CHI - VPS

$54 Find Cheap Flights from Chicago to Valparaiso

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 6/12. 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
1 adult, Economy, 0 bags

KAYAK searches 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
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Everything you should know

Cheapest round-trip
$88
Allegiant Air
Sun 4/26Thu 4/30
MDW - VPS • Non-stop
Cheapest one-way
$54
Allegiant Air
Fri 6/12
MDW - VPS • Non-stop
Advice from real travelers
AI-powered summary based on content written by travel experts. AI can make mistakes.
American Airlines' Main Cabin Extra includes early boarding.
Allegiant's Bonus bundle covers carry-on and seat choice.
Expert advice
Expert advice
Expert advice
Expert advice
Nonstop flights
You can fly direct with American Airlines and Allegiant Air. Average duration is 2h 17m
Direct flights
Direct flights
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Direct flights
Direct flights
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Top routes
Cheapest • 46% average savings
Most popular
Insights
Insights
Insights
Insights
Top layover airports
Cheapest • Avg $313 (round-trip)
Shortest trip • 4h 14m (one-way)
Insights
Insights
Insights
Insights
When to book
in advance
Our data shows that travelers who book at least 3 weeks in advance save around 35% compared to booking last minute.
Insights
Insights
Insights
Insights
When to travel
Cheapest • 42% price drop
Most popular
Good to know
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KAYAK searches 100s of sites at once to find you the best travel deals.
We hope you love your trip to Valparaiso!
Flight Deals
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Expert advice
Flight Deals

Cheap Flights 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 for you by selecting your travel dates on KAYAK.

Recent round-trip flight deals from Chicago to Valparaiso

Sun, Apr 26 - Thu, Apr 30
Allegiant Air Logo
5:47 pm - 7:56 pm
MDW
-
VPS
2h 09mnonstop
Allegiant Air Logo
4:05 pm - 6:22 pm
VPS
-
MDW
2h 17mnonstop
$88Allegiant Air
Sun, Apr 19 - Thu, Apr 23
Allegiant Air Logo
5:47 pm - 7:56 pm
MDW
-
VPS
2h 09mnonstop
Allegiant Air Logo
4:05 pm - 6:22 pm
VPS
-
MDW
2h 17mnonstop
$120Allegiant Air
Sun, Apr 5 - Thu, Apr 16
Allegiant Air Logo
5:47 pm - 7:56 pm
MDW
-
VPS
2h 09mnonstop
Allegiant Air Logo
4:05 pm - 6:22 pm
VPS
-
MDW
2h 17mnonstop
$137Allegiant Air
Sun, May 17 - Fri, May 22
Multiple Airlines Logo
6:00 am - 2:58 pm
MDW
-
VPS
32h 58m
3 stops
Multiple Airlines Logo
1:19 pm - 3:38 pm
VPS
-
MDW
2h 19mnonstop
$236Multiple Airlines
Mon, Apr 27 - Sun, May 10
Multiple Airlines Logo
11:28 am - 8:48 am
ORD
-
VPS
21h 20m
2 stops
Multiple Airlines Logo
6:15 pm - 7:06 pm
VPS
-
ORD
24h 51m
1 stop
$341Multiple Airlines
Sun, Apr 19 - Wed, Apr 22
Sun Country Air Logo
7:20 am - 5:12 pm
ORD
-
VPS
9h 52m
1 stop
Sun Country Air Logo
2:07 pm - 6:18 pm
VPS
-
ORD
28h 11m
1 stop
$346Sun Country Air
Tue, Apr 14 - Tue, Apr 21
Southwest Logo
2:40 pm - 9:00 pm
ORD
-
VPS
6h 20m
1 stop
Southwest Logo
7:15 am - 12:50 pm
VPS
-
ORD
5h 35m
1 stop
$355Southwest
Tue, May 19 - Wed, May 27
American Airlines Logo
9:41 am - 12:15 pm
ORD
-
VPS
2h 34mnonstop
American Airlines Logo
11:17 am - 2:00 pm
VPS
-
ORD
2h 43mnonstop
$356American Airlines
Tue, Apr 14 - Tue, Apr 21
Southwest Logo
2:40 pm - 9:00 pm
ORD
-
VPS
6h 20m
1 stop
Southwest Logo
7:15 am - 6:25 pm
VPS
-
ORD
11h 10m
2 stops
$361Southwest
Fri, May 15 - Mon, May 18
Sun Country Air Logo
8:06 pm - 11:06 am
ORD
-
VPS
15h 00m
1 stop
Sun Country Air Logo
12:06 pm - 7:06 pm
VPS
-
ORD
7h 00m
1 stop
$362Sun Country Air
Booking Insights

KAYAK's insights & trends for Chicago to Valparaiso flights

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.

