VPS - CHI

$69 Find Cheap Flights from Valparaiso to Chicago

This is the cheapest one-way flight price found by a KAYAK user in the last 72 hours by searching for a flight from Valparaiso to Chicago departing on 3/26. 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 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
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Everything you should know

Cheapest round-trip
$101
Allegiant Air
Thu 5/7Sun 5/10
VPS - MDW • Non-stop
Cheapest one-way
$69
Allegiant Air
Thu 3/26
VPS - MDW • 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 offers early boarding.
Allegiant's Bonus bundle includes carry-on and seat selection.
Expert advice
Expert advice
Expert advice
Expert advice
Top airlines
Cheapest • from $101 (round-trip)
Best reviews • 8.0 score
Airline reviews
Airline reviews
+1
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Airline reviews
Airline reviews
+1
Nonstop flights
Every day
You can fly direct with American Airlines and Allegiant Air. Average duration is 2h 31m
Direct flights
Direct flights
+1
+1
Direct flights
Direct flights
+1
Top routes
Cheapest • 22% average savings
Most popular
Insights
Insights
Insights
Insights
When to travel
Cheapest • 58% price drop
Most popular
Good to know
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+1
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Flight Deals

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

Recent round-trip flight deals from Valparaiso to Chicago

Thu, May 7 - Sun, May 10
Allegiant Air Logo
2:40 pm - 4:57 pm
VPS
-
MDW
2h 17mnonstop
Allegiant Air Logo
5:47 pm - 7:56 pm
MDW
-
VPS
2h 09mnonstop
$101Allegiant Air
Thu, Apr 30 - Thu, May 7
Allegiant Air Logo
4:05 pm - 6:22 pm
VPS
-
MDW
2h 17mnonstop
Allegiant Air Logo
5:47 pm - 7:56 pm
MDW
-
VPS
2h 09mnonstop
$111Allegiant Air
Sun, Mar 29 - Thu, Apr 2
Allegiant Air Logo
5:37 pm - 7:53 pm
VPS
-
MDW
2h 16mnonstop
Allegiant Air Logo
5:47 pm - 7:56 pm
MDW
-
VPS
2h 09mnonstop
$212Allegiant Air
Thu, Apr 9 - Thu, Apr 16
Allegiant Air Logo
2:40 pm - 4:57 pm
VPS
-
MDW
2h 17mnonstop
Allegiant Air Logo
7:12 pm - 9:21 pm
MDW
-
VPS
2h 09mnonstop
$226Allegiant Air
Thu, Mar 26 - Mon, Mar 30
Multiple Airlines Logo
5:37 pm - 7:53 pm
VPS
-
MDW
2h 16mnonstop
Multiple Airlines Logo
9:51 pm - 3:12 pm
MDW
-
VPS
17h 21m
2 stops
$329Multiple Airlines
Thu, Mar 26 - Mon, Mar 30
Multiple Airlines Logo
5:37 pm - 7:53 pm
VPS
-
MDW
2h 16mnonstop
Multiple Airlines Logo
9:51 pm - 3:12 pm
MDW
-
VPS
17h 21m
2 stops
$349Multiple Airlines
Tue, May 26 - Tue, Jun 2
Southwest Logo
7:15 am - 12:50 pm
VPS
-
ORD
5h 35m
1 stop
Southwest Logo
2:40 pm - 9:00 pm
ORD
-
VPS
6h 20m
1 stop
$355Southwest
Tue, May 26 - Wed, Jun 3
American Airlines Logo
11:20 am - 2:03 pm
VPS
-
ORD
2h 43mnonstop
American Airlines Logo
8:15 am - 10:50 am
ORD
-
VPS
2h 35mnonstop
$356American Airlines
Tue, May 26 - Tue, Jun 2
Southwest Logo
7:15 am - 12:50 pm
VPS
-
ORD
5h 35m
1 stop
Southwest Logo
11:55 am - 9:00 pm
ORD
-
VPS
9h 05m
2 stops
$361Southwest
Tue, May 26 - Wed, Jun 3
American Airlines Logo
12:59 pm - 6:53 pm
VPS
-
ORD
5h 54m
1 stop
American Airlines Logo
8:15 am - 10:50 am
ORD
-
VPS
2h 35mnonstop
$366American Airlines
Booking Insights

KAYAK's insights & trends for Valparaiso to Chicago flights

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 to Chicago flight route?

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

The cheapest return flight from Valparaiso to Chicago costs $230 on the route between Valparaiso (VPS) and Chicago Midway Airport (MDW). Over the past month, this route was, on average, 22% cheaper than other Valparaiso-Chicago routes. The most popular route is between Valparaiso (VPS) and Chicago O'Hare Intl Airport (ORD).

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

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

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

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

To calculate monthly average prices, KAYAK takes all prices for each month over the last year for round-trip flights from Valparaiso 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 to Chicago is May, where tickets cost $103 (return) on average. On the other hand, the most expensive months are December and January, where the average cost of round-trip tickets is $386 and $376 respectively.

