What is the cheapest airline that flies from Valparaiso Destin-Ft Walton Beach to Chicago?

Allegiant Air, Southwest, and Sun Country Air are the most popular carriers operating from Valparaiso Destin-Ft Walton Beach to Chicago

What airlines fly to Chicago?

United Airlines, American Airlines and Delta are the top three most popular airlines that fly to Chicago from Valparaiso, Florida according to our data. United Airlines is the first choice among our users, with 42% of people opting to fly with this airline when traveling to Chicago. Keep in mind that there are 6 different airlines that fly to Chicago on a routine basis, so you have a few additional options to choose from.

How many flights depart from Valparaiso, Florida to Chicago on average per week?

As of April 2026, there are 12 flights per week flying from Valparaiso, Florida to Chicago. The most common day of the week flights depart is Thu, with 25% of flights taking off on this day.

How many flights depart from Valparaiso, Florida to Chicago on average per day?

As of April 2026, 1 flights take off from Valparaiso, Florida and land in Chicago each day. The most common flight departure time for this route is 12:00PM, with 100% of daily flights taking off in the afternoon.

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?

As of April 2026, there are 3 operators available to choose from 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.

$64 Cheap Flights from Valparaiso to Chicago in 2026

Q: What is the typical price of a round-trip flight between Valparaiso, Florida and Chicago?

Prices are currently low for flights on this route. Typical prices usually range from $273 to $127. The lowest price recently found on this route was $101.

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Find the cheapest flights from Valparaiso, Florida to Chicago

Round-trip

One-way

Last minute

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Cheap round-trip flights

Enter your travel dates to find the best prices.

4:01 pm - 6:18 pm

VPS

MDW

2h 17mnonstop

9:30 pm - 11:37 pm

MDW

VPS

2h 07mnonstop

$101Allegiant Air

Thu, May 7 - Mon, May 25

6:12 pm - 8:33 pm

VPS

MDW

2h 21mnonstop

9:23 pm - 11:36 pm

MDW

VPS

2h 13mnonstop

$137Allegiant Air

Fri, Jun 19 - Mon, Jun 22

6:12 pm - 8:33 pm

VPS

MDW

2h 21mnonstop

9:23 pm - 11:36 pm

MDW

VPS

2h 13mnonstop

$167Allegiant Air

Fri, Jun 5 - Mon, Jun 8

6:21 pm - 8:40 pm

VPS

MDW

2h 19mnonstop

12:04 pm - 11:15 pm

MDW

VPS

35h 11m

3 stops

$237Multiple Airlines

Fri, May 29 - Wed, Jun 3

8:30 am - 10:02 pm

VPS

MDW

13h 32m

3 stops

5:47 pm - 7:56 pm

MDW

VPS

2h 09mnonstop

$271Multiple Airlines

Wed, May 6 - Sun, May 10

7:20 am - 12:50 pm

VPS

ORD

5h 30m

1 stop

2:40 pm - 9:00 pm

ORD

VPS

6h 20m

1 stop

$350Southwest

Fri, May 29 - Wed, Jun 3

6:04 pm - 11:19 am

VPS

ORD

17h 15m

1 stop

6:31 pm - 5:03 pm

ORD

VPS

22h 32m

1 stop

$353Sun Country Air

Mon, Jul 27 - Thu, Jul 30

11:17 am - 1:58 pm

VPS

ORD

2h 41mnonstop

8:14 am - 10:45 am

ORD

VPS

2h 31mnonstop

$356American Airlines

Wed, Jun 17 - Tue, Jun 23

12:48 pm - 5:40 pm

VPS

ORD

4h 52m

1 stop

8:15 am - 10:50 am

ORD

VPS

2h 35mnonstop

$366American Airlines

Tue, May 26 - Tue, Jun 2

7:20 am - 12:50 pm

VPS

ORD

5h 30m

1 stop

2:40 pm - 9:00 pm

ORD

VPS

6h 20m

1 stop

$378Southwest

Fri, May 8 - Tue, May 19

American Airlines flights from Valparaiso, Florida to Chicago

Our best American Airlines deals on Valparaiso, Florida to Chicago flight tickets

