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Cheap flights from Valparaiso, Florida to Chicago from $49

This is the cheapest one-way flight price found by a momondo user in the last 72 hours by searching for a flight from Valparaiso, Florida to Chicago departing on 12/23. 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 Valparaiso, Florida to Chicago

Cheap round-trip flights

Enter your travel dates to find the best prices.
Allegiant Air Logo
9:00 am - 11:17 amVPS-MDW
2h 17mnonstop
Allegiant Air Logo
12:07 pm - 2:12 pmMDW-VPS
2h 05mnonstop
$106Allegiant Air
Find Deal
jue., oct. 30 - dom., nov. 2
Allegiant Air Logo
9:00 am - 11:17 amVPS-MDW
2h 17mnonstop
Allegiant Air Logo
12:07 pm - 2:12 pmMDW-VPS
2h 05mnonstop
$113Allegiant Air
Find Deal
jue., oct. 30 - dom., nov. 2
Multiple Airlines Logo
6:35 am - 11:55 pmVPS-MDW
17h 20m1 stop
Multiple Airlines Logo
12:07 pm - 2:12 pmMDW-VPS
2h 05mnonstop
$166Multiple Airlines
Find Deal
jue., nov. 6 - dom., nov. 9
Multiple Airlines Logo
6:30 am - 11:25 pmVPS-MDW
16h 55m1 stop
Multiple Airlines Logo
12:07 pm - 2:12 pmMDW-VPS
2h 05mnonstop
$175Multiple Airlines
Find Deal
jue., oct. 30 - dom., nov. 2
Delta Logo
9:29 am - 8:35 pmVPS-ORD
11h 06m2 stops
Delta Logo
10:45 am - 9:40 pmORD-VPS
10h 55m2 stops
$284Delta
Find Deal
sáb., dic. 6 - sáb., dic. 13
American Airlines Logo
6:51 am - 7:18 pmVPS-ORD
12h 27m1 stop
American Airlines Logo
8:05 am - 8:30 pmORD-VPS
12h 25m1 stop
$294American Airlines
Find Deal
sáb., feb. 14 - mar., feb. 17
American Airlines Logo
11:37 am - 11:45 pmVPS-ORD
12h 08m1 stop
American Airlines Logo
8:35 pm - 10:04 amORD-VPS
13h 29m1 stop
$315American Airlines
Find Deal
mié., feb. 18 - vie., feb. 20
Southwest Logo
2:00 pm - 10:10 pmVPS-MDW
8h 10m2 stops
Southwest Logo
5:35 am - 10:20 amMDW-VPS
4h 45m1 stop
$325Southwest
Find Deal
lun., dic. 8 - jue., dic. 11
Southwest Logo
7:15 am - 12:15 pmVPS-ORD
5h 00m1 stop
Southwest Logo
6:05 am - 9:10 pmORD-VPS
15h 05m2 stops
$330Southwest
Find Deal
lun., dic. 8 - jue., dic. 11
Delta Logo
9:29 am - 10:30 pmVPS-ORD
13h 01m2 stops
Delta Logo
10:45 am - 9:40 pmORD-VPS
10h 55m2 stops
$335Delta
Find Deal
lun., dic. 8 - sáb., dic. 13

Delta flights from Valparaiso, Florida to Chicago

Our best Delta deals on Valparaiso, Florida to Chicago flight tickets
Delta
Dec 6
VPS9:29 amValparaiso Destin-Ft Walton Beach
11h 06m
2 stops
ORD8:35 pmChicago O'Hare Intl
Dec 13
ORD10:45 amChicago O'Hare Intl
10h 55m
2 stops
VPS9:40 pmValparaiso Destin-Ft Walton Beach
$284
Find similar
Delta
Dec 8
VPS9:29 amValparaiso Destin-Ft Walton Beach
13h 01m
2 stops
ORD10:30 pmChicago O'Hare Intl
Dec 13
ORD10:45 amChicago O'Hare Intl
10h 55m
2 stops
VPS9:40 pmValparaiso Destin-Ft Walton Beach
$335
Find similar
Delta
Dec 9
VPS6:00 amValparaiso Destin-Ft Walton Beach
12h 00m
2 stops
MDW6:00 pmChicago Midway
Dec 13
MDW9:59 amChicago Midway
11h 41m
2 stops
VPS9:40 pmValparaiso Destin-Ft Walton Beach
$354
Find similar

