HomeSearch by dateVacation packagesHotelsFlight dealsCar rentalTravel tips & news
Chicago

$89+ Cheap flights from Valparaiso, FL (VPS) to Chicago (CHI)

This is the cheapest round-trip flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 1/9. Fares are subject to change and may not be available on all flights or dates of travel.
VPS — CHI
Dec 24 — Dec 311
Tue 12/24
Tue 12/31
1 adult, Economy
We work with more than 300 partners to bring you better travel deals

Find cheap flights from Valparaiso to Chicago 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 Chicago

Discover tips and strategies to find the most affordable flight options for your journey from Valparaiso (VPS) to Chicago (CHI). 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 December 19, 2024.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$89
(Mytrip)

Popular in

September

Cheapest in

February

Average price

$400
Provider with most accurate pricing for Valparaiso Destin-Ft Walton Beach-Chicago (CHI) flight deals.
Search Deals
Provider most trusted by Cheapflights users for Valparaiso Destin-Ft Walton Beach-Chicago (CHI) flights.
Search Deals
From Valparaiso Destin-Ft Walton Beach to Chicago (CHI)
Search Deals
High demand for flights, 7% potential price rise
Search Deals
Best time to find cheap flights, 5% potential price drop
Search Deals
Average for round-trip flights in December 2024
Search Deals

Find flight deals from Valparaiso to Chicago

Cheapest flights from Valparaiso to Chicago
Explore the most affordable flight options available from Valparaiso to Chicago. Find the lowest fares from popular airlines and budget airlines, with prices last updated on December 19, 2024.

This Cheapflightsfares deal was found by Cheapflights users on 12/18. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 12/294:01 pmVPS - MDW
Nonstop2h 23mAllegiant Air
Tue 12/317:14 pmMDW - VPS
Nonstop2h 26mAllegiant Air
Deal found 12/18$170
This American Airlines deal was found by Cheapflights users on 12/18. 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 12/241:06 pmVPS - ORD
1 stop18h 13mAmerican Airlines
Wed 1/15:00 amORD - VPS
1 stop5h 56mAmerican Airlines
Deal found 12/18$495
This Southwest deal was found by Cheapflights users on 12/18. 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.
Sun 12/296:00 pmVPS - MDW
1 stop7h 00mSouthwest
Tue 12/316:20 amMDW - VPS
1 stop3h 55mSouthwest
Deal found 12/18$581
This Southwest deal was found by Cheapflights users on 12/18. 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.
Sun 12/297:40 amVPS - ORD
1 stop5h 20mSouthwest
Tue 12/315:45 amORD - VPS
2 stops15h 25mSouthwest
Deal found 12/18$586
This Delta deal was found by Cheapflights users on 12/18. 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.
Sun 12/297:30 pmVPS - ORD
1 stop4h 23mDelta
Tue 12/315:57 pmORD - VPS
1 stop5h 02mDelta
Deal found 12/18$632
This Sun Country Air deal was found by Cheapflights users on 12/18. 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 12/196:25 pmVPS - ORD
1 stop24h 07mSun Country Air
Sun 12/224:50 pmORD - VPS
1 stop17h 41mSun Country Air
Deal found 12/18$774
This Delta deal was found by Cheapflights users on 12/18. 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.
Sat 12/214:18 pmVPS - MDW
1 stop5h 48mDelta
Mon 12/235:03 pmMDW - VPS
1 stop5h 56mDelta
Deal found 12/18$921
This Mytrip deal was found by Cheapflights users on 12/18. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/196:25 pmVPS - ORD
2 stops25h 35mMultiple Airlines
Sun 12/2212:40 pmORD - VPS
3 stops34h 58mMultiple Airlines
Deal found 12/18$986

Find flights from Valparaiso to Chicago within your budget

Customize your flight search to find flights from Valparaiso to Chicago 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 December 19, 2024.