American Airlines

Jun 17

VPS11:17 amValparaiso Destin-Ft Walton Beach

2h 41m

ORD1:58 pmChicago O'Hare Intl

Jun 23

ORD8:14 amChicago O'Hare Intl

2h 31m

VPS10:45 amValparaiso Destin-Ft Walton Beach

$356

American Airlines

May 26

VPS12:48 pmValparaiso Destin-Ft Walton Beach

4h 52m

1 stop

ORD5:40 pmChicago O'Hare Intl

Jun 2

ORD8:15 amChicago O'Hare Intl

2h 35m

VPS10:50 amValparaiso Destin-Ft Walton Beach

$366

American Airlines

Aug 5

VPS10:00 amValparaiso Destin-Ft Walton Beach

2h 35m

ORD12:35 pmChicago O'Hare Intl

Aug 9

ORD7:08 amChicago O'Hare Intl

2h 12m

VPS9:20 amValparaiso Destin-Ft Walton Beach

$375

Southwest flights from Valparaiso, Florida to Chicago

Our best Southwest deals on Valparaiso, Florida to Chicago flight tickets

Southwest

May 29

VPS2:00 pmValparaiso Destin-Ft Walton Beach

8h 20m

1 stop

MDW10:20 pmChicago Midway

Jun 3

MDW4:50 pmChicago Midway

4h 10m

1 stop

VPS9:00 pmValparaiso Destin-Ft Walton Beach

$310

Southwest

Jun 4

VPS6:05 pmValparaiso Destin-Ft Walton Beach

6h 10m

1 stop

MDW12:15 amChicago Midway

Jun 8

MDW5:05 pmChicago Midway

4h 00m

1 stop

VPS9:05 pmValparaiso Destin-Ft Walton Beach

$322

Southwest

May 8

VPS12:35 pmValparaiso Destin-Ft Walton Beach

4h 25m

1 stop

MDW5:00 pmChicago Midway

May 12

MDW4:50 pmChicago Midway

4h 10m

1 stop

VPS9:00 pmValparaiso Destin-Ft Walton Beach

$343

momondo Fare Finder

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

Cheapest round-trip

Quickest round-trip

ValparaisoChicago

VPS - MDW

VPSMDW

Valparaiso Destin-Ft Walton Beach

Thu 5/7

4:01 pm-6:18 pm

Nonstop2h 17m

Chicago Midway

Mon 5/25

9:30 pm-11:37 pm

Nonstop2h 07m

$101

ValparaisoChicago

VPS - MDW

VPSMDW

Valparaiso Destin-Ft Walton Beach

Fri 6/19

6:12 pm-8:33 pm

Nonstop2h 21m

Chicago Midway

Mon 6/22

9:23 pm-11:36 pm

Nonstop2h 13m

$137

ValparaisoChicago

VPS - MDW

VPSMDW

Valparaiso Destin-Ft Walton Beach

Fri 6/5

6:12 pm-8:33 pm

Nonstop2h 21m

Chicago Midway

Mon 6/8

9:23 pm-11:36 pm

Nonstop2h 13m

$167

ValparaisoChicago

VPS - MDW

VPSMDW

Valparaiso Destin-Ft Walton Beach

Fri 5/29

6:21 pm-8:40 pm

Nonstop2h 19m

Chicago Midway

Wed 6/3

12:04 pm-11:15 pm

3 stops35h 11m

$237

ValparaisoChicago

VPS - MDW

VPSMDW

Valparaiso Destin-Ft Walton Beach

Wed 5/6

8:30 am-10:02 pm

3 stops13h 32m

Chicago Midway

Sun 5/10

5:47 pm-7:56 pm

Nonstop2h 09m

$271

ValparaisoChicago

VPS - ORD

VPSORD

Valparaiso Destin-Ft Walton Beach

Fri 5/29

7:20 am-12:50 pm

1 stop5h 30m

Chicago O'Hare Intl

Wed 6/3

2:40 pm-9:00 pm

1 stop6h 20m

$350

ValparaisoChicago

VPS - ORD

VPSORD

Valparaiso Destin-Ft Walton Beach

Mon 7/27

6:04 pm-11:19 am

1 stop17h 15m

Chicago O'Hare Intl

Thu 7/30

6:31 pm-5:03 pm

1 stop22h 32m

$353

ValparaisoChicago

VPS - ORD

VPSORD

Valparaiso Destin-Ft Walton Beach

Wed 6/17

11:17 am-1:58 pm

Nonstop2h 41m

Chicago O'Hare Intl

Tue 6/23

8:14 am-10:45 am

Nonstop2h 31m

$356

ValparaisoChicago

VPS - ORD

VPSORD

Valparaiso Destin-Ft Walton Beach

Tue 5/26

12:48 pm-5:40 pm

1 stop4h 52m

Chicago O'Hare Intl

Tue 6/2

8:15 am-10:50 am

Nonstop2h 35m

$366

ValparaisoChicago

VPS - ORD

VPSORD

Valparaiso Destin-Ft Walton Beach

Fri 5/8

7:20 am-12:50 pm

1 stop5h 30m

Chicago O'Hare Intl

Tue 5/19

2:40 pm-9:00 pm

1 stop6h 20m

$378

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 20 resultsSorted by cheapest first

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

Prices

Airlines

Other information

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 October is your next best option. Flight prices from Valparaiso, Florida to Chicago during October average around $139.

