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VPS - CHI

$103 Find cheap flights from Valparaiso, Florida to Chicago

This is the cheapest round-trip flight price found by a KAYAK user in the last 72 hours by searching for a flight from Valparaiso to Chicago departing on 5/17. Fares are subject to change and may not be available on all flights or dates of travel. Click the price to replicate the search for this deal.
1 adult
0 bags
Mon 5/27
Mon 6/3

Search hundreds of travel sites at once for deals on flights to Chicago

 
These are the airlines KAYAK users have selected most often from within our search results in flight searches from Valparaiso to Chicago, as well as popular online travel agencies
These are the airlines KAYAK users have selected most often from within our search results in flight searches from Valparaiso to Chicago, as well as popular online travel agencies
In the last 7 days travelers have searched 43,623,357 times on KAYAK, and here is why:

Save 22% or moreCompare multiple travel sites with one search.

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Filter your dealsChoose cabin class, free Wi-Fi and more.

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Cheap flight deals from Valparaiso to Chicago (VPS-CHI)

Here are some of the best deals found on KAYAK recently from the most popular airlines for round-trip flights from Valparaiso to Chicago that are departing in the next months. While these flights were available on KAYAK in the last 72 hours, prices and availability are subject to change and deals may expire.
Discover the best prices and deals for you by selecting your travel dates.
Choose your dates
4:24 pm - 6:42 pmVPS-MDW
2h 18mnonstop
7:32 pm - 9:35 pmMDW-VPS
2h 03mnonstop
$103Allegiant Air
Find Deal
Fri, May 17 - Mon, May 20
2:10 pm - 5:59 pmVPS-MDW
3h 49m1 stop
6:15 pm - 11:16 pmMDW-VPS
5h 01m1 stop
$196Delta
Find Deal
Wed, Sep 18 - Sat, Sep 21
5:05 pm - 11:54 pmVPS-ORD
6h 49m1 stop
7:05 am - 1:53 pmORD-VPS
6h 48m1 stop
$219Delta
Find Deal
Tue, Jun 4 - Fri, Jun 7
5:05 pm - 10:01 pmVPS-MDW
4h 56m1 stop
6:49 pm - 11:16 pmMDW-VPS
4h 27m1 stop
$219Delta
Find Deal
Tue, Jun 4 - Fri, Jun 7
1:02 pm - 5:21 pmVPS-ORD
4h 19m1 stop
3:00 pm - 9:04 pmORD-VPS
6h 04m1 stop
$239American Airlines
Find Deal
Wed, Sep 18 - Sat, Sep 21
4:23 pm - 11:59 pmVPS-ORD
7h 36m1 stop
6:30 am - 11:58 amORD-VPS
5h 28m1 stop
$276American Airlines
Find Deal
Wed, May 15 - Wed, May 22
7:50 pm - 11:56 pmVPS-ORD
4h 06m1 stop
5:59 pm - 11:16 pmORD-VPS
5h 17m1 stop
$289Delta
Find Deal
Thu, Jun 13 - Mon, Jun 17
4:38 pm - 11:59 pmVPS-ORD
7h 21m1 stop
3:20 pm - 9:05 pmORD-VPS
5h 45m1 stop
$333American Airlines
Find Deal
Sat, May 25 - Sat, Jun 1
11:30 am - 2:15 pmVPS-ORD
2h 45mnonstop
3:20 pm - 9:05 pmORD-VPS
5h 45m1 stop
$349American Airlines
Find Deal
Sat, May 25 - Sat, Jun 1
11:30 am - 2:15 pmVPS-ORD
2h 45mnonstop
10:32 am - 12:59 pmORD-VPS
2h 27mnonstop
$438American Airlines
Find Deal
Sat, May 25 - Sat, Jun 1

Flights from Valparaiso to Chicago - Travel Insights & Trends

Get data-powered insights and trends into flights from Valparaiso to Chicago to help you find the cheapest flights, the best time to fly and much more.

What is the cheapest Valparaiso, Florida to Chicago flight route?

The cheapest price for flight routes found by users searching on KAYAK in the last 2 weeks for one-way flights from Valparaiso, Florida to Chicago.
Our data shows that the cheapest route for a one-way flight from Valparaiso, Florida to Chicago cost $54 and was between Valparaiso, Florida and Chicago Midway Airport. On average, the best prices are found if you fly this route. The average price for a return flight for this route is $85.

