How many flights depart from Valparaiso, Florida to Chicago on average per week?

As of June 2026, there are 11 flights per week flying from Valparaiso, Florida to Chicago. The most common day of the week flights depart is Fri, with 27% of flights taking off on this day.

How many flights depart from Valparaiso, Florida to Chicago on average per day?

As of June 2026, 1 flights take off from Valparaiso, Florida and land in Chicago each day. The most common flight departure time for this route is 11:00AM, with 90% of daily flights taking off at noon.

What airlines fly to Chicago?

United Airlines, American Airlines and Delta are the top three most popular airlines that fly to Chicago from Valparaiso, Florida according to our data. United Airlines is the first choice among our users, with 43% of people opting to fly with this airline when traveling to Chicago. Keep in mind that there are 5 different airlines that fly to Chicago on a routine basis, so you have a few additional options to choose from.

What is the cheapest airline that flies from Valparaiso Destin-Ft Walton Beach to Chicago?

Allegiant Air and Delta are the most popular carriers operating from Valparaiso Destin-Ft Walton Beach to Chicago

When did momondo last update prices for flights from Valparaiso Destin-Ft Walton Beach Airport to Chicago?

Prices for flights from Valparaiso Destin-Ft Walton Beach Airport to Chicago are updated daily.

How many operators does momondo search for flights from Valparaiso Destin-Ft Walton Beach Airport to Chicago?

As of June 2026, there are 3 operators available to choose from for flights from Valparaiso Destin-Ft Walton Beach Airport to Chicago.

How old do you have to be to fly from Valparaiso Destin-Ft Walton Beach Airport to Chicago?

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.

What documentation or ID do you need to fly to Chicago?

The necessary travel and health documents for your Chicago trip may vary depending on your travel plans and individual circumstances. Generally, you should have various documents, such as a national ID card or driver's license and a passport that is valid for six months beyond your scheduled arrival date. We recommend seeking advice from your airline or a trusted third party, such as IATA.

$62 Cheap Flights from Valparaiso, Florida to Chicago in 2026

Q: What is the typical price of a round-trip flight between Valparaiso, Florida and Chicago?

Prices are currently low for flights on this route. Typical prices usually range from $509 to $388. The lowest price recently found on this route was $124.

Discover deals from 900+ travel sites with momondo.

Find the cheapest flights from Valparaiso, Florida to Chicago

Round-trip

One-way

Last minute

Direct

Cheap round-trip flights

Enter your travel dates to find the best prices.