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 $367. 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 $541.

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 $158. In contrast, the most expensive time of day to depart to Chicago is in the morning when prices are around $434.

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, Florida to Chicago flights?

There are 2 cabin classes available to choose from on Valparaiso, Florida 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?

You could potentially save up to 28% on your flight if you consider stops on a Valparaiso, Florida to Chicago flight.

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

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	$181
Fastest flight time	2h 19m
Direct flights	Every day
Airports in Chicago	3 airports

The best one-way flight to Chicago from Valparaiso, Florida in the past 72 hours is $181. The best round-trip flight deal from Valparaiso, Florida to Chicago found on momondo in the last 72 hours is $130.

The fastest flight from Valparaiso, Florida to Chicago takes 2h 19m

Direct flights go from Valparaiso, Florida to Chicago every day.

There are 3 airports in Chicago. From Valparaiso, Florida there are direct flights to Chicago O'Hare Intl (ORD), Chicago Midway (MDW).

Search flight deals

Frequently asked questions about flying from Valparaiso, Florida to Chicago

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 19m, 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?
As of April 2026, there are 3 operators available to choose from 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?
Based on momondo bookings for this flight route, the most popular plane model on flight routes from Valparaiso, Florida to Chicago is Embraer 175 (30.26% of total bookings). The next most popular plane models are Airbus A319 (25.00%), Boeing 737-800 (10.53%), and Airbus A320-100/200 (10.53%).
What is the most popular airline from Valparaiso, Florida to Chicago?
momondo data reveals that the most frequently booked airline on the route from Valparaiso, Florida to Chicago is American Airlines, representing 49% of all bookings. The subsequent popular airlines are Allegiant Air at 29% and Southwest at 22%.

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 Air	PriceFrom $86	Free Cancellation	Rating 7.3 707 reviews	Search Allegiant Air flights
American Airlines	PriceFrom $157	Free Cancellation	Rating 7.1 11,664 reviews	Search American Airlines flights
Southwest	PriceFrom $234	Free Cancellation	Rating 8.0 4,331 reviews	Search Southwest flights

Allegiant Air Flights From Valparaiso, Florida to Chicago
The lowest priced Allegiant Air flight from Valparaiso, Florida to Chicago from the last 72 hours was $86. Generally, Allegiant Air has 1 flight on this route every week with an average price of $188. Allegiant Air is rated 7.3/10 by our users.
American Airlines Flights From Valparaiso, Florida to Chicago
Another popular option for Valparaiso, Florida to Chicago flights is American Airlines (7.1/10, 11,664 ratings). American Airlines flies from Valparaiso, Florida to Chicago around 7 times per week, with deals starting from $157 round-trip and rising to an average price of around $380.

Merrillville

New Buffalo

Hammond

Saint Joseph

Benton Harbor

Portage

Lansing

Valparaiso

Munster

Schererville

Crown Point

Monticello

Chesterton

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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Cheap flights from Valparaiso, Florida to Chicago from $64

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 4/30. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.

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American Airlines flights from Valparaiso, Florida to Chicago

Our best American Airlines deals on Valparaiso, Florida to Chicago flight tickets

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Our best Southwest deals on Valparaiso, Florida to Chicago flight tickets

momondo Fare Finder

Use the filters below to find and compare flights from Valparaiso, Florida to Chicago that are best for you.

See travel insights to Chicago from

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

What is the typical price of a round-trip flight between Valparaiso, Florida and Chicago?

What is the cheapest month to fly to Chicago?

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

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

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

What cabin class options are available on Valparaiso, Florida to Chicago flights?

Can stopping save me money on Valparaiso, Florida to Chicago flights?

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

What is the cheapest airline that flies from Valparaiso Destin-Ft Walton Beach to Chicago?

What airlines fly to Chicago?

How many flights depart from Valparaiso, Florida to Chicago on average per day?

How many flights depart from Valparaiso, Florida to Chicago on average per week?

When to book flights from Valparaiso, Florida to Chicago

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

Fastest flight time

Direct flights

Airports in Chicago

Frequently asked questions about flying 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

Allegiant Air Flights From Valparaiso, Florida to Chicago

American Airlines Flights From Valparaiso, Florida to Chicago

Traveling to a place near Chicago?

Why use momondo?

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.

Get notified when prices go down

Daily price changes in your inbox - only with Price Alerts.

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

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List of cabin classes available on flights landing in Chicago. Availability may vary depending on flight origin and airline.

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