Latest deals
Insights
When to book
FAQs
Reviews
Price Alerts

Cheap flights from Valparaiso, Florida to Chicago from $48

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 10/30. 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

Discover deals from 900+ travel sites with momondo.

Save money when you book flights with momondo

Big names and deals

Big names and deals

Search 100s of travel sites to compare prices.

Filter for what you want

Filter for what you want

Free Wi-Fi? Stopover? Instantly customize your results.

Trusted and free

Trusted and free

We’re completely free to use - no hidden charges or fees.

Price Alerts

Price Alerts

Not ready to book? to track prices.
Search flight deals

Find the cheapest flights from Valparaiso, Florida to Chicago (VPS-CHI)

Cheap round-trip flights

Allegiant Air Logo
8:00 am - 10:17 amVPS-MDW
2h 17mnonstop
Allegiant Air Logo
11:07 am - 1:12 pmMDW-VPS
2h 05mnonstop
$121Allegiant Air
Find Deal
Thu, Oct 2 - Sun, Oct 5
Delta Logo
9:42 am - 2:33 pmVPS-ORD
4h 51m1 stop
Delta Logo
6:15 am - 12:00 pmORD-VPS
5h 45m1 stop
$187Delta
Find Deal
Wed, Sep 24 - Sat, Sep 27
Delta Logo
2:58 pm - 9:26 pmVPS-MDW
6h 28m1 stop
Delta Logo
6:00 am - 10:36 amMDW-VPS
4h 36m1 stop
$187Delta
Find Deal
Wed, Sep 10 - Sat, Sep 13
Southwest Logo
7:00 am - 12:45 pmVPS-ORD
5h 45m1 stop
Southwest Logo
2:55 pm - 6:45 pmORD-VPS
3h 50m1 stop
$221Southwest
Find Deal
Wed, Sep 24 - Sat, Sep 27
Southwest Logo
2:00 pm - 7:45 pmVPS-MDW
5h 45m1 stop
Southwest Logo
6:00 am - 10:55 amMDW-VPS
4h 55m1 stop
$221Southwest
Find Deal
Wed, Oct 1 - Sat, Oct 4
Logo
6:30 am - 9:58 pmVPS-ORD
15h 28m2 stops
Logo
5:17 pm - 1:55 pmORD-VPS
20h 38m2 stops
$296
Find Deal
Thu, Sep 18 - Sun, Sep 21
Sun Country Air Logo
6:17 pm - 7:21 pmVPS-ORD
25h 04m1 stop
Sun Country Air Logo
8:00 am - 4:17 pmORD-VPS
8h 17m1 stop
$304Sun Country Air
Find Deal
Wed, Oct 15 - Sun, Oct 19
Logo
6:30 am - 9:58 pmVPS-ORD
15h 28m2 stops
Logo
11:57 am - 1:55 pmORD-VPS
25h 58m3 stops
$333
Find Deal
Thu, Sep 18 - Sun, Sep 21
American Airlines Logo
7:00 am - 8:01 pmVPS-ORD
13h 01m1 stop
American Airlines Logo
8:45 am - 11:13 amORD-VPS
2h 28mnonstop
$356American Airlines
Find Deal
Wed, Sep 24 - Sat, Sep 27
American Airlines Logo
7:00 am - 5:18 pmVPS-ORD
10h 18m1 stop
American Airlines Logo
7:02 am - 11:54 amORD-VPS
4h 52m1 stop
$366American Airlines
Find Deal
Wed, Sep 17 - Sun, Sep 21

Southwest flights from Valparaiso, Florida to Chicago

Our best Southwest deals on Valparaiso, Florida to Chicago flight tickets
Southwest
Sep 24
VPS7:00 amValparaiso Destin-Ft Walton Beach
5h 45m
1 stop
ORD12:45 pmChicago O'Hare Intl
Sep 27
ORD2:55 pmChicago O'Hare Intl
3h 50m
1 stop
VPS6:45 pmValparaiso Destin-Ft Walton Beach
$221
Find similar
Southwest
Oct 1
VPS7:00 amValparaiso Destin-Ft Walton Beach
8h 00m
2 stops
MDW3:00 pmChicago Midway
Oct 4
MDW6:00 amChicago Midway
4h 55m
1 stop
VPS10:55 amValparaiso Destin-Ft Walton Beach
$226
Find similar
Southwest
Sep 9
VPS12:40 pmValparaiso Destin-Ft Walton Beach
6h 35m
1 stop
MDW7:15 pmChicago Midway
Sep 11
MDW12:00 pmChicago Midway
9h 05m
1 stop
VPS9:05 pmValparaiso Destin-Ft Walton Beach
$227
Find similar

Delta flights from Valparaiso, Florida to Chicago

Our best Delta deals on Valparaiso, Florida to Chicago flight tickets
Delta
Sep 24
VPS9:42 amValparaiso Destin-Ft Walton Beach
4h 51m
1 stop
ORD2:33 pmChicago O'Hare Intl
Sep 27
ORD6:15 amChicago O'Hare Intl
5h 45m
1 stop
VPS12:00 pmValparaiso Destin-Ft Walton Beach
$187
Find similar
Delta
Sep 17
VPS11:41 amValparaiso Destin-Ft Walton Beach
7h 19m
1 stop
ORD7:00 pmChicago O'Hare Intl
Sep 21
ORD7:20 amChicago O'Hare Intl
6h 49m
1 stop
VPS2:09 pmValparaiso Destin-Ft Walton Beach
$306
Find similar
Delta
Sep 12
VPS2:55 pmValparaiso Destin-Ft Walton Beach
6h 41m
1 stop
MDW9:36 pmChicago Midway
Sep 14
MDW6:00 amChicago Midway
4h 36m
1 stop
VPS10:36 amValparaiso Destin-Ft Walton Beach
$425
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 August 11, 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

