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O'Hare Intl

$116+ Cheap flights from Valparaiso, FL (VPS) to O'Hare Intl (ORD)

This is the cheapest one-way flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 10/29. Fares are subject to change and may not be available on all flights or dates of travel.
VPS — ORD
Aug 28 — Sep 41
Fri 8/28
Fri 9/4
1 adult, Economy
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Cheap flight deals from Valparaiso to O'Hare Intl

Cheapest flights from Valparaiso to O'Hare Intl
Explore the most affordable flight options available from Valparaiso to O'Hare Intl. Find the lowest fares from popular airlines and budget airlines, with prices last updated on July 29, 2026.

This Kiwi.com deal was found by Cheapflights users on 7/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/212:09 pm
VPS
-
ORD
2 stops23h 42m
Multiple Airlines
Sun 10/46:30 am
ORD
-
VPS
1 stop17h 07m
Multiple Airlines
Deal found 7/28$331
This American Airlines deal was found by Cheapflights users on 7/26. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 11/2411:44 am
VPS
-
ORD
Nonstop2h 55m
American Airlines
Wed 12/28:33 am
ORD
-
VPS
Nonstop2h 26m
American Airlines
Deal found 7/26$386
This Kiwi.com deal was found by Cheapflights users on 7/26. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/2410:56 am
VPS
-
ORD
1 stop13h 27m
Multiple Airlines
Sat 10/37:21 pm
ORD
-
VPS
2 stops37h 06m
Multiple Airlines
Deal found 7/26$390
This American Airlines deal was found by Cheapflights users on 7/25. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/811:28 am
VPS
-
ORD
Nonstop2h 45m
American Airlines
Tue 9/158:59 am
ORD
-
VPS
1 stop7h 21m
American Airlines
Deal found 7/25$395
This American Airlines deal was found by Cheapflights users on 7/26. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 11/2411:44 am
VPS
-
ORD
Nonstop2h 55m
American Airlines
Tue 12/15:19 am
ORD
-
VPS
1 stop7h 02m
American Airlines
Deal found 7/26$396
This Delta deal was found by Cheapflights users on 7/27. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 11/242:49 pm
VPS
-
ORD
1 stop4h 13m
Delta
Wed 12/21:30 pm
ORD
-
VPS
1 stop5h 13m
Delta
Deal found 7/27$405
This American Airlines deal was found by Cheapflights users on 7/27. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/54:39 pm
VPS
-
ORD
1 stop7h 32m
American Airlines
Mon 9/78:25 am
ORD
-
VPS
Nonstop2h 28m
American Airlines
Deal found 7/27$425
This American Airlines deal was found by Cheapflights users on 7/26. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/2412:24 pm
VPS
-
ORD
1 stop9h 36m
American Airlines
Sat 10/35:29 pm
ORD
-
VPS
1 stop6h 14m
American Airlines
Deal found 7/26$428
This American Airlines deal was found by Cheapflights users on 7/25. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/2011:28 am
VPS
-
ORD
Nonstop2h 45m
American Airlines
Tue 8/258:25 am
ORD
-
VPS
Nonstop2h 28m
American Airlines
Deal found 7/25$444
This American Airlines deal was found by Cheapflights users on 7/27. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/1911:28 am
VPS
-
ORD
Nonstop2h 45m
American Airlines
Tue 8/258:25 am
ORD
-
VPS
Nonstop2h 28m
American Airlines
Deal found 7/27$452

Find flight deals from Valparaiso to O'Hare Intl

Discover tips and strategies to find the most affordable flight options for your journey from Valparaiso (VPS) to O'Hare Intl (ORD). Learn about various techniques such as flexible date searches, comparing prices across and setting up price alerts. Use these methods to find the cheapest flights available for your travel needs. Data last updated July 29, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$331
(Kiwi.com)

One-way from

$116
(Kiwi.com)