American Airlines flights from Valparaiso, Florida to Chicago

Our best American Airlines deals on Valparaiso, Florida to Chicago flight tickets
American Airlines
Feb 14
VPS6:51 amValparaiso Destin-Ft Walton Beach
12h 27m
1 stop
ORD7:18 pmChicago O'Hare Intl
Feb 17
ORD8:05 amChicago O'Hare Intl
12h 25m
1 stop
VPS8:30 pmValparaiso Destin-Ft Walton Beach
$294
Find similar
American Airlines
Feb 18
VPS11:37 amValparaiso Destin-Ft Walton Beach
12h 08m
1 stop
ORD11:45 pmChicago O'Hare Intl
Feb 20
ORD8:35 pmChicago O'Hare Intl
13h 29m
1 stop
VPS10:04 amValparaiso Destin-Ft Walton Beach
$315
Find similar
American Airlines
Dec 8
VPS6:28 amValparaiso Destin-Ft Walton Beach
11h 42m
1 stop
ORD6:10 pmChicago O'Hare Intl
Dec 11
ORD10:24 amChicago O'Hare Intl
12h 24m
1 stop
VPS10:48 pmValparaiso Destin-Ft Walton Beach
$316
Find similar

momondo Fare Finder

 
Customize your flight search to find flights from Valparaiso, Florida to Chicago 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 octubre 22, 2025.
Use the filters below to find and compare flights from Valparaiso, Florida to Chicago that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

ValparaisoChicago

VPS - MDW

VPSMDW

Valparaiso Destin-Ft Walton Beach

jue. 10/30

9:00 am-11:17 am

Nonstop2h 17m

Chicago Midway

dom. 11/2

12:07 pm-2:12 pm

Nonstop2h 05m

$106

ValparaisoChicago

VPS - MDW

VPSMDW

Valparaiso Destin-Ft Walton Beach

jue. 10/30

9:00 am-11:17 am

Nonstop2h 17m

Chicago Midway

dom. 11/2

12:07 pm-2:12 pm

Nonstop2h 05m

$113

ValparaisoChicago

VPS - MDW

VPSMDW

Valparaiso Destin-Ft Walton Beach

jue. 11/6

6:35 am-11:55 pm

1 stop17h 20m

Chicago Midway

dom. 11/9

12:07 pm-2:12 pm

Nonstop2h 05m

$166

ValparaisoChicago

VPS - MDW

VPSMDW

Valparaiso Destin-Ft Walton Beach

jue. 10/30

6:30 am-11:25 pm

1 stop16h 55m

Chicago Midway

dom. 11/2

12:07 pm-2:12 pm

Nonstop2h 05m

$175

ValparaisoChicago

VPS - ORD

VPSORD

Valparaiso Destin-Ft Walton Beach

sáb. 12/6

9:29 am-8:35 pm

2 stops11h 06m

Chicago O'Hare Intl

sáb. 12/13

10:45 am-9:40 pm

2 stops10h 55m

$284

ValparaisoChicago

VPS - ORD

VPSORD

Valparaiso Destin-Ft Walton Beach

sáb. 2/14

6:51 am-7:18 pm

1 stop12h 27m

Chicago O'Hare Intl

mar. 2/17

8:05 am-8:30 pm

1 stop12h 25m

$294

ValparaisoChicago

VPS - ORD

VPSORD

Valparaiso Destin-Ft Walton Beach

mié. 2/18

11:37 am-11:45 pm

1 stop12h 08m

Chicago O'Hare Intl

vie. 2/20

8:35 pm-10:04 am

1 stop13h 29m

$315

ValparaisoChicago

VPS - MDW

VPSMDW

Valparaiso Destin-Ft Walton Beach

lun. 12/8

2:00 pm-10:10 pm

2 stops8h 10m

Chicago Midway

jue. 12/11

5:35 am-10:20 am

1 stop4h 45m

$325

ValparaisoChicago

VPS - ORD

VPSORD

Valparaiso Destin-Ft Walton Beach

lun. 12/8

7:15 am-12:15 pm

1 stop5h 00m

Chicago O'Hare Intl

jue. 12/11

6:05 am-9:10 pm

2 stops15h 05m

$330

ValparaisoChicago

VPS - ORD

VPSORD

Valparaiso Destin-Ft Walton Beach

lun. 12/8

9:29 am-10:30 pm

2 stops13h 01m

Chicago O'Hare Intl

sáb. 12/13

10:45 am-9:40 pm

2 stops10h 55m

$335

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 Chicago from

How to get the cheapest flight ticket from Valparaiso, Florida to Chicago

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 Valparaiso, Florida and Chicago?

What is the cheapest month to fly to Chicago?

The month of May is, on average, the cheapest month to fly to Chicago from Valparaiso, Florida, with most prices found around $103. If you’re not able to fly to Chicago in May, then February is your next best option. Flight prices from Valparaiso, Florida to Chicago during February average around $105.

What is the cheapest day to depart on your flight to Chicago?

The cheapest day to depart on your flight to Chicago is on a Thursday when prices can be found for as low as $212. This is often the case because there is less demand to fly during this day of the week. When flying out on a Monday, the most expensive travel day of the week, you can expect to see flight prices from Valparaiso, Florida to Chicago for around $582.