How much is a round-trip flight from Chicago to Valparaiso, Florida?

This analysis is based on the cheapest round-trip price found on KAYAK in the last 12 months by searching for a flight from Chicago to Valparaiso, Florida departing in April.

What is the cheapest Chicago to Valparaiso flight route?

Data is based on round-trip flight searches on KAYAK over the past month.

The cheapest return flight from Chicago to Valparaiso costs $138 on the route between Chicago Midway Airport (MDW) and Valparaiso (VPS). Over the past month, this route was, on average, 46% cheaper than other Chicago-Valparaiso routes. It is also the most popular route.

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

The average price of all round-trip flights from Chicago to Valparaiso clicked on KAYAK for each day over the last 12 months.

When flying from Chicago to Valparaiso, you should consider leaving on a Tuesday and avoid Sundays if you are looking for the best rates. For your return to Chicago, you’ll find the best rates on Wednesdays and the most expensive ones on Mondays.

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

To calculate monthly average prices, KAYAK takes all prices for each month over the last year for round-trip flights from Chicago to Valparaiso, 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 is October, where tickets cost $199 (return) on average. On the other hand, the most expensive months are March and January, where the average cost of round-trip tickets is $453 and $397 respectively.

Can I save money by flying with a layover from Chicago to Valparaiso?

The average round-trip price for all non-stop flights, flights with one layover, and flights with two layovers for the route found by users searching on KAYAK in the last 2 weeks.

No, with an average price for the route of $317, prices are generally cheapest when you fly direct.

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

To calculate weekly average prices, KAYAK takes all prices for each week before departure over the last year for round-trip flights from Chicago to Valparaiso, removes the top 0.1% to account for outliers, and then takes the average of all the values for each week.

To get a below average price on the flight from Chicago to Valparaiso, you should book around 3 weeks before departure, which saves you about 35% compared to booking last minute. For the absolute cheapest price, our data suggests you should book 6 weeks before departure.

Expert advice

Expert advice for your flight from Chicago to Valparaiso

 
AI-powered summary based on content written by travel experts. AI can make mistakes.
KAYAK teamed up with top travel experts to share the best tips for your journey.
Our travel experts
Harriet Baskas

Harriet Baskas

Expert on American Airlines

Harriet is an award-winning journalist who is happiest in an airport or an unusual museum. Her stories about airports, air travel, and the business of travel have appeared on NBC News, CNBC, USA TODAY, The Points Guy and other outlets. She is the creator of the StuckatTheAirport.com blog and the author of nine books. When not out on the road or exploring the latest airport amenities, she’s home in Seattle getting ready for the next adventure.

Daniel Scheffler

Daniel Scheffler

Expert on Allegiant Air

Daniel Scheffler is a travel writer, podcaster, and producer. Born in Africa, bred in Europe and now living in America he has traveled to 140 countries (and all 50 U.S. states). Plus he has stayed at over 2500 hotels across the globe. His original shows Everywhere and Without Maps (available on Spotify) showcase his beliefs, travel is about humanity and sharing that beauty. And thus it reminds you that you shouldn’t believe everything you think.

Good to know

Low seasonJanuary
Cheapest flight$54
Best time to beat the crowds but there is an average 16% increase in price.
Most popular time to fly and prices are also 32% lower on average.
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?

    In the last 3 days, the lowest price for a flight from Chicago to Valparaiso was $54 for a one-way ticket and $88 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 Embraer 175 is the aircraft model that flies most regularly on the Chicago to Valparaiso flight route.

  • Which airline alliances offer flights from Chicago to Valparaiso?

    SkyTeam, and oneworld are the airline alliances operating flights between Chicago and Valparaiso, with SkyTeam being the most commonly used for this route.

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

    There are nonstop flights from Chicago to Valparaiso on a daily basis.