6:10 pm - 8:30 pm

VPS

MDW

2h 20mnonstop

9:21 pm - 11:35 pm

MDW

VPS

2h 14mnonstop

$124Allegiant Air

Mon, Jul 20 - Fri, Jul 24

6:10 pm - 8:30 pm

VPS

MDW

2h 20mnonstop

9:21 pm - 11:35 pm

MDW

VPS

2h 14mnonstop

$125Allegiant Air

Mon, Jul 20 - Fri, Jul 24

5:05 pm - 11:50 pm

VPS

ORD

6h 45m

1 stop

1:15 pm - 6:28 pm

ORD

VPS

5h 13m

1 stop

$325Delta

Tue, Nov 24 - Wed, Dec 2

6:27 pm - 8:20 am

VPS

ORD

13h 53m

1 stop

8:15 pm - 9:11 am

ORD

VPS

12h 56m

1 stop

$334Sun Country Air

Wed, Nov 25 - Sat, Nov 28

7:45 am - 12:06 pm

VPS

ORD

4h 21m

1 stop

1:15 pm - 6:28 pm

ORD

VPS

5h 13m

1 stop

$346Delta

Wed, Nov 18 - Sat, Nov 21

6:03 pm - 5:29 pm

VPS

ORD

23h 26m

1 stop

7:25 am - 5:03 pm

ORD

VPS

9h 38m

1 stop

$354Sun Country Air

Sun, Jul 12 - Thu, Jul 23

6:05 pm - 5:24 pm

VPS

ORD

23h 19m

1 stop

9:48 pm - 4:19 pm

ORD

VPS

18h 31m

1 stop

$356Multiple Airlines

Sun, Aug 16 - Wed, Aug 19

11:29 am - 1:58 pm

VPS

ORD

2h 29mnonstop

8:33 am - 10:59 am

ORD

VPS

2h 26mnonstop

$376American Airlines

Tue, Nov 24 - Tue, Dec 1

6:03 pm - 5:29 pm

VPS

ORD

23h 26m

1 stop

9:57 pm - 5:05 pm

ORD

VPS

19h 08m

1 stop

$384Multiple Airlines

Sun, Jul 12 - Wed, Jul 22

11:29 am - 1:58 pm

VPS

ORD

2h 29mnonstop

4:05 pm - 9:10 pm

ORD

VPS

5h 05m

1 stop

$386American Airlines

Tue, Nov 24 - Tue, Dec 1

Save money when you book flights with momondo

Big names and deals

Search 100s of travel sites to compare prices.

Filter for what you want

Free Wi-Fi? Stopover? Instantly customize your results.

Trusted and free

We’re completely free to use - no hidden charges or fees.

Price Alerts

Not ready to book? to track prices.

Search flight deals

Delta flights from Valparaiso, Florida to Chicago

Our best Delta deals on Valparaiso, Florida to Chicago flight tickets

Delta

Nov 24

VPS5:05 pmValparaiso Destin-Ft Walton Beach

6h 45m

1 stop

ORD11:50 pmChicago O'Hare Intl

Dec 2

ORD1:15 pmChicago O'Hare Intl

5h 13m

1 stop

VPS6:28 pmValparaiso Destin-Ft Walton Beach

$325

Delta

Nov 18

VPS7:45 amValparaiso Destin-Ft Walton Beach

4h 21m

1 stop

ORD12:06 pmChicago O'Hare Intl

Nov 21

ORD1:15 pmChicago O'Hare Intl

5h 13m

1 stop

VPS6:28 pmValparaiso Destin-Ft Walton Beach

$346

Delta

Nov 18

VPS7:45 amValparaiso Destin-Ft Walton Beach

4h 11m

1 stop

MDW11:56 amChicago Midway

Nov 23

MDW1:05 pmChicago Midway

5h 23m

1 stop

VPS6:28 pmValparaiso Destin-Ft Walton Beach

$354

Sun Country Air flights from Valparaiso, Florida to Chicago

Our best Sun Country Air deals on Valparaiso, Florida to Chicago flight tickets

Sun Country Air

Nov 25

VPS6:27 pmValparaiso Destin-Ft Walton Beach

13h 53m

1 stop

ORD8:20 amChicago O'Hare Intl

Nov 28

ORD8:15 pmChicago O'Hare Intl

12h 56m

1 stop

VPS9:11 amValparaiso Destin-Ft Walton Beach

$334

Sun Country Air

Jul 12

VPS6:03 pmValparaiso Destin-Ft Walton Beach

23h 26m

1 stop

ORD5:29 pmChicago O'Hare Intl

Jul 23

ORD7:25 amChicago O'Hare Intl

9h 38m

1 stop

VPS5:03 pmValparaiso Destin-Ft Walton Beach

$354

Sun Country Air

Aug 2

VPS6:05 pmValparaiso Destin-Ft Walton Beach

23h 19m

1 stop

ORD5:24 pmChicago O'Hare Intl

Aug 6

ORD9:00 pmChicago O'Hare Intl

20h 03m

1 stop

VPS5:03 pmValparaiso Destin-Ft Walton Beach

$364

momondo Fare Finder

Use the filters below to find and compare flights from Valparaiso, Florida to Chicago that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip

Quickest round-trip

ValparaisoChicago

VPS - MDW

VPSMDW

Valparaiso Destin-Ft Walton Beach

Mon 7/20

6:10 pm-8:30 pm

Nonstop2h 20m

Chicago Midway

Fri 7/24

9:21 pm-11:35 pm

Nonstop2h 14m

$124

ValparaisoChicago

VPS - MDW

VPSMDW

Valparaiso Destin-Ft Walton Beach

Mon 7/20

6:10 pm-8:30 pm

Nonstop2h 20m

Chicago Midway

Fri 7/24

9:21 pm-11:35 pm

Nonstop2h 14m

$125

ValparaisoChicago

VPS - ORD

VPSORD

Valparaiso Destin-Ft Walton Beach

Tue 11/24

5:05 pm-11:50 pm

1 stop6h 45m

Chicago O'Hare Intl

Wed 12/2

1:15 pm-6:28 pm

1 stop5h 13m

$325

ValparaisoChicago

VPS - ORD

VPSORD

Valparaiso Destin-Ft Walton Beach

Wed 11/25

6:27 pm-8:20 am

1 stop13h 53m

Chicago O'Hare Intl

Sat 11/28

8:15 pm-9:11 am

1 stop12h 56m

$334

ValparaisoChicago

VPS - ORD

VPSORD

Valparaiso Destin-Ft Walton Beach

Wed 11/18

7:45 am-12:06 pm

1 stop4h 21m

Chicago O'Hare Intl

Sat 11/21

1:15 pm-6:28 pm

1 stop5h 13m

$346

ValparaisoChicago

VPS - ORD

VPSORD

Valparaiso Destin-Ft Walton Beach

Sun 7/12

6:03 pm-5:29 pm

1 stop23h 26m

Chicago O'Hare Intl

Thu 7/23

7:25 am-5:03 pm

1 stop9h 38m

$354

ValparaisoChicago

VPS - ORD

VPSORD

Valparaiso Destin-Ft Walton Beach

Sun 8/16

6:05 pm-5:24 pm

1 stop23h 19m

Chicago O'Hare Intl

Wed 8/19

9:48 pm-4:19 pm

1 stop18h 31m

$356

ValparaisoChicago

VPS - ORD

VPSORD

Valparaiso Destin-Ft Walton Beach

Tue 11/24

11:29 am-1:58 pm

Nonstop2h 29m

Chicago O'Hare Intl

Tue 12/1

8:33 am-10:59 am

Nonstop2h 26m

$376

ValparaisoChicago

VPS - ORD

VPSORD

Valparaiso Destin-Ft Walton Beach

Sun 7/12

6:03 pm-5:29 pm

1 stop23h 26m

Chicago O'Hare Intl

Wed 7/22

9:57 pm-5:05 pm

1 stop19h 08m

$384

ValparaisoChicago

VPS - ORD

VPSORD

Valparaiso Destin-Ft Walton Beach

Tue 11/24

11:29 am-1:58 pm

Nonstop2h 29m

Chicago O'Hare Intl

Tue 12/1

4:05 pm-9:10 pm

1 stop5h 05m

$386

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 20 resultsSorted by cheapest first

How to get the cheapest flight ticket from Valparaiso, Florida to Chicago

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

Prices

Airlines

Other information

What is the typical price of a round-trip flight between Valparaiso, Florida and Chicago?

What is the cheapest month to fly to Chicago?

The month of March is, on average, the cheapest month to fly to Chicago from Valparaiso, Florida, with most prices found around $68. If you’re not able to fly to Chicago in March, then April is your next best option. Flight prices from Valparaiso, Florida to Chicago during April average around $96.

What is the cheapest day to depart on your flight to Chicago?

The cheapest day to depart on your flight to Chicago is on a Wednesday when prices can be found for as low as $370. This is often the case because there is less demand to fly during this day of the week. When flying out on a Saturday, the most expensive travel day of the week, you can expect to see flight prices from Valparaiso, Florida to Chicago for around $562.

What is the cheapest time of day to depart on your flight to Chicago?

Our most recent data shows that the best time of day to fly to Chicago is in the afternoon. Flights from Valparaiso, Florida to Chicago during this time can be as low as $144. In contrast, the most expensive time of day to depart to Chicago is in the morning when prices are around $477.

What is the cheapest Valparaiso Destin-Ft Walton Beach to Chicago flight route?

Fly from Valparaiso Destin-Ft Walton Beach to Chicago Midway for the best Valparaiso Destin-Ft Walton Beach - Chicago flight prices

What cabin class options are available on Valparaiso, Florida to Chicago flights?

There are 2 cabin classes available to choose from on Valparaiso, Florida to Chicago 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 flights?

No. A direct flight is the cheapest option for a flight between Valparaiso, Florida to Chicago.

How have Valparaiso, Florida to Chicago flight prices changed over time?

When to book flights from Valparaiso, Florida to Chicago

Are you open to changing your travel dates? Check out the ideal times to fly from Valparaiso, Florida to Chicago according to our flight data. Find out which month and days have the cheapest flights.

