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

4 flights are operational weekly from Chicago to Valparaiso, Florida as of March 2026. The most popular departure day for this route is Mon, with 25% of flights per week taking off on this day.

What airlines fly to Valparaiso, Florida?

United Airlines, American Airlines and Delta are the top three most popular airlines that fly to Valparaiso, Florida from Chicago 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 Valparaiso, Florida. Keep in mind that there are 6 different airlines that fly to Valparaiso, Florida on a routine basis, so you have a few additional options to choose from.

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

Allegiant Air, Southwest, and Sun Country Air are the most popular carriers operating from Chicago to Valparaiso Destin-Ft Walton Beach

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

Prices for flights from Chicago to Valparaiso Destin-Ft Walton Beach Airport were last updated today.

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

As of March 2026, there are 4 operators available to choose from for flights from Chicago to Valparaiso Destin-Ft Walton Beach Airport.

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

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 Chicago to Valparaiso Destin-Ft Walton Beach Airport.

What documentation or ID do you need to fly to Valparaiso Destin-Ft Walton Beach Airport?

The travel and health documents required for your trip to Valparaiso Destin-Ft Walton Beach Airport can vary based on your itinerary and personal situation. As a rule, consider having multiple documents such as a national ID card or driver’s license, and a passport valid for six-months after you plan to arrive at Valparaiso Destin-Ft Walton Beach Airport. We always recommend checking with your airline or a trusted third party such as IATA to get advice.

$58 Cheap Flights from Chicago to Valparaiso in 2026

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

Prices are currently low for flights on this route. Typical prices usually range from $423 to $618. The lowest price recently found on this route was $120.

1 adult

0 bags

Discover deals from 900+ travel sites with momondo.

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

Find the cheapest flights from Chicago to Valparaiso

Round-trip

One-way

Last minute

Direct

Cheap round-trip flights

Enter your travel dates to find the best prices.