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

    The two airlines most popular with KAYAK users for flights from Chicago to Valparaiso are Southwest and Delta. With an average price for the route of $346 and an overall rating of 8.0, Southwest is the most popular choice. Delta is also a great choice for the route, with an average price of $383 and an overall rating of 7.9.

  • 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.

KAYAK’s 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 $115 or less one-way and $304 or less round-trip.

Prefer to fly direct from Chicago to Valparaiso?

 
Direct data is based off flight results for the next 60 days. Find direct flights from all airlines flying direct from Chicago to Valparaiso Destin-Ft Walton Beach.
Find which airlines fly direct from Chicago to Valparaiso Destin-Ft Walton Beach Airport, which days they fly and book direct flights.

Direct departures

Chicago to Valparaiso Destin-Ft Walton Beach

Monday

American Airlines,Allegiant Air

American Airlines,Allegiant Air

Tuesday

American Airlines

American Airlines

Wednesday

American Airlines

American Airlines

Thursday

Allegiant Air,American Airlines

Allegiant Air,American Airlines

Friday

American Airlines,Allegiant Air

American Airlines,Allegiant Air

Saturday

American Airlines

American Airlines

Sunday

Allegiant Air,American Airlines

Allegiant Air,American Airlines

See more direct flights

Direct returns

Valparaiso Destin-Ft Walton Beach to Chicago

Monday

American Airlines,Allegiant Air

American Airlines,Allegiant Air

Tuesday

American Airlines

American Airlines

Wednesday

American Airlines

American Airlines

Thursday

Allegiant Air,American Airlines

Allegiant Air,American Airlines

Friday

American Airlines,Allegiant Air

American Airlines,Allegiant Air

Saturday

American Airlines

American Airlines

Sunday

Allegiant Air,American Airlines

Allegiant Air,American Airlines

See more direct flights

Reviews of the 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
SouthwestOverall score based on 4318 reviews
8.1Boarding
8.6Crew
7.5Entertainment
8.0Comfort
7.0Food
Airline reviews

It was canceled. Supposedly weather. But there was no snow in Baltimore. At least we found out before driving to airport

2.0 MediocreAnonymous, Feb 2026
BWI - PBI
Read more Southwest reviews

It was canceled. Supposedly weather. But there was no snow in Baltimore. At least we found out before driving to airport

The staff was very friendly, professional, and courteous. The overall flight was a great experience.

Okay, not wonderful. Short flight. Wi-fi didn't work properly. Stuck waiting for a gate to open upon arrival for 20 or so minutes.

They sent a notice that they were boarding an hour early. We had to leave the club and run to the gate. They said sorry, that came from corporate and was a mistake. They did not have enough seating because the flight before it had not taken off on time. They moved our gate and delayed it for an hour.

Plane crashed into a bus or some other vehicle on the ground while pulling out of the gate. No injuries, but wing tip was damaged and returned to gate for “maintenance issues” and we departed 5 hours later because the plane went out of service and new plane was flown in from a nearby airport, Midway.

All was good. I just had a hard time getting connected to the WiFi/internet during the flight

Better and more food and drinks. Put msnbc and free speech tv on the news channel selection list.

The quality of Southwest Airlines continues to degrade each time I fly with them. If it were not for the free luggage, I would probably choose another airline. Their prices are a little bit competitive, but way too high for the quality of the service. Southwest is not unique in this way. Domestic flight in the United States of America has continued to be a lower and lower quality product. Very sad when you compare the quality of domestic airlines to that of many international airlines around the world.

after landing, we stay 2 hours on the taxi way before reaching the gate The airline and the crew were good though

I'm not a fan of Southwest's model. I don't like the herding style of boarding.

Stop changing gates. Stop cancelling flights Stop moving my seat.

The whole experience was excellent. As it most often is with Delta

We waited an hour on the runway to get a gate in Orlando

Flight was delayed by 3-hours and their fix was… complimentary pretzels.

The staff on board and gate was nice - a welcome change from the usual. We also arrived early, which was a great benefit, given that it takes 30 minutes plus to get bags at SRQ.

The staff was frielndly. The plane was terrible, it was too small and should be decommissioned. There were no back seat screens at all. The only beverages we had a choice from was coffee, tea or water. The only bathroom in the back was behind the flight attendant's jump seat and wasn't working. And I literally felt like I was sitting on top of the guy next to me. It was terribly hot in the plane and we had to sit on the tarmac in Chicago for 1/2 hour due to congestion in Mpls. Wouldn't they have know that before they even boarded us so that we could have sat in comfort in the terminal?

