CHI - VPS

$50 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 10/19. 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 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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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, Oct 19 - Thu, Oct 23
Allegiant Air Logo
11:07 am - 1:12 pmMDW-VPS
2h 05mnonstop
Allegiant Air Logo
8:00 am - 10:17 amVPS-MDW
2h 17mnonstop
$134Allegiant Air
Find Deal
Thu, Nov 6 - Sun, Nov 9
Allegiant Air Logo
12:07 pm - 2:12 pmMDW-VPS
2h 05mnonstop
Allegiant Air Logo
9:00 am - 11:17 amVPS-MDW
2h 17mnonstop
$210Allegiant Air
Find Deal
Sat, Oct 18 - Tue, Oct 21
Southwest Logo
7:30 am - 3:35 pmORD-VPS
8h 05m1 stop
Southwest Logo
2:00 pm - 9:30 pmVPS-ORD
7h 30m1 stop
$235Southwest
Find Deal
Wed, Aug 27 - Sat, Aug 30
Southwest Logo
2:05 pm - 7:00 pmMDW-VPS
4h 55m1 stop
Southwest Logo
10:30 am - 2:50 pmVPS-MDW
4h 20m1 stop
$235Southwest
Find Deal
Sun, Aug 24 - Thu, Aug 28
Sun Country Air Logo
8:00 am - 5:02 pmORD-VPS
9h 02m1 stop
Sun Country Air Logo
6:08 pm - 12:20 pmVPS-ORD
18h 12m1 stop
$261Sun Country Air
Find Deal
Thu, Dec 18 - Mon, Dec 22
Sun Country Air Logo
8:08 pm - 10:29 amORD-VPS
14h 21m1 stop
Sun Country Air Logo
11:26 am - 10:26 amVPS-ORD
23h 00m1 stop
$301Sun Country Air
Find Deal
Sat, Sep 13 - Sat, Sep 20
Delta Logo
2:25 pm - 8:37 amORD-VPS
18h 12m2 stops
Delta Logo
12:55 pm - 9:30 pmVPS-ORD
8h 35m1 stop
$316Delta
Find Deal
Sat, Sep 6 - Mon, Sep 15
Delta Logo
8:25 am - 12:00 pmORD-VPS
27h 35m1 stop
Delta Logo
7:06 pm - 8:05 amVPS-ORD
12h 59m2 stops
$317Delta
Find Deal
Tue, Aug 19 - Tue, Aug 26
American Airlines Logo
10:10 pm - 10:38 amORD-VPS
12h 28m1 stop
American Airlines Logo
7:00 am - 3:50 pmVPS-ORD
8h 50m1 stop
$366American Airlines
Find Deal
Wed, Aug 27 - Sat, Aug 30
American Airlines Logo
8:03 am - 10:18 amORD-VPS
2h 15mnonstop
American Airlines Logo
4:47 pm - 7:23 pmVPS-ORD
2h 36mnonstop
$371American Airlines
Find Deal
Expert advice

Expert advice for your flight from Chicago to Valparaiso

 
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
American Airlines

American Airlines' Main Cabin Extra offers early boarding and complimentary drinks for a small fee.


American Airlines provides high-speed Wi-Fi for purchase, with free options for T-Mobile customers.

Allegiant Air

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


Allegiant offers Trip Flex for free flight changes or cancellations, providing flexibility for travelers.

Our travel experts
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
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
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.

What is the cheapest Chicago to Valparaiso flight route?

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

Our data shows that the cheapest route for a return flight from Chicago to Valparaiso cost $82 and was between Chicago Midway Airport (MDW) and Valparaiso (VPS). On average, the best prices are found if you fly this route. The average price for a return flight for this route is $82.

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 Thursdays 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 January, where tickets cost $121 (return) on average. On the other hand, the most expensive months are March and April, where the average cost of round-trip tickets is $537 and $420 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 $270, 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 51% compared to booking last minute. For the absolute cheapest price, our data suggests you should book 6 weeks before departure.

Good to know

Low seasonJanuary
Cheapest flight$50
Best time to beat the crowds with an average 61% drop in price.
Most popular time to fly with an average 74% 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?