Estimated round-trip price

Cheap Valparaiso, Florida to Chicago (VPS to CHI) flight deals and tips

Find info about flight duration, direct flights, and airports for your flight from Valparaiso, Florida to Chicago

Best Price Found	$57
Fastest flight time	2h 20m
Direct flights	Every day
Airports in Chicago	3 airports

The best one-way flight to Chicago from Valparaiso, Florida in the past 72 hours is $57. The best round-trip flight deal from Valparaiso, Florida to Chicago found on momondo in the last 72 hours is $154.

The fastest flight from Valparaiso, Florida to Chicago takes 2h 20m

Direct flights go from Valparaiso, Florida to Chicago every day.

There are 3 airports in Chicago. From Valparaiso, Florida there are direct flights to Chicago O'Hare Intl (ORD), Chicago Midway (MDW).

Search flight deals

Frequently asked questions about flying from Valparaiso, Florida to Chicago

How far is Valparaiso Destin-Ft Walton Beach to Chicago by plane?
Valparaiso Destin-Ft Walton Beach and Chicago are 787.3 mi apart from one another. Flights usually cover this in 2h 20m, 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?
Prices for flights from Valparaiso Destin-Ft Walton Beach Airport to Chicago are updated daily.
How many operators does momondo search for flights from Valparaiso Destin-Ft Walton Beach Airport to Chicago?
As of June 2026, there are 3 operators available to choose from for flights from Valparaiso Destin-Ft Walton Beach Airport to Chicago.
How old do you have to be to fly from Valparaiso Destin-Ft Walton Beach Airport to Chicago?
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.
What documentation or ID do you need to fly to Chicago?
The necessary travel and health documents for your Chicago trip may vary depending on your travel plans and individual circumstances. Generally, you should have various documents, such as a national ID card or driver's license and a passport that is valid for six months beyond your scheduled arrival date. We recommend seeking advice from your airline or a trusted third party, such as IATA.
What is the most popular plane model from Valparaiso, Florida to Chicago?
Based on momondo bookings for this flight route, the most popular plane model on flight routes from Valparaiso, Florida to Chicago is Embraer 175 (26.39% of total bookings). The next most popular plane models are Airbus A320-100/200 (25.00%), Airbus A319 (12.50%), and Boeing 737-800 (11.11%).
What is the most popular airline from Valparaiso, Florida to Chicago?
momondo data reveals that the most frequently booked airline on the route from Valparaiso, Florida to Chicago is American Airlines, representing 49% of all bookings. The subsequent popular airlines are Allegiant Air at 30% and Southwest at 21%.

Best airlines flying from Valparaiso, Florida to Chicago

Compare and see reviews for airlines that fly from Valparaiso, Florida to Chicago with momondo

Airline	Rating	Free Cancellation	Price
Allegiant Air	PriceFrom $86	Free Cancellation	Rating 7.3 700 reviews	Search Allegiant Air flights
American Airlines	PriceFrom $152	Free Cancellation	Rating 7.1 11,651 reviews	Search American Airlines flights
Southwest	PriceFrom $234	Free Cancellation	Rating 7.9 4,237 reviews	Search Southwest flights

Allegiant Air Flights From Valparaiso, Florida to Chicago
The lowest priced Allegiant Air flight from Valparaiso, Florida to Chicago from the last 72 hours was $86. Generally, Allegiant Air has 1 flight on this route every week with an average price of $188. Allegiant Air is rated 7.3/10 by our users.
American Airlines Flights From Valparaiso, Florida to Chicago
Another popular option for Valparaiso, Florida to Chicago flights is American Airlines (7.1/10, 11,651 ratings). American Airlines flies from Valparaiso, Florida to Chicago around 5 times per week, with deals starting from $152 round-trip and rising to an average price of around $431.

Merrillville

New Buffalo

Hammond

Portage

Benton Harbor

Saint Joseph

Lansing

Valparaiso

Schererville

Munster

Crown Point

Chesterton

Monticello

Porter

Griffith

Saint John

Why use momondo?

Why should I use momondo to find a flight deal from Valparaiso to Chicago?

Finding the right flight to Chicago from Valparaiso is quick and easy when you have a range of options in front of you, from reputable agents and recognisable airlines. Options that can then be filtered down to find the best fit. That is what momondo does. We make finding flights to Chicago quick and easy, saving you time and money.

Can I find flights from Valparaiso to Chicago with flexible booking policies on momondo?