They took all carry-on luggage from Groups 6 -9 - I was group 5 and waiting in line to board - they made me check my luggage too. That then went to baggage claim and delayed departure from the airport. There was overhead room in my seating area - Delta over reacted. Also, had a gentleman next to me that took up 1/2 my seat.

Sorry I didn't realize I was writing a review for each leg. Please see my previous review - it applies to the entire flight, not just a single leg.

boarded at 5:30 pm, pushed away from gate at 6pm ... takeoff was not until ~6:45pm; disappointing

Paid for wifi that didn't work. No plug in seat to work. No entertainment.

Superb. Staff great. Great flight. As with other airlines, seating too tight and restrictive.

There is not one likable thing about this airline. It’s starts with the deceptive pricing and continues through the whole flight. The worst staff I’ve ever experienced way over priced bags absolutely no food or drink (unacceptable and you should be embarrassed) the seats are cramped and uncomfortable there is no entertainment there is nothing about this trash airline that constitutes any amount of money. It’s worse than spirit and way more expensive it is disgraceful. Do not travel with Allegiant I repeat do not bother no matter what they say the price is it is never ever going to be the right choice I’m mind blown at how awful the entire experience was I’m embarrassed that I chose so poorly I cannot reiterate enough how beyond horrible this company and its staff are, not one person on this flight or at the airport is qualified to sweep up trash on a city sidewalk they should certainly never be given any job that requires a brain or manners or communication with human beings, what a disgrace to the human race. Your criminal chiselers and should be put out to pasture

Great flight. Friendly staff. Free snacks and drinks would be nice. I would love fewer taxes and fees added on.

My 90 year old father flew with me. He needed wheel chair assistance and is nearly deaf. The staff was amazing with him.

It was fine. Nobody was outstandingly friendly but no one was rude and everything was smooth . The captain thanked us for flying but no one greeted me as I walked on the plane or as I exited which is the least they could do lol

Clean, friendly, roomy. But check-in from the phone link was terrible. Repeated attempts wouldn’t save at the final step. Just kept spinning! It was very frustrating. Finally, I used the app (vs website link) to check-in which worked very smoothly on the first attempt.

Check in on the web portal was cumbersome! After several attempts I finally got the boarding pass.

Excellent flight and even arrived 23 min early. No entertainment , or wi fi on board, but I downloaded a couple of movies beforehand which kept me entertained. Really like flying Allegiant airlines.

WE were delayed about an hour and never any communications from the employees working the gate. We also were moved to a total of three gates.

I love how they show love to their customers and care about them too.

The gate got changed several times and the flight was delayed over an hour. Awful experience

American continues to decline in their customer service and its beyond disappointing.

It was an older plane. First Class was not especially roomy or comfortable. It was a short flight so there were no meal but they did offer mixed nuts which used to be normal but now is rare. Crew member was very polite and professional.

Flight to Tampa was delayed taking off due to plane arriving late but no other issues

As previously stated the delay I experienced flying from Wichita to Chicago caused a host of issues. When I finally was able to be booked on the last remaining American flight from Chicago to Cincinnati, the gate changed four times with the last change occurring very near the scheduled boarding time. While I didn't have a problem moving from gate to gate, I did notice and make note of others that had mobility issues and had to move each time for the gate change.

Maintenance took a very long time and then we were in a holding pattern. While a one-off maintenance issue is standard, there were delays on both of my flights for this trip based on maintenance issues with the planes, which delayed both flights over 45 minutes. Thankfully, I didn't have any connections but it wasn't an experience that would make me pick AA if I have other options.

No Snacks or Entertainment. The flight was short, snacks should still be given.

See prior comment about how Kayak mishandled my reservation and delayed my arrival by 6 hours.

Boarding delayed 20 minutes for no reason, no wifi, in flight entertainment, or snacks / waters?

Delayed an hour due to operational issues. Minimal apologies or care for the significant inconvenience caused. Landed at nearly 1am and they still couldn’t find ground staff to get us off the plane promptly.

Everything you need to know for your flight from Chicago to Valparaiso

Information on your arrival and departure airports