Thu 10/2

8:00 am-10:17 am

Nonstop2h 17m

Chicago Midway

Sun 10/5

11:07 am-1:12 pm

Nonstop2h 05m

$121

ValparaisoChicago

VPS - ORD

VPSORD

Valparaiso Destin-Ft Walton Beach

Wed 9/24

9:42 am-2:33 pm

1 stop4h 51m

Chicago O'Hare Intl

Sat 9/27

6:15 am-12:00 pm

1 stop5h 45m

$187

ValparaisoChicago

VPS - MDW

VPSMDW

Valparaiso Destin-Ft Walton Beach

Wed 9/10

2:58 pm-9:26 pm

1 stop6h 28m

Chicago Midway

Sat 9/13

6:00 am-10:36 am

1 stop4h 36m

$187

ValparaisoChicago

VPS - ORD

VPSORD

Valparaiso Destin-Ft Walton Beach

Wed 9/24

7:00 am-12:45 pm

1 stop5h 45m

Chicago O'Hare Intl

Sat 9/27

2:55 pm-6:45 pm

1 stop3h 50m

$221

ValparaisoChicago

VPS - MDW

VPSMDW

Valparaiso Destin-Ft Walton Beach

Wed 10/1

2:00 pm-7:45 pm

1 stop5h 45m

Chicago Midway

Sat 10/4

6:00 am-10:55 am

1 stop4h 55m

$221

ValparaisoChicago

VPS - ORD

VPSORD

Valparaiso Destin-Ft Walton Beach

Thu 9/18

6:30 am-9:58 pm

2 stops15h 28m

Chicago O'Hare Intl

Sun 9/21

5:17 pm-1:55 pm

2 stops20h 38m

$296

ValparaisoChicago

VPS - ORD

VPSORD

Valparaiso Destin-Ft Walton Beach

Wed 10/15

6:17 pm-7:21 pm

1 stop25h 04m

Chicago O'Hare Intl

Sun 10/19

8:00 am-4:17 pm

1 stop8h 17m

$304

ValparaisoChicago

VPS - ORD

VPSORD

Valparaiso Destin-Ft Walton Beach

Thu 9/18

6:30 am-9:58 pm

2 stops15h 28m

Chicago O'Hare Intl

Sun 9/21

11:57 am-1:55 pm

3 stops25h 58m

$333

ValparaisoChicago

VPS - ORD

VPSORD

Valparaiso Destin-Ft Walton Beach

Wed 9/24

7:00 am-8:01 pm

1 stop13h 01m

Chicago O'Hare Intl

Sat 9/27

8:45 am-11:13 am

Nonstop2h 28m

$356

ValparaisoChicago

VPS - ORD

VPSORD

Valparaiso Destin-Ft Walton Beach

Wed 9/17

7:00 am-5:18 pm

1 stop10h 18m

Chicago O'Hare Intl

Sun 9/21

7:02 am-11:54 am

1 stop4h 52m

$366

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 20 resultsSorted by cheapest first
1
2

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 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 Wednesday when prices can be found for as low as $190. This is often the case because there is less demand to fly during this day of the week. When flying out on a Saturday, the most expensive travel day of the week, you can expect to see flight prices from Valparaiso, Florida to Chicago for around $621.

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 at noon. Flights from Valparaiso, Florida to Chicago during this time can be as low as $123. 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 August 2025, prices for Valparaiso, Florida to Chicago flights are approximately 0% 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

$48

Fastest flight time

2h 17m

Direct flights

Every day

Airports in Chicago

2 airports
The best one-way flight to Chicago from Valparaiso, Florida in the past 72 hours is $48. The best round-trip flight deal from Valparaiso, Florida to Chicago found on momondo in the last 72 hours is $121.
The fastest flight from Valparaiso, Florida to Chicago takes 2h 17m
Direct flights go from Valparaiso, Florida to Chicago every day.
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
American AirlinesPriceFrom $157Free CancellationRating
7.2
10,000 reviews
Search American Airlines flights
DeltaPriceFrom $294Free CancellationRating
8.0
7,979 reviews
Search Delta flights

  • American Airlines Flights From Valparaiso, Florida to Chicago

    The lowest priced American Airlines flight from Valparaiso, Florida to Chicago from the last 72 hours was $157. Generally, American Airlines has 6 flights on this route every week with an average price of $375. American Airlines is rated 7.2/10 by our users.

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.

An easier way to manage your Chicago trip

We make it super easy to schedule, organize and travel with friends or family. Trips is free — and available to use no matter where you book.
Start using Trips
Find my bookings

Get notified when prices go down

Daily price changes in your inbox - only with Price Alerts.
1 adult
Sat 8/16
Sat 8/23
By creating a price alert you accept our terms of use and privacy policy.

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