What’s the cheapest day of the week to fly from Valparaiso to Chicago?

The average price of all flights from Valparaiso, Florida to Chicago clicked on KAYAK for each day over the last 12 months.
For Valparaiso to Chicago, Tuesday is the cheapest day to fly on average and Sunday is the most expensive. Flying from Chicago back to Valparaiso, the best deals are generally found on Monday, with Saturday being the most expensive.

What is the cheapest month to fly from Valparaiso, Florida to Chicago?

To calculate monthly average prices, KAYAK takes all prices for each month over the last year for flights from Valparaiso, Florida to Chicago, removes the top 0.1% to account for outliers, and then takes the median of all values for each month.
The cheapest month for flights from Valparaiso, Florida to Chicago is February, where tickets cost $95 on average. On the other hand, the most expensive months are August and October, where the average cost of tickets is $558 and $483 respectively.

How far in advance should I book a flight from Valparaiso, Florida to Chicago?

To calculate daily average prices, KAYAK takes all prices for each day before departure over the last year for flights from Valparaiso, Florida to Chicago, removes the top 0.1% to account for outliers, and then takes the average of all the values for each month.
To get a below average price on the flight from Valparaiso, Florida to Chicago, you should book around 1 day before departure. For the absolute cheapest price, our data suggests you should book 45 days before departure.

Which airlines fly non-stop between Valparaiso, Florida and Chicago?

Airline and price data is aggregated from results in KAYAK’s search results from the last 2 weeks for flights from Valparaiso, Florida to Chicago.
There are 2 airlines that fly nonstop from Valparaiso, Florida to Chicago. They are Allegiant Air and American Airlines. The cheapest airline for this route is Allegiant Air, with the best one-way deal found costing $77. On average, the best prices for this route can be found at Allegiant Air.

How many flights are there between Valparaiso, Florida and Chicago per day?

Each day, there are between 1 and 2 nonstop flights that take off from Valparaiso, Florida and land in Chicago, with an average flight time of 2h 25m. The most common departure time is 4:00 pm and most flights take off in the morning, while the most flights land at Chicago Midway Airport. Each week, there are 8 flights. The most frequent day of departure is Monday, when 25% of all weekly flights depart. The fewest flights depart on a Thursday.

Which cabin class options are there for flights between Valparaiso, Florida and Chicago?

The average price of flights for each cabin class for the route found by users searching on KAYAK over the last 2 weeks.
There are 2 cabin class options for the route. These are First and Economy. Perform a search on KAYAK to find the latest prices and availability for all cabin fares, which differ across airlines.

How long does a flight from Valparaiso to Chicago take?

A direct flight to Chicago will take on average 2h 18m to travel the 789 miles flying distance from Valparaiso.

What’s the earliest departure time from Valparaiso to Chicago?

Early birds can take the earliest flight from Valparaiso, Florida at 8:59 am and will be landing in Chicago at 11:18 am.

What’s the latest departure time from Valparaiso to Chicago?

If you prefer to fly at night, the latest flight from Valparaiso, Florida to Chicago jets off at 6:13 pm and lands at 8:33 pm.

Good to know

Low season

April

High season

May

Cheapest flight

$103
Best time to beat the crowds but there is an average 16% increase in price.
Most popular time to fly and prices are also 36% lower on average.
Flight from Valparaiso to Chicago Midway Airport

When to book flights from Valparaiso to Chicago

Are your dates flexible? Find out the best times to travel from Valparaiso to Chicago based on our flight data from the last year. Discover the cheapest month and even day to fly.
Estimated round-trip price
KAYAK looks at all historical flight data for each date to provide a predicted price for one-way trips or round-trips with a duration up to 40 days. While we try to provide actual minimum prices for each date, some prices are predictions and actual prices may differ.

FAQs for booking flights from Valparaiso to Chicago

  • What is the cheapest flight from Valparaiso, Florida to Chicago?

    In the last 3 days, the lowest price for a flight from Valparaiso, Florida to Chicago was $103 for a round-trip ticket.

  • Do I need a passport to fly between Valparaiso and Chicago?

    Even though you are not required to have a passport, keep in mind that an official ID is needed to board the airplane.