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

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 $297, prices are generally cheapest when you fly direct.

Expert advice

Expert advice for your flight from Valparaiso to Chicago

 
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 seasonApril
Cheapest flight$69
Best time to beat the crowds but there is an average 35% increase in price.
Most popular time to fly and prices are also 59% 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 to Chicago?

    In the last 3 days, the lowest price for a flight from Valparaiso to Chicago was $69 for a one-way ticket and $101 for a round-trip.

  • 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?

    American Airlines, and Delta offer inflight Wi-Fi service on the Valparaiso to Chicago flight route.

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

    The Embraer 175 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?

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

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

    The two airlines most popular with KAYAK users for flights from Valparaiso to Chicago are Southwest and Allegiant Air. With an average price for the route of $280 and an overall rating of 8.0, Southwest is the most popular choice. Allegiant Air is also a great choice for the route, with an average price of $124 and an overall rating of 7.3.

  • 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.

KAYAK’s 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 $287 or less one-way and $298 or less round-trip.

Prefer to fly direct from Valparaiso to Chicago?

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

Direct departures

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

Direct returns

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

Reviews of the 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
SouthwestOverall score based on 4319 reviews
8.0Comfort
8.6Crew
8.1Boarding
7.5Entertainment
7.0Food
Airline reviews

Long layover between flights to Long Island from BWI - need better coordination between flights

4.0 OkayKenny, Mar 2026
TPA - BWI
Read more Southwest reviews

Long layover between flights to Long Island from BWI - need better coordination between flights

I realize they are still working out kinks with the new boarding process, but by the time I boarded in group 5, most of the bins were full. All airlines should better enforce small bags and jackets going under the seats until everyone has boarded.

WiFi was not working and didn’t have a beverage service

An entire day of delays. Cost lots of money. Meals and a hotel.

I appreciate the staff who allowed me to board though I arrived a little late! Regarding the assigned seating, I had booked my flight before this change and wasn't aware of the change at the time, and so I didn't select a seat at booking as I didn't realize it was relevant. Better communication about the change would have been helpful for preparing.

All good except once again bags took an hour at Midway Airport Happens all the time. Ridiculous

The seats were comfortable, and the boarding process was pretty smooth.

Departure was delayed more than 1/2 hour while we waited for luggage (only) transfer from another flight/plane. Once approved for takeoff, the flight was excellent.

Flight was on time. Wi-fi was a little spotty/slow. Boarding and exit were efficient.

It was rough. The staff was unprofessional, the choice of on board drinks terrible, it was cramped in space at every airport, they always ran out of overhead bin space so they pressured people to check bags for free or we couldn’t leave on the plane— so I did check my bag to help, and they nearly lost my bag. My bag did not arrive on the luggage belt, another man on my flight and I had to waste our time going to the baggage office to search for our bags. I would only fly southwest again if it was my last choice. Also, my flights were consistently delayed over and over again— at one point they straight up told us we were waiting for the pilot to arrive.

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.

There was no inflight service. Once we landed we were delayed to find a gate for an hour and a half which was 1/2 the total time in the air.

The chicken wrap was tiny ($13 for what looked like a 1/3 of a normal wrap?) and disgusting.

It was good experience this time. The flight was on time.

There was a delay with the plan which cause the flight to leave later and once arrived in Chicago there was another delay and some passengers missed their connecting flights

The gate agent had a really bad attitude and refused to help me get on the standby list. She just handed me a card and said I needed to call a number. I asked her to help with the AA app on my phone and she just shrugged and said she didnt know. After a few phone calls, I eventually just went to a different gate agent on the other side of the terminal and got the help I needed.

Overall, my last three trips on American Airlines have all been either delayed or "rescheduled" due to mechanical issues. At least on delay caused me to miss two possible connecting flights each later than the first. My last option for my last connection required the assistance of the onsite service desk (O'Hare Airport). The wait time for the service desk was such that it jeopardized getting booked on the last connecting flight available for the night. Suffice it to say, my latest experiences with American Airlines have caused me extensive loss of productive business and personal time and can therefore be classified as significantly less than satisfactory.

Waiting for gate in RDU for more than 20mins is crazy.

American Airlines was great and worked very hard to change my ticket so I could get an earlier, direct flight back to Dallas. However, I was informed that Kayak made mistakes with my itinerary and classified my ticket as desiring to be on the earlier flight instead of taking the necessary step of calling AA to get me on the standby list. This ended up keeping me from being added to the standby list and delayed me getting home by 6 hours. I am happy to discuss this further with Kayak so they can correct their procedures so this won't happen again.

Waited for oxygen tanks for 30 minutes after boarding was complete.

We flew in first class. The crew did not offer drinks before the flight took off, but they treated us well during the flight. The food was excellent. There was actually too much food served, but it was nice to have all the options.

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

Information on your arrival and departure airports