VPS - CHI

$53 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 10/30. 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

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
Travelers love KAYAK
41,299,237 searches in the past 7 days on KAYAK

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

Track pricesNot ready to book? Create a price alert for when prices drop.

Bundle and saveSave money when you bundle your flight + hotel.

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

Flight Deals
Expert advice
Booking Insights
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, Oct 23 - Sun, Oct 26
Allegiant Air Logo
8:00 am - 10:17 amVPS-MDW
2h 17mnonstop
Allegiant Air Logo
11:07 am - 1:12 pmMDW-VPS
2h 05mnonstop
$155Allegiant Air
Find Deal
Thu, Nov 20 - Mon, Dec 1
Allegiant Air Logo
5:24 pm - 7:43 pmVPS-MDW
2h 19mnonstop
Allegiant Air Logo
9:24 am - 11:37 amMDW-VPS
2h 13mnonstop
$158Allegiant Air
Find Deal
Thu, Oct 23 - Sun, Oct 26
Multiple Airlines Logo
6:30 am - 11:25 pmVPS-MDW
16h 55m1 stop
Multiple Airlines Logo
11:07 am - 1:12 pmMDW-VPS
2h 05mnonstop
$241Multiple Airlines
Find Deal
Thu, Oct 23 - Sun, Oct 26
Multiple Airlines Logo
8:00 am - 10:17 amVPS-MDW
2h 17mnonstop
Multiple Airlines Logo
11:57 am - 1:32 pmMDW-VPS
25h 35m2 stops
$244Multiple Airlines
Find Deal
Sun, Nov 23 - Thu, Nov 27
Sun Country Air Logo
4:56 pm - 10:39 amVPS-ORD
17h 43m1 stop
Sun Country Air Logo
9:20 am - 9:08 amORD-VPS
23h 48m1 stop
$278Sun Country Air
Find Deal
Thu, Nov 20 - Thu, Nov 27
Sun Country Air Logo
10:35 am - 6:32 pmVPS-ORD
7h 57m1 stop
Sun Country Air Logo
9:20 am - 9:08 amORD-VPS
23h 48m1 stop
$311Sun Country Air
Find Deal
Mon, Oct 27 - Mon, Nov 3
Southwest Logo
7:05 am - 4:25 pmVPS-ORD
9h 20m1 stop
Southwest Logo
1:45 pm - 9:10 pmORD-VPS
7h 25m1 stop
$361Southwest
Find Deal
Wed, Feb 18 - Fri, Feb 20
American Airlines Logo
12:30 pm - 2:59 pmVPS-ORD
2h 29mnonstop
American Airlines Logo
9:34 am - 12:00 pmORD-VPS
2h 26mnonstop
$363American Airlines
Find Deal
Wed, Feb 18 - Fri, Feb 20
American Airlines Logo
12:30 pm - 2:59 pmVPS-ORD
2h 29mnonstop
American Airlines Logo
9:34 am - 12:00 pmORD-VPS
2h 26mnonstop
$364American Airlines
Find Deal
Fri, Oct 17 - Sun, Oct 19
Southwest Logo
12:00 pm - 5:40 pmVPS-MDW
5h 40m1 stop
Southwest Logo
6:15 am - 11:55 amMDW-VPS
5h 40m1 stop
$402Southwest
Find Deal

Everything you should know

Our travelers' advice
AI-generated summary based on content written by travel experts
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
Allegiant Air
Cheapest • from $155 (round-trip)
Southwest
Best reviews • 8.0 score
Airline reviews
Airline reviews
+1
+1
Airline reviews
Airline reviews
+1
Top routes
VPS-MDW
Cheapest • 74% average savings
VPS-ORD
Most popular
Insights
Insights
Insights
Insights
When to travel
May
Cheapest • 58% price drop
May
Most popular
Good to know
Good to know
+1
+1
Good to know
Good to know
+1
Cheapest round-trip
$155
Allegiant Air
Thu 10/23Sun 10/26
VPS - MDW • Non-stop
Cheapest one-way
$53
Allegiant Air
Thu 10/30
VPS - MDW • Non-stop
Start a new search
KAYAK searches 100s of sites at once to find you the best travel deals.
We hope you love your trip to Chicago!
Expert advice

Expert advice for your flight from Valparaiso to Chicago

 
Snippets provided in this section are AI-generated based on a summarization of KAYAK-commissioned articles. The articles are presented as-is, for general informational purposes only, and may not be up-to-date. The opinions contained in the articles are original to the author and reflect their authentic experience, which may vary significantly from the experience of others.
KAYAK teamed up with top travel experts to share the best tips for your journey.
Airlines
Allegiant Air

Allegiant's Bonus bundle includes carry-on, seat selection, and ticket change flexibility, enhancing travel convenience.


