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CHI - VPS

Find cheap flights from Chicago to Valparaiso from $48

This is the cheapest one-way flight price found by a KAYAK user in the last 72 hours by searching for a flight from Chicago to Valparaiso departing on 5/20. 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
Sun 5/19
Sun 5/26

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

 
These are the airlines KAYAK users have selected most often from within our search results in flight searches from Chicago to Valparaiso, 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 Chicago to Valparaiso, as well as popular online travel agencies
In the last 7 days travelers have searched 44,212,662 times on KAYAK, and here is why:

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

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

Here are some of the best deals found on KAYAK recently from the most popular airlines for round-trip flights from Chicago to Valparaiso 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
12:08 pm - 2:11 pmMDW-VPS
2h 03mnonstop
8:59 am - 11:18 amVPS-MDW
2h 19mnonstop
$127Allegiant Air
Find Deal
Fri, May 31 - Mon, Jun 3
12:08 pm - 2:11 pmMDW-VPS
2h 03mnonstop
8:59 am - 11:18 amVPS-MDW
2h 19mnonstop
$128Allegiant Air
Find Deal
Fri, May 31 - Mon, Jun 3
12:03 pm - 2:06 pmMDW-VPS
2h 03mnonstop
9:00 am - 11:18 amVPS-MDW
2h 18mnonstop
$145Allegiant Air
Find Deal
Fri, Jun 28 - Fri, Jul 5
12:15 pm - 7:19 pmORD-VPS
7h 04m1 stop
7:00 am - 12:40 pmVPS-ORD
5h 40m1 stop
$239American Airlines
Find Deal
Tue, May 7 - Wed, May 22
6:30 am - 11:58 amORD-VPS
5h 28m1 stop
3:49 pm - 11:00 pmVPS-ORD
7h 11m1 stop
$241American Airlines
Find Deal
Mon, May 13 - Thu, May 16
9:36 am - 5:06 pmORD-VPS
7h 30m1 stop
5:05 pm - 11:55 pmVPS-ORD
6h 50m1 stop
$242Delta
Find Deal
Tue, May 7 - Wed, May 8
6:00 am - 11:02 amMDW-VPS
5h 02m1 stop
4:30 pm - 10:50 pmVPS-MDW
6h 20m1 stop
$242Delta
Find Deal
Sun, Apr 28 - Thu, May 2
8:00 am - 5:08 pmORD-VPS
9h 08m1 stop
1:49 pm - 9:55 amVPS-ORD
20h 06m2 stops
Sun, May 12 - Fri, May 17
10:57 pm - 8:01 pmORD-VPS
21h 04m2 stops
1:49 pm - 9:55 amVPS-ORD
20h 06m2 stops
Sun, May 12 - Fri, May 17
7:00 am - 5:25 pmORD-VPS
10h 25m1 stop
6:20 pm - 6:19 pmVPS-ORD
23h 59m1 stop
$314Sun Country Air
Find Deal
Thu, Jul 18 - Sun, Jul 21

Flights from Chicago to Valparaiso - Travel Insights & Trends

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

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

The cheapest price for flight routes found by users searching on KAYAK in the last 2 weeks for one-way flights from Chicago to Valparaiso, Florida.
Our data shows that the cheapest route for a one-way flight from Chicago to Valparaiso, Florida cost $48 and was between Chicago Midway Airport and Valparaiso, Florida. On average, the best prices are found if you fly this route. The average price for a return flight for this route is $98.

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

The average price of all flights from Chicago to Valparaiso, Florida clicked on KAYAK for each day over the last 12 months.
Your flight ticket price will generally be cheaper if you fly to Valparaiso on a Monday and more expensive on a Sunday. On your return trip to Chicago, you should consider flying back on a Tuesday, and avoid Sundays for better deals.

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

To calculate monthly average prices, KAYAK takes all prices for each month over the last year for flights from Chicago to Valparaiso, Florida, 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 Chicago to Valparaiso, Florida is January, where tickets cost $176 on average. On the other hand, the most expensive months are March and December, where the average cost of tickets is $435 and $434 respectively.