Fly from

Any airport

Fly to

Any airport

Route

Depart

Return

Price

ValparaisoChicago

VPS - MDW

VPSMDW

Valparaiso Destin-Ft Walton Beach

Thu 1/9

1:18 pm-3:41 pm

Nonstop2h 23m

Chicago Midway

Sun 1/12

4:31 pm-6:57 pm

Nonstop2h 26m

$89

ValparaisoChicago

VPS - ORD

VPSORD

Valparaiso Destin-Ft Walton Beach

Thu 1/16

1:50 pm-9:58 pm

1 stop8h 08m

Chicago O'Hare Intl

Sun 1/19

5:45 am-9:59 am

1 stop4h 14m

$370

ValparaisoChicago

VPS - ORD

VPSORD

Valparaiso Destin-Ft Walton Beach

Thu 1/23

9:00 am-9:52 pm

1 stop12h 52m

Chicago O'Hare Intl

Thu 1/30

1:35 pm-3:31 pm

3 stops25h 56m

$376

ValparaisoChicago

VPS - MDW

VPSMDW

Valparaiso Destin-Ft Walton Beach

Thu 1/9

6:00 am-10:12 am

1 stop4h 12m

Chicago Midway

Sun 1/12

10:57 am-3:52 pm

1 stop4h 55m

$385

ValparaisoChicago

VPS - ORD

VPSORD

Valparaiso Destin-Ft Walton Beach

Thu 1/16

12:54 pm-8:04 pm

2 stops7h 10m

Chicago O'Hare Intl

Sun 1/19

8:10 am-2:02 pm

1 stop5h 52m

$390

ValparaisoChicago

VPS - ORD

VPSORD

Valparaiso Destin-Ft Walton Beach

Thu 1/9

7:30 am-11:30 am

1 stop4h 00m

Chicago O'Hare Intl

Sun 1/12

11:25 am-9:00 pm

2 stops9h 35m

$420

ValparaisoChicago

VPS - MDW

VPSMDW

Valparaiso Destin-Ft Walton Beach

Thu 1/9

1:00 pm-10:40 pm

2 stops9h 40m

Chicago Midway

Sun 1/12

5:55 am-10:50 am

1 stop4h 55m

$420

ValparaisoChicago

VPS - MDW

VPSMDW

Valparaiso Destin-Ft Walton Beach

Sun 12/29

4:01 pm-6:24 pm

Nonstop2h 23m

$102

ValparaisoChicago

VPS - ORD

VPSORD

Valparaiso Destin-Ft Walton Beach

Sun 6/15

6:05 pm-7:11 pm

1 stop25h 06m

$147

ValparaisoChicago

VPS - ORD

VPSORD

Valparaiso Destin-Ft Walton Beach

Wed 1/15

5:00 pm-11:59 pm

1 stop6h 59m

$172

Flights are sorted by cheapest round-trip flights first.

Deals found on 12/18

Showing 1-10 of 15 results
1
2

Compare providers for flights from Valparaiso to Chicago

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 Chicago in December.
ProviderPrice AccuracyTrust Score*
FlightHubPrice Accuracy3 starsTrust Score*3 stars
ExpediaPrice Accuracy1 starTrust Score*3 stars
eDreamsPrice 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 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 flight deals on Cheapflights vs. FlightHub >95% of the time. Price accuracy is based on data collected from Valparaiso, Florida-Chicago flight searches over the past month and is updated monthly.
  • Most trusted provider: When it comes to deals on Valparaiso, Florida-Chicago 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 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 Chicago

Have a flexible travel schedule? Discover the best time to fly to Chicago 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.

Travel insights for flights from Valparaiso to Chicago

Get recent, data-driven insights about flights from Valparaiso to Chicago including ideal travel times, pricing trends, and more.

What is the cheapest month to book a flight from Valparaiso, Florida to Chicago?

Currently, September is the cheapest month in which you can book a flight from Valparaiso, Florida to Chicago (average of $232). Flying from Valparaiso, Florida to Chicago in June is currently the most expensive (average of $308). 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 CHI?

Find hourly flight availability from Valparaiso to Chicago. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated December 19, 2024.

One of the essential ways to save on airfare from Valparaiso, Florida to Chicago is to remain as flexible as possible. Flights that are in the evening tend to be the most expensive. A flight at noon could potentially save you up to 38% on airfare.

Rainfall in Chicago by month

Plan your trip to Chicago by taking into account the average rainfall totals by month.

In terms of precipitation, rainfall in Chicago ranges from 1.7 - 4.9 inches per month. August is typically the wettest month, when rainfall can reach 4.9 in. January is typically the driest time to visit Chicago when rainfall is around 1.7 in.

Temperature in Chicago by month

Plan your trip to Chicago by taking into account the average temperature totals by month.

If weather is an important factor for your trip to Chicago, use this chart to help with planning. For those seeking warmer temperatures, July is the ideal time of year to visit, when temperatures reach an average of 73.4 F. Travelers looking to avoid the cold should look outside of January, when temperatures are typically at their lowest (around 23.0 F).

Reviews of airlines servicing Chicago

Get insights into the airlines that provide service to Chicago. 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 Chicago. Reviews last updated December 19, 2024.
See what other customers who have flown with Delta, American Airlines and Southwest from Valparaiso to Chicago have to say. Users have also rated airlines in terms of entertainment options, comfort, food, crew/service, and boarding process.
Southwest
8.1
Very good
4,836 reviews

