Latest deals
Insights
When to book
FAQs
Reviews
Price Alerts

Cheap flights from Chicago to Valparaiso from $83

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 12/1. 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
6:54 pm - 9:07 pmMDW-VPS
2h 13mnonstop
Allegiant Air Logo
1:01 pm - 3:20 pmVPS-MDW
2h 19mnonstop
$153Allegiant Air
Find Deal
Thu, Dec 18 - Tue, Dec 30
Allegiant Air Logo
8:43 pm - 10:51 pmMDW-VPS
2h 08mnonstop
Allegiant Air Logo
5:37 pm - 7:53 pmVPS-MDW
2h 16mnonstop
$211Allegiant Air
Find Deal
Thu, Mar 12 - Sun, Mar 15
Multiple Airlines Logo
6:12 am - 10:15 pmMDW-VPS
16h 03m2 stops
Multiple Airlines Logo
1:01 pm - 3:20 pmVPS-MDW
2h 19mnonstop
$269Multiple Airlines
Find Deal
Thu, Dec 18 - Tue, Dec 30
Allegiant Air Logo
5:47 pm - 7:56 pmMDW-VPS
2h 09mnonstop
Allegiant Air Logo
2:40 pm - 4:57 pmVPS-MDW
2h 17mnonstop
$288Allegiant Air
Find Deal
Thu, Apr 9 - Sun, Apr 12
Multiple Airlines Logo
7:44 am - 2:55 pmMDW-VPS
7h 11m1 stop
Multiple Airlines Logo
1:01 pm - 3:20 pmVPS-MDW
2h 19mnonstop
$289Multiple Airlines
Find Deal
Thu, Dec 18 - Tue, Dec 30
American Airlines Logo
9:29 am - 12:00 pmORD-VPS
2h 31mnonstop
American Airlines Logo
1:00 pm - 3:40 pmVPS-ORD
2h 40mnonstop
$296American Airlines
Find Deal
Sat, Jan 10 - Tue, Jan 13
American Airlines Logo
9:29 am - 12:00 pmORD-VPS
2h 31mnonstop
American Airlines Logo
10:47 am - 4:50 pmVPS-ORD
6h 03m1 stop
$306American Airlines
Find Deal
Sat, Jan 10 - Tue, Jan 13
Southwest Logo
6:00 am - 10:05 amMDW-VPS
4h 05m1 stop
Southwest Logo
12:15 pm - 6:05 pmVPS-MDW
5h 50m1 stop
$315Southwest
Find Deal
Sat, Jan 10 - Tue, Jan 13
Delta Logo
5:59 pm - 11:02 pmORD-VPS
5h 03m1 stop
Delta Logo
7:05 am - 1:18 pmVPS-ORD
6h 13m1 stop
$315Delta
Find Deal
Sat, Mar 14 - Sat, Mar 21
Southwest Logo
6:00 am - 10:05 amMDW-VPS
4h 05m1 stop
Southwest Logo
12:15 pm - 8:40 pmVPS-MDW
8h 25m2 stops
$321Southwest
Find Deal
Sat, Jan 10 - Tue, Jan 13

Southwest flights from Chicago to Valparaiso, Florida

Our best Southwest deals on Chicago to Valparaiso, Florida flight tickets
Southwest
Jan 10
MDW6:00 amChicago Midway
4h 05m
1 stop
VPS10:05 amValparaiso Destin-Ft Walton Beach
Jan 13
VPS12:15 pmValparaiso Destin-Ft Walton Beach
5h 50m
1 stop
MDW6:05 pmChicago Midway
$315
Find similar
Southwest
Jan 10
MDW6:00 amChicago Midway
4h 05m
1 stop
VPS10:05 amValparaiso Destin-Ft Walton Beach
Jan 13
VPS12:15 pmValparaiso Destin-Ft Walton Beach
8h 25m
2 stops
MDW8:40 pmChicago Midway
$321
Find similar
Southwest
Jan 10
MDW9:05 amChicago Midway
8h 15m
2 stops
VPS5:20 pmValparaiso Destin-Ft Walton Beach
Jan 13
VPS2:00 pmValparaiso Destin-Ft Walton Beach
8h 05m
2 stops
MDW10:05 pmChicago Midway
$326
Find similar

