CHI - VPS

$59 Find Cheap Flights from Chicago to Valparaiso - Compare and Save

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 10/2. 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

Save 20% or more on flights. Compare deals from all over the web.

Never overpay with our price tracking tools.

Filter searches by price, airline and more to find your best flights.

Everything you should know

Cheapest round-trip
$82
Typical prices: $184-$271
Allegiant Air
Mon 10/26Thu 11/19
MDW - VPS • Non-stop
Cheapest one-way
$59
Allegiant Air
Fri 10/2
MDW - VPS • Non-stop
Nonstop flights
You can fly direct with American Airlines and Allegiant Air. Average duration is 2h 18m
Direct flights
Direct flights
+1
+1
Direct flights
Direct flights
+1
Top routes
Cheapest • 62% average savings
Most popular
Insights
Insights
Insights
Insights
Top layover airports
Cheapest • Avg $332 (round-trip)
Shortest trip • 4h 13m (one-way)
Insights
Insights
Insights
Insights
When to book
in advance
Our data shows that travelers who book at least 8 weeks in advance save around 13% compared to booking last minute.
Insights
Insights
Insights
Insights
When to travel
Cheapest • 42% price drop
Most popular
Good to know
Good to know
+1
+1
Good to know
Good to know
+1
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 Valparaiso!
Flight Deals
Booking Insights
Expert advice
Flight Deals

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

Mon, Oct 26 - Thu, Nov 19
Allegiant Air Logo
6:44 pm - 8:55 pm
MDW
-
VPS
2h 11mnonstop
Allegiant Air Logo
6:30 am - 8:54 am
VPS
-
MDW
2h 24mnonstop
$82Allegiant Air
Fri, Oct 23 - Fri, Nov 6
Allegiant Air Logo
9:15 pm - 11:26 pm
MDW
-
VPS
2h 11mnonstop
Allegiant Air Logo
7:30 am - 9:48 am
VPS
-
MDW
2h 18mnonstop
$87Allegiant Air
Mon, Oct 5 - Fri, Oct 16
Multiple Airlines Logo
6:20 am - 8:17 pm
ORD
-
VPS
13h 57m
1 stop
Multiple Airlines Logo
12:17 pm - 12:32 pm
VPS
-
ORD
24h 15m
1 stop
$222Multiple Airlines
Fri, Oct 23 - Fri, Nov 6
Multiple Airlines Logo
9:15 pm - 11:26 pm
MDW
-
VPS
2h 11mnonstop
Multiple Airlines Logo
1:39 pm - 9:53 pm
VPS
-
MDW
32h 14m
2 stops
$236Multiple Airlines
Mon, Sep 14 - Mon, Sep 21
Southwest Logo
5:30 pm - 9:00 pm
MDW
-
VPS
3h 30m
1 stop
Southwest Logo
12:40 pm - 7:20 pm
VPS
-
MDW
6h 40m
1 stop
$317Southwest
Thu, Aug 20 - Mon, Aug 24
Southwest Logo
5:30 pm - 9:00 pm
MDW
-
VPS
3h 30m
1 stop
Southwest Logo
12:40 pm - 7:20 pm
VPS
-
MDW
6h 40m
1 stop
$317Southwest
Tue, Oct 20 - Wed, Oct 28
Delta Logo
6:20 am - 11:19 pm
ORD
-
VPS
16h 59m
2 stops
Delta Logo
2:07 pm - 8:53 am
VPS
-
ORD
18h 46m
1 stop
$329Delta
Tue, Sep 29 - Tue, Oct 6
Delta Logo
6:10 am - 11:22 pm
ORD
-
VPS
17h 12m
2 stops
Delta Logo
2:07 pm - 8:53 am
VPS
-
ORD
18h 46m
1 stop
$329Delta
Tue, Nov 24 - Tue, Dec 1
American Airlines Logo
8:34 am - 11:10 am
ORD
-
VPS
2h 36mnonstop
American Airlines Logo
11:44 am - 2:39 pm
VPS
-
ORD
2h 55mnonstop
$386American Airlines
Wed, Oct 28 - Wed, Nov 4
American Airlines Logo
5:29 pm - 11:48 pm
ORD
-
VPS
6h 19m
1 stop
American Airlines Logo
11:44 am - 2:35 pm
VPS
-
ORD
2h 51mnonstop
$396American Airlines
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.

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

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

Flight prices are below average for this route right now.

Flights to Valparaiso, Florida from Chicago usually cost between $383 and $509 in October.
The lowest price found in the past 5 days was $82 on Allegiant Air (Oct 26-Nov 19).

What is the cheapest Chicago to Valparaiso flight route?

