VPS - CHI

$52 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 5/16. 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.
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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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Flights Deals

Cheap Flights from Valparaiso to Chicago

 
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.

Recent round-trip flight deals from Valparaiso to Chicago

KAYAK's recommended round-trip deals from the most popular airlines that fly from Valparaiso to Chicago.
Discover the best prices for you by selecting your travel dates on KAYAK.
Allegiant Air Logo
6:00 am - 8:22 amVPS-MDW
2h 22mnonstop
Allegiant Air Logo
9:12 am - 11:23 amMDW-VPS
2h 11mnonstop
$91Allegiant Air
Find Deal
Fri, Jun 13 - Mon, Jun 16
Allegiant Air Logo
6:00 am - 8:22 amVPS-MDW
2h 22mnonstop
Allegiant Air Logo
9:12 am - 11:23 amMDW-VPS
2h 11mnonstop
$97Allegiant Air
Find Deal
Fri, Jun 6 - Mon, Jun 9
American Airlines Logo
11:08 am - 1:37 pmVPS-ORD
2h 29mnonstop
American Airlines Logo
7:43 am - 9:59 amORD-VPS
2h 16mnonstop
$158American Airlines
Find Deal
Wed, Jun 4 - Wed, Jun 11
Delta Logo
4:59 pm - 9:20 pmVPS-ORD
4h 21m1 stop
Delta Logo
6:00 am - 12:04 pmORD-VPS
6h 04m1 stop
$177Delta
Find Deal
Wed, Jun 4 - Wed, Jun 11
American Airlines Logo
11:08 am - 1:37 pmVPS-ORD
2h 29mnonstop
American Airlines Logo
5:29 am - 11:44 amORD-VPS
6h 15m1 stop
$178American Airlines
Find Deal
Wed, Jun 4 - Wed, Jun 11
Delta Logo
7:23 pm - 11:58 pmVPS-ORD
4h 35m1 stop
Delta Logo
1:30 pm - 6:33 pmORD-VPS
5h 03m1 stop
$217Delta
Find Deal
Fri, May 30 - Sat, May 31
 Logo
8:32 am - 11:04 pmVPS-ORD
38h 32m2 stops
 Logo
9:08 pm - 2:45 pmORD-VPS
17h 37m1 stop
Mon, Jun 2 - Sat, Jun 7
Southwest Logo
12:00 pm - 7:50 pmVPS-MDW
7h 50m1 stop
Southwest Logo
5:35 am - 10:55 amMDW-VPS
5h 20m1 stop
$297Southwest
Find Deal
Fri, Sep 26 - Sun, Sep 28
 Logo
8:32 am - 11:04 pmVPS-ORD
38h 32m2 stops
 Logo
1:59 pm - 11:26 pmORD-VPS
33h 27m2 stops
Mon, Jun 2 - Sat, Jun 7
Southwest Logo
12:00 pm - 7:30 pmVPS-MDW
7h 30m2 stops
Southwest Logo
5:35 am - 10:55 amMDW-VPS
5h 20m1 stop
$303Southwest
Find Deal
Fri, Sep 26 - Sun, Sep 28
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
Useful Info

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?

The cheapest price for flight routes found by users searching on KAYAK in the last 2 weeks for round-trip flights from Valparaiso to Chicago.

Our data shows that the cheapest route for a return flight from Valparaiso to Chicago cost $89 and was between Valparaiso (VPS) and Chicago Midway Airport (MDW). On average, the best prices are found if you fly this route. The average price for a return flight for this route is $89.

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 Thursday 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 Fridays.

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 February, where tickets cost $105 (return) on average. On the other hand, the most expensive months are September and March, where the average cost of round-trip tickets is $432 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 $358, prices are generally cheapest when you fly direct.

Good to know

Low seasonApril
High seasonAugust
Cheapest flight$52
Best time to beat the crowds with an average 25% drop in price.
Most popular time to fly and prices are also 17% 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 $52 for a one-way ticket and $91 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?

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

  • 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 $414 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 $167 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 $110 or less one-way and $96 or less round-trip.

Prefer to fly direct from Valparaiso 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

Allegiant Air, American Airlines

Allegiant Air, American Airlines

Tuesday

American Airlines

American Airlines

Wednesday

American Airlines, Allegiant Air

American Airlines, Allegiant Air

Thursday

Allegiant Air, American Airlines

Allegiant Air, American Airlines

Friday

Allegiant Air, American Airlines

Allegiant Air, American Airlines

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

Allegiant Air, American Airlines

Allegiant Air, American Airlines

Tuesday

American Airlines

American Airlines

Wednesday

American Airlines, Allegiant Air

American Airlines, Allegiant Air

Thursday

Allegiant Air, American Airlines

Allegiant Air, American Airlines

Friday

Allegiant Air, American Airlines

Allegiant Air, American Airlines

Saturday

American Airlines

American Airlines

Sunday

Allegiant Air, American Airlines

Allegiant Air, American Airlines

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 7934 reviews
7.3Food
8.2Boarding
8.5Crew
7.9Entertainment
7.9Comfort
Airline reviews

This had nothing to do with Delta… The flights were on time and flawless. The service was excellent. We purchased seats in (aisle/middle) comfort plus since this was a cross country flight. Unfortunately, the woman seated at the window was 300+ pounds and, as might be expected, covered up about a third of the middle seat also. there was absolutely nothing that Delta could have done about that… I just don’t know what the answer should be. If you purchase a seat, you should should be able to use the entire seat and not just the portion that someone else is not sitting/oozing in. Disappointing…there should be something that could be done….I'm just not sure what solution could be.

