How long is the flight from Chicago to Valparaiso, Florida?

Airlines like Sun Country Air, Southwest, and Delta fly from Chicago to Valparaiso, Florida in about 5h 44m. The time it takes to get you to your destination can typically vary by up to 5h 44m. Chicago and Valparaiso, Florida are separated by a distance of 797 mi. When browsing for deals, the options you’ll see will be for both nonstop flights and flights with stops.

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

Currently priced at $82, Allegiant Air will fly you from Chicago to Valparaiso, Florida and back. In addition to Allegiant Air, many other airlines offer competitively priced options for your trip. Search Cheapflights for deals from Delta and Southwest - these airlines can fly you to your destination from $207 and $212, respectively. Allegiant Air is 74% cheaper than the average price of flights available within the next 90 days to this destination.

What is the cheapest day to fly from Chicago to Valparaiso, Florida?

Travelers seeking maximum savings on their Chicago to Valparaiso, Florida flight should consider departing on Sunday afternoons when fares are most often at their lowest. Sunday mornings flights should be avoided if possible as fares are typically the most expensive at this time.

In terms of precipitation, rainfall in Valparaiso, Florida ranges from 3.1 - 7.5 inches per month. July is typically the wettest month, when rainfall can reach 7.5 in. October is typically the driest time to visit Valparaiso, Florida when rainfall is around 3.1 in.

If weather is an important factor for your trip to Valparaiso, Florida, 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 80.6 F. Travelers looking to avoid the cold should look outside of January, when temperatures are typically at their lowest (around 50.0 F).

What are the cheapest flights from Chicago to Valparaiso, Florida?

The cheapest flight price from Chicago to Valparaiso, Florida is $124. On average you can expect to pay $471. The most popular route, (Chicago O'Hare Intl - Valparaiso Destin-Ft Walton Beach), can usually be booked for $298.

What is the cheapest day to fly round-trip from Chicago to Valparaiso, Florida?

It’s generally more expensive to depart on a Tuesday, if you have to leave on this day you can still search on Cheapflights to find great options that meet your needs.

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

When searching for a good deal, it’s best to be prepared for potential fluctuations in price. We recommend booking at least 18 days in advance, which can save you up to 302% on flights from Chicago to Valparaiso, Florida compared to booking the week you need them. Waiting 18 days out may not be for everyone, so we have options available for flights within the next two weeks, with the lowest price starting at $105. For sooner than that we have options available in the next 3 days from $604.

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

January is one of the best times of the year to fly to Valparaiso, Florida from Chicago. Prices for January average $320 per person but you can even find prices for as low as $85. The most expensive prices can be found in the month of March. Opting for a January flight can save you 67% on your journey compared to booking in March

What airport do you fly into for flights to Valparaiso from Chicago?

Most people fly into Valparaiso Destin-Ft Walton Beach (VPS) if they book a flight to Valparaiso from Chicago. On average, Destin-Ft Walton Beach has 0 inbound flights from Chicago per day from 4 airlines. Valparaiso Destin-Ft Walton Beach is conveniently located just 3.1 mi from Valparaiso’s city center.

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

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

How can I find direct flights from Chicago to Valparaiso?

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

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

Yes. Cheapflights offers flight deals from Chicago to Valparaiso by cabin class. In addition to browsing deals, you can also filter by cabin class on the search results page after making a search.

$54+ Cheap Flights from Chicago to Valparaiso, FL

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Cheapflights Tip: The best prices from Chicago to Valparaiso Destin-Ft Walton Beach are usually found in January or October, booked 17 days in advance, depart on a Wednesday or Monday and return on a Thursday

Cheap flight deals from Chicago to Valparaiso

Round-trip from	$172 (Kiwi.com)
One-way from	$54 (Cheapflightsfares)
Popular in	March
Cheapest in	January
Average price	$263
Good round-trip deal	$180 or less
Good one-way deal	$64 or less

From Chicago (CHI) to Valparaiso Destin-Ft Walton Beach

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One-way flight from Chicago (CHI) to Valparaiso Destin-Ft Walton Beach

Search Deals

Highest demand for flights based on searches. 22% potential increase in price ($95 potential increase over avg. RT price).

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Cheapest flight prices on average. 6% potential price decrease ($20 potential savings vs. average RT price).