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

To calculate daily average prices, KAYAK takes all prices for each day before departure over the last year for flights from Chicago to Valparaiso, Florida, 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 Chicago to Valparaiso, Florida, you should book around 1 day before departure. For the absolute cheapest price, our data suggests you should book 66 days before departure.

Which airlines provide the cheapest flights from Chicago to Valparaiso?

The cheapest price for the route for each airline clicked by KAYAK users in the last 72 hours.
In the last 72 hours, the best return deals on flights connecting Chicago to Valparaiso were found on Allegiant Air ($127) and American Airlines ($239). Allegiant Air proposed the cheapest one-way flight at $48.

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

Airline and price data is aggregated from results in KAYAK’s search results from the last 2 weeks for flights from Chicago to Valparaiso, Florida.
There are 2 airlines that fly nonstop from Chicago to Valparaiso, Florida. They are Allegiant Air and American Airlines. The cheapest airline for this route is Allegiant Air, with the best one-way deal found costing $82. On average, the best prices for this route can be found at Allegiant Air.

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

Each day, there are between 1 and 2 nonstop flights that take off from Chicago and land in Valparaiso, Florida, with an average flight time of 2h 15m. The most common departure time is 7:00 pm and most flights take off in the evening. Each week, there are 6 flights. The most frequent day of departure is Saturday, when 33% of all weekly flights depart. The fewest flights depart on a Sunday.

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

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 Economy and Prem 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 Chicago to Valparaiso take?

Nonstop flights from Chicago generally make it to Valparaiso in 2h 03m. The flying distance between the two cities is 789 miles.

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

Early birds can take the earliest flight from Chicago at 8:20 am and will be landing in Valparaiso, Florida at 10:52 am.

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

If you prefer to fly at night, the latest flight from Chicago to Valparaiso, Florida jets off at 9:23 pm and lands at 11:38 pm.

Good to know

Low season

September

High season

June

Cheapest flight

$48
Best time to beat the crowds but there is an average 2% increase in price.
Most popular time to fly with an average 11% increase in price.
Flight from Chicago Midway Airport to Valparaiso

When to book flights from Chicago to Valparaiso

Are your dates flexible? Find out the best times to travel from Chicago to Valparaiso 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 Chicago to Valparaiso

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

    In the last 3 days, the lowest price for a flight from Chicago to Valparaiso, Florida was $48 for a one-way ticket and $127 for a round-trip.

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

    No, a passport isn't needed to fly from Chicago to Valparaiso. However, local authorities might ask for an official ID.

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

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

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

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

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

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

  • Which airline alliances offer flights from Chicago to Valparaiso?

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

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

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

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

    The two airlines most popular with KAYAK users for flights from Chicago to Valparaiso are Delta and Allegiant Air. With an average price for the route of $383 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 $170 and an overall rating of 7.4.

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

    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 Chicago to Valparaiso.

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

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight to Valparaiso from Chicago 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 Chicago to Valparaiso?

    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 Valparaiso with an airline and back to Chicago with another airline.

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

    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 Valparaiso from Chicago 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 Chicago to Valparaiso

  • Looking for a cheap flight? 25% of our users found flights on this route for $51 or less one-way and $132 or less round-trip.

Prefer to fly non-stop from Chicago to Valparaiso?

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

Nonstop departures

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

Nonstop returns

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
See more direct flights

Top 4 airlines serving from Chicago to Valparaiso

 
See real verified KAYAK customer reviews for airlines flying from Chicago to Valparaiso. 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 Chicago to Valparaiso? 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 11094 reviews
7.9comfort
8.0entertainment
7.5food
8.6crew
8.2boarding
Airline reviews

Seat back monitors and outlets were dead and not working.

8.0 ExcellentCarl, Apr 2024JFK - FLL
Read more about Delta reviews

Seat back monitors and outlets were dead and not working.

