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Cheap flights from Chicago O'Hare Intl Airport to Valparaiso from $135

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 O'Hare Intl Airport to Valparaiso departing on 11/27. 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 O'Hare Intl Airport to Valparaiso

Cheap round-trip flights

Sun Country Air Logo
8:08 pm - 10:29 amORD-VPS
14h 21m1 stop
Sun Country Air Logo
11:26 am - 10:26 amVPS-ORD
23h 00m1 stop
$298Sun Country Air
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Thu, Dec 18 - Mon, Dec 22
Southwest Logo
1:45 pm - 9:15 pmORD-VPS
7h 30m1 stop
Southwest Logo
11:20 am - 9:50 pmVPS-ORD
10h 30m2 stops
$343Southwest
Find Deal
Mon, Nov 10 - Wed, Nov 12
Multiple Airlines Logo
6:58 pm - 3:18 pmORD-VPS
20h 20m2 stops
Multiple Airlines Logo
6:30 am - 12:45 pmVPS-ORD
30h 15m1 stop
$346Multiple Airlines
Find Deal
Tue, Oct 14 - Tue, Oct 21
Multiple Airlines Logo
5:11 am - 7:30 pmORD-VPS
14h 19m2 stops
Multiple Airlines Logo
6:35 am - 7:13 amVPS-ORD
24h 38m1 stop
$363Multiple Airlines
Find Deal
Thu, Nov 13 - Sun, Nov 16
Delta Logo
9:30 am - 3:42 pmORD-VPS
6h 12m1 stop
Delta Logo
6:00 am - 10:06 amVPS-ORD
4h 06m1 stop
$375Delta
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Wed, Feb 18 - Sat, Feb 21
Delta Logo
6:45 am - 11:05 amORD-VPS
4h 20m1 stop
Delta Logo
1:15 pm - 5:04 pmVPS-ORD
27h 49m1 stop
$385Delta
Find Deal
Tue, Dec 2 - Sun, Dec 14
American Airlines Logo
12:52 pm - 8:07 pmORD-VPS
7h 15m1 stop
American Airlines Logo
11:18 am - 1:58 pmVPS-ORD
2h 40mnonstop
$402American Airlines
Find Deal
Fri, Oct 31 - Fri, Nov 7
Delta Logo
11:23 am - 4:39 pmORD-VPS
5h 16m1 stop
Delta Logo
1:35 pm - 6:49 pmVPS-ORD
5h 14m1 stop
$410Delta
Find Deal
Fri, Oct 31 - Fri, Nov 7
Southwest Logo
3:10 pm - 9:10 pmORD-VPS
6h 00m1 stop
Southwest Logo
2:00 pm - 9:30 pmVPS-ORD
7h 30m1 stop
$414Southwest
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Wed, Oct 15 - Wed, Oct 22
American Airlines Logo
11:40 am - 8:07 pmORD-VPS
8h 27m2 stops
American Airlines Logo
7:59 am - 3:56 pmVPS-ORD
7h 57m1 stop
$418American Airlines
Find Deal
Fri, Oct 31 - Fri, Nov 7

Southwest flights from Chicago O'Hare Intl Airport to Valparaiso, Florida

Our best Southwest deals on Chicago O'Hare Intl Airport to Valparaiso, Florida flight tickets
Southwest
Nov 10
ORD1:45 pmChicago O'Hare Intl
7h 30m
1 stop
VPS9:15 pmValparaiso Destin-Ft Walton Beach
Nov 12
VPS11:20 amValparaiso Destin-Ft Walton Beach
10h 30m
2 stops
ORD9:50 pmChicago O'Hare Intl
$343
Find similar
Southwest
Oct 15
ORD3:10 pmChicago O'Hare Intl
6h 00m
1 stop
VPS9:10 pmValparaiso Destin-Ft Walton Beach
Oct 22
VPS2:00 pmValparaiso Destin-Ft Walton Beach
7h 30m
1 stop
ORD9:30 pmChicago O'Hare Intl
$414
Find similar
Southwest
Nov 19
ORD1:45 pmChicago O'Hare Intl
7h 25m
1 stop
VPS9:10 pmValparaiso Destin-Ft Walton Beach
Nov 23
VPS7:10 amValparaiso Destin-Ft Walton Beach
5h 05m
1 stop
ORD12:15 pmChicago O'Hare Intl
$420
Find similar

American Airlines flights from Chicago O'Hare Intl Airport to Valparaiso, Florida