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Average for round-trip flights in September 2025

Search Deals

Price to beat on a round-trip flight from Chicago (CHI) to Valparaiso Destin-Ft Walton Beach.

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Price to beat on a one-way flight from Chicago (CHI) to Valparaiso Destin-Ft Walton Beach.

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Find flight deals from Chicago to Valparaiso

Cheapest flights from Chicago to Valparaiso
Explore the most affordable flight options available from Chicago to Valparaiso. Find the lowest fares from popular airlines and budget airlines, with prices last updated on September 15, 2025.

Sun 11/912:07 pmMDW - VPS

Nonstop2h 05mAllegiant Air

Thu 11/139:00 amVPS - MDW

Nonstop2h 17mAllegiant Air

Deal found 9/14

$172

Sun 10/511:07 amMDW - VPS

Nonstop2h 05mAllegiant Air

Sun 10/128:00 amVPS - MDW

Nonstop2h 17mAllegiant Air

Deal found 9/15

$194

Thu 11/1312:07 pmMDW - VPS

Nonstop2h 05mAllegiant Air

Sun 11/169:00 amVPS - MDW

Nonstop2h 17mAllegiant Air

Deal found 9/15

$200

Sun 11/912:07 pmMDW - VPS

Nonstop2h 05mMultiple Airlines

Thu 11/136:35 amVPS - MDW

1 stop17h 20mMultiple Airlines

Deal found 9/14

$215

Thu 10/2311:07 amMDW - VPS

Nonstop2h 05mAllegiant Air

Sun 10/268:00 amVPS - MDW

Nonstop2h 17mAllegiant Air

Deal found 9/15

$221

Sun 11/912:07 pmMDW - VPS

Nonstop2h 05mAllegiant Air

Sun 11/169:00 amVPS - MDW

Nonstop2h 17mAllegiant Air

Deal found 9/14

$230

Sun 11/912:07 pmMDW - VPS

Nonstop2h 05mMultiple Airlines

Sun 11/163:02 pmVPS - MDW

2 stops44h 36mMultiple Airlines

Deal found 9/14

$271

Thu 10/236:20 amMDW - VPS

2 stops13h 22mMultiple Airlines

Sun 10/268:00 amVPS - MDW

Nonstop2h 17mMultiple Airlines

Deal found 9/15

$287

Sat 11/156:15 amMDW - VPS

2 stops12h 48mMultiple Airlines

Sun 11/169:00 amVPS - MDW

Nonstop2h 17mMultiple Airlines

Deal found 9/14

$291

Thu 12/1811:45 amORD - VPS

1 stop5h 44mSun Country Air

Mon 12/2211:26 amVPS - ORD

1 stop23h 00mSun Country Air

Deal found 9/13

$298

Wed 11/127:05 pmORD - VPS

1 stop17h 45mMultiple Airlines

Mon 11/174:16 pmVPS - ORD

2 stops31h 56mMultiple Airlines

Deal found 9/14

$299

Sun 9/286:10 amORD - VPS

1 stop13h 46mMultiple Airlines

Wed 10/11:07 pmVPS - ORD

2 stops51h 11mMultiple Airlines

Deal found 9/13

$306

Best flights from Chicago to Valparaiso
Discover carefully curated flight deals from Chicago to Valparaiso that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated September 15, 2025.