Allegiant offers Legroom+ seats for extra space and faster deplaning, ideal for short flights.

American Airlines

American Airlines' Main Cabin Extra offers early boarding and complimentary drinks, enhancing short flight comfort.


American Airlines provides high-speed Wi-Fi for purchase, ensuring connectivity during flights.

Our travel experts
Daniel Scheffler

Daniel Scheffler

Expert on Allegiant Air

Daniel Scheffler

Daniel Scheffler

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.

Read more
Harriet Baskas

Harriet Baskas

Expert on American Airlines

Harriet Baskas

Harriet Baskas

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.

Read more
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.

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

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 $52 on the route between Valparaiso (VPS) and Chicago Midway Airport (MDW). Over the past month, this route was, on average, 74% 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 Thursdays.

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 November and March, where the average cost of round-trip tickets is $451 and $395 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 $272, prices are generally cheapest when you fly direct.

Good to know

Low seasonApril
Cheapest flight$53
Best time to beat the crowds with an average 54% drop in price.
Most popular time to fly and prices are also 58% 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 $53 for a one-way ticket and $155 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 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 Thursday, Saturday, and Sunday.

  • 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 $158 and an overall rating of 7.2.

  • 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 $478 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

American Airlines

Tuesday

Allegiant Air, American Airlines

Allegiant Air, American Airlines

Wednesday

American Airlines

American Airlines

Thursday

Allegiant Air, American Airlines

Allegiant Air, American Airlines

Friday

American Airlines

American Airlines

Saturday

American Airlines, Allegiant Air

American Airlines, Allegiant Air

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

American Airlines

Tuesday

Allegiant Air, American Airlines

Allegiant Air, American Airlines

Wednesday

American Airlines

American Airlines

Thursday

Allegiant Air, American Airlines

Allegiant Air, American Airlines

Friday

American Airlines

American Airlines

Saturday

American Airlines, Allegiant Air

American Airlines, Allegiant Air

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 4242 reviews
7.5Entertainment
8.1Boarding
8.0Comfort
8.6Crew
7.0Food
Airline reviews

Near 4 hour flight with only 1 service. Had to use call button to request water. Internet and power not working until into flight. Internet would stop working during flight.

6.0 GoodDavid, Aug 2025MCO - DEN
Read more Southwest reviews

Near 4 hour flight with only 1 service. Had to use call button to request water. Internet and power not working until into flight. Internet would stop working during flight.

My flight was delayed 50 minutes and we were rushed to board to then sit for 15 minutes until the pilot arrived. Unacceptable since we could have waited to board. Also the delayed flight was updated AFTER we boarded to more than the 10 minutes as originally stated.

If we are going to have to pay for luggage, make it easier to do. Put something on the app during check-in so I don't need to do it at the kiosk. I've done it twice recently and I ended up having to pay at the desk because something went wrong at the kiosk in Tampa.

Worst experience I had on Southwest. Still better than most, but the seating was barely tolerable.

It was okay. The plane was delayed from earlier in the day, but they kept updating the departure time, sometimes later, sometimes earlier. That was stressful. Once we finally got on and took off, it was fine. I was supposed to have a connection in Chicago to Los Angeles, and the time for so late I was rebooked to arrive in LA 3 hours late. The departure time to Chicago later became early enough to have taken my original connection and arrive earlier but that wasn't an option.

Everything was on time. I was disappointed by the front section female, African American flight attendant. I did not see her name tag or would have identified by name not race. As passengers moved to the bathroom early in flight, she would say with a disdainful tone “I have to say the seat belt light is on” then go back to her book. Better trained flight attendants say something like be careful the seat belt light is on.

The price of the tickets isn't matching the flight experience. No matter how long the flight is, you're only getting pretzels. The flight attendants looked unkept and over it.

WiFi on the flight was not working. Thus, entertainment options were limited.