10.0 ExcellentGary, Apr 2025TPA - LAX
Read more Delta reviews

This had nothing to do with Delta… The flights were on time and flawless. The service was excellent. We purchased seats in (aisle/middle) comfort plus since this was a cross country flight. Unfortunately, the woman seated at the window was 300+ pounds and, as might be expected, covered up about a third of the middle seat also. there was absolutely nothing that Delta could have done about that… I just don’t know what the answer should be. If you purchase a seat, you should should be able to use the entire seat and not just the portion that someone else is not sitting/oozing in. Disappointing…there should be something that could be done….I'm just not sure what solution could be.

The worst part was I was NOT allowed in the lounge even though I was holding a first class ticket and have a premium American Express card. I have flown Business or First Class with many airlines. Delta is the ONLY one who does not extend this courtesy to anyone except people who hold the very expensive American Express card. As a result, I won’t fly Delta if I have any other choice.

The Dekta Rep that checked us in was great. She's very personable, pleasant, and can tell she enjoys her job.

The young man who was our flight attendant in first class was lazy and did not do his job well at all. Never offered drinks upon boarding - actually I take that back... said "are you okay with water" as if I do not want to get you anything else, only passed the snacks around once, got my drink order wrong and then never offered a second round of drinks. He was the worst I have ever seen on Delta and we fly a lot.

Flight left early and arrived early. the whole trip was excellent.

Newer plane, relatively easy boarding, not a full flight and was told that we could not be moved up because of weight and balance issues. Otherwise, a very good experience.

Everything was great. Great service, excellent communication, and early arrival

I sat in comfort plus. It was fine. Seats were comfortable. I got drinks and snacks.

Good and consistent Printer in lounge did not work for me :(

Great - This was the last flight before hurricane closures and did a quick turnaround to get the plane heading north. Much appreciated.

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!

First time flying with them and will definitely fly again in the future. Crew was so nice and friendly, fought was seamless. They are simple planes, no entertainment, but it’s fine for a short flight or if you have personal devices Rates are competitive, and they did so well with keeping the flight on time after a tropical storm, where other airlines had delays and cancellations.

They boarded passengers that sat in the back of the plane first, making boarding very efficient.

I didn't even take this flight. My plans changed and I couldn't get ahold of customer service and the website kept breaking down during the attempt to change the flight. I wound up taking another airline entirely and eating the cost.

The worst flying experience ever 3 delays. No accommodations. Had to deboard the plane after being delayed.

Posted a 20minute delay but didn’t delay at all. Caused boarding issues and confusion. Also, didn’t release baggage. Took over an hour and 20 minutes to get luggage.

Flight was good, boarding was a breeze, flight attendants were friendly and professional. There was a medical issue with another passenger and the crew handled it in a calm and professional way.

To start, I’d like to say that every American Airline personnel I interacted with on the ground, especially flight crew, was very friendly and did their best to help me out. Despite this, however, my experience with the airline was an entire mess. The 7:19 PM flight was heavily delayed due to weather, and pushed to 10:30 AM the next morning. Because of this, I had to spend the night inside of the airport. At some point later in the night, I got an email saying that the flight had been canceled. I called the support number, and the representative on the other line told me that the flight was still on and that I didn’t need to rebook. The next morning, no one came to the gate to open the door for the crew until almost 11 AM. By this time the flight crew had been waiting for over an hour, and they had called management to get someone to open the door for them multiple times. Around 11:30, the gate screen had changed to a different flight. I ended up buying a last minute ticket with Southwest airline just to get to Chicago, because the next flight with American wasn’t until 7:19 pm that day. Now, earlier that morning my suitcase had been sent ahead of me to ORD. I went to baggage claim to ask them if I could have my suitcase forwarded to where I was staying. The representative at SDF baggage claim said they could and put the claim in for me. As I was going back through TSA, I got an email that the airline had found my suitcase, but the next step was to send it BACK to SDF. I called the airline support number again, and I made it clear that my suitcase needed to stay in Chicago and to not come back to SDF. The representative told me that they would hold my suitcase at ORD and that it wasn’t going to be forwarded anywhere. Once I got there, I found that they had loaded my suitcase onto a plane to send it back to SDF. Thankfully, I had gotten to the baggage claim counter in time for them to put in a request to bring my suitcase back up. My refund with the airline is processing already, but because of this entire experience and miscommunication at every turn of the way, I will not book with American Airlines in the future.

The plane was late and then sat on the runway for almost 45 minutes before taking off.

Crew professional. Easy bag drop off. On time. Good entertainment.

Everything was great. Boarding, early departure, early arrival, and deplaning were smooth. Smooth flight.

Per usual, flight status, staff courtesy and professionalism were excellent

The only thing is if Wi-Fi is available after you land and taxi to the gate. It takes forever to get to the gate, and having the Wi-Fi continue would be great to bide the time at least 5 minutes before you arrive at the entrance. That is my only comment; otherwise, everything was good.

Had to wait on pilot and crew to depart and had to wait to arrive at the gate because they only had 2 crews working. Delays, delays....Planes just keep getting smaller and tighter and they nickle and dime for everything. When will an airline actually wake up and make flying more enjoyable?

Seating was horrible. Small seats. Access to flight information and extras very iser unfriendly. Kept losing internet after paying for it. Staff in madison was as unprofessional and unhelpful.

Delayed due to no crew. On a major holiday travel day.

Other than being delayed 5.5 hours and having to get a hotel because I missed my connecting flight, it was an okay flight. No in-flight Wi-Fi or entertainment.

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

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