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Cheap flights from Chicago to Valparaiso, Florida from $148

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, Florida departing on 2/19. 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

These are some of the best round-trip flight deals from Chicago to Valparaiso that have been recently found on momondo from popular airlines, departing in the coming months.

Cheap one-way flights

Flying one-way? These are some of the best deals recently discovered on momondo for flights from Chicago to Valparaiso.

Cheap last minute flights

Planning a quick getaway from Chicago to Valparaiso? These are the last-minute flight deals available now.

Cheap direct flights

If you prefer a non-stop journey, check out our latest direct flight deals to Valparaiso, so you can enjoy a seamless trip without layovers.

Cheap bus & train deals from Chicago to Valparaiso

Find recent round-trip train or bus tickets from Chicago to Valparaiso.

All round-trip flight deals to Valparaiso

The cheapest plane tickets to Valparaiso found on KAYAK recently.
5:45 am - 10:02 amORD-VPS
4h 17m1 stop
5:00 pm - 11:59 pmVPS-ORD
6h 59m1 stop
$315Delta
Find Deal
Sat, Jan 11 - Tue, Jan 14
6:00 am - 10:02 amMDW-VPS
4h 02m1 stop
6:00 am - 10:12 amVPS-MDW
4h 12m1 stop
$315Delta
Find Deal
Sat, Jan 11 - Wed, Jan 15
2:22 pm - 4:34 pmMDW-VPS
2h 12mnonstop
11:15 am - 1:32 pmVPS-MDW
2h 17mnonstop
$334Allegiant Air
Find Deal
Sun, Mar 23 - Thu, Mar 27
7:05 am - 2:10 pmORD-VPS
7h 05m1 stop
7:15 pm - 11:59 pmVPS-ORD
4h 44m1 stop
$335Delta
Find Deal
Mon, Jan 6 - Thu, Jan 9
7:00 am - 5:00 pmORD-VPS
10h 00m2 stops
7:55 am - 3:20 pmVPS-ORD
7h 25m1 stop
$340Southwest
Find Deal
Sat, Feb 1 - Sat, Feb 8
4:30 pm - 9:49 pmORD-VPS
5h 19m1 stop
7:19 am - 3:04 pmVPS-ORD
7h 45m2 stops
$341American Airlines
Find Deal
Sat, Jan 11 - Sat, Jan 18
7:00 am - 5:00 pmORD-VPS
10h 00m2 stops
7:55 am - 7:40 pmVPS-ORD
11h 45m2 stops
$346Southwest
Find Deal
Sat, Feb 1 - Sat, Feb 8
3:56 pm - 6:58 pmORD-VPS
27h 02m3 stops
9:00 am - 9:52 pmVPS-ORD
12h 52m1 stop
Sun, Jan 26 - Thu, Jan 30
3:56 pm - 6:58 pmORD-VPS
27h 02m3 stops
9:00 am - 10:17 amVPS-ORD
25h 17m2 stops
Sun, Jan 26 - Thu, Jan 30
7:00 am - 12:19 pmORD-VPS
5h 19m1 stop
4:28 pm - 12:09 amVPS-ORD
7h 41m1 stop
$387American Airlines
Find Deal
Sat, Jan 4 - Tue, Jan 7
5:45 am - 11:14 amORD-VPS
5h 29m1 stop
$148Delta
Find Deal
Wed, Feb 19
8:05 pm - 11:06 amORD-VPS
15h 01m1 stop
$150Sun Country Air
Find Deal
Thu, May 1
5:45 am - 11:14 amORD-VPS
5h 29m1 stop
$168Delta
Find Deal
Thu, Feb 20
10:57 am - 3:52 pmMDW-VPS
4h 55m1 stop
$168Delta
Find Deal
Sat, Feb 8
7:30 am - 6:55 pmORD-VPS
11h 25m2 stops
$173Southwest
Find Deal
Tue, Jan 21
8:35 am - 5:00 pmMDW-VPS
8h 25m2 stops
$173Southwest
Find Deal
Sat, Feb 8
2:19 pm - 4:29 pmMDW-VPS
2h 10mnonstop
$183Allegiant Air
Find Deal
Thu, May 1