9:23 pm - 11:36 pm

MDW

VPS

2h 13mnonstop

6:12 pm - 8:33 pm

VPS

MDW

2h 21mnonstop

$120Allegiant Air

Mon, Jun 8 - Fri, Jun 12

9:23 pm - 11:36 pm

MDW

VPS

2h 13mnonstop

6:12 pm - 8:33 pm

VPS

MDW

2h 21mnonstop

$131Allegiant Air

Mon, Jun 8 - Mon, Jun 15

5:47 pm - 7:56 pm

MDW

VPS

2h 09mnonstop

4:05 pm - 6:22 pm

VPS

MDW

2h 17mnonstop

$133Allegiant Air

Sun, Apr 12 - Thu, Apr 16

2:40 pm - 9:05 pm

ORD

VPS

6h 25m

1 stop

7:15 am - 12:50 pm

VPS

ORD

5h 35m

1 stop

$311Southwest

Mon, May 18 - Wed, May 20

9:41 am - 12:15 pm

ORD

VPS

2h 34mnonstop

11:27 am - 2:10 pm

VPS

ORD

2h 43mnonstop

$316American Airlines

Wed, May 20 - Wed, May 27

8:35 am - 11:06 am

ORD

VPS

2h 31mnonstop

7:13 am - 2:20 pm

VPS

ORD

7h 07m

1 stop

$326American Airlines

Wed, May 27 - Sat, May 30

6:25 am - 1:27 pm

ORD

VPS

7h 02m

1 stop

1:53 pm - 8:16 pm

VPS

ORD

6h 23m

1 stop

$335Delta

Tue, Apr 14 - Tue, Apr 21

7:10 pm - 11:48 am

ORD

VPS

16h 38m

1 stop

2:01 pm - 7:20 pm

VPS

ORD

5h 19m

1 stop

$339Delta

Fri, May 29 - Tue, Jun 2

2:40 pm - 9:05 pm

ORD

VPS

6h 25m

1 stop

10:00 am - 3:30 pm

VPS

ORD

5h 30m

1 stop

$341Southwest

Mon, Apr 20 - Fri, Apr 24

12:53 pm - 12:55 pm

ORD

VPS

24h 02m

1 stop

6:00 am - 9:12 pm

VPS

ORD

15h 12m

2 stops

$342Multiple Airlines

Sat, May 23 - Sat, May 30

Allegiant Air flights from Chicago to Valparaiso, Florida

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

Allegiant Air

Jun 8

MDW9:23 pmChicago Midway

2h 13m

VPS11:36 pmValparaiso Destin-Ft Walton Beach

Jun 12

VPS6:12 pmValparaiso Destin-Ft Walton Beach

2h 21m

MDW8:33 pmChicago Midway

$120

Allegiant Air

Jun 8

MDW9:23 pmChicago Midway

2h 13m

VPS11:36 pmValparaiso Destin-Ft Walton Beach

Jun 15

VPS6:12 pmValparaiso Destin-Ft Walton Beach

2h 21m

MDW8:33 pmChicago Midway

$131

Allegiant Air

Apr 12

MDW5:47 pmChicago Midway

2h 09m

VPS7:56 pmValparaiso Destin-Ft Walton Beach

Apr 16

VPS4:05 pmValparaiso Destin-Ft Walton Beach

2h 17m

MDW6:22 pmChicago Midway

$133

Southwest flights from Chicago to Valparaiso, Florida

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

Southwest

May 18

ORD2:40 pmChicago O'Hare Intl

6h 25m

1 stop

VPS9:05 pmValparaiso Destin-Ft Walton Beach

May 20

VPS7:15 amValparaiso Destin-Ft Walton Beach

5h 35m

1 stop

ORD12:50 pmChicago O'Hare Intl

$311

Southwest

Apr 26

ORD2:40 pmChicago O'Hare Intl

6h 25m

1 stop

VPS9:05 pmValparaiso Destin-Ft Walton Beach

May 2

VPS7:00 amValparaiso Destin-Ft Walton Beach

8h 30m

1 stop

ORD3:30 pmChicago O'Hare Intl

$331

Southwest

Apr 20

ORD2:40 pmChicago O'Hare Intl

6h 25m

1 stop

VPS9:05 pmValparaiso Destin-Ft Walton Beach

Apr 24

VPS10:00 amValparaiso Destin-Ft Walton Beach

5h 30m

1 stop

ORD3:30 pmChicago O'Hare Intl

$341

momondo Fare Finder

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

Fly from

Fly to

Route

Depart

Return

Price

ChicagoValparaiso

MDW - VPS

MDWVPS

Chicago Midway

Mon 6/8

9:23 pm-11:36 pm

Nonstop2h 13m

Valparaiso Destin-Ft Walton Beach

Fri 6/12

6:12 pm-8:33 pm

Nonstop2h 21m

$120

ChicagoValparaiso

MDW - VPS

MDWVPS

Chicago Midway

Mon 6/8

9:23 pm-11:36 pm

Nonstop2h 13m

Valparaiso Destin-Ft Walton Beach

Mon 6/15

6:12 pm-8:33 pm

Nonstop2h 21m

$131

ChicagoValparaiso

MDW - VPS

MDWVPS

Chicago Midway

Sun 4/12

5:47 pm-7:56 pm

Nonstop2h 09m

Valparaiso Destin-Ft Walton Beach

Thu 4/16

4:05 pm-6:22 pm

Nonstop2h 17m

$133

ChicagoValparaiso

ORD - VPS

ORDVPS

Chicago O'Hare Intl

Mon 5/18

2:40 pm-9:05 pm

1 stop6h 25m

Valparaiso Destin-Ft Walton Beach

Wed 5/20

7:15 am-12:50 pm

1 stop5h 35m

$311

ChicagoValparaiso

ORD - VPS

ORDVPS

Chicago O'Hare Intl

Wed 5/20

9:41 am-12:15 pm

Nonstop2h 34m

Valparaiso Destin-Ft Walton Beach

Wed 5/27

11:27 am-2:10 pm

Nonstop2h 43m

$316

ChicagoValparaiso

ORD - VPS

ORDVPS

Chicago O'Hare Intl

Wed 5/27

8:35 am-11:06 am

Nonstop2h 31m

Valparaiso Destin-Ft Walton Beach

Sat 5/30

7:13 am-2:20 pm

1 stop7h 07m

$326

ChicagoValparaiso

ORD - VPS

ORDVPS

Chicago O'Hare Intl

Tue 4/14

6:25 am-1:27 pm

1 stop7h 02m

Valparaiso Destin-Ft Walton Beach

Tue 4/21

1:53 pm-8:16 pm

1 stop6h 23m

$335

ChicagoValparaiso

ORD - VPS

ORDVPS

Chicago O'Hare Intl

Fri 5/29

7:10 pm-11:48 am

1 stop16h 38m

Valparaiso Destin-Ft Walton Beach

Tue 6/2

2:01 pm-7:20 pm

1 stop5h 19m

$339

ChicagoValparaiso

ORD - VPS

ORDVPS

Chicago O'Hare Intl

Mon 4/20

2:40 pm-9:05 pm

1 stop6h 25m

Valparaiso Destin-Ft Walton Beach

Fri 4/24

10:00 am-3:30 pm

1 stop5h 30m

$341

ChicagoValparaiso

ORD - VPS

ORDVPS

Chicago O'Hare Intl

Sat 5/23

12:53 pm-12:55 pm

1 stop24h 02m

Valparaiso Destin-Ft Walton Beach

Sat 5/30

6:00 am-9:12 pm

2 stops15h 12m

$342

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 Chicago to Valparaiso, Florida

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 Chicago and Valparaiso, Florida?

What is the cheapest month to fly to Valparaiso, Florida?