  • Which airports will I be using when flying from Valparaiso to Chicago?

    When flying out of Valparaiso you will be using Valparaiso Destin-Ft Walton Beach. You will be landing at one of these airports: Chicago Midway or Chicago O'Hare Intl.

  • Which airlines offer Wi-Fi service onboard planes from Valparaiso to Chicago?

    Only American Airlines offers inflight Wi-Fi service on the Valparaiso to Chicago flight route.

  • Which aircraft models fly most regularly from Valparaiso to Chicago?

    The Airbus A319 is the aircraft model that flies most regularly on the Valparaiso to Chicago flight route.

  • Which airline alliances offer flights from Valparaiso to Chicago?

    oneworld is the only airline alliance operating flights between Valparaiso and Chicago.

  • On which days can I fly direct from Valparaiso to Chicago?

    You can catch a nonstop flight from Valparaiso to Chicago on on Monday, Thursday, Friday, Saturday, and Sunday.

  • Which is the best airline for flights from Valparaiso to Chicago, Delta or Allegiant Air?

    The two airlines most popular with KAYAK users for flights from Valparaiso to Chicago are Delta and Allegiant Air. With an average price for the route of $419 and an overall rating of 8.0, Delta is the most popular choice. Allegiant Air is also a great choice for the route, with an average price of $140 and an overall rating of 7.4.

  • How does KAYAK find such low prices on flights from Valparaiso to Chicago?

    KAYAK is a travel search engine. That means we look across the web to find the best prices we can find for our users. With over 2 billion flight queries processed yearly, we are able to display a variety of prices and options on flights from Valparaiso to Chicago.

  • How does KAYAK's flight Price Forecast tool help me choose the right time to buy my flight ticket from Valparaiso to Chicago?

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight to Chicago from Valparaiso is likely to change within 7 days, so travelers know whether to wait or book now.

  • What is the Hacker Fare option on flights from Valparaiso to Chicago?

    Hacker Fares allow you to combine one-way tickets in order to save you money over a traditional round-trip ticket. You could then fly to Chicago with an airline and back to Valparaiso with another airline.

  • What is KAYAK's "flexible dates" feature and why should I care when looking for a flight from Valparaiso to Chicago?

    Sometimes travel dates aren't set in stone. If your preferred travel dates have some wiggle room, flexible dates will show you all the options when flying to Chicago from Valparaiso up to 3 days before/after your preferred dates. You can then pick the flights that suit you best.

See more FAQs

Top tips for finding a cheap flight from Valparaiso to Chicago

  • Looking for a cheap flight? 25% of our users found flights on this route for $67 or less one-way and $91 or less round-trip.

Prefer to fly non-stop from Valparaiso to Chicago?

Find which airlines fly direct from Destin-Ft Walton Beach to Chicago, which days they fly and book direct flights.

Nonstop departures

Valparaiso Destin-Ft Walton Beach to Chicago

Monday

Allegiant Air

Allegiant Air

Thursday

Allegiant Air

Allegiant Air

Friday

Allegiant Air

Allegiant Air

Saturday

American Airlines, Qatar Airways

American Airlines, Qatar Airways

Sunday

Allegiant Air

Allegiant Air

See more direct flights

Nonstop returns

Chicago to Valparaiso Destin-Ft Walton Beach

Monday

Allegiant Air

Allegiant Air

Thursday

Allegiant Air

Allegiant Air

Friday

Allegiant Air

Allegiant Air

Saturday

American Airlines

American Airlines

Sunday

Allegiant Air

Allegiant Air

See more direct flights
See more direct flights

Top 3 airlines serving from Valparaiso to Chicago

 
See real verified KAYAK customer reviews for airlines flying from Valparaiso to Chicago. Airline scores are aggregated from all reviews left by passengers on KAYAK after flying with an airline. KAYAK doesn’t show reviews that are older than 5 years. Learn how KAYAK collects reviews.
Need help choosing which airline to fly with from Valparaiso to Chicago? KAYAK airline reviews give an overall score for each airline based on loads of factors, including comfort, boarding, in-flight entertainment and more, to make your decision easier. See airline scores according to verified KAYAK customer reviews.
8.0
DeltaOverall score based on 10951 reviews
7.9comfort
7.4food
8.2boarding
8.0entertainment
8.6crew
Airline reviews

I liked the ease of checking in, luggage check in, wheel chair assistance, boarding and flight.

