VPS - CHI

$75 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 3/12. 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 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
$269
Allegiant Air
Thu 4/2Sun 4/5
VPS - MDW • Non-stop
Cheapest one-way
$75
Allegiant Air
Thu 3/12
VPS - MDW • Non-stop
Our travelers' advice
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
American Airlines
Cheapest • from $296 (round-trip)
Southwest
Best reviews • 7.9 score
Airline reviews
Airline reviews
+1
+1
Airline reviews
Airline reviews
+1
Top routes
VPS-MDW
Cheapest • 35% average savings
VPS-ORD
Most popular
Insights
Insights
Insights
Insights
When to travel
May
Cheapest • 48% price drop
May
Most popular
Good to know
Good to know
+1
+1
Good to know
Good to know
+1
Start a new search
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Flight Deals
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Expert advice
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, Apr 2 - Sun, Apr 5
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
$269Allegiant Air
Wed, Jan 21 - Wed, Jan 28
American Airlines Logo
1:31 pm - 4:11 pm
VPS
-
ORD
2h 40mnonstop
American Airlines Logo
10:30 am - 1:01 pm
ORD
-
VPS
2h 31mnonstop
$296American Airlines
Sat, Feb 14 - Tue, Feb 17
American Airlines Logo
12:15 pm - 2:59 pm
VPS
-
ORD
2h 44mnonstop
American Airlines Logo
9:15 am - 11:45 am
ORD
-
VPS
2h 30mnonstop
$301American Airlines
Wed, Jan 21 - Wed, Jan 28
American Airlines Logo
11:00 am - 6:01 pm
VPS
-
ORD
7h 01m1 stop
American Airlines Logo
10:30 am - 1:01 pm
ORD
-
VPS
2h 31mnonstop
$306American Airlines
Sat, Feb 14 - Wed, Feb 18
American Airlines Logo
12:15 pm - 2:59 pm
VPS
-
ORD
2h 44mnonstop
American Airlines Logo
9:25 am - 3:12 pm
ORD
-
VPS
5h 47m1 stop
$311American Airlines
Sat, Feb 14 - Wed, Feb 18
Delta Logo
3:00 pm - 7:19 pm
VPS
-
ORD
4h 19m1 stop
Delta Logo
9:52 am - 4:03 pm
ORD
-
VPS
6h 11m1 stop
$315Delta
Tue, Mar 31 - Tue, Apr 7
Delta Logo
5:10 pm - 10:29 pm
VPS
-
MDW
5h 19m1 stop
Delta Logo
5:38 pm - 11:02 pm
MDW
-
VPS
5h 24m1 stop
$315Delta
Wed, Jan 21 - Wed, Jan 28
Southwest Logo
12:15 pm - 9:50 pm
VPS
-
ORD
9h 35m2 stops
Southwest Logo
1:45 pm - 6:55 pm
ORD
-
VPS
5h 10m1 stop
$321Southwest
Tue, Mar 31 - Sat, Apr 4
Southwest Logo
7:15 am - 5:05 pm
VPS
-
MDW
9h 50m1 stop
Southwest Logo
5:30 am - 3:55 pm
MDW
-
VPS
10h 25m2 stops
$326Southwest
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
$346Allegiant Air
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?

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

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 $144 on the route between Valparaiso (VPS) and Chicago Midway Airport (MDW). Over the past month, this route was, on average, 35% 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 March and January, where the average cost of round-trip tickets is $395 and $349 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.

Yes, flying with a layover may cost you more time, but you can also save money on the route, with a 1 stop layover the cheapest option at $337 on average.

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.
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

Good to know

Low seasonFebruary
Cheapest flight$75
Best time to beat the crowds with an average 48% drop in price.
Most popular time to fly and prices are also 49% 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 $75 for a one-way ticket and $215 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?

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

  • 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 7.9, Southwest is the most popular choice. Allegiant Air is also a great choice for the route, with an average price of $138 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 $153 or less one-way and $370 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

American Airlines

American Airlines

Wednesday

American Airlines

American Airlines

Thursday

American Airlines, Allegiant Air

American Airlines, Allegiant Air

Friday

American Airlines

American Airlines

Saturday

Allegiant Air, American Airlines

Allegiant Air, American Airlines

Sunday

American Airlines, Allegiant Air

American Airlines, Allegiant Air

See more direct flights

Direct returns

Chicago to Valparaiso Destin-Ft Walton Beach

Monday

American Airlines

American Airlines

Tuesday

American Airlines

American Airlines

Wednesday

American Airlines

American Airlines

Thursday

American Airlines, Allegiant Air

American Airlines, Allegiant Air

Friday

American Airlines

American Airlines

Saturday

Allegiant Air, American Airlines

Allegiant Air, American Airlines

Sunday

American Airlines, Allegiant Air

American Airlines, Allegiant Air

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.
7.9
SouthwestOverall score based on 4250 reviews
8.6Crew
8.0Comfort
8.1Boarding
7.5Entertainment
7.0Food
Airline reviews

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.

2.0 MediocreCharity, Nov 2025
MSP - MDW
Read more Southwest reviews

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.

Excellent. Would encourage Southwest to keep current boarding procedures with free style seating. Makes for a fantastic experience

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.

Awful. They won’t help me with anything. I booked on American but they abdicated to Iberia. The ticket was overpriced. Everything negative

I enjoyed the extra leg room compared to other airlines. The first stewards made my daughter’s birthday special by giving her an extra snack. Then the last one coming home from Chicago to Appleton made our night really enjoyable Thanks for making our trip enjoyable

It was good..clean, comfy seat. Friendly warm welcoming crew. Was able to check my cabin luggage at the gate which I was able to pickup in a decent time from baggage claim. The app gave all updates from delays to baggage claim info. Overall smooth flight.

It was a typical flight. We had a delay which seems to be the normality now. And we had no in flight service due to conditions.

After we landed we sat on the tarmac for 1.5 hours waiting to get to our gate. Ridiculous.

Terrible. Flight delayed for more than 8 hours with only a $12 meal voucher provided for the inconvenience. The airplane did not have breaks on arrival yet they still made us go through the motions and board on time knowing we could not take off then sit for 40+ minutes before having to get of the time. A complete waste of my time. I cannot believe they can stay business with these shenanigans. I’ll avoid this company like the plague moving forward as the lack of accountability is disgraceful.

This was the best 2 flights I have had with American out of SGF. Great crew both flights.

Excellent - explanations were clear staff was nice and flight was comfortable

Lost bag and 2 days no word leaving for cruise no clothes or stuff

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.

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.

I liked how when I got on board how fast we ended up taking off but what I truly disliked was how uncomfortable the seats were. There was truly never a time that I could ever get comfortable during both of my flights. The seats could get away during shorter flights but flights 3 hour plus makes it hard to enjoy.

The crew was great and the flight was very smooth. Can’t really judge food since I did not get any because it costs money. The seat was comfortable for what we bought. Thanks!

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.

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

Information on your arrival and departure airports