    In the last 3 days, the lowest price for a flight from Chicago to Valparaiso was $50 for a one-way ticket and $134 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?

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

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

    The two airlines most popular with KAYAK users for flights from Chicago to Valparaiso are Delta and Southwest. With an average price for the route of $379 and an overall rating of 8.0, Delta is the most popular choice. Southwest is also a great choice for the route, with an average price of $412 and an overall rating of 8.0.

  • 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 $147 or less one-way and $204 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

Allegiant Air, American Airlines

Allegiant Air, American Airlines

Tuesday

American Airlines

American Airlines

Wednesday

Allegiant Air, American Airlines

Allegiant Air, American Airlines

Thursday

American Airlines

American Airlines

Friday

Allegiant Air, American Airlines

Allegiant Air, American Airlines

Saturday

American Airlines

American Airlines

Sunday

American Airlines

American Airlines

See more direct flights

Direct returns

Valparaiso Destin-Ft Walton Beach to Chicago

Monday

Allegiant Air, American Airlines

Allegiant Air, American Airlines

Tuesday

American Airlines

American Airlines

Wednesday

Allegiant Air, American Airlines

Allegiant Air, American Airlines

Thursday

American Airlines

American Airlines

Friday

Allegiant Air, American Airlines

Allegiant Air, American Airlines

Saturday

American Airlines

American Airlines

Sunday

American Airlines

American Airlines

See more direct flights

Reviews of the top 5 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 4241 reviews
7.5Entertainment
7.0Food
8.0Comfort
8.6Crew
8.1Boarding
Airline reviews

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.

6.0 GoodDavid, Jul 2025BWI - RSW
Read more Southwest reviews

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.

It is southwest seat was ok. Not the most comfortable seat

Plz don't take away free bags and free seating

My flight to Chicago left and landed early. My return flight left two minutes late and arrived 2 minutes late. My seat selections were ideal! There were no snacks going to Chicago and no snacks on the return trip. There are no charging outlets on board.

Excellent! Only question is how we check in at exactly 24 hours in advance and end up at the end of the B boarding group

It went well. Plane wasn't full. Will be great when assigned seating is in place

One of the crew performed a hilarious skit to accompany the standard instructions. Passengers enjoyed it so much they applauded at the end!

Excellent experience. WiFi worked on this leg of My trip

Delayed and took off even later than the scheduled delay time

For a 69 year old with health problems I had the worse experience, no wheelchair when I entered a lady told me to sit and wait while a gentleman told me I had to walk to the Delta station, which I did. I had a carry on and a bag, and I was traveling with my service dog, which was on his carrier and the lady charged me for my carry on luggage, beside all the waiting cause of the delay, I had to walk to get my luggage cause no wheelchair showed up, I am so disappointed. I will get in touch with the company. I got home at 3:00 am, not good for my health situation.

Great experience on Delta. Staff from baggage check to flight attendants were very courteous and professional. My only issue was a personal preference for pretzels instead of the chips and cookies that were offered.

Always good but we must do something about people in rows ahead of you that don't put their seats back up when they are suppose to. And It's rough to not be able to even lean over to get something out of my purse.

this crew didn't care much. bumping carts into seats more times than i care to remember

Everything was fine except the entertainment was not working for half of the flight.

Easy boarding with an extremely kind attendant. Seats were spacious and we had 3 seats for 2 people so we could stretch out. Comfortable air flow and very attentive and hospital attendants. Bathrooms and food were the only negative. Bathrooms were so small you could hardly get in and close the door. I don’t think an obese person would fit or a person with a movement disability. Food was the trending food for flights, nonexistent. We spent $40 getting sandwich and snack at airport for our 6 hour flught.

I am very bothered by the events today. I can't believe the flight attendants allowed someone to take my seat and made me move. It was embarrassing. I was in the right. The lady just didn't want move. I can't believe delta would allow this to stand and disrespect my rights as a passenger. The lady complained about her leg and that she couldn't move. Firstly somehow she was able to make it to row 24. Not sure how much her leg could have hurt. Secondly, I'm in plenty of pain myself. I just finished chemotherapy a several weeks ago. My body is constantly sore. Yet deltas flight attendants didn't appropriately protect my rights. In the end they found me a seat on the plane but I want to understand how delta can operate this way. They in essence allowed a bully to get their way.