Our best American Airlines deals on Chicago O'Hare Intl Airport to Valparaiso, Florida flight tickets
American Airlines
Oct 31
ORD12:52 pmChicago O'Hare Intl
7h 15m
1 stop
VPS8:07 pmValparaiso Destin-Ft Walton Beach
Nov 7
VPS11:18 amValparaiso Destin-Ft Walton Beach
2h 40m
ORD1:58 pmChicago O'Hare Intl
$402
Find similar
American Airlines
Oct 31
ORD11:40 amChicago O'Hare Intl
8h 27m
2 stops
VPS8:07 pmValparaiso Destin-Ft Walton Beach
Nov 7
VPS7:59 amValparaiso Destin-Ft Walton Beach
7h 57m
1 stop
ORD3:56 pmChicago O'Hare Intl
$418
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

momondo Fare Finder

 
Customize your flight search to find flights from Chicago O'Hare Intl Airport 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 September 17, 2025.
Use the filters below to find and compare flights from Chicago O'Hare Intl Airport to Valparaiso, Florida that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

ChicagoValparaiso

ORD - VPS

ORDVPS

Chicago O'Hare Intl

Thu 12/18

8:08 pm-10:29 am

1 stop14h 21m

Valparaiso Destin-Ft Walton Beach

Mon 12/22

11:26 am-10:26 am

1 stop23h 00m

$298

ChicagoValparaiso

ORD - VPS

ORDVPS

Chicago O'Hare Intl

Mon 11/10

1:45 pm-9:15 pm

1 stop7h 30m

Valparaiso Destin-Ft Walton Beach

Wed 11/12

11:20 am-9:50 pm

2 stops10h 30m

$343

ChicagoValparaiso

ORD - VPS

ORDVPS

Chicago O'Hare Intl

Tue 10/14

6:58 pm-3:18 pm

2 stops20h 20m

Valparaiso Destin-Ft Walton Beach

Tue 10/21

6:30 am-12:45 pm

1 stop30h 15m

$346

ChicagoValparaiso

ORD - VPS

ORDVPS

Chicago O'Hare Intl

Thu 11/13

5:11 am-7:30 pm

2 stops14h 19m

Valparaiso Destin-Ft Walton Beach

Sun 11/16

6:35 am-7:13 am

1 stop24h 38m

$363

ChicagoValparaiso

ORD - VPS

ORDVPS

Chicago O'Hare Intl

Wed 2/18

9:30 am-3:42 pm

1 stop6h 12m

Valparaiso Destin-Ft Walton Beach

Sat 2/21

6:00 am-10:06 am

1 stop4h 06m

$375

ChicagoValparaiso

ORD - VPS

ORDVPS

Chicago O'Hare Intl

Tue 12/2

6:45 am-11:05 am

1 stop4h 20m

Valparaiso Destin-Ft Walton Beach

Sun 12/14

1:15 pm-5:04 pm

1 stop27h 49m

$385

ChicagoValparaiso

ORD - VPS

ORDVPS

Chicago O'Hare Intl

Fri 10/31

12:52 pm-8:07 pm

1 stop7h 15m

Valparaiso Destin-Ft Walton Beach

Fri 11/7

11:18 am-1:58 pm

Nonstop2h 40m

$402

ChicagoValparaiso

ORD - VPS

ORDVPS

Chicago O'Hare Intl

Fri 10/31

11:23 am-4:39 pm

1 stop5h 16m

Valparaiso Destin-Ft Walton Beach

Fri 11/7

1:35 pm-6:49 pm

1 stop5h 14m

$410

ChicagoValparaiso

ORD - VPS

ORDVPS

Chicago O'Hare Intl

Wed 10/15

3:10 pm-9:10 pm

1 stop6h 00m

Valparaiso Destin-Ft Walton Beach

Wed 10/22

2:00 pm-9:30 pm

1 stop7h 30m

$414

ChicagoValparaiso

ORD - VPS

ORDVPS

Chicago O'Hare Intl

Fri 10/31

11:40 am-8:07 pm

2 stops8h 27m

Valparaiso Destin-Ft Walton Beach

Fri 11/7

7:59 am-3:56 pm

1 stop7h 57m

$418

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 O'Hare Intl Airport 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 February, then book flights to Valparaiso, Florida from Chicago O'Hare Intl Airport during January instead. Flights to Valparaiso, Florida in January, while not as cheap as those in February, still average around $390.

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 O'Hare Intl Airport 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 O'Hare Intl Airport 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 $390.

What is the cheapest Chicago O'Hare Intl to Valparaiso Destin-Ft Walton Beach flight route?