Popular in

October

Cheapest in

September

Average price

$501

Good round-trip deal

$501 or less
Provider with most accurate pricing for Valparaiso Destin-Ft Walton Beach-Chicago O'Hare Intl flight deals.
Search Deals
Provider most trusted by Cheapflights users for Valparaiso Destin-Ft Walton Beach-Chicago O'Hare Intl flights.
Search Deals
From Valparaiso Destin-Ft Walton Beach to Chicago O'Hare Intl
Search Deals
One-way flight from Valparaiso Destin-Ft Walton Beach to Chicago O'Hare Intl
Search Deals
Highest demand for flights based on searches. 4% potential increase in price ($22 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 6% potential price decrease ($28 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in July 2026
Search Deals
Price to beat on a round-trip flight from Valparaiso Destin-Ft Walton Beach to Chicago O'Hare Intl.
Search Deals

Cheapflights Fare Finder

 
Customize your flight search to find flights from Valparaiso to O'Hare Intl 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, Cheapflights users made 2,558,603 searches. Data last updated July 29, 2026.
Use the filters below to find and compare flights from Valparaiso 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

10:56 am-12:23 am

1 stop13h 27m

Chicago O'Hare Intl

Sat 10/3

7:21 pm-8:27 am

2 stops37h 06m

$390

ValparaisoChicago

VPS - ORD

VPSORD

Valparaiso Destin-Ft Walton Beach

Tue 11/24

2:49 pm-7:02 pm

1 stop4h 13m

Chicago O'Hare Intl

Wed 12/2

1:30 pm-6:43 pm

1 stop5h 13m

$405

ValparaisoChicago

VPS - ORD

VPSORD

Valparaiso Destin-Ft Walton Beach

Tue 11/24

5:00 pm-11:59 pm

1 stop6h 59m

Chicago O'Hare Intl

Tue 12/1

6:19 pm-11:20 pm

1 stop5h 01m

$405
Quickest round-trip

ValparaisoChicago

VPS - ORD

VPSORD

Valparaiso Destin-Ft Walton Beach

Thu 8/20

11:28 am-2:13 pm

Nonstop2h 45m

Chicago O'Hare Intl

Tue 8/25

8:25 am-10:53 am

Nonstop2h 28m

$444

ValparaisoChicago

VPS - ORD

VPSORD

Valparaiso Destin-Ft Walton Beach

Fri 9/4

4:50 pm-9:57 pm

1 stop5h 07m

Chicago O'Hare Intl

Mon 9/7

8:25 am-10:53 am

Nonstop2h 28m

$454

ValparaisoChicago

VPS - ORD

VPSORD

Valparaiso Destin-Ft Walton Beach

Sat 8/15

2:45 pm-8:55 pm

1 stop6h 10m

Chicago O'Hare Intl

Mon 8/17

11:23 am-4:01 pm

1 stop4h 38m

$496

ValparaisoChicago

VPS - ORD

VPSORD

Valparaiso Destin-Ft Walton Beach

Fri 8/14

5:59 pm-11:52 pm

1 stop5h 53m

Chicago O'Hare Intl

Sun 8/16

6:49 am-11:51 am

1 stop5h 02m

$521

ValparaisoChicago

VPS - ORD

VPSORD

Valparaiso Destin-Ft Walton Beach

Fri 8/14

7:00 am-12:40 pm

1 stop5h 40m

Chicago O'Hare Intl

Sun 8/23

5:30 am-11:15 am

1 stop5h 45m

$521

ValparaisoChicago

VPS - ORD

VPSORD

Valparaiso Destin-Ft Walton Beach

Fri 8/14

5:06 pm-11:57 pm

1 stop6h 51m

Chicago O'Hare Intl

Sun 8/16

5:30 am-11:15 am

1 stop5h 45m

$521

ValparaisoChicago

VPS - ORD

VPSORD

Valparaiso Destin-Ft Walton Beach

Tue 9/8

5:05 pm-11:59 pm

1 stop6h 54m

Chicago O'Hare Intl

Tue 9/15

8:25 am-6:42 pm

2 stops10h 17m

$924

Flights are sorted by cheapest round-trip flights first.