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

The cheapest return flight from Chicago to Valparaiso costs $86 on the route between Chicago Midway Airport (MDW) and Valparaiso (VPS). Over the past month, this route was, on average, 62% cheaper than other Chicago-Valparaiso routes. It is also the most popular route.

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 Sundays 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 Thursdays.

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 October, where tickets cost $235 (return) on average. On the other hand, the most expensive months are May and August, where the average cost of round-trip tickets is $499 and $455 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 $397, 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 8 weeks before departure, which saves you about 13% compared to booking last minute. For the absolute cheapest price, our data suggests you should book 24 weeks before departure.

Expert advice

Expert advice for your flight from Chicago to Valparaiso

 
AI-powered summary based on content written by travel experts. AI can make mistakes.
KAYAK teamed up with top travel experts to share the best tips for your journey.
Our travel experts
Daniel Scheffler

Daniel Scheffler

Expert on Allegiant Air

Daniel Scheffler is a travel writer, podcaster, and producer. Born in Africa, bred in Europe and now living in America he has traveled to 140 countries (and all 50 U.S. states). Plus he has stayed at over 2500 hotels across the globe. His original shows Everywhere and Without Maps (available on Spotify) showcase his beliefs, travel is about humanity and sharing that beauty. And thus it reminds you that you shouldn’t believe everything you think.

Harriet Baskas

Harriet Baskas

Expert on American Airlines

Harriet is an award-winning journalist who is happiest in an airport or an unusual museum. Her stories about airports, air travel, and the business of travel have appeared on NBC News, CNBC, USA TODAY, The Points Guy and other outlets. She is the creator of the StuckatTheAirport.com blog and the author of nine books. When not out on the road or exploring the latest airport amenities, she’s home in Seattle getting ready for the next adventure.

Good to know

Low season

January

Cheapest flight

$59
Best time to beat the crowds but there is an average 1% increase in price.
Most popular time to fly with an average 2% 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 5 days, the lowest price for a flight from Chicago to Valparaiso was $59 for a one-way ticket and $82 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 Embraer 175 is the aircraft model that flies most regularly on the Chicago to Valparaiso flight route.

  • Which airline alliances offer flights from Chicago to Valparaiso?

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

  • 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, Southwest or Delta?

    The two airlines most popular with KAYAK users for flights from Chicago to Valparaiso are Southwest and Delta. With an average price for the route of $453 and an overall rating of 8.0, Southwest is the most popular choice. Delta is also a great choice for the route, with an average price of $445 and an overall rating of 7.8.

  • 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 $90 or less one-way and $279 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

American Airlines

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

American Airlines

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 4 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 4227 reviews
8.0Comfort
7.5Entertainment
8.1Boarding
8.6Crew
7.0Food
Airline reviews

Boarding process of asking for volunteers to check bags goes against the system you had before with 2 bags checked free. This process is more of a guilt trip than a caring attitude toward the customer. In addition bag-size scrutiny has increased which also slows down the process of boarding. My wife said she will not fly on your airline again unless there is no other option.

10.0 ExcellentDenis, Aug 2026
MDW - ATL
Read more Southwest reviews

Boarding process of asking for volunteers to check bags goes against the system you had before with 2 bags checked free. This process is more of a guilt trip than a caring attitude toward the customer. In addition bag-size scrutiny has increased which also slows down the process of boarding. My wife said she will not fly on your airline again unless there is no other option.

Overall good, just screaming kids in the area the whole flight.

OKay. I sat in the back of the plane and it was really loud between babies and little kids, and adults who.like to talk a lot and loudly most of the flight.

The first time I flew in the extra legroom section. It was difficult to notice a difference. I had bad luck with my neighbors. The crew was okay. Southwest has reduced the live TV options.

I flew twice this week on Southwest, was delayed over 2 hours both ways. From Pittsburgh to Chicago it was due to weather but the gate agents, pilot etc were great at updating everyone. Today from Midway to Pittsburgh the plane had come from an international location, kept getting delayed, no information was given until we were delayed for the third time. It was ridiculous, whoever scheduled that plane to fly to Pittsburgh after didn’t consider a lot of things.

The staff was very friendly, professional, and courteous. The overall flight was a great experience.

Plane crashed into a bus or some other vehicle on the ground while pulling out of the gate. No injuries, but wing tip was damaged and returned to gate for “maintenance issues” and we departed 5 hours later because the plane went out of service and new plane was flown in from a nearby airport, Midway.

I'm not a fan of Southwest's model. I don't like the herding style of boarding.

Excellent experience. WiFi worked on this leg of My trip

Very helpful, convenient, nice crew members, no extra fees, helped us saving 4 hrs of travel by booking is on an earlier flight

The crew was very inconsiderate and rude. My flight was scheduled to depart at 6:00am. I received a call from the crew at 5:40am, asking if I was going to make the flight because I was the only one that hasn't boarded yet and boarding ends at 5:50am. I let them know that I will be at the gate in a few minutes, before the 5:50am cutoff. When I arrived at the gate at 5:45am the gate was closed. Departing early on last minute notice without having all passengers on board is inconsiderate and unprofessional.