Fly from Chicago O'Hare Intl to Valparaiso Destin-Ft Walton Beach for the best Chicago O'Hare Intl - 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 O'Hare Intl Airport when booking weeks ahead of your departure date. In general, you can expect to find flights to Valparaiso, Florida for around $425 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 O'Hare Intl Airport for as low as $333 on momondo.

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

There is only 1 cabin class available to choose from on Chicago O'Hare Intl 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 O'Hare Intl Airport to Valparaiso, Florida flights?

No. A direct flight is the cheapest option for a flight between Chicago O'Hare Intl Airport to Valparaiso, Florida.

How have Chicago O'Hare Intl Airport to Valparaiso, Florida flight prices changed over time?

As of September 2025, prices for Chicago O'Hare Intl Airport to Valparaiso, Florida flights are approximately 13% cheaper when compared to flights at the same time last year.

When to book flights from Chicago O'Hare Intl Airport to Valparaiso, Florida

Are you open to changing your travel dates? Check out the ideal times to fly from Chicago O'Hare Intl Airport to Valparaiso, Florida according to our flight data. Find out which month and days have the cheapest flights.
Estimated round-trip price

Cheap Chicago O'Hare Intl Airport to Valparaiso, Florida (ORD to VPS) flight deals and tips

Find info about flight duration, direct flights, and airports for your flight from Chicago O'Hare Intl Airport to Valparaiso, Florida

Best Price Found

$235

Fastest flight time

2h 26m

Direct flights

Every day

Airports in Valparaiso, Florida

1 airport
The best one-way flight to Valparaiso, Florida from Chicago O'Hare Intl Airport in the past 72 hours is $235. The best round-trip flight deal from Chicago O'Hare Intl Airport to Valparaiso, Florida found on momondo in the last 72 hours is $485.
The fastest flight from Chicago O'Hare Intl Airport to Valparaiso, Florida takes 2h 26m
Direct flights go from Chicago O'Hare Intl Airport 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 O'Hare Intl to Valparaiso Destin-Ft Walton Beach by plane?

    The straight-line distance from Chicago O'Hare Intl to Valparaiso Destin-Ft Walton Beach is 795.8 mi. Flights usually cover this in 2h 26m, depending on flying conditions and air traffic around both airports.

  • When did momondo last update prices for flights from Chicago O'Hare Intl Airport to Valparaiso Destin-Ft Walton Beach Airport?

    Prices for flights from Chicago O'Hare Intl Airport to Valparaiso Destin-Ft Walton Beach Airport refresh daily.

  • How many operators does momondo search for flights from Chicago O'Hare Intl Airport to Valparaiso Destin-Ft Walton Beach Airport?

  • How old do you have to be to fly from Chicago O'Hare Intl Airport to Valparaiso Destin-Ft Walton Beach Airport?

    Although the minimum age for a child to fly alone is five, airlines that offer an unaccompanied minor (UMNR) service may have their own age limits, which could be impacted by factors such as flight length, timing, and layovers. It is recommended that you verify with the airline you are booking with for travel from Chicago O'Hare Intl Airport 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 O'Hare Intl Airport to Valparaiso, Florida?

  • What is the most popular airline from Chicago O'Hare Intl Airport to Valparaiso, Florida?

Best airlines flying from Chicago O'Hare Intl Airport to Valparaiso, Florida

Compare and see reviews for airlines that fly from Chicago O'Hare Intl Airport to Valparaiso, Florida with momondo
Airline
Rating
Free Cancellation
Price
DeltaPriceFrom $207Free CancellationRating
7.9
7,961 reviews
Search Delta flights
American AirlinesPriceFrom $236Free CancellationRating
7.2
10,000 reviews
Search American Airlines flights

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?

momondo compares prices from hundreds of airlines and agents so you can find and book the best deal on flights from Chicago to Valparaiso. Millions of users trust and use momondo every year so you are in good hands.

Can I find flights from Chicago to Valparaiso with flexible booking policies on momondo?

Yes. All flights to Valparaiso from Chicago on momondo can be compared and filtered by various policies on offer, including flexible booking.

How can momondo help me find flights from Chicago to Valparaiso?

momondo offers useful filters to help you find the right flight. Choose specific flight times, airports or even what payment method you prefer. We have numerous options to help you book your ideal flight from Chicago to Valparaiso.

I’m not ready to book a flight from Chicago to Valparaiso right now. Can momondo alert me if prices change?

Price alerts on flights to Valparaiso from Chicago are quick and easy to set up on momondo. Simply perform a search and select the price alert feature. It is as simple as that.

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