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 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.
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Find the cheapest flights from Chicago to Valparaiso

Cheap round-trip flights

Allegiant Air Logo
4:27 pm - 6:38 pmMDW-VPS
2h 11mnonstop
Allegiant Air Logo
6:00 am - 8:22 amVPS-MDW
2h 22mnonstop
$91Allegiant Air
Find Deal
Wed, Jul 30 - Fri, Aug 1
Allegiant Air Logo
4:27 pm - 6:38 pmMDW-VPS
2h 11mnonstop
Allegiant Air Logo
1:15 pm - 3:37 pmVPS-MDW
2h 22mnonstop
$134Allegiant Air
Find Deal
Wed, Jul 30 - Wed, Aug 6
Southwest Logo
3:10 pm - 9:10 pmORD-VPS
6h 00m1 stop
Southwest Logo
7:15 am - 12:45 pmVPS-ORD
5h 30m1 stop
$235Southwest
Find Deal
Tue, Oct 14 - Tue, Oct 21
Southwest Logo
6:25 am - 11:55 amMDW-VPS
5h 30m1 stop
Southwest Logo
10:35 am - 4:25 pmVPS-MDW
5h 50m1 stop
$235Southwest
Find Deal
Tue, Aug 5 - Tue, Aug 12
 Logo
11:36 am - 12:48 pmORD-VPS
25h 12m2 stops
 Logo
6:30 am - 4:51 pmVPS-ORD
10h 21m1 stop
Wed, Sep 3 - Sun, Sep 14
 Logo
8:12 pm - 9:40 pmORD-VPS
25h 28m3 stops
 Logo
4:07 pm - 7:07 pmVPS-ORD
27h 00m2 stops
Sat, Aug 23 - Sat, Aug 30
Delta Logo
8:55 am - 9:27 pmORD-VPS
12h 32m2 stops
Delta Logo
12:45 pm - 9:52 pmVPS-ORD
9h 07m1 stop
$343Delta
Find Deal
Tue, Oct 14 - Fri, Oct 24
American Airlines Logo
10:10 pm - 10:41 amORD-VPS
12h 31m1 stop
American Airlines Logo
4:47 pm - 7:23 pmVPS-ORD
2h 36mnonstop
$350American Airlines
Find Deal
Sat, Aug 23 - Sat, Aug 30
American Airlines Logo
10:15 am - 10:44 pmORD-VPS
12h 29m1 stop
American Airlines Logo
6:58 am - 5:31 pmVPS-ORD
10h 33m1 stop
$362American Airlines
Find Deal
Mon, Nov 3 - Wed, Nov 5
Delta Logo
9:25 am - 10:04 pmMDW-VPS
12h 39m2 stops
Delta Logo
7:06 pm - 8:35 amVPS-MDW
13h 29m2 stops
$370Delta
Find Deal
Sat, Aug 9 - Fri, Aug 15

Allegiant Air flights from Chicago to Valparaiso, Florida

Our best Allegiant Air deals on Chicago to Valparaiso, Florida flight tickets
Allegiant Air
Jul 30
MDW4:27 pmChicago Midway
2h 11m
VPS6:38 pmValparaiso Destin-Ft Walton Beach
Aug 1
VPS6:00 amValparaiso Destin-Ft Walton Beach
2h 22m
MDW8:22 amChicago Midway
Allegiant Air
Jul 30
MDW4:27 pmChicago Midway
2h 11m
VPS6:38 pmValparaiso Destin-Ft Walton Beach
Aug 6
VPS1:15 pmValparaiso Destin-Ft Walton Beach
2h 22m
MDW3:37 pmChicago Midway
Allegiant Air
Aug 8
MDW9:12 amChicago Midway
2h 11m
VPS11:23 amValparaiso Destin-Ft Walton Beach
Aug 11
VPS6:00 amValparaiso Destin-Ft Walton Beach
2h 22m
MDW8:22 amChicago Midway

Southwest flights from Chicago to Valparaiso, Florida

Our best Southwest deals on Chicago to Valparaiso, Florida flight tickets
Southwest
Oct 14
ORD3:10 pmChicago O'Hare Intl
6h 00m
1 stop
VPS9:10 pmValparaiso Destin-Ft Walton Beach
Oct 21
VPS7:15 amValparaiso Destin-Ft Walton Beach
5h 30m
1 stop
ORD12:45 pmChicago O'Hare Intl
Southwest
Oct 14
ORD3:10 pmChicago O'Hare Intl
6h 00m
1 stop
VPS9:10 pmValparaiso Destin-Ft Walton Beach
Oct 21
VPS7:15 amValparaiso Destin-Ft Walton Beach
10h 40m
2 stops
ORD5:55 pmChicago O'Hare Intl
Southwest
Aug 23
ORD2:55 pmChicago O'Hare Intl
3h 50m
1 stop
VPS6:45 pmValparaiso Destin-Ft Walton Beach
Aug 30
VPS7:05 amValparaiso Destin-Ft Walton Beach
9h 20m
1 stop
ORD4:25 pmChicago O'Hare Intl

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 February instead. Flights to Valparaiso, Florida in February, while not as cheap as those in January, still average around $223.

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, 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 $391.

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 $123. In contrast, the most expensive time of day to depart to Valparaiso, Florida is in the morning when prices are around $355.

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 $406 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 $323 on momondo.

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

There are 1 cabin classes 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 July 2025, prices for Chicago to Valparaiso, Florida flights are approximately 21% 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

$50

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 $50. The best round-trip flight deal from Chicago to Valparaiso, Florida found on momondo in the last 72 hours is $91.
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)

  • 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
702 reviews
Search Allegiant Air flights
DeltaPriceFrom $202Free CancellationRating
8.0
7,959 reviews
Search Delta flights
SouthwestPriceFrom $212Free CancellationRating
8.0
4,239 reviews
Search Southwest flights
American AirlinesPriceFrom $214Free CancellationRating
7.2
10,000 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 $176. Allegiant Air is rated 7.2/10 by our users.

  • American Airlines Flights From Chicago to Valparaiso, Florida

    American Airlines (7.2/10 from 10,000 reviews) operates around 3 flights from Chicago to Valparaiso, Florida in any given week. The average American Airlines airfare for this route is around $404, with deals from around $214 rare but found on momondo. Referenced prices are for round-trip Chicago to Valparaiso, Florida flight searches in the last 72 hours.


Traveling to a place near Valparaiso?

Book flights to Valparaiso if you plan to visit one of these locations
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.


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1 adult
Tue 7/22
Tue 7/29

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