Latest deals
Insights
When to book
FAQs
Reviews
Price Alerts

Cheap flights from Chicago to Valparaiso from $50

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 11/16. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.
1 adult
0 bags

Discover deals from 900+ travel sites with momondo.

Save money when you book flights with momondo

Big names and deals

Big names and deals

Search 100s of travel sites to compare prices.

Filter for what you want

Filter for what you want

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

Trusted and free

Trusted and free

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

Price Alerts

Price Alerts

Not ready to book? to track prices.
Search flight deals

Find the cheapest flights from Chicago to Valparaiso

Cheap round-trip flights

Enter your travel dates to find the best prices.
Allegiant Air Logo
11:07 am - 1:12 pmMDW-VPS
2h 05mnonstop
Allegiant Air Logo
9:00 am - 11:17 amVPS-MDW
2h 17mnonstop
$138Allegiant Air
Find Deal
Sun, Oct 26 - Thu, Oct 30
Allegiant Air Logo
11:07 am - 1:12 pmMDW-VPS
2h 05mnonstop
Allegiant Air Logo
8:00 am - 10:17 amVPS-MDW
2h 17mnonstop
$174Allegiant Air
Find Deal
Sun, Oct 19 - Thu, Oct 23
Multiple Airlines Logo
11:07 am - 1:12 pmMDW-VPS
2h 05mnonstop
Multiple Airlines Logo
6:30 am - 11:25 pmVPS-MDW
16h 55m1 stop
$198Multiple Airlines
Find Deal
Sun, Oct 26 - Thu, Oct 30
Multiple Airlines Logo
5:20 pm - 4:50 pmMDW-VPS
23h 30m2 stops
Multiple Airlines Logo
9:00 am - 11:17 amVPS-MDW
2h 17mnonstop
$215Multiple Airlines
Find Deal
Thu, Oct 23 - Thu, Oct 30
Delta Logo
6:00 am - 12:12 pmORD-VPS
6h 12m1 stop
Delta Logo
1:52 pm - 9:34 pmVPS-ORD
7h 42m1 stop
$317Delta
Find Deal
Fri, Dec 19 - Thu, Dec 25
Delta Logo
6:00 am - 12:12 pmORD-VPS
6h 12m1 stop
Delta Logo
7:24 pm - 9:01 amVPS-ORD
13h 37m2 stops
$337Delta
Find Deal
Thu, Dec 18 - Mon, Dec 29
Southwest Logo
5:35 am - 10:20 amMDW-VPS
4h 45m1 stop
Southwest Logo
7:00 am - 11:20 amVPS-MDW
4h 20m1 stop
$349Southwest
Find Deal
Thu, Nov 20 - Thu, Nov 27
Southwest Logo
1:45 pm - 9:10 pmORD-VPS
7h 25m1 stop
Southwest Logo
7:00 am - 1:00 pmVPS-ORD
6h 00m1 stop
$355Southwest
Find Deal
Thu, Nov 20 - Thu, Nov 27
American Airlines Logo
8:29 am - 10:57 amORD-VPS
2h 28mnonstop
American Airlines Logo
6:34 am - 10:20 pmVPS-ORD
15h 46m1 stop
$424American Airlines
Find Deal
Sun, Nov 16 - Wed, Nov 19
American Airlines Logo
8:33 am - 10:59 amORD-VPS
2h 26mnonstop
American Airlines Logo
11:29 am - 2:12 pmVPS-ORD
2h 43mnonstop
$426American Airlines
Find Deal
Fri, Dec 12 - Mon, Dec 15

American Airlines flights from Chicago to Valparaiso, Florida

Our best American Airlines deals on Chicago to Valparaiso, Florida flight tickets
American Airlines
Nov 16
ORD8:29 amChicago O'Hare Intl
2h 28m
VPS10:57 amValparaiso Destin-Ft Walton Beach
Nov 19
VPS6:34 amValparaiso Destin-Ft Walton Beach
15h 46m
1 stop
ORD10:20 pmChicago O'Hare Intl
$424
Find similar
American Airlines
Dec 12
ORD8:33 amChicago O'Hare Intl
2h 26m
VPS10:59 amValparaiso Destin-Ft Walton Beach
Dec 15
VPS11:29 amValparaiso Destin-Ft Walton Beach
2h 43m
ORD2:12 pmChicago O'Hare Intl
$426
Find similar
American Airlines
Oct 18
ORD8:49 amChicago O'Hare Intl
2h 35m
VPS11:24 amValparaiso Destin-Ft Walton Beach
Oct 25
VPS12:02 pmValparaiso Destin-Ft Walton Beach
2h 44m
ORD2:46 pmChicago O'Hare Intl
$659
Find similar

Southwest flights from Chicago to Valparaiso, Florida

Our best Southwest deals on Chicago to Valparaiso, Florida flight tickets
Southwest
Nov 20
MDW5:35 amChicago Midway
4h 45m
1 stop
VPS10:20 amValparaiso Destin-Ft Walton Beach
Nov 27
VPS7:00 amValparaiso Destin-Ft Walton Beach
4h 20m
1 stop
MDW11:20 amChicago Midway
$349
Find similar
Southwest
Nov 20
ORD1:45 pmChicago O'Hare Intl
7h 25m
1 stop
VPS9:10 pmValparaiso Destin-Ft Walton Beach
Nov 27
VPS7:00 amValparaiso Destin-Ft Walton Beach
6h 00m
1 stop
ORD1:00 pmChicago O'Hare Intl
$355
Find similar
Southwest
Dec 3
MDW5:35 amChicago Midway
4h 45m
1 stop
VPS10:20 amValparaiso Destin-Ft Walton Beach
Dec 7
VPS6:05 pmValparaiso Destin-Ft Walton Beach
6h 05m
1 stop
MDW12:10 amChicago Midway
$402
Find similar

momondo Fare Finder

 
Customize your flight search to find flights from Chicago to Valparaiso, Florida 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, momondo users made 832,500 searches. Data last updated October 9, 2025.
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