Deals found on 7/29

Showing 1-10 of 17 resultsSorted by cheapest first
1
2

Compare providers for flights from Valparaiso to O'Hare Intl

Provider information is updated monthly. Please note that these providers often have deals for this flight, but the availability may vary on a day-by-day basis on Cheapflights.
Use the table below to compare price accuracy, trust ratings, and cancellation policies for each provider offering flight deals from Valparaiso to O'Hare Intl in July.
ProviderPrice AccuracyTrust Score*
ExpediaPrice Accuracy1 starTrust Score*3 stars
FlightHubPrice Accuracy3 starsTrust Score*3 stars

*The Trust Score is based on feedback from users after their booking experience. It measures overall satisfaction, helping us identify issues like hidden fees, problems during the ticketing process, and the quality of customer service. This score is our best indicator of the provider's quality and reliability.

  • Most accurate provider: When it comes to deals on Valparaiso, Florida-Chicago O'Hare Intl Airport flights, users find the pricing of FlightHub to be most consistent on Cheapflights vs. FlightHub Users can find the same prices on Valparaiso, Florida-Chicago O'Hare Intl Airport flight deals on Cheapflights vs. FlightHub >95% of the time. Price accuracy is based on data collected from Valparaiso, Florida-Chicago O'Hare Intl Airport flight searches over the past month and is updated monthly.
  • Most trusted provider: When it comes to deals on Valparaiso, Florida-Chicago O'Hare Intl Airport flights, Cheapflights users trust FlightHub the most. FlightHub has received a user feedback score of 3 out of 3 stars (3 being the best), meaning they have been trusted the most by Cheapflights users looking for Valparaiso, Florida-Chicago O'Hare Intl Airport flight deals. Provider user feedback score is based on Cheapflights searches over the past month and is updated monthly.

Best time to book a flight from Valparaiso to O'Hare Intl

Have a flexible travel schedule? Discover the best time to fly to O'Hare Intl from Valparaiso with our price prediction graph.
Estimated round-trip price
Rates are based on past data. Find the cheapest month and day to book your flight based on your travel requirements, then search for cheap deals.

Cheapflights Insights

Everything you need to know about your flight from Valparaiso to Chicago O'Hare Intl Airport

What is the cheapest time of day to fly from VPS to ORD?

Find hourly flight availability from Valparaiso to O'Hare Intl. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated July 29, 2026.

Regardless of the time of day you decide to fly, the ticket price will remain around the same. Book flights from Valparaiso, Florida to Chicago O'Hare Intl Airport as you normally would.

Reviews of airlines servicing O'Hare Intl

Get insights into the airlines that provide service to O'Hare Intl. Read reviews, discover amenities, and learn about the overall travel experience offered by airlines. Use this information to make informed decisions when choosing an airline for your flight to O'Hare Intl. Reviews last updated July 29, 2026.
Read through reviews of airlines operating flights from Valparaiso to Chicago O'Hare Intl Airport, such as Southwest and American Airlines. Reviews also offer insight into each airline's entertainment options, comfort, food, crew/service, and boarding process.
Southwest
8.0
Very good
4,228 reviews

Crew

8.6

Boarding

8.1

Comfort

8.0

Food

7.0

Overall

8.0

Entertainment

7.5

Reviews

1 / 20
6.0
Good

Reza,Jun 2026

TPA - MDW

The seats were super cramped and couldn’t move without hitting other passengers
Southwest
8.0
Very good
4,228 reviews
Southwest
8.0
Very good
4,228 reviews

Crew

8.6

Boarding

8.1

Comfort

8.0

Food

7.0

Overall

8.0

Entertainment

7.5

Reviews

1 / 20
6.0
Good

Reza,Jun 2026

TPA - MDW

The seats were super cramped and couldn’t move without hitting other passengers
American Airlines
7.1
Good
11,845 reviews
Southwest
8.0
Very good
4,228 reviews

Crew

8.6

Boarding

8.1

Comfort

8.0

Food

7.0

Overall

8.0

Entertainment

7.5

Reviews

1 / 20
6.0
Good

Reza,Jun 2026

TPA - MDW

The seats were super cramped and couldn’t move without hitting other passengers

Related info for your journey

Find useful and relevant information for your journey from Valparaiso to O'Hare Intl. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.