Very easy to use and convenient, you can perform any action within the same portal

Okay considering we had weather delays which the Pilot notified us of immediately!

The boarding was organized and informative but the plane was tight meaning that you were sitting on one another and extremely uncomfortable. It’s disappointing that can’t have common seating comfort on the plane.

Everything could have benn better. Short fly, no food, no entertainment and no wifi.

Stop changing gates. Stop cancelling flights Stop moving my seat.

The staff was frielndly. The plane was terrible, it was too small and should be decommissioned. There were no back seat screens at all. The only beverages we had a choice from was coffee, tea or water. The only bathroom in the back was behind the flight attendant's jump seat and wasn't working. And I literally felt like I was sitting on top of the guy next to me. It was terribly hot in the plane and we had to sit on the tarmac in Chicago for 1/2 hour due to congestion in Mpls. Wouldn't they have know that before they even boarded us so that we could have sat in comfort in the terminal?

This was one of the worst flights I’ve been on in years. I upgraded to comfort and had such an uncomfortable experience. The person next to me was oversized - which I understand - however, they took up their space and mine. I could only use about 50% of my seat space to not be physically touching this person the entire flight and there was no spatial awareness. I also could not use the seat outlet because their body was obstructing it. It was very inconvenient. Their body kept touching me repeatedly during the flight and I felt very uncomfortable. To pay more for an upgraded space and then not even being able to use it was highly disappointing.

It was very cold because the air conditioner was on high power, and my son got sick.

Excellent customer service and in flight experience as stated in previous comment Mke-Atl.

It was poor a four hour delay and no explanation for the delay. What’s a 35 dollars going to do. It also made me miss my car rental,

It was on time. Flight was comfortable. Staff was nice. It was the way a flight should always be.

Allegiant canceled the flight. The flight the next day was full. Allegiant did not provide any compensation besides a refund. Last time on Allegiant.

Great. No choice for n/a. No food or entertainment options

just had water and there was plenty of leg & seat room. But then i don't weight 220#s!!

Not totally their fault- screaming kids that had zero parent intervention.

Check in on the web portal was cumbersome! After several attempts I finally got the boarding pass.

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.

My TSA number was missing from my ticket which shouldn’t have happened since it’s in my file. The on board flight attendant who was a male, did not want to help me put my luggage in the overhead bin and made a very rude comment and was very unpleasant. The good… the woman who fixed my ticket with the TSA number was excellent and I had extra legroom which was perfect.

I went to lower my tray table and it was very nasty. Looks like some one had left some food on it and then just closed it up.

I had my flight of Cedar Rapids. THen Chicago to Boston. Flight out of Cedar rapids was delayed by 12 hrs. Had to drive to Chicago to catch my flight

Long delays to board due to mechanical issues with plane.

Flight was delayed, boarded, sat at the gate for more than 30 minutes, left the gate then waited on the pad for another 30 to 60 minutes then returned to the gate, deboarded and was cancelled... alternative flight was not booked automatically. Waited in line for 30 minutes but fortunately an alternate flight to a different destination was found ... no thanks to the travel agent used by kayak

The flight from Milwaukee to Dallas was great the staff absolutely amazing. After that EVERYTHING WENT DOWN HILL!!! ABSOLUTELY HORRIBLE!!! WILL NOT FLY THIS AIRLINE AGAIN

The flight was delayed significantly. Communication during the flight was abrupt and caused some panic as we were navigating turbulence. It was also too loud and every announcement felt startling. The flight attendants did not offer any assurances and I felt unsettled most of the flight. The seats, floor and tray table was very dirty. The seat next to me was broken and the passenger sitting there was very uncomfortable. He had a spring in his back and his seat made terrible squeaking noises through the flight.

Flight to Tampa was delayed taking off due to plane arriving late but no other issues

We experienced gate changes and a long delay. My seat was dirty when I boarded and I had to use wipes to clean it myself. There was an unpleasant and overpowering cleaning product scent on the plane as well that lingered through the flight.

Departure down was really rough and ended up getting motion sickness on the flight

The Airline was not prepared for weather delays. We were held up due to an incoming flight being delayed and so we did not have a flight crew. This caused an extra delay for departure by 2 hours.

From the moment I walked into the airport in Chicago to the moment I was walking off the plane in Florida I had an unforgettable experience! I was traveling with my 3 month old by myself and everyone just made sure I was taken care of. I couldn’t thank them enough!

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

Information on your arrival and departure airports