Sun Country Air flights from Chicago to Valparaiso, Florida

Our best Sun Country Air deals on Chicago to Valparaiso, Florida flight tickets
Sun Country Air
Dec 18
ORD11:45 amChicago O'Hare Intl
5h 44m
1 stop
VPS5:29 pmValparaiso Destin-Ft Walton Beach
Dec 21
VPS6:23 pmValparaiso Destin-Ft Walton Beach
15h 27m
1 stop
ORD9:50 amChicago O'Hare Intl
$294
Find similar
Sun Country Air
Dec 18
ORD11:45 amChicago O'Hare Intl
5h 44m
1 stop
VPS5:29 pmValparaiso Destin-Ft Walton Beach
Dec 25
VPS6:11 pmValparaiso Destin-Ft Walton Beach
15h 03m
1 stop
ORD9:14 amChicago O'Hare Intl
$304
Find similar
Sun Country Air
Dec 18
ORD8:08 pmChicago O'Hare Intl
14h 21m
1 stop
VPS10:29 amValparaiso Destin-Ft Walton Beach
Dec 22
VPS11:26 amValparaiso Destin-Ft Walton Beach
23h 00m
1 stop
ORD10:26 amChicago O'Hare Intl
$314
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 November 26, 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

Thu 12/18

6:54 pm-9:07 pm

Nonstop2h 13m

Valparaiso Destin-Ft Walton Beach

Tue 12/30

1:01 pm-3:20 pm

Nonstop2h 19m

$153

ChicagoValparaiso

MDW - VPS

MDWVPS

Chicago Midway

Thu 3/12

8:43 pm-10:51 pm

Nonstop2h 08m

Valparaiso Destin-Ft Walton Beach

Sun 3/15

5:37 pm-7:53 pm

Nonstop2h 16m

$211

ChicagoValparaiso

MDW - VPS

MDWVPS

Chicago Midway

Thu 12/18

6:12 am-10:15 pm

2 stops16h 03m

Valparaiso Destin-Ft Walton Beach

Tue 12/30

1:01 pm-3:20 pm

Nonstop2h 19m

$269

ChicagoValparaiso

MDW - VPS

MDWVPS

Chicago Midway

Thu 4/9

5:47 pm-7:56 pm

Nonstop2h 09m

Valparaiso Destin-Ft Walton Beach

Sun 4/12

2:40 pm-4:57 pm

Nonstop2h 17m

$288

ChicagoValparaiso

MDW - VPS

MDWVPS

Chicago Midway

Thu 12/18

7:44 am-2:55 pm

1 stop7h 11m

Valparaiso Destin-Ft Walton Beach

Tue 12/30

1:01 pm-3:20 pm

Nonstop2h 19m

$289

ChicagoValparaiso

ORD - VPS

ORDVPS

Chicago O'Hare Intl

Sat 1/10

9:29 am-12:00 pm

Nonstop2h 31m

Valparaiso Destin-Ft Walton Beach

Tue 1/13

1:00 pm-3:40 pm

Nonstop2h 40m

$296

ChicagoValparaiso

ORD - VPS

ORDVPS

Chicago O'Hare Intl

Sat 1/10

9:29 am-12:00 pm

Nonstop2h 31m

Valparaiso Destin-Ft Walton Beach

Tue 1/13

10:47 am-4:50 pm

1 stop6h 03m

$306

ChicagoValparaiso

MDW - VPS

MDWVPS

Chicago Midway

Sat 1/10

6:00 am-10:05 am

1 stop4h 05m

Valparaiso Destin-Ft Walton Beach

Tue 1/13

12:15 pm-6:05 pm

1 stop5h 50m

$315

ChicagoValparaiso

ORD - VPS

ORDVPS

Chicago O'Hare Intl

Sat 3/14

5:59 pm-11:02 pm

1 stop5h 03m

Valparaiso Destin-Ft Walton Beach

Sat 3/21

7:05 am-1:18 pm

1 stop6h 13m

$315

ChicagoValparaiso

MDW - VPS

MDWVPS

Chicago Midway

Sat 1/10

6:00 am-10:05 am

1 stop4h 05m

Valparaiso Destin-Ft Walton Beach

Tue 1/13

12:15 pm-8:40 pm

2 stops8h 25m

$321

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 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 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 $199.

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 $201. 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 $121. 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 $435 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 November 2025, prices for Chicago to Valparaiso, Florida flights are approximately 31% 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

$255

Fastest flight time

2h 08m

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 $255. The best round-trip flight deal from Chicago to Valparaiso, Florida found on momondo in the last 72 hours is $210.
The fastest flight from Chicago to Valparaiso, Florida takes 2h 08m
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 08m.

  • 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 $85Free CancellationRating
7.2
700 reviews
Search Allegiant Air flights
DeltaPriceFrom $207Free CancellationRating
7.9
7,998 reviews
Search Delta flights
SouthwestPriceFrom $212Free CancellationRating
8.0
4,253 reviews
Search Southwest flights
American AirlinesPriceFrom $238Free CancellationRating
7.2
11,038 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 $238. Generally, American Airlines has 3 flights on this route every week with an average price of $420. American Airlines 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
Fri 12/26
Fri 1/2
By creating a price alert you accept our terms of use and privacy policy.

Find better results for your trip to the United States