Sun 11/912:07 pmMDW - VPS

Nonstop2h 05mMultiple Airlines

Thu 11/136:35 amVPS - MDW

2 stops12h 04mMultiple Airlines

Deal found 9/14

$246

Thu 12/1811:45 amORD - VPS

1 stop5h 44mSun Country Air

Mon 12/2211:26 amVPS - ORD

1 stop23h 00mSun Country Air

Deal found 9/13

$298

Tue 12/25:00 amMDW - VPS

1 stop8h 15mSouthwest

Wed 12/32:00 pmVPS - MDW

1 stop5h 25mSouthwest

Deal found 9/15

$315

Sat 10/1810:30 amORD - VPS

2 stops11h 28mDelta

Wed 10/226:00 amVPS - ORD

2 stops10h 11mDelta

Deal found 9/13

$316

Fri 11/712:14 pmMDW - VPS

3 stops30h 49mMultiple Airlines

Sun 11/99:00 amVPS - MDW

Nonstop2h 17mMultiple Airlines

Deal found 9/15

$319

Tue 10/73:00 pmMDW - VPS

2 stops6h 10mSouthwest

Tue 10/147:15 amVPS - MDW

1 stop6h 10mSouthwest

Deal found 9/14

$321

Sat 10/1810:30 amORD - VPS

2 stops11h 28mDelta

Fri 10/247:00 amVPS - ORD

2 stops11h 14mDelta

Deal found 9/13

$353

Wed 11/125:00 amMDW - VPS

1 stop8h 15mSouthwest

Sat 11/1511:00 amVPS - MDW

1 stop8h 05mSouthwest

Deal found 9/14

$332

Thu 11/135:11 amORD - VPS

2 stops14h 19mMultiple Airlines

Sun 11/166:35 amVPS - ORD

1 stop24h 38mMultiple Airlines

Deal found 9/15

$363

Wed 12/39:34 amMDW - VPS

2 stops12h 07mDelta

Sat 12/136:00 amVPS - MDW

2 stops12h 18mDelta

Deal found 9/15

$365

Thu 12/115:35 amMDW - VPS

1 stop4h 45mSouthwest

Wed 12/1711:20 amVPS - MDW

1 stop4h 40mSouthwest

Deal found 9/14

$332

Sat 10/1810:30 amORD - VPS

2 stops11h 28mDelta

Mon 10/204:56 pmVPS - ORD

1 stop7h 02mDelta

Deal found 9/13

$380

Last-minute flights from Chicago to Valparaiso
Discover last-minute flight deals from Chicago to Valparaiso. Data last updated September 15, 2025 and is based on user searches.

Sun 9/286:10 amORD - VPS

1 stop13h 46mMultiple Airlines

Wed 10/11:07 pmVPS - ORD

2 stops51h 11mMultiple Airlines

Deal found 9/13

$306

Sun 10/511:07 amMDW - VPS

Nonstop2h 05mAllegiant Air

Sun 10/128:00 amVPS - MDW

Nonstop2h 17mAllegiant Air

Deal found 9/15

$194

Mon 10/612:08 pmMDW - VPS

1 stop8h 22mMultiple Airlines

Tue 10/146:30 amVPS - MDW

1 stop16h 55mMultiple Airlines

Deal found 9/14

$311

Tue 10/73:10 pmORD - VPS

1 stop6h 00mSouthwest

Tue 10/142:00 pmVPS - ORD

1 stop7h 30mSouthwest

Deal found 9/14

$315

Tue 10/78:40 amMDW - VPS

1 stop6h 55mSouthwest

Tue 10/142:00 pmVPS - MDW

1 stop5h 05mSouthwest

Deal found 9/14

$315

Fri 10/107:43 pmORD - VPS

2 stops17h 05mMultiple Airlines

Sun 10/122:02 pmVPS - ORD

1 stop8h 15mMultiple Airlines

Deal found 9/13

$357

Mon 10/136:00 amMDW - VPS

1 stop3h 40mSouthwest

Mon 10/206:30 pmVPS - MDW

1 stop6h 15mSouthwest

Deal found 9/15

$349

Sat 10/1810:30 amORD - VPS

2 stops11h 28mDelta

Wed 10/226:00 amVPS - ORD

2 stops10h 11mDelta

Deal found 9/13

$316

Sat 10/1810:30 amORD - VPS

2 stops11h 28mDelta

Fri 10/247:00 amVPS - ORD

2 stops11h 14mDelta

Deal found 9/13

$353

Sat 10/1810:30 amORD - VPS

2 stops11h 28mDelta

Mon 10/204:56 pmVPS - ORD

1 stop7h 02mDelta

Deal found 9/13

$380

Thu 10/2311:07 amMDW - VPS

Nonstop2h 05mAllegiant Air

Sun 10/268:00 amVPS - MDW

Nonstop2h 17mAllegiant Air

Deal found 9/15

$221

Thu 10/236:20 amMDW - VPS

2 stops13h 22mMultiple Airlines

Sun 10/268:00 amVPS - MDW

Nonstop2h 17mMultiple Airlines

Deal found 9/15

$287

One-way flights from Chicago to Valparaiso
Search for one-way flight options from Chicago to Valparaiso. Find affordable one-way fares based on user searches. Data last updated September 15, 2025.