Yes. momondo enables you to select and highlight flights to Chicago from Valparaiso with this policy.

How can momondo help me find flights from Valparaiso to Chicago?

momondo provides multiple filters to help you find the best flight to Chicago from Valparaiso. Filter by price, airline, airports, cabin, aircraft, payment method, number of stops and more.

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.

An easier way to manage your Chicago trip

We make it super easy to schedule, organize and travel with friends or family. Trips is free — and available to use no matter where you book.

Start using Trips

Find my bookings

Get notified when prices go down

Daily price changes in your inbox - only with Price Alerts.

1 adult

Mon 7/13

Mon 7/20

Email me momondo's favorite deals

By creating a price alert you accept our terms of use and privacy policy.

Find better results for your trip to the United States

Nearby airports

Airlines

Cabin classes

Other United States destinations

Other flights from Valparaiso, Florida

Complete your trip

Feeling lucky

Fly into one of these airports located in Chicago

Chicago Midway Airport

Chicago O'Hare Intl Airport

Chicago Greater Rockford Airport

Cheap flights from Valparaiso, Florida to Chicago from $62

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 7/27. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.

Find the cheapest flights from Valparaiso, Florida to Chicago

Cheap round-trip flights

Cheap one-way flights

Cheap last minute flights

Cheap direct flights

Big names and deals

Big names and deals

Filter for what you want

Filter for what you want

Trusted and free

Trusted and free

Price Alerts

Price Alerts

Delta flights from Valparaiso, Florida to Chicago

Our best Delta deals on Valparaiso, Florida to Chicago flight tickets

Sun Country Air flights from Valparaiso, Florida to Chicago

Our best Sun Country Air deals on Valparaiso, Florida to Chicago flight tickets

momondo Fare Finder

Use the filters below to find and compare flights from Valparaiso, Florida to Chicago that are best for you.

See travel insights to Chicago from

How to get the cheapest flight ticket from Valparaiso, Florida to Chicago

What is the typical price of a round-trip flight between Valparaiso, Florida and Chicago?

What is the cheapest month to fly to Chicago?

What is the cheapest day to depart on your flight to Chicago?

What is the cheapest time of day to depart on your flight to Chicago?

What is the cheapest Valparaiso Destin-Ft Walton Beach to Chicago flight route?

What cabin class options are available on Valparaiso, Florida to Chicago flights?

Can stopping save me money on Valparaiso, Florida to Chicago flights?

How have Valparaiso, Florida to Chicago flight prices changed over time?

What is the cheapest airline that flies from Valparaiso Destin-Ft Walton Beach to Chicago?

What airlines fly to Chicago?

How many flights depart from Valparaiso, Florida to Chicago on average per day?

How many flights depart from Valparaiso, Florida to Chicago on average per week?

When to book flights from Valparaiso, Florida to Chicago

Cheap Valparaiso, Florida to Chicago (VPS to CHI) flight deals and tips

Find info about flight duration, direct flights, and airports for your flight from Valparaiso, Florida to Chicago

Best Price Found

Fastest flight time

Direct flights

Airports in Chicago

Frequently asked questions about flying from Valparaiso, Florida to Chicago

Best airlines flying from Valparaiso, Florida to Chicago

Compare and see reviews for airlines that fly from Valparaiso, Florida to Chicago with momondo

Allegiant Air Flights From Valparaiso, Florida to Chicago

American Airlines Flights From Valparaiso, Florida to Chicago

Traveling to a place near Chicago?

Why use momondo?

An easier way to manage your Chicago trip

We make it super easy to schedule, organize and travel with friends or family. Trips is free — and available to use no matter where you book.

Get notified when prices go down

Daily price changes in your inbox - only with Price Alerts.

Find better results for your trip to the United States

Fly into one of these airports located in Chicago

Airports listed have a maximum distance of 78.5 mi from Chicago

Fly your favorite airline to Chicago

Airlines are sorted and displayed according to clicks in the past 7 days on momondo

Cabin classes currently available on flights to Chicago

List of cabin classes available on flights landing in Chicago. Availability may vary depending on flight origin and airline.

Popular cities in the United States

Popular flights according to clicks in the last 7 days on momondo

Fly to other destinations from Valparaiso, Florida

According to popular flight searches on momondo this year

Complete your trip to Chicago

Explore popular destinations other users love

According to popular flight searches on momondo this year