The experience was good and the flight departed on time and landed early

The flight was delayed but we got to our final destination.

public website still broken for years randomly blocking browsers with privacy options active after loading a page maybe once. check-in on laptop was almost impossible but eventually randomly worked. had to print pass at airport since couldn't get back in to load digital pass on mobile firefox or chrome. red eye flight so smooth onboarding, plenty of room to spread out, easy offboarding. onboard wifi instructions mention vpn can cause problems connecting but fails to also mention private dns. no printed or built in menu list, seems weird to require personal device to point at qr code link for menu which does not even allow direct ordering. people with health condition risk related dietary restrictions trying to avoid for example cholesterol and sugar are left guessing what they can order either way without nutritional info highlights (cranberry juice was minute maid cocktail with as much suger as typical can of soda). tap to pay wasn't working and always seems sketchy to manually enter card info. good movie variety, so limited tv was okay.

Horrible. Flight ORD to CGH was okay, but Paris was a nightmare. Old planes, delays, involuntary downgrades, broken planes, terrible communication. CGH to CPT was my worst flight ever.

Boarding super slow with people allowed to linger in aisles

There were choices for the snacks. Good choices and tasty lunch and breakfast as well.

First time travel in economy and the worst experience I ever had ! Shame on paying 600 dollars to be in a tuna can ! Service was terrible no even water no even class no even matters your flight attendants were lazy and sloppy very bad experience! After all these years traveling in first and once I try this cause I need to go to a destination for an emergency wow shame on you !

Everything was smooth and easy to fly. No complains and a lot of thanks!

More space in the cabin. The guy in front of me leaned his seat back and I felt he was sitting in my lap.

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.

No complaints. It’s a budget airline so can’t expect any frills.

My TSA number was missing from my ticket which shouldn’t have happened since it’s in my file. The on board flight attendant who was a male, did not want to help me put my luggage in the overhead bin and made a very rude comment and was very unpleasant. The good… the woman who fixed my ticket with the TSA number was excellent and I had extra legroom which was perfect.

The flight experience was very good! Especially the United Club!

I was not able to buy food in the flight. They refer to include your Credit card in the APP, and if you are not from USA (i have a credit card form Canada) it is not possible

The flight from Ottawa to Chicago took a lot longer due to DC in Ottawa. We got to Chicago and went to our gate to catch our flight. We only had nine minutes I found that very stressful.

Good boarding. Crew started quick with drinks and food. They came around several times for trash which I really liked. Other than turbulence due to storms in the area, flight was great.

The control panel for the seat back screen did not work at all after takeoff.

Plane was so old it had cigarette butt trays in the seat

Everything was good, hard to really comfortable on a flight that long.

Unfortunately our flight was delayed by 45 minutes due to Kate arriving aircraft. Once we stated everything was great.

For some strange reason I was put in zone 5 for boarding even though I had paid premium price for a premium seat right behind business class. This must have been a flaw because everyone else around me in the same zone (row) had been placed in zone 3.

Nothing bad to say about the actual crew or airline. It was nice to have a complimentary FULL can of soda, as well as a snack. Blankets and earbuds were also provided at no cost for this red eye flight. I especially appreciated the free WiFi and movie selection with the Bluetooth option. It helped the flight pass more quickly. No matter who you fly, boarding and disembarking are always SUCH a pain. As I mentioned, this is on the passengers and not the crew!!

Good flights. Departure and arrivals were on time. DFW was a little problematic in that the Skytrain without prior notice bypassed the Echo terminal so that delayed my arrival at my connecting flight.

Because I can’t stand very long in one place, I was allowed to reword.

5 hour flight - full flight - not enough room to use my computer - slightly delayed - Admirals club was excellent quality food, drink made up for flight seating. No food offerred on flight, you ahd to prebook.

Excellent- plan was barely populated. I cannot remember a flight where I was able/encouraged to stretch out!

Great flight. Boarding was efficient and quick. On time departure and smooth flight. Flight arrived early at destination. Good experience.