Crew was friendly Love the entertainment in the seat head rest.

Other then mechanical/ computer problem and 3.5 hours flight delay the flight was great. I guess that what happened when you fly an old airplane now a day.

It was delayed instead of departing at 9:20pm, we departed at 11pm… putting us in Columbus after 2am! It was awful. Had I known about the delay, I could have spent some time in the United Lounge… I was starving because I started my journey in Budapest… so I was exhausted and hungry. Plus I had to make new arrangements to be picked up at the airport in Columbus, instead of midnight it was 2:30 am after getting luggage and out of airport. Not feasible. I would have just stayed in Chicago for the night and gotten a morning flight.

It was great, I’m very grateful for the pilots and crew flight attendants for everything.

Evidently, my seat had the only broken TV. I couldn’t plug it in, get it to come on, or watch anything, and of course, no one could fix it while we were on the plane. The service was good and the boarding was quick

I was charged for my daughters bag when I am supposed to receive two free checked bags with my United Explorer card.

The schedule to Moline changed 5 times. The gate changed 6 times. That is a pathetic way to run an airline. No wonder that no one in our company flies on United Express to or from Moline. Changes happen most of the time. I learned my lesson on this trip…never again!

Flight was great. Efficient boarding. Short flight. Early arrival. Friendly flight crew. The entertainment system did not work well. Could not access it until the aircraft reached 10K feet or more. Lots of glitches.

A bit rush for transit. Food and entertainment are not available

Smooth boarding process. Early departure, smooth flight, early arrival. The entertainment package has very good recent movie options. The flight crew were friendly and professional.

My flight was scheduled for about 6:05 departure. There were 11 gate changes from 4-7pm and the flight was 3 hours delayed due to operational issues. The plane taxied around the airport for about half an hour before stopping to be de-iced. It would have been nice if we were alerted of the plan to de-ice prior to the 30 minute drive around the airport. The flight attendant was friendly, which was the only redeeming thing about this flight. As a former flight attendant for United, I was extremely disappointed.

Delays took 2hours and thirty minutes making me miss my connecting flight and make me sit in the Chicago airport for 9 hours

3 hour weather delay followed by 1 hour (and counting) maintenance delay. UGH!

After we'd boarded , they canceled the flight. The crew didn't even know , we just all received text messages. Then after they deplaned us , AA was just like "too bad, go F your self, we sure ain't gonna help you"

After a two hour delay, my flight was CANCELLED! No pilot available. Such BS.

Amazing food, great staff, with one noticable detail missing ...but no seat entertainment in any of aircraft ...I am not a fan

I wish American Airlines would change the airline industry by loading the plane back to front instead of front to back. Planes would board so much more smoothly and quickly.

I have long legs, my foot was out in the aisle and when a flight attendant came walking by and I didn't notice, instead of saying "excuse me" or anything like that, she kicked my foot. Extremely rude

Excellent! The gate agents were kind enough to rebook me on an earlier flight saving me from a 6 hour layover. Even my luggage made it despite the fact that the connection was technically too narrow. The flight itself was very comfortable, roomy, and clean. Plenty of space for my carryon items with plugs to charge my phone. After a long international flight of 14 hours, this was an excellent way to end my travels!

Great experience. Flight boarded easily. Departed early. Smooth flight. Great arrival in DC--almost no taxing! Almost direct to gate from runway. Crew was terrific. Same cookies and beverages in main cabin. I did not use the entertainment system on this flight.

Most of the delay was due to weather which is not what was at issue here. One delay was due to a missing flashlight and in the end the flashlight was actually found on the plane. The entertainment system is very limited. Live TV options offer only a few channels that are not very appealing. Boarding and deplaning are always difficult. It just takes too much time to get on and off the plane. On the plus side, I missed my connecting flight, but was easily able to book a later flight from the app while enroute.

You were more on time than United. I'm so over united delays.

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!

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.

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

Information on your arrival and departure airports

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