Sun 11/1612:07 pmMDW - VPS

Nonstop2h 05mAllegiant Air

Deal found 9/14

$54

Thu 11/612:07 pmMDW - VPS

Nonstop2h 05mAllegiant Air

Deal found 9/14

$70

Mon 12/19:24 amMDW - VPS

Nonstop2h 13mAllegiant Air

Deal found 9/14

$74

Thu 10/3012:07 pmMDW - VPS

Nonstop2h 05mAllegiant Air

Deal found 9/14

$76

Sun 11/912:07 pmMDW - VPS

Nonstop2h 05mAllegiant Air

Deal found 9/14

$83

Sun 10/1911:07 amMDW - VPS

Nonstop2h 05mAllegiant Air

Deal found 9/13

$90

Sun 3/13:40 pmMDW - VPS

Nonstop2h 06mAllegiant Air

Deal found 9/14

$93

Sun 2/223:40 pmMDW - VPS

Nonstop2h 06mAllegiant Air

Deal found 9/15

$97

Thu 12/186:54 pmMDW - VPS

Nonstop2h 13mAllegiant Air

Deal found 9/14

$98

Sun 11/238:33 pmMDW - VPS

Nonstop2h 13mAllegiant Air

Deal found 9/14

$106

Thu 12/188:08 pmORD - VPS

1 stop14h 21mSun Country Air

Deal found 9/15

$129

Thu 11/279:20 amORD - VPS

1 stop23h 48mSun Country Air

Deal found 9/14

$135

Cheapflights Fare Finder

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

Fly from

Fly to

Route

Depart

Return

Price

ChicagoValparaiso

MDW - VPS

MDWVPS

Chicago Midway

Sun 11/9

12:07 pm-2:12 pm

Nonstop2h 05m

Valparaiso Destin-Ft Walton Beach

Thu 11/13

6:35 am-6:39 pm

2 stops12h 04m

$246

ChicagoValparaiso

ORD - VPS

ORDVPS

Chicago O'Hare Intl

Thu 12/18

11:45 am-5:29 pm

1 stop5h 44m

Valparaiso Destin-Ft Walton Beach

Mon 12/22

11:26 am-10:26 am

1 stop23h 00m

$298

ChicagoValparaiso

MDW - VPS

MDWVPS

Chicago Midway

Tue 12/2

5:00 am-1:15 pm

1 stop8h 15m

Valparaiso Destin-Ft Walton Beach

Wed 12/3

2:00 pm-7:25 pm

1 stop5h 25m

$315

ChicagoValparaiso

ORD - VPS

ORDVPS

Chicago O'Hare Intl

Sat 10/18

10:30 am-9:58 pm

2 stops11h 28m

Valparaiso Destin-Ft Walton Beach

Wed 10/22

6:00 am-4:11 pm

2 stops10h 11m

$316

ChicagoValparaiso

MDW - VPS

MDWVPS

Chicago Midway

Fri 11/7

12:14 pm-7:03 pm

3 stops30h 49m

Valparaiso Destin-Ft Walton Beach

Sun 11/9

9:00 am-11:17 am

Nonstop2h 17m

$319

ChicagoValparaiso

MDW - VPS

MDWVPS

Chicago Midway

Tue 10/7

3:00 pm-9:10 pm

2 stops6h 10m

Valparaiso Destin-Ft Walton Beach

Tue 10/14

7:15 am-1:25 pm

1 stop6h 10m

$321

ChicagoValparaiso

MDW - VPS

MDWVPS

Chicago Midway

Wed 11/12

5:00 am-1:15 pm

1 stop8h 15m

Valparaiso Destin-Ft Walton Beach

Sat 11/15

11:00 am-7:05 pm

1 stop8h 05m

$332

ChicagoValparaiso

MDW - VPS

MDWVPS

Chicago Midway

Thu 12/11

5:35 am-10:20 am

1 stop4h 45m

Valparaiso Destin-Ft Walton Beach

Wed 12/17

11:20 am-4:00 pm

1 stop4h 40m

$332

ChicagoValparaiso

MDW - VPS

MDWVPS

Chicago Midway

Mon 10/13

6:00 am-9:40 am

1 stop3h 40m

Valparaiso Destin-Ft Walton Beach

Mon 10/20

6:30 pm-12:45 am

1 stop6h 15m

$349

ChicagoValparaiso

ORD - VPS

ORDVPS

Chicago O'Hare Intl

Sat 10/18

10:30 am-9:58 pm

2 stops11h 28m

Valparaiso Destin-Ft Walton Beach

Fri 10/24

7:00 am-6:14 pm

2 stops11h 14m

$353

Flights are sorted by cheapest round-trip flights first.