7:20 am - 9:56 amORD-VPS
2h 36mnonstop
$242American Airlines
Find Deal
Thu, May 1
11:40 am - 2:18 pmORD-VPS
2h 38mnonstop
$362American Airlines
Find Deal
Fri, Mar 21
7:50 pm - 11:40 pmORD-VPS
27h 50m3 stops
Thu, Dec 26
7:14 pm - 9:40 pmMDW-VPS
2h 26mnonstop
4:01 pm - 6:24 pmVPS-MDW
2h 23mnonstop
$180Allegiant Air
Find Deal
Tue, Dec 24 - Tue, Dec 31
7:14 pm - 9:40 pmMDW-VPS
2h 26mnonstop
4:01 pm - 6:24 pmVPS-MDW
2h 23mnonstop
$190Allegiant Air
Find Deal
Tue, Dec 24 - Tue, Dec 31
11:25 am - 9:05 pmORD-VPS
9h 40m2 stops
7:35 am - 1:00 pmVPS-ORD
5h 25m1 stop
$605Southwest
Find Deal
Thu, Dec 26 - Wed, Jan 1
5:30 am - 11:25 amMDW-VPS
5h 55m1 stop
7:35 am - 12:15 pmVPS-MDW
4h 40m1 stop
$651Southwest
Find Deal
Thu, Dec 26 - Wed, Jan 1
11:05 am - 9:05 pmMDW-VPS
10h 00m2 stops
7:35 am - 12:15 pmVPS-MDW
4h 40m1 stop
$656Southwest
Find Deal
Thu, Dec 26 - Wed, Jan 1
9:45 am - 3:25 pmORD-VPS
5h 40m1 stop
7:21 am - 12:12 pmVPS-ORD
4h 51m1 stop
$670American Airlines
Find Deal
Thu, Dec 26 - Wed, Jan 1
8:05 am - 3:33 pmORD-VPS
7h 28m1 stop
4:05 pm - 9:52 pmVPS-ORD
5h 47m1 stop
$705American Airlines
Find Deal
Tue, Dec 24 - Tue, Dec 31
6:00 am - 3:33 pmORD-VPS
9h 33m2 stops
4:05 pm - 11:37 pmVPS-ORD
7h 32m1 stop
$710American Airlines
Find Deal
Tue, Dec 24 - Tue, Dec 31
5:57 pm - 10:59 pmORD-VPS
5h 02m1 stop
7:30 pm - 11:53 pmVPS-ORD
4h 23m1 stop
$791Delta
Find Deal
Wed, Dec 25 - Sat, Dec 28
10:08 am - 3:31 pmMDW-VPS
5h 23m1 stop
4:18 pm - 10:06 pmVPS-MDW
5h 48m1 stop
$801Delta
Find Deal
Tue, Dec 24 - Tue, Dec 31
2:22 pm - 4:34 pmMDW-VPS
2h 12mnonstop
11:15 am - 1:32 pmVPS-MDW
2h 17mnonstop
$334Allegiant Air
Find Deal
Sun, Mar 23 - Thu, Mar 27
8:00 am - 10:35 amORD-VPS
2h 35mnonstop
1:30 pm - 4:00 pmVPS-ORD
2h 30mnonstop
$396American Airlines
Find Deal
Sun, Mar 9 - Sat, Mar 15
2:19 pm - 4:29 pmMDW-VPS
2h 10mnonstop
11:16 am - 1:29 pmVPS-MDW
2h 13mnonstop
$417Allegiant Air
Find Deal
Thu, May 1 - Sun, May 4
7:20 am - 9:56 amORD-VPS
2h 36mnonstop
10:40 am - 12:53 pmVPS-ORD
2h 13mnonstop
$439American Airlines
Find Deal
Fri, May 9 - Mon, May 12
7:20 am - 9:56 amORD-VPS
2h 36mnonstop
10:40 am - 12:53 pmVPS-ORD
2h 13mnonstop
$469American Airlines
Find Deal
Thu, Apr 17 - Mon, Apr 21
9:40 am - 12:22 pmORD-VPS
2h 42mnonstop
11:10 am - 1:43 pmVPS-ORD
2h 33mnonstop
$491American Airlines
Find Deal
Mon, Mar 24 - Fri, Mar 28
7:20 am - 9:56 amORD-VPS
2h 36mnonstop
10:40 am - 12:53 pmVPS-ORD
2h 13mnonstop
$502American Airlines
Find Deal
Thu, May 1 - Sun, May 4
10:00 am - 12:40 pmORD-VPS
2h 40mnonstop
1:30 pm - 4:00 pmVPS-ORD
2h 30mnonstop
$507American Airlines
Find Deal
Sat, Mar 15 - Sat, Mar 22
8:00 am - 10:35 amORD-VPS
2h 35mnonstop
2:59 pm - 5:32 pmVPS-ORD
2h 33mnonstop
$511American Airlines
Find Deal
Sun, Mar 23 - Thu, Mar 27
7:20 am - 9:56 amORD-VPS
2h 36mnonstop
10:40 am - 12:53 pmVPS-ORD
2h 13mnonstop
$568American Airlines
Find Deal
Thu, Apr 24 - Sun, Apr 27