If you aren’t able to travel during the month of October, then book flights to Valparaiso, Florida from Chicago during September instead. Flights to Valparaiso, Florida in September, while not as cheap as those in October, still average around $235.

What is the cheapest day to depart on your flight to Valparaiso, Florida?

The cheapest day to depart on your flight to Valparaiso, Florida is on a Monday when prices can be found for as low as $272. This is often the case because there is less demand to fly during this day of the week. On the other hand, Sunday is the most expensive day to depart from Chicago because it is more convenient for both business and leisure travelers. As a result, prices tend to be around $395.

What is the cheapest time of day to depart on your flight to Valparaiso, Florida?

Our data shows that the cheapest Chicago to Valparaiso, Florida flights are usually those with departure times in the afternoon. Our users have found flights to Valparaiso, Florida in the afternoon for as low as $166. In contrast, the most expensive time of day to depart to Valparaiso, Florida is in the morning when prices are around $393.

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

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

How far in advance should I book a flight to Valparaiso, Florida?

You are more likely to see cheaper flights to Valparaiso, Florida from Chicago when booking weeks ahead of your departure date. In general, you can expect to find flights to Valparaiso, Florida for around $415 when searching weeks out. However, flight prices might be lower outside of this timeframe. For example, people recently found flights to Valparaiso, Florida from Chicago for as low as $324 on momondo.

What cabin class options are available on Chicago to Valparaiso Destin-Ft Walton Beach flights?

There is only 1 cabin class available to choose from on Chicago to Valparaiso Destin-Ft Walton Beach 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 Chicago to Valparaiso, Florida flights?

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

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

When to book flights from Chicago to Valparaiso, Florida

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

Estimated round-trip price

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

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

Best Price Found	$115
Fastest flight time	2h 07m
Direct flights	Every day
Airports in Valparaiso, Florida	1 airport

The best one-way flight to Valparaiso, Florida from Chicago in the past 72 hours is $115. The best round-trip flight deal from Chicago to Valparaiso, Florida found on momondo in the last 72 hours is $180.

The fastest flight from Chicago to Valparaiso, Florida takes 2h 07m

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

There is 1 airport in Valparaiso, Florida. From Chicago there are direct flights to Valparaiso Destin-Ft Walton Beach (VPS).

Search flight deals

How far is Chicago to Valparaiso Destin-Ft Walton Beach by plane?
The distance between Chicago and Valparaiso Destin-Ft Walton Beach is about 787.3 mi. In terms of flight time, this usually takes a little over 2h 07m.
When did momondo last update prices for flights from Chicago to Valparaiso Destin-Ft Walton Beach Airport?
Prices for flights from Chicago to Valparaiso Destin-Ft Walton Beach Airport were last updated today.
How many operators does momondo search for flights from Chicago to Valparaiso Destin-Ft Walton Beach Airport?
As of March 2026, there are 4 operators available to choose from for flights from Chicago to Valparaiso Destin-Ft Walton Beach Airport.
How old do you have to be to fly from Chicago to Valparaiso Destin-Ft Walton Beach Airport?
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 Chicago to Valparaiso Destin-Ft Walton Beach Airport.
What documentation or ID do you need to fly to Valparaiso Destin-Ft Walton Beach Airport?
The travel and health documents required for your trip to Valparaiso Destin-Ft Walton Beach Airport can vary based on your itinerary and personal situation. As a rule, consider having multiple documents such as a national ID card or driver’s license, and a passport valid for six-months after you plan to arrive at Valparaiso Destin-Ft Walton Beach Airport. We always recommend checking with your airline or a trusted third party such as IATA to get advice.
What is the most popular plane model from Chicago to Valparaiso, Florida?
Based on momondo bookings for flights between Chicago and Valparaiso, Florida, the leading plane model is Embraer 175, making up 43.72% of the total bookings. Other popular models include Airbus A319 with 29.30%, Boeing 737-800 with 5.58%, and Airbus A320-100/200 with 5.58%.
What is the most popular airline from Chicago to Valparaiso, Florida?
Based on momondo bookings for flights between Chicago and Valparaiso, Florida, the leading airline is American Airlines, making up 50% of the total bookings. Other popular airlines include Allegiant Air with 32%, Delta with 10%, and Southwest with 8%.

