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O'Hare Intl

$133+ 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 8/10. Fares are subject to change and may not be available on all flights or dates of travel.
VPS — ORD
Jul 16 — Jul 231
Thu 7/16
Thu 7/23
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 June 16, 2026.

This Kiwi.com deal was found by Cheapflights users on 6/14. 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 9/255:53 pm
VPS
-
ORD
2 stops25h 51m
Multiple Airlines
Wed 9/3010:40 pm
ORD
-
VPS
1 stop24h 57m
Multiple Airlines
Deal found 6/14$325
This Kiwi.com deal was found by Cheapflights users on 6/15. 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 8/131:07 pm
VPS
-
ORD
1 stop7h 45m
Multiple Airlines
Sun 8/168:05 am
ORD
-
VPS
2 stops15h 12m
Multiple Airlines
Deal found 6/15$343
This Delta deal was found by Cheapflights users on 6/11. 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.
Wed 11/187:45 am
VPS
-
ORD
1 stop4h 21m
Delta
Sat 11/211:15 pm
ORD
-
VPS
1 stop5h 13m
Delta
Deal found 6/11$346
This Delta deal was found by Cheapflights users on 6/11. 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.
Wed 11/186:00 am
VPS
-
ORD
1 stop4h 07m
Delta
Mon 11/235:55 pm
ORD
-
VPS
1 stop5h 12m
Delta
Deal found 6/11$354
This Kiwi.com deal was found by Cheapflights users on 6/13. 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 10/912:32 pm
VPS
-
ORD
1 stop24h 00m
Multiple Airlines
Sun 10/1111:06 am
ORD
-
VPS
1 stop12h 31m
Multiple Airlines
Deal found 6/13$364
This Kiwi.com deal was found by Cheapflights users on 6/14. 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.
Wed 9/234:40 pm
VPS
-
ORD
2 stops27h 04m
Multiple Airlines
Wed 9/3010:40 pm
ORD
-
VPS
1 stop24h 57m
Multiple Airlines
Deal found 6/14$371
This Delta deal was found by Cheapflights users on 6/15. 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 7/711:15 am
VPS
-
ORD
1 stop5h 57m
Delta
Tue 7/146:35 am
ORD
-
VPS
1 stop5h 54m
Delta
Deal found 6/15$373
This Sun Country Air deal was found by Cheapflights users on 6/15. 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 Sun Country Air is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 7/96:03 pm
VPS
-
ORD
1 stop23h 26m
Sun Country Air
Wed 7/156:39 pm
ORD
-
VPS
1 stop22h 24m
Sun Country Air
Deal found 6/15$374
This American Airlines deal was found by Cheapflights users on 6/11. 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 11/2411:29 am
VPS
-
ORD
Nonstop2h 29m
American Airlines
Tue 12/18:33 am
ORD
-
VPS
Nonstop2h 26m
American Airlines
Deal found 6/11$376
This Delta deal was found by Cheapflights users on 6/11. 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.
Fri 9/257:10 pm
VPS
-
ORD
1 stop4h 49m
Delta
Mon 9/285:30 am
ORD
-
VPS
1 stop5h 28m
Delta
Deal found 6/11$381
This Delta deal was found by Cheapflights users on 6/12. 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 11/245:05 pm
VPS
-
ORD
1 stop6h 45m
Delta
Tue 12/13:35 pm
ORD
-
VPS
1 stop5h 06m
Delta
Deal found 6/12$384
This Kiwi.com deal was found by Cheapflights users on 6/14. 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 8/61:07 pm
VPS
-
ORD
1 stop7h 45m
Multiple Airlines
Sat 8/88:05 am
ORD
-
VPS
2 stops30h 18m
Multiple Airlines
Deal found 6/14$385

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 June 16, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$325
(Kiwi.com)

One-way from

$133
(Kiwi.com)

Popular in

October

Cheapest in

June

Average price

$109

Good round-trip deal

$491 or less

Good one-way deal

$317 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. 8% potential increase in price ($40 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 4% potential price decrease ($17 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in June 2026
Search Deals
Price to beat on a round-trip flight from Valparaiso Destin-Ft Walton Beach to Chicago O'Hare Intl.
Search Deals
Price to beat on a one-way 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 June 16, 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
Quickest round-trip

