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Cheap flights from Chicago to Valparaiso from $106

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 2/12. 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

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Find the cheapest flights from Chicago to Valparaiso

Cheap round-trip flights

Enter your travel dates to find the best prices.
Allegiant Air Logo
3:40 pm - 5:46 pm
MDW
-
VPS
2h 06mnonstop
Allegiant Air Logo
12:31 pm - 2:50 pm
VPS
-
MDW
2h 19mnonstop
$111Allegiant Air
dom., feb. 22 - jue., feb. 26
Allegiant Air Logo
4:10 pm - 6:16 pm
MDW
-
VPS
2h 06mnonstop
Allegiant Air Logo
12:31 pm - 2:50 pm
VPS
-
MDW
2h 19mnonstop
$152Allegiant Air
jue., feb. 19 - dom., feb. 22
Multiple Airlines Logo
3:40 pm - 5:46 pm
MDW
-
VPS
2h 06mnonstop
Multiple Airlines Logo
8:40 pm - 3:19 pm
VPS
-
MDW
42h 39m
2 stops
$220Multiple Airlines
dom., feb. 22 - jue., feb. 26
Allegiant Air Logo
4:10 pm - 6:16 pm
MDW
-
VPS
2h 06mnonstop
Allegiant Air Logo
12:31 pm - 2:50 pm
VPS
-
MDW
2h 19mnonstop
$228Allegiant Air
jue., feb. 19 - jue., feb. 26
Multiple Airlines Logo
9:04 pm - 2:37 pm
MDW
-
VPS
17h 33m
3 stops
Multiple Airlines Logo
12:31 pm - 2:50 pm
VPS
-
MDW
2h 19mnonstop
$255Multiple Airlines
dom., feb. 22 - jue., feb. 26
Southwest Logo
4:35 pm - 9:05 pm
MDW
-
VPS
4h 30m
1 stop
Southwest Logo
5:15 pm - 11:05 pm
VPS
-
MDW
5h 50m
1 stop
$289Southwest
sáb., abr. 4 - mié., abr. 8
Southwest Logo
9:20 am - 9:05 pm
MDW
-
VPS
11h 45m
2 stops
Southwest Logo
10:25 am - 3:25 pm
VPS
-
MDW
5h 00m
1 stop
$294Southwest
sáb., abr. 4 - mié., abr. 8
American Airlines Logo
9:31 am - 12:00 pm
ORD
-
VPS
2h 29mnonstop
American Airlines Logo
1:00 pm - 3:44 pm
VPS
-
ORD
2h 44mnonstop
$296American Airlines
mié., feb. 18 - mié., feb. 25
American Airlines Logo
8:38 am - 11:07 am
ORD
-
VPS
2h 29mnonstop
American Airlines Logo
4:53 pm - 11:59 pm
VPS
-
ORD
7h 06m
1 stop
$306American Airlines
mié., may. 27 - sáb., may. 30
Delta Logo
6:00 am - 11:34 am
ORD
-
VPS
5h 34m
1 stop
Delta Logo
6:00 am - 12:09 pm
VPS
-
ORD
6h 09m
1 stop
$316Delta
mié., may. 27 - sáb., may. 30

Delta flights from Chicago to Valparaiso, Florida

Our best Delta deals on Chicago to Valparaiso, Florida flight tickets
Delta
Mar 25
MDW10:45 amChicago Midway
5h 23m
1 stop
VPS4:08 pmValparaiso Destin-Ft Walton Beach
Mar 31
VPS6:00 amValparaiso Destin-Ft Walton Beach
3h 56m
1 stop
MDW9:56 amChicago Midway
$316
Delta
Mar 19
ORD2:38 pmChicago O'Hare Intl
6h 14m
1 stop
VPS8:52 pmValparaiso Destin-Ft Walton Beach
Mar 24
VPS3:00 pmValparaiso Destin-Ft Walton Beach
6h 10m
1 stop
ORD9:10 pmChicago O'Hare Intl
$335
Delta
Mar 3
ORD9:52 amChicago O'Hare Intl
4h 10m
1 stop
VPS2:02 pmValparaiso Destin-Ft Walton Beach
Mar 10
VPS3:00 pmValparaiso Destin-Ft Walton Beach
6h 10m
1 stop
ORD9:10 pmChicago O'Hare Intl
$336

