HomeSearch by dateVacation packagesHotelsFlight dealsCar rentalTravel tips & news
O'Hare Intl

$131+ 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 5/23. Fares are subject to change and may not be available on all flights or dates of travel.
VPS — ORD
Jun 1 — Jun 81
Mon 6/1
Mon 6/8
1 adult, Economy
We work with more than 300 partners to bring you better travel deals

Find cheap flights from Valparaiso to O'Hare Intl with Cheapflights

1. Tell us where you want to go

Enter your travel information like dates, passengers, trip type (one-way or round trip), and preferred cabin class then click “Find deals”

2. Select your favorite providers

We find the providers serving your travel needs. Choose up to four travel providers to compare side-by-side for flights, hotels, or car rentals.

3. Compare prices and book

Review each provider’s pricing and select the best option for you! Book through your favorite provider’s website for a seamless experience.

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 May 2, 2026.

This Kiwi.com deal was found by Cheapflights users on 5/1. 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.
Mon 6/228:23 pm
VPS
-
ORD
2 stops23h 27m
Multiple Airlines
Sat 7/46:19 pm
ORD
-
VPS
1 stop22h 44m
Multiple Airlines
Deal found 5/1$318
This Kiwi.com deal was found by Cheapflights users on 4/27. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/296:15 am
VPS
-
ORD
2 stops13h 26m
Multiple Airlines
Wed 6/39:37 pm
ORD
-
VPS
1 stop19h 47m
Multiple Airlines
Deal found 4/27$319
This Kiwi.com deal was found by Cheapflights users on 4/29. 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.
Mon 6/228:23 pm
VPS
-
ORD
2 stops23h 30m
Multiple Airlines
Mon 6/297:20 am
ORD
-
VPS
1 stop12h 53m
Multiple Airlines
Deal found 4/29$354
This American Airlines deal was found by Cheapflights users on 4/28. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/297:13 am
VPS
-
ORD
1 stop5h 05m
American Airlines
Sat 5/308:15 am
ORD
-
VPS
Nonstop2h 35m
American Airlines
Deal found 4/28$366
This Delta deal was found by Cheapflights users on 4/27. 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.
Fri 5/292:55 pm
VPS
-
ORD
1 stop6h 58m
Delta
Wed 6/38:10 am
ORD
-
VPS
1 stop5h 50m
Delta
Deal found 4/27$375
This Delta deal was found by Cheapflights users on 4/28. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 5/261:17 pm
VPS
-
ORD
1 stop7h 09m
Delta
Tue 6/29:49 am
ORD
-
VPS
1 stop4h 11m
Delta
Deal found 4/28$384
This American Airlines deal was found by Cheapflights users on 4/30. 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 7/111:16 am
VPS
-
ORD
Nonstop2h 41m
American Airlines
Thu 7/912:00 pm
ORD
-
VPS
1 stop6h 04m
American Airlines
Deal found 4/30$385
This Southwest deal was found by Cheapflights users on 4/30. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 6/17:20 am
VPS
-
ORD
1 stop5h 30m
Southwest
Tue 6/22:40 pm
ORD
-
VPS
1 stop6h 20m
Southwest
Deal found 4/30$388
This Southwest deal was found by Cheapflights users on 4/28. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 5/287:20 am
VPS
-
ORD
1 stop5h 30m
Southwest
Mon 6/12:40 pm
ORD
-
VPS
1 stop6h 25m
Southwest
Deal found 4/28$389
This Kiwi.com deal was found by Cheapflights users on 4/28. 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.
Mon 6/89:03 pm
VPS
-
ORD
1 stop32h 04m
Multiple Airlines
Fri 6/127:33 pm
ORD
-
VPS
2 stops17h 51m
Multiple Airlines
Deal found 4/28$390
This Delta deal was found by Cheapflights users on 4/30. 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 7/17:00 am
VPS
-
ORD
1 stop5h 36m
Delta
Thu 7/95:30 am
ORD
-
VPS
1 stop6h 59m
Delta
Deal found 4/30$394
This American Airlines deal was found by Cheapflights users on 4/28. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 5/264:45 pm
VPS
-
ORD
1 stop4h 52m
American Airlines
Tue 6/28:15 am
ORD
-
VPS
Nonstop2h 35m
American Airlines
Deal found 4/28$399

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 May 2, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$318
(Kiwi.com)

One-way from

$131
(Kiwi.com)

Popular in

October

Cheapest in

June

Average price

$349

Good round-trip deal

$432 or less

Good one-way deal

$246 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. 11% potential increase in price ($51 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 4% potential price decrease ($18 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in May 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 May 2, 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