What is the cheapest time of day to depart on your flight to Chicago?

Our most recent data shows that the best time of day to fly to Chicago is in the afternoon. Flights from Valparaiso, Florida to Chicago during this time can be as low as $194. In contrast, the most expensive time of day to depart to Chicago is in the evening when prices are around $401.

What is the cheapest Valparaiso Destin-Ft Walton Beach to Chicago flight route?

Fly from Valparaiso Destin-Ft Walton Beach to Chicago Midway for the best Valparaiso Destin-Ft Walton Beach - Chicago flight prices

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

There are 2 cabin classes available to choose from on Valparaiso Destin-Ft Walton Beach to Chicago 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 Valparaiso, Florida to Chicago flights?

No. A direct flight is the cheapest option for a flight between Valparaiso, Florida to Chicago.

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

As of October 2025, prices for Valparaiso, Florida to Chicago flights are approximately 11% more expensive when compared to flights at the same time last year.

When to book flights from Valparaiso, Florida to Chicago

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

Cheap Valparaiso, Florida to Chicago (VPS to CHI) flight deals and tips

Find info about flight duration, direct flights, and airports for your flight from Valparaiso, Florida to Chicago

Best Price Found

$190

Fastest flight time

2h 16m

Direct flights

Mon, Wed, Thu, Fri, Sat and Sun

Airports in Chicago

2 airports
The best one-way flight to Chicago from Valparaiso, Florida in the past 72 hours is $190. The best round-trip flight deal from Valparaiso, Florida to Chicago found on momondo in the last 72 hours is $138.
The fastest flight from Valparaiso, Florida to Chicago takes 2h 16m
Direct flights go from Valparaiso, Florida to Chicago on Monday, Wednesday, Thursday, Friday, Saturday and Sunday. The only airline offering direct flights is American Airlines.
There are 2 airports near Chicago: Chicago O'Hare Intl (ORD), Chicago Midway (MDW)
Search flight deals

  • How far is Valparaiso Destin-Ft Walton Beach to Chicago by plane?

    Valparaiso Destin-Ft Walton Beach and Chicago are 787.3 mi apart from one another. Flights usually cover this in 2h 17m, depending on flying conditions and air traffic around both airports.

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

    Prices for flights from Valparaiso Destin-Ft Walton Beach Airport to Chicago are updated daily.

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

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

    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 Valparaiso Destin-Ft Walton Beach Airport to Chicago.

  • What documentation or ID do you need to fly to Chicago?

    The necessary travel and health documents for your Chicago trip may vary depending on your travel plans and individual circumstances. Generally, you should have various documents, such as a national ID card or driver's license and a passport that is valid for six months beyond your scheduled arrival date. We recommend seeking advice from your airline or a trusted third party, such as IATA.

  • What is the most popular plane model from Valparaiso, Florida to Chicago?

  • What is the most popular airline from Valparaiso, Florida to Chicago?

Best airlines flying from Valparaiso, Florida to Chicago

Compare and see reviews for airlines that fly from Valparaiso, Florida to Chicago with momondo
Airline
Rating
Free Cancellation
Price
Allegiant AirPriceFrom $84Free CancellationRating
7.2
694 reviews
Search Allegiant Air flights
American AirlinesPriceFrom $157Free CancellationRating
7.2
11,028 reviews
Search American Airlines flights
DeltaPriceFrom $323Free CancellationRating
7.9
7,980 reviews
Search Delta flights

Traveling to a place near Chicago?

Book flights to Chicago if you plan to visit one of these locations
Merrillville
New Buffalo
Hammond
Benton Harbor
Saint Joseph
Lansing
Portage
Schererville
Valparaiso
Crown Point
Munster
Chesterton
Monticello
Porter
Griffith
Saint John

Why use momondo?

Why should I use momondo to find a flight deal from Valparaiso to Chicago?

Finding the right flight to Chicago from Valparaiso 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 Chicago quick and easy, saving you time and money.

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

Yes. momondo enables you to select and highlight flights to Chicago from Valparaiso with this policy.

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

momondo provides multiple filters to help you find the best flight to Chicago from Valparaiso. Filter by price, airline, airports, cabin, aircraft, payment method, number of stops and more.

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

Yes momondo offers price alerts on flights to Chicago from Valparaiso. After performing a search on this page you should be able to see the price alert set up feature. Simply provide a valid email address and momondo will instantly alert you when prices change.

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Find better results for your trip to the United States

Fly into one of these airports located in Chicago

Airports listed have a maximum distance of 78.5 mi from Chicago
Chicago Midway Airport
Chicago O'Hare Intl Airport
Chicago Greater Rockford Airport