Had technical issue which delayed the flight period. Flight crew knew there was 5 passengers that the connecting flight was within 15 minutes once at the gate. Rather than identify the 5 passengers to assure they got first. The flight attended mentioned it but didn't assist to assure passengers with connecting flights off first. This caused a hardship and our party of 3 missed the connecting flight.

I don't like that I have to pay if I want extra leg room. The seats are so expensive; I sit in normal seats and my legs and knees cramp the entire flight. I never feel comfortable on AA flights.

Flight was delayed at departure due to weather and the need for de-icing. The flight was smooth but there was a delay at arrival due to weather. We were in a hold for 20 minutes or more. The flight arrived more than 30 minutes late. Airlines have no control over the weather and I'm glad that they follow all safety procedures. Had to wait a long time for my checked luggage. Whole process was slow and the bags arrived wet due to the rain. The onboard wifi and entertainment access was spotty and the signal was dropped several times. Otherwise the crew was great and friendly. They tried to get everyone's bags stowed and seated so we could take off.

Regarding the boarding: it needs more efforts to make it more convenient

Deicing in Denver took forever and I almost missed my connection. De-ice faster! Not Americans fault.

Book cheap flights from Chicago to Valparaiso

Recent one-way flight deals

 
Only flying one-way? Below are some of the best one-way flight deals from Chicago to Valparaiso found on KAYAK in the last 72 hours.
5/20Mon
nonstopAllegiant Air
2h 03mMDW-VPS
$48
5/2Thu
nonstopAllegiant Air
2h 15mMDW-VPS
$77
5/17Fri
nonstopAllegiant Air
2h 03mMDW-VPS
$83
6/7Fri
nonstopAllegiant Air
2h 03mMDW-VPS
$112
4/25Thu
1 stopAmerican Airlines
7h 41mORD-VPS
$121
4/28Sun
1 stopDelta
5h 30mORD-VPS
$122
6/7Fri
1 stopDelta
4h 27mMDW-VPS
$122
6/29Sat
nonstopAmerican Airlines
2h 25mORD-VPS
$160
5/17Fri
2 stops
18h 10mORD-VPS
$187
5/2Thu
2 stops
23h 51mORD-VPS
$202

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Last minute flights from Chicago to Valparaiso

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 Chicago to Valparaiso that are departing in the next 10 days.
4/23Tue
multi-stopDelta
6h 51mORD-VPS
4/24Wed
multi-stopDelta
7h 52mVPS-ORD
$256
4/20Sat
multi-stopAmerican Airlines
5h 53mORD-VPS
4/23Tue
multi-stopAmerican Airlines
5h 01mVPS-ORD
$267
4/20Sat
nonstopAmerican Airlines
2h 27mORD-VPS
4/23Tue
multi-stopAmerican Airlines
5h 01mVPS-ORD
$339
4/21Sun
multi-stopAmerican Airlines
5h 51mORD-VPS
4/22Mon
multi-stopAmerican Airlines
5h 45mVPS-ORD
$352
4/21Sun
multi-stopDelta
5h 30mMDW-VPS
4/22Mon
multi-stopDelta
7h 26mVPS-MDW
$388
4/21Sun
multi-stopDelta
6h 51mORD-VPS
4/22Mon
multi-stopDelta
4h 19mVPS-ORD
$388
4/23Tue
multi-stop
17h 38mORD-VPS
4/24Wed
multi-stop
31h 11mVPS-ORD
$557
4/21Sun
multi-stopAmerican Airlines
7h 37mORD-VPS
4/22Mon
multi-stopAmerican Airlines
5h 27mVPS-ORD
$620
4/21Sun
multi-stopAmerican Airlines
9h 10mORD-VPS
4/22Mon
multi-stopAmerican Airlines
10h 48mVPS-ORD
$626
4/21Sun
multi-stopAmerican Airlines
6h 46mORD-VPS
4/23Tue
multi-stopAmerican Airlines
5h 24mVPS-ORD
$718

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Flights to Valparaiso

Destination:

Valparaiso (VPS)United States

Return flight deals:

Valparaiso - Chicago

Cabin classes:

$739
$98