Flight was awfully bumpy and landing was a bit jolting. I was in the restroom when snacks and drinks were served and was not asked if i wanted any. I had to ask for water finally.

Crew was great flight was great baggage claim was a failure. It took over 1 hour for bags to arrive. Poor communication poor effort when I spoke to the supervisor about the delay

Any flight to ORD after about 2pm this summer has been challenging. Flight was delayed getting in (coming from ORD) and that led to it not leaving before a ground stop due to lightening before they could fuel the plane, and so forth. They made up some time but we were still late in arriving at ORD, and that led to missed connections.

Food was ok, but not as good as I have had before on AA.

Pretty good. The food was just mediocre, the boarding and crew were good.

My flight got switched and my prepaid bag didnt transfer over properly so I paid to check ANOTHER BAG. I was placed in a middle seat and it was just miserable. At least it was a bulkhead row so I had legroom. The flight just never seem3d to end

Was not able to watch most shows on the entertainment site. They would not load

On Wednesday, July 30 we were in mid flight from Manchester to Charlotte and we turned around because the right engine was malfunctioning. That was the last flight out of Manchester that night. I was rebooked for Thursday, which became a weather event Friday. There were no seats left on the flight from Manchester to Charlotte. Consequently I didn’t leave Manchester until Saturday morning and we flew to Chicago so to say the least my scheduled flight and return to Iowa was three days off and it messed with my business schedule. Consequently cash flow. I would like some sort of acknowledgment of this event.

Dreadful experience. Our flight was delayed more than 8 hours due to a maintenance issue and the assistance from rebooking was poor. I was travelling with a bad knee and needed assistance waited in one place more than 3 hours before someone came with a wheelchair. The woman next to me was a 91 year old great grandmother who had waited more than 4 hours. There were moments of support from the staff but it appeared as they were going against the direction of management. It was apathy, lack of ownership and dismissive responses with small moments of kindness and understanding typically from grey haired, female, veteran staff..

Couldn’t get the door on the plane to close leading to a nearly 2 hour delay. But, hey at least they didn’t cancel the flight.

The flight was fine and the crew awesome. The problem is ORD and AA. Computers went down, ORD fell apart and a 40 min flight turned into a 3 hour trip. Guess the answer is to not try and fly to ORD after noon. But, as I said, crew was awesome and did everything they could to lesson the flight time.

The flight was fine but the 8 hour delay in Chicago was awful - 5 gate changes and repeated delays without an explanation. No vouchers. Nothing.

Crew was great. No entertainment and food and beverage was for purchase only, even water

It was canceled. The flight wasn’t rescheduled, everyone had to figure out their own new arrangements. They said we would get refunded our original fare and receive an additional $150. We received links for $100 only and they expired before we could activate them.

The plane had originated in Las Vegas at 6:30 in the morning and flew to Moline where we boarded. The flight left around 12:30 PM and there were no boxed snacks available and many of the alcoholic beverages were unavailable. I would find it hard to believe that that many of the passengers coming from Las Vegas at 6:30 in the morning, drank and ate that much of the items. I can only come to the conclusion that someone failed to stock the plane for the round-trip. This is a huge revenue failure for the airline and disappointment for the passengers. The flight crew did not seem happy to be there and did not engage with passengers. Allegiant you can do better.

They did not let my husband on the plane with our service animal at the last minute. Do NOT fly this airline with a service animal!

Tight! Seats are not designed for those of us who wear extra-large clothes.

The non-stop flight from Grand Rapids was excellent. I neither expected or needed a budget flight and Allegiant made the trip easy and for an affordable price, Arriving at the Mesa Airport (AZA) is a delight compared to the international airport. For our return flight, we were able to arrive 75 minutes before the flight, return the rental car, check our bag and make it to the gate in plenty of time. That would never happen at most airports.

Easiest flights I’ve ever taken. Plane was comfortable without overly crowded seating.

Terrible. Still have not received the refund from them. They sent it to some account that I don't even know. Spoke with costumer service and they are unable to help.

I didn’t like it at all. I miss my second flight because of the delay on Allegiant Air now I m stuck in MCO.

Good, but a bit late on take off after loading. Don't like charging for carry ons!

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

Information on your arrival and departure airports

Not what you’re looking for? Find thousands of other hotels, flights, car rentals and package deals with KAYAK.