Overall

8.1

Entertainment

7.7

Crew

8.7

Comfort

8.1

Food

7.2

Boarding

8.2

Reviews

1 / 10

No tray tables for food or drink not convenient nor comfortable

Southwest
8.1
Very good
4,836 reviews
Southwest
8.1
Very good
4,836 reviews

Overall

8.1

Entertainment

7.7

Crew

8.7

Comfort

8.1

Food

7.2

Boarding

8.2

Reviews

1 / 10

No tray tables for food or drink not convenient nor comfortable

Delta
8.0
Very good
8,600 reviews
Southwest
8.1
Very good
4,836 reviews

Overall

8.1

Entertainment

7.7

Crew

8.7

Comfort

8.1

Food

7.2

Boarding

8.2

Reviews

1 / 10

No tray tables for food or drink not convenient nor comfortable

Allegiant Air
7.4
Good
829 reviews
Southwest
8.1
Very good
4,836 reviews

Overall

8.1

Entertainment

7.7

Crew

8.7

Comfort

8.1

Food

7.2

Boarding

8.2

Reviews

1 / 10

No tray tables for food or drink not convenient nor comfortable

American Airlines
7.2
Good
10,000 reviews
Southwest
8.1
Very good
4,836 reviews

Overall

8.1

Entertainment

7.7

Crew

8.7

Comfort

8.1

Food

7.2

Boarding

8.2

Reviews

1 / 10

No tray tables for food or drink not convenient nor comfortable

Sun Country Air
7.0
Good
399 reviews
Southwest
8.1
Very good
4,836 reviews

Overall

8.1

Entertainment

7.7

Crew

8.7

Comfort

8.1

Food

7.2

Boarding

8.2

Reviews

1 / 10

No tray tables for food or drink not convenient nor comfortable

Related info for your journey

Find useful and relevant information for your journey from Valparaiso to Chicago. 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?

    Valparaiso Destin-Ft Walton Beach (VPS), located 3.1 mi from the city center, is the airport you fly out of when you book flights from Valparaiso to Chicago. 3 airlines have flights from Destin-Ft Walton Beach to Chicago on a regular basis. Booking flights from Valparaiso Destin-Ft Walton Beach to Chicago should not be difficult; the airport handles an average of 0 outbound flights to Chicago per day.

  • What are the cheapest airlines flying from Valparaiso, Florida to Chicago round-trip?

    Cheapflights users have booked flights from Valparaiso, Florida to Chicago round-trip from $89. Other airlines that can offer you cheap pricing are Delta, from $370, and American Airlines, from $390. Users have found that Allegiant Air is 67% cheaper than the other options available to this destination.

  • What are the cheapest airlines to fly from Valparaiso, Florida to Chicago one-way?

    To fly one-way, consider booking your trip with Allegiant Air, which is currently one of the cheapest options available, starting at $102. Sun Country Air flights start at $147 while deals on Delta start at $172 one-way.

  • Can I find deals for flights from Valparaiso to Chicago that include hotel bookings?

    Yes. In addition to deals on Valparaiso to Chicago flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from Valparaiso to Chicago?

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

  • Can I find deals for business class flights from Valparaiso to Chicago?

    Yes. Cheapflights offers flight deals from Valparaiso to Chicago 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?

    Currently, September is the cheapest month in which you can book a flight from Valparaiso, Florida to Chicago (average of $232). Flying from Valparaiso, Florida to Chicago in June is currently the most expensive (average of $308). 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

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.

Alternative routes for Valparaiso to Chicago

See prices for flight routes from nearby airports that may be better suited for you.
Orlando to O'Hare Intl flights
Miami to O'Hare Intl flights
Fort Lauderdale to O'Hare Intl flights
Tampa to O'Hare Intl flights
Miami to Midway flights
Orlando to Midway flights
Tampa to Midway flights
Jacksonville to O'Hare Intl flights
West Palm Beach to O'Hare Intl flights
Fort Lauderdale to Midway flights
Fort Myers to O'Hare Intl flights
Orlando to St. Louis flights
Sarasota to O'Hare Intl flights
Pensacola to O'Hare Intl flights
Miami to St. Louis flights
West Palm Beach to Midway flights
Jacksonville to Midway flights
Tampa to St. Louis flights
Panama City to O'Hare Intl flights
Fort Lauderdale to St. Louis flights
Pensacola to Midway flights
Fort Myers to Midway flights
Jacksonville to Peoria flights
Orlando Sanford Intl to Rockford flights
Jacksonville to St. Louis flights
Fort Lauderdale to Peoria flights
Fort Myers to St. Louis flights
Valparaiso to O'Hare Intl flights
Jacksonville to Moline flights
Tallahassee to O'Hare Intl flights
Fort Myers to Moline flights
West Palm Beach to St. Louis flights
St Petersburg to Rockford flights
Sarasota to Midway flights
Daytona Beach to O'Hare Intl flights
Tallahassee to Midway flights
Panama City to Midway flights
Orlando to Moline flights
Pensacola to St. Louis flights
Orlando to Peoria flights
Daytona Beach to Midway flights
Gainesville to O'Hare Intl flights
Sarasota to St. Louis flights
Miami to Bloomington flights
Key West to O'Hare Intl flights
Miami to Peoria flights
Tampa to Moline flights
Gainesville to Midway flights
Orlando to Evansville flights
Sarasota to Moline flights

Top 3 airlines flying from Valparaiso to Chicago

Discover the top 3 airlines that operate flights from Valparaiso to Chicago. 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 December 19, 2024.
AirlineCheapestAverageFlexibilityOn-time
Allegiant AirCheapest$74Average$134FlexibilityNo cancel feeOn-time88%
DeltaCheapest$196Average$419FlexibilityNo cancel feeOn-timeN/A
American AirlinesCheapest$239Average$334FlexibilityNo cancel feeOn-time71%
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.