10.0 ExcellentAnonymous, Apr 2024PNS - ATL
Read more about Delta reviews

I liked the ease of checking in, luggage check in, wheel chair assistance, boarding and flight.

I usually have a positive experience with Delta. Complimentary upgrades are always nice!

The main person that was coordinating everything was a short white/light skin Spanish man and he was very rude. It honestly made me feel like it was everyone’s First day at work. His announcements were very not reasonable and they did not make sense. The stewardess on the flight that made the announcements she didn’t even know what she was talking about she sounded inebriated. There were no snacks or drinks on our flight there wasn’t even much turbulence. This flight was not enjoyable nor was it what a Delta flight should be and just this past week I flew with Delta 3 times.

nothing Delta could do... the person sitting next to me was huge and overflowing into my seat

Crew was great! I need wheelchair assistance and they knew who I was and updated me that my chair was on its way and to just hang tight. There was some turbulence but the captain announced we would be going thru it and he handled the plane well. Landing was soft and his.

Aircraft very cramped. Check-in was great with an agent helping us. Food was almost non-existent. Pre-flight went well once I got the app reloaded on my phone since we don’t fly much anymore.

I like that it got us where we were going. Everything else needed work. It was 1/2 hour late and we took off an hour late. The plane had to be cleaned and the disabled loaded on board before we could take off which took forever and then we sat at the terminal FOREVER before we took off. The ride was so bumpy that they couldn’t serve drinks and snack but to about 1/2 the plane. Seriously we should have flown out of Fort Lauderdale. We probably would’ve gotten home several hours earlier.

Flight was on time, the staff was personable & professional, & the plane arrived on time.

Flight was great. DELTA did a fantastic job! FLL airport was chaotic!

You lost my luggage!!! How frustrating!!! Now they can’t find one of our bags!!!! I really don’t have time for this!!!

The net issue I had was with the gate agent. We had added a carryon to our boarding pass when we checked bags. When I got to the boarding gate the agent was rude asking why I had a backpack - I said I added it - even had an orange tag on it. She ripped my tag off and swung her monitor around to show me how she was right- saying it isn’t wasn’t listed - only a checked bag. I explained again that I wasn’t sure what the issue was but I wouldn’t have an orange tag if I hadn’t added it. Then she finally checked my husband’s boarding pass and found that the agent at checkin had added my carryon to his boarding pass instead of mine. She sent me on my way without my orange tag. Was a bit embarrassing for me the tone she used with me assuming I was trying to get away with something.

Gate agent asked if I could switch seats so a family could sit together. Agent moved me to a seat in the front of the plane, no charge. It was easy. The agent did a great job.

Great seat space. However food and drink prices outrageous. Jabbing to pay for a carry on bag or stuck paying at the gate too much.

Every Allegiant Air flight I've ever taken has been delayed. This flight was delayed a full 2 hours. It was excuse after excuse after excuse. It was a flight from southern Florida. They made us board the plane on time, but made us wait for 2 hours on the tarmac. Because the engines were kept shut off, so was the air conditioning. One can only imagine how hot the air was in the cabin over those 2 hours on the tarmac, while in the hot Florida sun. Just terrible.

Actually, for the price, I'm willing to put up with a little discomfort (upright chairs) and at times inconveniences (like any airline), lack of entertainment (I can bring my own). My flight was non stop and smooth. I would fly this route again.

The flight was delayed 6 hours and we were only offered an $8 food credit. My husband stood in line to get the credit for 45 minutes and when he got close to the end of the line the computers went down.

Worst ever! Flight cancelled supposedly for weather even though we k ow of many others who flew into Bangor same time no problem. At the airport there was no customer service at all just refund and no possibility of rebook for 3-4 days. Aweful won’t fly with them again!!

It’s a budget airline so adjust expectations accordingly. Nothing is without a fee but such is necessary for tickets to remain so affordable.

My daughter dropped her cell phone right through the crack between walkway and plane. Right in front of myself, the lead flight attendant and crew below. In slow motion we all watched. The crew was on it as they got her phone back to her. Surprisingly, not damaged! This same head flight attendant was hilarious on the speaker! Loved his humor! Pilots were very clear to hear. Sometimes there’s a lot of noise interference or they sound muffled, but this time I could understand everything that was spoken. One more positive experience was renting a car through Allegiant which was my first time. We got a great car deal through Alamo and the car was really nice too, 2024 Blazer.