American Airlines flights from Chicago to Valparaiso, Florida

Our best American Airlines deals on Chicago to Valparaiso, Florida flight tickets
American Airlines
Jan 11
ORD4:30 pmChicago O'Hare Intl
5h 19m
1 stop
VPS9:49 pmValparaiso Destin-Ft Walton Beach
Jan 18
VPS7:19 amValparaiso Destin-Ft Walton Beach
7h 45m
2 stops
ORD3:04 pmChicago O'Hare Intl
American Airlines
Jan 4
ORD7:00 amChicago O'Hare Intl
5h 19m
1 stop
VPS12:19 pmValparaiso Destin-Ft Walton Beach
Jan 7
VPS4:28 pmValparaiso Destin-Ft Walton Beach
7h 41m
1 stop
ORD12:09 amChicago O'Hare Intl
American Airlines
Jan 4
ORD6:00 amChicago O'Hare Intl
5h 42m
1 stop
VPS11:42 amValparaiso Destin-Ft Walton Beach
Jan 7
VPS12:54 pmValparaiso Destin-Ft Walton Beach
7h 10m
2 stops
ORD8:04 pmChicago O'Hare Intl

Delta flights from Chicago to Valparaiso, Florida

Our best Delta deals on Chicago to Valparaiso, Florida flight tickets
Delta
Jan 11
ORD5:45 amChicago O'Hare Intl
4h 17m
1 stop
VPS10:02 amValparaiso Destin-Ft Walton Beach
Jan 14
VPS5:00 pmValparaiso Destin-Ft Walton Beach
6h 59m
1 stop
ORD11:59 pmChicago O'Hare Intl
Delta
Jan 6
ORD7:05 amChicago O'Hare Intl
7h 05m
1 stop
VPS2:10 pmValparaiso Destin-Ft Walton Beach
Jan 9
VPS7:15 pmValparaiso Destin-Ft Walton Beach
4h 44m
1 stop
ORD11:59 pmChicago O'Hare Intl
Delta
Jan 29
ORD6:35 pmChicago O'Hare Intl
4h 18m
1 stop
VPS10:53 pmValparaiso Destin-Ft Walton Beach
Feb 7
VPS7:15 pmValparaiso Destin-Ft Walton Beach
18h 30m
1 stop
ORD1:45 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 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 $234.

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 Monday when prices can be found for as low as $245. 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 $383.

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 evening. Our users have found flights to Valparaiso, Florida in the evening for as low as $174. In contrast, the most expensive time of day to depart to Valparaiso, Florida is in the afternoon when prices are around $374.

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?

Most flyers found that booking tickets 31 days in advance of their planned departure date is the best time to get cheap flights to Valparaiso, Florida. During this timeframe, flight prices are around $370. 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 $233 on momondo.

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

There are 2 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?

You could potentially save up to 19% on your flight if you consider stops on a Chicago to Valparaiso, Florida flight.

How have Chicago to Valparaiso, Florida flight prices changed over time?

As of December 2024, prices for Chicago to Valparaiso, Florida flights are approximately 105% more expensive 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

$148

Fastest flight time

2h 10m

Direct flights

Mon, Tue, Fri, Sat and Sun

Airports in Valparaiso, Florida

1 airport
The best one-way flight to Valparaiso, Florida from Chicago in the past 72 hours is $148. The best round-trip flight deal from Chicago to Valparaiso, Florida found on momondo in the last 72 hours is $315.
The fastest flight from Chicago to Valparaiso, Florida takes 2h 10m
Direct flights go from Chicago to Valparaiso, Florida on Monday, Tuesday, Friday, Saturday and Sunday. Airlines offering direct flights are: Allegiant Air and American Airlines.
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 12m.

  • 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
7.3
823 reviews
Search Allegiant Air flights
DeltaPriceFrom $199Free CancellationRating
8.0
8,594 reviews
Search Delta flights
American AirlinesPriceFrom $233Free 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 2 flights on this route every week with an average price of $175. Allegiant Air is rated 7.3/10 by our users.


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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