Deals found on 9/15

Showing 1-10 of 38 results

Best time to book a flight from Chicago to Valparaiso

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

How far ahead should I book a flight from Chicago to Valparaiso, Florida?

Booking 17 days in advance of your planned departure date is, on average, the best time to get cheap flights from Chicago to Valparaiso, Florida. The general trend is that the closer you book to the departure date, the more expensive your flight will be.

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

Currently, September is the cheapest month in which you can book a flight from Chicago to Valparaiso, Florida (average of $274). Flying from Chicago to Valparaiso, Florida in March is currently the most expensive (average of $386). 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 CHI to VPS?

A simple way to save on the total cost of your ticket is to fly from Chicago to Valparaiso, Florida in the afternoon. If you’re flexible enough to do this you can expect to save up to 72% on your trip compared to booking a flight in the morning.

Reviews of airlines servicing Valparaiso

Get a feel of what it's like to fly with Southwest, Delta, and American Airlines from Chicago to Valparaiso by reading reviews from past customers. Users have also rated airlines in terms of entertainment options, comfort, food, crew/service, and boarding process.

Southwest

8.0

Very good

4,242 reviews

Reviews

1 / 20

10.0

Excellent

Sarah,Aug 2024

MDW - AUS

My first time, surprisingly good! It was a good ride overall. Coming from Singapore, this budget flight is better than the budget airline for our national carrier Singapore Airlines.

Southwest

8.0

Very good

4,242 reviews

Southwest

8.0

Very good

4,242 reviews

Reviews

1 / 20

10.0

Excellent

Sarah,Aug 2024

MDW - AUS

My first time, surprisingly good! It was a good ride overall. Coming from Singapore, this budget flight is better than the budget airline for our national carrier Singapore Airlines.

Delta

8.0

Very good

7,954 reviews

Southwest

8.0

Very good

4,242 reviews

Reviews

1 / 20

10.0

Excellent

Sarah,Aug 2024

MDW - AUS

My first time, surprisingly good! It was a good ride overall. Coming from Singapore, this budget flight is better than the budget airline for our national carrier Singapore Airlines.

American Airlines

7.2

Good

10,000 reviews

Southwest

8.0

Very good

4,242 reviews

Reviews

1 / 20

10.0

Excellent

Sarah,Aug 2024

MDW - AUS

My first time, surprisingly good! It was a good ride overall. Coming from Singapore, this budget flight is better than the budget airline for our national carrier Singapore Airlines.

Allegiant Air

7.2

Good

699 reviews

Southwest

8.0

Very good

4,242 reviews

Reviews

1 / 20

10.0

Excellent

Sarah,Aug 2024

MDW - AUS

My first time, surprisingly good! It was a good ride overall. Coming from Singapore, this budget flight is better than the budget airline for our national carrier Singapore Airlines.