ValparaisoChicago

VPS - ORD

VPSORD

Valparaiso Destin-Ft Walton Beach

Wed 11/18

6:00 am-10:07 am

1 stop4h 07m

Chicago O'Hare Intl

Mon 11/23

5:55 pm-11:07 pm

1 stop5h 12m

$354

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

$381

ValparaisoChicago

VPS - ORD

VPSORD

Valparaiso Destin-Ft Walton Beach

Tue 11/24

7:45 am-12:06 pm

1 stop4h 21m

Chicago O'Hare Intl

Tue 12/1

5:55 pm-11:07 pm

1 stop5h 12m

$384

ValparaisoChicago

VPS - ORD

VPSORD

Valparaiso Destin-Ft Walton Beach

Tue 11/17

5:05 pm-11:50 pm

1 stop6h 45m

Chicago O'Hare Intl

Fri 11/20

3:35 pm-8:41 pm

1 stop5h 06m

$386

ValparaisoChicago

VPS - ORD

VPSORD

Valparaiso Destin-Ft Walton Beach

Thu 7/23

6:03 pm-5:19 pm

1 stop23h 16m

Chicago O'Hare Intl

Sun 7/26

7:30 am-5:08 pm

1 stop9h 38m

$444

ValparaisoChicago

VPS - ORD

VPSORD

Valparaiso Destin-Ft Walton Beach

Thu 7/23

11:32 am-2:14 pm

Nonstop2h 42m

Chicago O'Hare Intl

Sun 7/26

5:07 am-12:02 pm

1 stop6h 55m

$444

ValparaisoChicago

VPS - ORD

VPSORD

Valparaiso Destin-Ft Walton Beach

Tue 7/7

11:15 am-5:12 pm

1 stop5h 57m

Chicago O'Hare Intl

Sat 7/18

7:00 am-11:03 pm

2 stops16h 03m

$444

ValparaisoChicago

VPS - ORD

VPSORD

Valparaiso Destin-Ft Walton Beach

Wed 7/8

5:06 pm-11:53 pm

1 stop6h 47m

Chicago O'Hare Intl

Sat 7/18

7:00 am-11:03 pm

2 stops16h 03m

$444

ValparaisoChicago

VPS - ORD

VPSORD

Valparaiso Destin-Ft Walton Beach

Sat 7/11

2:56 pm-8:33 pm

1 stop5h 37m

Chicago O'Hare Intl

Thu 7/16

6:35 am-12:29 pm

1 stop5h 54m

$457

ValparaisoChicago

VPS - ORD

VPSORD

Valparaiso Destin-Ft Walton Beach

Mon 7/20

5:06 pm-11:53 pm

1 stop6h 47m

Chicago O'Hare Intl

Fri 7/24

6:35 am-12:29 pm

1 stop5h 54m

$471

Flights are sorted by cheapest round-trip flights first.

Deals found on 6/11

Showing 1-10 of 21 resultsSorted by cheapest first
1
2
3

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 June.
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 month to book a flight from Valparaiso, Florida to Chicago O'Hare Intl Airport?

Currently, June is the cheapest month in which you can book a flight from Valparaiso, Florida to Chicago O'Hare Intl Airport (average of $109). Flying from Valparaiso, Florida to Chicago O'Hare Intl Airport in October is currently the most expensive (average of $601). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

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 June 16, 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 June 16, 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
7.9
Good
4,237 reviews

Comfort

8.0

Entertainment

7.5

Boarding

8.1

Crew

8.6

Food

7.0

Overall

7.9

Reviews

1 / 20
2.0
Mediocre

Dominic,Mar 2026

MCO - SMF

I had to try and sleep on the floor of the Austin airport. I spent 12 hours there. The airline policies were so poor, that a near violent argument broke out between the people in front of me and the flight attendants - making for a super stressful situation at 30,000 feet. Garbage airline choice by Kayak Garbage idea to book a flight with a layover. Next time I will pay for a quality booking myself, and somehow force the company to reimburse it.
Southwest
7.9
Good
4,237 reviews
Southwest
7.9
Good
4,237 reviews

Comfort

8.0

Entertainment

7.5

Boarding

8.1

Crew

8.6

Food

7.0

Overall

7.9

Reviews

1 / 20
2.0
Mediocre

Dominic,Mar 2026

MCO - SMF

I had to try and sleep on the floor of the Austin airport. I spent 12 hours there. The airline policies were so poor, that a near violent argument broke out between the people in front of me and the flight attendants - making for a super stressful situation at 30,000 feet. Garbage airline choice by Kayak Garbage idea to book a flight with a layover. Next time I will pay for a quality booking myself, and somehow force the company to reimburse it.
American Airlines
7.1
Good
11,668 reviews
Southwest
7.9
Good
4,237 reviews

Comfort

8.0

Entertainment

7.5

Boarding

8.1

Crew

8.6

Food

7.0

Overall

7.9

Reviews

1 / 20
2.0
Mediocre

Dominic,Mar 2026

MCO - SMF

I had to try and sleep on the floor of the Austin airport. I spent 12 hours there. The airline policies were so poor, that a near violent argument broke out between the people in front of me and the flight attendants - making for a super stressful situation at 30,000 feet. Garbage airline choice by Kayak Garbage idea to book a flight with a layover. Next time I will pay for a quality booking myself, and somehow force the company to reimburse it.

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 $354, Delta can have you in Chicago O'Hare Intl Airport from Valparaiso, Florida in 4h 07m. The distance from Valparaiso, Florida to Chicago O'Hare Intl Airport is about 797 mi.

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

    Currently priced at $152, American Airlines will fly you from Valparaiso, Florida to Chicago O'Hare Intl Airport and back. In addition to American Airlines, many other airlines offer competitively priced options for your trip. Check Cheapflights for deals on Southwest for as low as $234. American Airlines is priced at 63% 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 American Airlines (81%), Envoy Air (81%) or Qatar Airways (81%) 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 $192. While the most popular route (Valparaiso Destin-Ft Walton Beach - Chicago O'Hare Intl) can be booked for $325 on average, our data indicates $734 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.

  • What is the cheapest month to book a flight from Valparaiso, Florida to Chicago O'Hare Intl Airport?

    Currently, June is the cheapest month in which you can book a flight from Valparaiso, Florida to Chicago O'Hare Intl Airport (average of $109). Flying from Valparaiso, Florida to Chicago O'Hare Intl Airport in October is currently the most expensive (average of $601). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

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
Gurnee
Delavan
Oakbrook Terrace
Downers Grove
Des Plaines
Hoffman Estates
Oak Brook
South Holland
Libertyville
Racine
Warrenville
Rockford
Great Lakes
Northbrook
Waukegan

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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 June 16, 2026.
AirlineCheapestAverageFlexibilityOn-time
American AirlinesCheapest$152Average$431FlexibilityNo cancel feeOn-time71%
SouthwestCheapest$234Average$400FlexibilityNo cancel feeOn-time63%

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