American Airlines flights from Chicago to Valparaiso, Florida

Our best American Airlines deals on Chicago to Valparaiso, Florida flight tickets
American Airlines
Feb 18
ORD9:31 amChicago O'Hare Intl
2h 29m
VPS12:00 pmValparaiso Destin-Ft Walton Beach
Feb 25
VPS1:00 pmValparaiso Destin-Ft Walton Beach
2h 44m
ORD3:44 pmChicago O'Hare Intl
$296
American Airlines
Feb 10
ORD9:17 amChicago O'Hare Intl
2h 31m
VPS11:48 amValparaiso Destin-Ft Walton Beach
Feb 17
VPS4:38 pmValparaiso Destin-Ft Walton Beach
7h 28m
1 stop
ORD12:06 amChicago O'Hare Intl
$306
American Airlines
Feb 18
ORD4:49 pmChicago O'Hare Intl
6h 29m
1 stop
VPS11:18 pmValparaiso Destin-Ft Walton Beach
Feb 23
VPS12:10 pmValparaiso Destin-Ft Walton Beach
2h 44m
ORD2:54 pmChicago O'Hare Intl
$325

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 enero 12, 2026.
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

dom. 2/22

3:40 pm-5:46 pm

Nonstop2h 06m

Valparaiso Destin-Ft Walton Beach

jue. 2/26

12:31 pm-2:50 pm

Nonstop2h 19m

$111

ChicagoValparaiso

MDW - VPS

MDWVPS

Chicago Midway

jue. 2/19

4:10 pm-6:16 pm

Nonstop2h 06m

Valparaiso Destin-Ft Walton Beach

dom. 2/22

12:31 pm-2:50 pm

Nonstop2h 19m

$152

ChicagoValparaiso

MDW - VPS

MDWVPS

Chicago Midway

dom. 2/22

3:40 pm-5:46 pm

Nonstop2h 06m

Valparaiso Destin-Ft Walton Beach

jue. 2/26

8:40 pm-3:19 pm

2 stops42h 39m

$220

ChicagoValparaiso

MDW - VPS

MDWVPS

Chicago Midway

jue. 2/19

4:10 pm-6:16 pm

Nonstop2h 06m

Valparaiso Destin-Ft Walton Beach

jue. 2/26

12:31 pm-2:50 pm

Nonstop2h 19m

$228

ChicagoValparaiso

MDW - VPS

MDWVPS

Chicago Midway

dom. 2/22

9:04 pm-2:37 pm

3 stops17h 33m

Valparaiso Destin-Ft Walton Beach

jue. 2/26

12:31 pm-2:50 pm

Nonstop2h 19m

$255

ChicagoValparaiso

MDW - VPS

MDWVPS

Chicago Midway

sáb. 4/4

4:35 pm-9:05 pm

1 stop4h 30m

Valparaiso Destin-Ft Walton Beach

mié. 4/8

5:15 pm-11:05 pm

1 stop5h 50m

$289

ChicagoValparaiso

MDW - VPS

MDWVPS

Chicago Midway

sáb. 4/4

9:20 am-9:05 pm

2 stops11h 45m

Valparaiso Destin-Ft Walton Beach

mié. 4/8

10:25 am-3:25 pm

1 stop5h 00m

$294

ChicagoValparaiso

ORD - VPS

ORDVPS

Chicago O'Hare Intl

mié. 2/18

9:31 am-12:00 pm

Nonstop2h 29m

Valparaiso Destin-Ft Walton Beach

mié. 2/25

1:00 pm-3:44 pm

Nonstop2h 44m

$296

ChicagoValparaiso

ORD - VPS

ORDVPS

Chicago O'Hare Intl

mié. 5/27

8:38 am-11:07 am

Nonstop2h 29m

Valparaiso Destin-Ft Walton Beach

sáb. 5/30

4:53 pm-11:59 pm

1 stop7h 06m

$306

ChicagoValparaiso

ORD - VPS

ORDVPS

Chicago O'Hare Intl

mié. 5/27

6:00 am-11:34 am

1 stop5h 34m

Valparaiso Destin-Ft Walton Beach

sáb. 5/30

6:00 am-12:09 pm

1 stop6h 09m

$316

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 20 resultsSorted by cheapest first
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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 October, then book flights to Valparaiso, Florida from Chicago during June instead. Flights to Valparaiso, Florida in June, 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 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, 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 $132. In contrast, the most expensive time of day to depart to Valparaiso, Florida is in the morning when prices are around $389.

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 $414 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 $330 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

$150

Fastest flight time

2h 06m

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 $150. The best round-trip flight deal from Chicago to Valparaiso, Florida found on momondo in the last 72 hours is $170.
The fastest flight from Chicago to Valparaiso, Florida takes 2h 06m
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 06m.

  • 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
702 reviews
Search Allegiant Air flights
DeltaPriceFrom $207Free CancellationRating
7.9
8,038 reviews
Search Delta flights
SouthwestPriceFrom $212Free CancellationRating
8.0
4,256 reviews
Search Southwest flights
American AirlinesPriceFrom $240Free CancellationRating
7.2
11,114 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 $240. Generally, American Airlines has 4 flights on this route every week with an average price of $411. 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.

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