Related info for your journey

What airport do you fly into for flights to Valparaiso from Chicago?
Most people fly into Valparaiso Destin-Ft Walton Beach (VPS) if they book a flight to Valparaiso from Chicago. On average, Destin-Ft Walton Beach has 0 inbound flights from Chicago per day from 4 airlines. Valparaiso Destin-Ft Walton Beach is conveniently located just 3.1 mi from Valparaiso’s city center.
How long is the flight from Chicago to Valparaiso, Florida?
Airlines like Sun Country Air, Southwest, and Delta fly from Chicago to Valparaiso, Florida in about 5h 44m. The time it takes to get you to your destination can typically vary by up to 5h 44m. Chicago and Valparaiso, Florida are separated by a distance of 797 mi. When browsing for deals, the options you’ll see will be for both nonstop flights and flights with stops.
What are the cheapest airlines flying from Chicago to Valparaiso, Florida round-trip?
Currently priced at $82, Allegiant Air will fly you from Chicago to Valparaiso, Florida and back. In addition to Allegiant Air, many other airlines offer competitively priced options for your trip. Search Cheapflights for deals from Delta and Southwest - these airlines can fly you to your destination from $207 and $212, respectively. Allegiant Air is 74% cheaper than the average price of flights available within the next 90 days to this destination.
What are the cheapest flights from Chicago to Valparaiso, Florida?
The cheapest flight price from Chicago to Valparaiso, Florida is $124. On average you can expect to pay $471. The most popular route, (Chicago O'Hare Intl - Valparaiso Destin-Ft Walton Beach), can usually be booked for $298.
Can I find deals for flights from Chicago to Valparaiso that include hotel bookings?
Yes. In addition to deals on Chicago to Valparaiso flights, Cheapflights offers vacation packages that include both flights and hotel.
How can I find direct flights from Chicago to Valparaiso?
After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Chicago to Valparaiso.
Can I find deals for business class flights from Chicago to Valparaiso?
Yes. Cheapflights offers flight deals from Chicago to Valparaiso 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 Chicago to Valparaiso, Florida?
Currently, September is the cheapest month in which you can book a flight from Chicago to Valparaiso, Florida (average of $274). Flying from Chicago to Valparaiso, Florida in March is currently the most expensive (average of $386). 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.

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Top 4 airlines flying from Chicago to Valparaiso

Airline	Cheapest	Average	Flexibility	On-time
Allegiant Air	Cheapest$82	Average$138	FlexibilityNo cancel fee	On-time88%
Delta	Cheapest$207	Average$495	FlexibilityNo cancel fee	On-timeN/A
Southwest	Cheapest$212	Average$388	FlexibilityNo cancel fee	On-time63%
American Airlines	Cheapest$236	Average$416	FlexibilityNo cancel fee	On-time71%

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$54+ Cheap flights from Chicago (CHI) to Valparaiso, FL (VPS)

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 11/16. Fares are subject to change and may not be available on all flights or dates of travel.

Find cheap flights from Chicago to Valparaiso with Cheapflights

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3. Compare prices and book

Cheapflights Tip: The best prices from Chicago to Valparaiso Destin-Ft Walton Beach are usually found in January or October, booked 17 days in advance, depart on a Wednesday or Monday and return on a Thursday

Cheap flight deals from Chicago to Valparaiso

Round-trip from

One-way from

Popular in

Cheapest in

Average price

Good round-trip deal

Good one-way deal

Find flight deals from Chicago to Valparaiso

Cheapest flights from Chicago to ValparaisoExplore the most affordable flight options available from Chicago to Valparaiso. Find the lowest fares from popular airlines and budget airlines, with prices last updated on September 15, 2025.

Explore the most affordable flight options available from Chicago to Valparaiso. Find the lowest fares from popular airlines and budget airlines, with prices last updated on September 15, 2025.

Cheapflights Fare Finder

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

Best time to book a flight from Chicago to Valparaiso

Have a flexible travel schedule? Discover the best time to fly to Valparaiso from Chicago with our price prediction graph.

Cheapflights Insights

Everything you need to know about your flight from Chicago to Valparaiso

How far ahead should I book a flight from Chicago to Valparaiso, Florida?

Use this chart to determine the optimal time to book a round-trip flight from Chicago to Valparaiso. Price data was last updated on September 12, 2025.

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

What is the cheapest time of day to fly from CHI to VPS?

Find hourly flight availability from Chicago to Valparaiso. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated September 15, 2025.

Reviews of airlines servicing Valparaiso

Get a feel of what it's like to fly with Southwest, Delta, and American Airlines from Chicago to Valparaiso by reading reviews from past customers. Users have also rated airlines in terms of entertainment options, comfort, food, crew/service, and boarding process.

Related info for your journey

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

How long is the flight from Chicago to Valparaiso, Florida?

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

What are the cheapest flights from Chicago to Valparaiso, Florida?

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

How can I find direct flights from Chicago to Valparaiso?

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

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Top 4 airlines flying from Chicago to Valparaiso

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Cheapest flights from Chicago to Valparaiso
Explore the most affordable flight options available from Chicago to Valparaiso. Find the lowest fares from popular airlines and budget airlines, with prices last updated on September 15, 2025.