop2h 44m

Chicago O'Hare Intl

Mi 4/1

2:57 pm-11:59 pm

1 stop9h 02m

$326

ValparaisoChicago

VPS - ORD

VPSORD

Valparaiso Destin-Ft Walton Beach

Do 3/5

7:40 am-12:40 am

1 stop17h 00m

Chicago O'Hare Intl

Mo 3/9

4:44 pm-12:54 pm

2 stops44h 10m

$330

ValparaisoChicago

VPS - ORD

VPSORD

Valparaiso Destin-Ft Walton Beach

Mi 3/25

7:15 am-12:50 pm

1 stop5h 35m

Chicago O'Hare Intl

Mi 4/1

2:40 pm-9:15 pm

1 stop6h 35m

$333

ValparaisoChicago

VPS - ORD

VPSORD

Valparaiso Destin-Ft Walton Beach

Sa 2/28

7:15 am-9:50 pm

2 stops14h 35m

Chicago O'Hare Intl

Sa 3/7

7:20 pm-8:45 am

2 stops13h 25m

$334

ValparaisoChicago

VPS - ORD

VPSORD

Valparaiso Destin-Ft Walton Beach

Di 3/17

7:24 pm-11:54 pm

1 stop4h 30m

Chicago O'Hare Intl

Di 3/24

9:50 am-4:08 pm

1 stop6h 18m

$335

ValparaisoChicago

VPS - ORD

VPSORD

Valparaiso Destin-Ft Walton Beach

Mi 3/25

12:35 pm-9:55 pm

2 stops9h 20m

Chicago O'Hare Intl

Mi 4/1

2:40 pm-9:15 pm

1 stop6h 35m

$339

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 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 $368. 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 $635.

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 in the morning is the least expensive time of day to depart. momondo users have found prices as low as $470 when looking at flights departing in the morning. 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

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

There are 2 cabin classes available to choose from on Valparaiso Destin-Ft Walton Beach to Chicago O'Hare Intl 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 14% 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

$169

Fastest flight time

2h 44m

Direct flights

Every day
The best one-way flight to Chicago O'Hare Intl Airport from Valparaiso, Florida in the past 72 hours is $169. The best round-trip flight deal from Valparaiso, Florida to Chicago O'Hare Intl Airport found on momondo in the last 72 hours is $376.
The fastest flight from Valparaiso, Florida to Chicago O'Hare Intl Airport takes 2h 44m
Direct flights go from Valparaiso, Florida to Chicago O'Hare Intl Airport every day.
Search flight deals

  • 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 44m, 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
7.2
11,211 reviews
Search American Airlines flights

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

    Across 3 American Airlines flights from Valparaiso, Florida to Chicago O'Hare Intl Airport this week, the average price was $376, with the best American Airlines deals starting from $157 round-trip. 11,211 users have rated American Airlines on momondo, with an average score of 7.2/10.

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
Naperville
Rosemont
New Buffalo
Kenosha
Joliet
Oak Brook
Orland Park
Racine
Hammond
Janesville
Tinley Park
Elgin
Aurora
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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