  • What airport do you fly from for flights from Valparaiso to Chicago O'Hare Intl?

    If you book a flight to Chicago O'Hare Intl from Valparaiso, you will be flying from Destin-Ft Walton Beach, which is the city’s only airport. Valparaiso Destin-Ft Walton Beach (VPS) is located 3.1 mi from the center of Valparaiso. There is 1 flight from Destin-Ft Walton Beach to Chicago O'Hare Intl per day from 2 different airlines.

  • How long is the flight from Valparaiso, Florida to Chicago O'Hare Intl Airport?

    For as low as $395, American Airlines can have you in Chicago O'Hare Intl Airport from Valparaiso, Florida in 2h 45m. The distance from Valparaiso, Florida to Chicago O'Hare Intl Airport is about 797 mi. Both multi-stop and nonstop flights can be found to your destination and back.

  • What are the cheapest airlines flying from Valparaiso, Florida to Chicago O'Hare Intl Airport round-trip?

    Currently priced at $234, Southwest will fly you from Valparaiso, Florida to Chicago O'Hare Intl Airport and back. In addition to Southwest, many other airlines offer competitively priced options for your trip. Check Cheapflights for deals on American Airlines for as low as $374. Southwest is priced at 50% lower than the current average price of a flight leaving 3 months from now.

  • What are the most reliable airlines from Valparaiso, Florida to Chicago O'Hare Intl Airport?

    No one likes to see their flight delayed. When booking a flight from Valparaiso, Florida to Chicago O'Hare Intl Airport consider choosing Qatar Airways (80%), American Airlines (73%) or Envoy Air (73%) as they are the most reliable in getting you off to your destination on time.

  • What are the cheapest flights from Valparaiso, Florida to Chicago O'Hare Intl Airport?

    Looking at all options, your cheapest flight can be booked for $405. While the most popular route (Valparaiso Destin-Ft Walton Beach - Chicago O'Hare Intl) can be booked for $331 on average, our data indicates $553 when flying from Valparaiso, Florida to Chicago O'Hare Intl Airport.

  • Can I find deals for flights from Valparaiso to O'Hare Intl that include hotel bookings?

    Yes. In addition to deals on Valparaiso to O'Hare Intl flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from Valparaiso to O'Hare Intl?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Valparaiso to O'Hare Intl.

  • Can I find deals for business class flights from Valparaiso to O'Hare Intl?

    Yes. Cheapflights offers flight deals from Valparaiso to O'Hare Intl by cabin class. In addition to browsing deals, you can also filter by cabin class on the search results page after making a search.

See more FAQs

Traveling to a place near Chicago O'Hare Intl Airport?

Book flights to Chicago O'Hare Intl Airport if you plan to visit one of these locations
Benton Harbor
Rosemont
Schaumburg
Naperville
Lake Geneva
Oak Brook
Delavan
Oakbrook Terrace
Gurnee
South Holland
Libertyville
Orland Park
Hoffman Estates
Beloit
Downers Grove
Rockford
Aurora
Racine
Great Lakes
Janesville

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Top 2 airlines flying from Valparaiso to O'Hare Intl

Discover the top 2 airlines that operate flights from Valparaiso to O'Hare Intl. Compare their services, reliability, and customer satisfaction ratings to choose the airline that best suits your travel preferences and needs. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated July 29, 2026.
AirlineCheapestAverageFlexibilityOn-time
SouthwestCheapest$234Average$400FlexibilityNo cancel feeOn-time63%
American AirlinesCheapest$374Average$477FlexibilityNo cancel feeOn-time71%

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