Best airlines flying from Chicago to Valparaiso, Florida

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

Airline	Rating	Free Cancellation	Price
Allegiant Air	PriceFrom $82	Free Cancellation	Rating 7.3 714 reviews	Search Allegiant Air flights
Southwest	PriceFrom $212	Free Cancellation	Rating 8.0 4,307 reviews	Search Southwest flights
Delta	PriceFrom $236	Free Cancellation	Rating 7.9 8,237 reviews	Search Delta flights
American Airlines	PriceFrom $237	Free Cancellation	Rating 7.1 11,369 reviews	Search American Airlines flights

American Airlines Flights From Chicago to Valparaiso, Florida
The lowest priced American Airlines flight from Chicago to Valparaiso, Florida from the last 72 hours was $237. Generally, American Airlines has 4 flights on this route every week with an average price of $403. American Airlines is rated 7.1/10 by our users.

Fort Walton Beach

Crestview

Niceville

Andalusia

DeFuniak Springs

Why use momondo?

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

Finding the right flight to Valparaiso from Chicago 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 Valparaiso quick and easy, saving you time and money.

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

Yes. momondo allows you to filter the results for Chicago to Valparaiso flights to just show those with flexible booking policies.

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

Once all potential Chicago to Valparaiso flight options are in front of you, momondo lets you sort and filter flights based on preferences such as airline, price and flight times amongst many other options.

I’m not ready to book a flight from Chicago to Valparaiso right now. Can momondo alert me if prices change?

Of course. momondo tracks the price of Chicago to Valparaiso flights. All you need is a valid email address and we will do the rest; it is that quick and easy.

An easier way to manage your Valparaiso, Florida 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

Wed 4/1

Wed 4/8

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 Chicago

Complete your trip

Feeling lucky

Cheap flights from Chicago to Valparaiso from $58

This is the cheapest one-way flight price found by a momondo user in the last 72 hours by searching for a flight from Chicago to Valparaiso departing on 3/8. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.

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

Find the cheapest flights from Chicago to Valparaiso

Cheap round-trip flights

Cheap one-way flights

Cheap last minute flights

Cheap direct flights

Allegiant Air flights from Chicago to Valparaiso, Florida

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

Southwest flights from Chicago to Valparaiso, Florida

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

momondo Fare Finder

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

See travel insights to Valparaiso from

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

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

What is the cheapest month to fly to Valparaiso, Florida?

What is the cheapest day to depart on your flight to Valparaiso, Florida?

What is the cheapest time of day to depart on your flight to Valparaiso, Florida?

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

How far in advance should I book a flight to Valparaiso, Florida?

What cabin class options are available on Chicago to Valparaiso Destin-Ft Walton Beach flights?

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

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

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

What airlines fly to Valparaiso, Florida?

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

When to book flights from Chicago to Valparaiso, Florida

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

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

Best Price Found

Fastest flight time

Direct flights

Airports in Valparaiso, Florida

Best airlines flying from Chicago to Valparaiso, Florida

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

American Airlines Flights From Chicago to Valparaiso, Florida

Traveling to a place near Valparaiso?

Why use momondo?

An easier way to manage your Valparaiso, Florida 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

Airports servicing Florida

Fly your favorite airline to Valparaiso

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

Cabin classes currently available on flights to Valparaiso

List of cabin classes available on flights landing in Valparaiso. 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 Chicago

According to popular flight searches on momondo this year

Complete your trip to Valparaiso

Explore popular destinations other users love

According to popular flight searches on momondo this year