We waited for our captain to arrive and she made our flight take off 20 minutes late.

This flight is frequently delayed. The connections seemingly are more frequently delayed. I’ve missed connections as a result twice on the same route to charlotte then Charleston. Final destination arrival has been the next day, twice in a row. No pilots, no crew. Too many excuses. Unfortunately, my days with American are over.

Entertainment was okay not because anything was wrong but it is a short flight so having no wifi is annoying but understandable. Crew was outstanding as usual

Those seats were way too narrow. I had the middle seat, one person was a very skinny person and we still couldn’t avoid touching each other anytime one of us moved. The other person was larger and we were basically sitting in each others lap the entire flight. There was zero entertainment. The flight was long enough to justify tvs, but no. Gotta sit there in your infant seat and twiddle your thumbs.

Flight was fine. It took an unusually long time to have baggage delivered to the carousel in ORD.

Average - flew with Jet Blue internal and it was far more comfortable and better food and entertainment. Notable difference

The flight got canceled due to mechanical issues, and he to be rebooked and missed my appointments for that day

The flight was scheduled to depart DCA at 12:30 pm but was delayed twice on the ground so that we were finally scheduled to depart at around 4:00 pm. Once we boarded, it was announced that takeoff would be delayed again to fix a hydraulic problem which delayed our eventual takeoff until around 5:00 pm. Once we departed, it was a smooth flight back to ORD. We did not get any explanation about what caused the original significant delay. In my experience, this happens frequently with AA.

The only problem experienced was a ground stop in Chicago due to weather. But the crew handled everything professionally. They prioritized rebooking those passengers who had connecting flights and then deplaning the other passengers. When the hold was lifted, they efficiently re-boarded all the passengers so that we could depart before our departure limit expired.

Our second leg to Jackson WY was unable to land due to weather. We were flown back to Dallas after stopping in SLC. We were given hotel rooms and vouchers. We were told that we would be back on the same plane in the morning. Instead we were given a different flight with different seats. Not a good experience. No one knew what was going on.

Turn on the heat. Flight was way too cold from Arizona to Chicago.

Last minute flights from Valparaiso to Chicago

Last minute flight, train and bus deals

 
These last-minute flight deals are the cheapest flights found on KAYAK in the last 72 hours for flights from Valparaiso to Chicago that are departing in the next 10 days.
5/2Thu
nonstopAllegiant Air
2h 20mVPS-MDW
5/5Sun
nonstopAllegiant Air
2h 15mMDW-VPS
$98
5/1Wed
multi-stopDelta
4h 46mVPS-ORD
5/4Sat
multi-stopDelta
6h 31mORD-VPS
$256
5/2Thu
multi-stopDelta
5h 55mVPS-MDW
5/5Sun
multi-stopDelta
5h 02mMDW-VPS
$256
5/2Thu
multi-stopDelta
7h 09mVPS-MDW
5/5Sun
multi-stopDelta
5h 02mMDW-VPS
$289
5/2Thu
multi-stopDelta
7h 09mVPS-MDW
5/5Sun
multi-stopDelta
5h 02mMDW-VPS
$303
4/29Mon
multi-stopDelta
4h 19mVPS-ORD
5/3Fri
multi-stopDelta
6h 49mORD-VPS
$386
4/29Mon
multi-stopDelta
5h 44mVPS-MDW
5/3Fri
multi-stopDelta
4h 26mMDW-VPS
$464
5/1Wed
multi-stopAmerican Airlines
5h 02mVPS-ORD
5/4Sat
nonstopAmerican Airlines
2h 27mORD-VPS
$585
4/29Mon
multi-stopAmerican Airlines
7h 26mVPS-ORD
5/3Fri
multi-stopAmerican Airlines
8h 42mORD-VPS
$598
4/29Mon
multi-stopAmerican Airlines
11h 49mVPS-ORD
5/3Fri
multi-stopAmerican Airlines
13h 03mORD-VPS
$767

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Valparaiso - Chicago Flights

Departure:

Valparaiso (VPS)United States

Return flight deals:

Chicago - Valparaiso

Cabin classes:

$85