Sun 10/26

11:07 am-1:12 pm

Nonstop2h 05m

Valparaiso Destin-Ft Walton Beach

Thu 10/30

9:00 am-11:17 am

Nonstop2h 17m

$138

ChicagoValparaiso

MDW - VPS

MDWVPS

Chicago Midway

Sun 10/19

11:07 am-1:12 pm

Nonstop2h 05m

Valparaiso Destin-Ft Walton Beach

Thu 10/23

8:00 am-10:17 am

Nonstop2h 17m

$174

ChicagoValparaiso

MDW - VPS

MDWVPS

Chicago Midway

Sun 10/26

11:07 am-1:12 pm

Nonstop2h 05m

Valparaiso Destin-Ft Walton Beach

Thu 10/30

6:30 am-11:25 pm

1 stop16h 55m

$198

ChicagoValparaiso

MDW - VPS

MDWVPS

Chicago Midway

Thu 10/23

5:20 pm-4:50 pm

2 stops23h 30m

Valparaiso Destin-Ft Walton Beach

Thu 10/30

9:00 am-11:17 am

Nonstop2h 17m

$215

ChicagoValparaiso

ORD - VPS

ORDVPS

Chicago O'Hare Intl

Fri 12/19

6:00 am-12:12 pm

1 stop6h 12m

Valparaiso Destin-Ft Walton Beach

Thu 12/25

1:52 pm-9:34 pm

1 stop7h 42m

$317

ChicagoValparaiso

ORD - VPS

ORDVPS

Chicago O'Hare Intl

Thu 12/18

6:00 am-12:12 pm

1 stop6h 12m

Valparaiso Destin-Ft Walton Beach

Mon 12/29

7:24 pm-9:01 am

2 stops13h 37m

$337

ChicagoValparaiso

MDW - VPS

MDWVPS

Chicago Midway

Thu 11/20

5:35 am-10:20 am

1 stop4h 45m

Valparaiso Destin-Ft Walton Beach

Thu 11/27

7:00 am-11:20 am

1 stop4h 20m

$349

ChicagoValparaiso

ORD - VPS

ORDVPS

Chicago O'Hare Intl

Thu 11/20

1:45 pm-9:10 pm

1 stop7h 25m

Valparaiso Destin-Ft Walton Beach

Thu 11/27

7:00 am-1:00 pm

1 stop6h 00m

$355

ChicagoValparaiso

ORD - VPS

ORDVPS

Chicago O'Hare Intl

Sun 11/16

8:29 am-10:57 am

Nonstop2h 28m

Valparaiso Destin-Ft Walton Beach

Wed 11/19

6:34 am-10:20 pm

1 stop15h 46m

$424

ChicagoValparaiso

ORD - VPS

ORDVPS

Chicago O'Hare Intl

Fri 12/12

8:33 am-10:59 am

Nonstop2h 26m

Valparaiso Destin-Ft Walton Beach

Mon 12/15

11:29 am-2:12 pm

Nonstop2h 43m

$426

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 20 resultsSorted by cheapest first
1
2

See travel insights to Valparaiso from

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

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

If you aren’t able to travel during the month of January, then book flights to Valparaiso, Florida from Chicago during October instead. Flights to Valparaiso, Florida in October, while not as cheap as those in January, still average around $202.

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 Wednesday when prices can be found for as low as $192. This is often the case because there is less demand to fly during this day of the week. On the other hand, Saturday 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 $112. In contrast, the most expensive time of day to depart to Valparaiso, Florida is in the morning when prices are around $388.

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 $432 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 $333 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?

As of October 2025, prices for Chicago to Valparaiso, Florida flights are approximately 27% cheaper when compared to flights at the same time last year.

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

$64

Fastest flight time

2h 05m

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 $64. The best round-trip flight deal from Chicago to Valparaiso, Florida found on momondo in the last 72 hours is $182.
The fastest flight from Chicago to Valparaiso, Florida takes 2h 05m
Direct flights go from Chicago to Valparaiso, Florida every day.
There is 1 airport near Valparaiso, Florida: 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 05m.

  • 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?

  • 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?

  • What is the most popular airline from Chicago to 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
Airline
Rating
Free Cancellation
Price
Allegiant AirPriceFrom $82Free CancellationRating
7.2
697 reviews
Search Allegiant Air flights
DeltaPriceFrom $207Free CancellationRating
7.9
7,969 reviews
Search Delta flights
SouthwestPriceFrom $212Free CancellationRating
8.0
4,237 reviews
Search Southwest flights
American AirlinesPriceFrom $237Free CancellationRating
7.2
11,043 reviews
Search American Airlines flights

  • Allegiant Air Flights From Chicago to Valparaiso, Florida

    The lowest priced Allegiant Air flight from Chicago to Valparaiso, Florida from the last 72 hours was $82. Generally, Allegiant Air has 1 flight on this route every week with an average price of $138. Allegiant Air is rated 7.2/10 by our users.

Traveling to a place near Valparaiso?

Book flights to Valparaiso if you plan to visit one of these locations
Fort Walton Beach
Crestview
Niceville
DeFuniak Springs
Andalusia

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
Sat 11/8
Sat 11/15
By creating a price alert you accept our terms of use and privacy policy.

Find better results for your trip to the United States