Fri 5/29

3:53 pm-12:42 am

1 stop8h 49m

Chicago O'Hare Intl

Wed 6/3

9:05 am-4:01 pm

1 stop6h 56m

$375

ValparaisoChicago

VPS - ORD

VPSORD

Valparaiso Destin-Ft Walton Beach

Fri 7/3

2:45 pm-8:32 pm

1 stop5h 47m

Chicago O'Hare Intl

Tue 7/7

1:44 pm-6:42 pm

1 stop4h 58m

$375

ValparaisoChicago

VPS - ORD

VPSORD

Valparaiso Destin-Ft Walton Beach

Sat 6/20

5:07 pm-12:04 am

1 stop6h 57m

Chicago O'Hare Intl

Tue 6/30

5:30 am-10:29 am

1 stop4h 59m

$375

ValparaisoChicago

VPS - ORD

VPSORD

Valparaiso Destin-Ft Walton Beach

Mon 6/1

7:20 am-12:50 pm

1 stop5h 30m

Chicago O'Hare Intl

Tue 6/2

2:40 pm-9:00 pm

1 stop6h 20m

$388

ValparaisoChicago

VPS - ORD

VPSORD

Valparaiso Destin-Ft Walton Beach

Wed 8/5

11:10 am-6:45 pm

1 stop7h 35m

Chicago O'Hare Intl

Sun 8/9

5:15 am-10:25 am

1 stop5h 10m

$394

ValparaisoChicago

VPS - ORD

VPSORD

Valparaiso Destin-Ft Walton Beach

Thu 5/28

2:55 pm-8:26 pm

1 stop5h 31m

Chicago O'Hare Intl

Thu 6/4

7:07 am-2:00 pm

1 stop6h 53m

$399

ValparaisoChicago

VPS - ORD

VPSORD

Valparaiso Destin-Ft Walton Beach

Wed 7/1

6:00 am-12:36 pm

1 stop6h 36m

Chicago O'Hare Intl

Thu 7/9

8:03 am-12:29 pm

1 stop4h 26m

$404

ValparaisoChicago

VPS - ORD

VPSORD

Valparaiso Destin-Ft Walton Beach

Thu 6/4

1:17 pm-6:35 pm

1 stop5h 18m

Chicago O'Hare Intl

Mon 6/8

6:30 am-1:10 pm

1 stop6h 40m

$413

ValparaisoChicago

VPS - ORD

VPSORD

Valparaiso Destin-Ft Walton Beach

Mon 6/22

6:00 am-10:13 am

1 stop4h 13m

Chicago O'Hare Intl

Mon 6/29

6:30 am-1:10 pm

1 stop6h 40m

$413
Quickest round-trip

ValparaisoChicago

VPS - ORD

VPSORD

Valparaiso Destin-Ft Walton Beach

Thu 5/21

2:01 pm-7:20 pm

1 stop5h 19m

Chicago O'Hare Intl

Mon 5/25

5:30 am-10:22 am

1 stop4h 52m

$423

Flights are sorted by cheapest round-trip flights first.

Deals found on 4/29

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 May.
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 $249). 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 May 2, 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.

How much does it cost to fly round-trip from Valparaiso, Florida to Chicago O'Hare Intl Airport?

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 May 2, 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
4,314 reviews

Crew

8.6

Overall

8.0

Entertainment

7.5

Food

7.0

Comfort

8.0

Boarding

8.1

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
8.0
Very good
4,314 reviews
Southwest
8.0
Very good
4,314 reviews

Crew

8.6

Overall

8.0

Entertainment

7.5

Food

7.0

Comfort

8.0

Boarding

8.1

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
11,673 reviews
Southwest
8.0
Very good
4,314 reviews

Crew

8.6

Overall

8.0

Entertainment

7.5

Food

7.0

Comfort

8.0

Boarding

8.1

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 are 2 flights 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 $388, Delta can have you in Chicago O'Hare Intl Airport from Valparaiso, Florida in 5h 30m. 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 $157, 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 61% 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 (89%), Envoy Air (89%) or Qatar Airways (86%) 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 $243. While the most popular route (Valparaiso Destin-Ft Walton Beach - Chicago O'Hare Intl) can be booked for $354 on average, our data indicates $469 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 $249). 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
Rosemont
Schaumburg
Naperville
Lake Geneva
Gurnee
Delavan
Downers Grove
Oakbrook Terrace
Benton Harbor
Hoffman Estates
Des Plaines
Oak Brook
South Holland
Libertyville
Warrenville
Elk Grove Village
Bridgeview
Great Lakes
Lansing
Arlington Heights

Browse thousands of different options on Cheapflights for your next trip

Toggle through the tabs below to find thousands of options on Cheapflights for your next trip.

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 May 2, 2026.
AirlineCheapestAverageFlexibilityOn-time
American AirlinesCheapest$157Average$384FlexibilityNo cancel feeOn-time71%
SouthwestCheapest$234Average$400FlexibilityNo cancel feeOn-time63%

100% Free

Cheapflights is completely free to use, so you can start saving the moment you arrive.

Book with Flexibility

Our users can plan ahead with confidence and find flights with no change fees

Travel Smart

Millions of people come to us for their flight needs every year. We help make travel planning easy by providing useful insights and data-driven graphs that can inform your decisions.