MDW - VPS

$91 Find Cheap Flights from Chicago Midway Airport 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 Midway to Valparaiso departing on 3/1. 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 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
Travelers love KAYAK
41.299.237 searches in the past 7 days on KAYAK

Save 23% or moreCompare multiple travel sites with one search.

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

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

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

Everything you should know

Cheapest round-trip
$101
Overall average: $378
Allegiant Air
Sun 3/8Thu 3/12
MDW - VPS • Non-stop
Cheapest one-way
$91
Allegiant Air
Sun 3/1
MDW - VPS • Non-stop
Top airlines
Allegiant Air
Cheapest • from $101 (round-trip)
Southwest
Best reviews • 8.0 score
Airline reviews
Airline reviews
+1
+1
Airline reviews
Airline reviews
+1
When to travel
July
Cheapest • 60% price drop
July
Most popular
Good to know
Good to know
+1
+1
Good to know
Good to know
+1
Nonstop flights
2 days a week
There are direct flights from Midway to Valparaiso 2 days a week: Thu, Sun.
Direct flights
Direct flights
Direct flights
Direct flights
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
Flight Deals

Cheap Flights from Midway to Valparaiso (MDW-VPS)

 
Here are some of the best deals found on KAYAK recently from the most popular airlines for round-trip flights from Midway 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 Midway to Valparaiso

Sun, Mar 8 - Thu, Mar 12
Allegiant Air Logo
8:46 pm - 10:54 pm
MDW
-
VPS
2h 08mnonstop
Allegiant Air Logo
5:37 pm - 7:53 pm
VPS
-
MDW
2h 16mnonstop
$101Allegiant Air
Sun, Feb 15 - Thu, Feb 19
Allegiant Air Logo
3:40 pm - 5:46 pm
MDW
-
VPS
2h 06mnonstop
Allegiant Air Logo
1:01 pm - 3:20 pm
VPS
-
MDW
2h 19mnonstop
$113Allegiant Air
Sun, Feb 15 - Thu, Feb 19
Allegiant Air Logo
3:40 pm - 5:46 pm
MDW
-
VPS
2h 06mnonstop
Allegiant Air Logo
1:01 pm - 3:20 pm
VPS
-
MDW
2h 19mnonstop
$139Allegiant Air
Thu, Feb 19 - Thu, Feb 26
Allegiant Air Logo
4:10 pm - 6:16 pm
MDW
-
VPS
2h 06mnonstop
Allegiant Air Logo
12:31 pm - 2:50 pm
VPS
-
MDW
2h 19mnonstop
$164Allegiant Air
Thu, Apr 2 - Thu, Apr 9
Allegiant Air Logo
5:47 pm - 7:56 pm
MDW
-
VPS
2h 09mnonstop
Allegiant Air Logo
2:40 pm - 4:57 pm
VPS
-
MDW
2h 17mnonstop
$193Allegiant Air
Sun, Mar 8 - Thu, Mar 12
Multiple Airlines Logo
7:30 am - 1:52 pm
MDW
-
VPS
6h 22m
1 stop
Multiple Airlines Logo
5:37 pm - 7:53 pm
VPS
-
MDW
2h 16mnonstop
$197Multiple Airlines
Thu, Feb 12 - Thu, Feb 19
Allegiant Air Logo
4:10 pm - 6:16 pm
MDW
-
VPS
2h 06mnonstop
Allegiant Air Logo
1:01 pm - 3:20 pm
VPS
-
MDW
2h 19mnonstop
$219Allegiant Air
Thu, Feb 12 - Sun, Feb 15
Allegiant Air Logo
4:10 pm - 6:16 pm
MDW
-
VPS
2h 06mnonstop
Allegiant Air Logo
12:31 pm - 2:50 pm
VPS
-
MDW
2h 19mnonstop
$225Allegiant Air
Thu, Feb 19 - Sun, Feb 22
Allegiant Air Logo
4:10 pm - 6:16 pm
MDW
-
VPS
2h 06mnonstop
Allegiant Air Logo
12:31 pm - 2:50 pm
VPS
-
MDW
2h 19mnonstop
$243Allegiant Air
Sun, Feb 15 - Thu, Feb 19
Multiple Airlines Logo
3:40 pm - 5:46 pm
MDW
-
VPS
2h 06mnonstop
Multiple Airlines Logo
8:48 pm - 5:53 pm
VPS
-
MDW
21h 05m
2 stops
$244Multiple Airlines
Booking Insights

KAYAK's insights & trends for Midway to Valparaiso flights

Get data-powered insights and trends into flights from Midway to Valparaiso to help you find the cheapest flights, the best time to fly and much more.

What’s the cheapest day of the week to fly from Chicago Midway Airport to Valparaiso?

The average price of all round-trip flights from Chicago Midway Airport to Valparaiso clicked on KAYAK for each day over the last 12 months.

When flying from Chicago Midway Airport to Valparaiso, you should consider leaving on a Wednesday and avoid Saturdays if you are looking for the best rates. For your return to Chicago Midway Airport, you’ll find the best rates on Thursdays and the most expensive ones on Wednesdays.

What is the cheapest month to fly from Chicago Midway Airport to Valparaiso?

To calculate monthly average prices, KAYAK takes all prices for each month over the last year for round-trip flights from Chicago Midway Airport 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 Midway Airport to Valparaiso is July, where tickets cost $97 (return) on average. On the other hand, the most expensive months are November and March, where the average cost of round-trip tickets is $423 and $378 respectively.

Good to know

Low seasonJanuary
Cheapest flight$91
Best time to beat the crowds but there is an average 2% increase in price.
Most popular time to fly and prices are also 61% lower on average.
Flight from Chicago Midway Airport to Valparaiso

When to book flights from Midway to Valparaiso

Are your dates flexible? Find out the best times to travel from Midway 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 Chicago Midway Airport to Valparaiso flights

  • How many flights are there between Chicago Midway Airport and Valparaiso per day?

    There is a maximum of 1 nonstop flight a day that takes off from Chicago Midway Airport and lands in Valparaiso, with an average flight time of 2h 06m. The most common departure time is 3:00 pm and most flights take off in the afternoon. Each week, there are 2 flights.

  • What is the cheapest flight from Chicago Midway Airport to Valparaiso?

    In the last 3 days, the lowest price for a flight from Chicago Midway Airport to Valparaiso was $91 for a one-way ticket and $101 for a round-trip.

  • Do I need a passport to fly between Chicago Midway Airport and Valparaiso?

    No

  • Which airports will I be using when flying from Chicago Midway Airport to Valparaiso?

    Chicago Midway Airport and Valparaiso are both served by 1 main airport. You will leave Chicago Midway Airport from Chicago Midway and will be arriving at Valparaiso Destin-Ft Walton Beach.

  • Which airlines offer Wi-Fi service onboard planes from Chicago Midway Airport to Valparaiso?

    Only American Airlines offers inflight Wi-Fi service on the Chicago Midway Airport to Valparaiso flight route.

  • Which aircraft models fly most regularly from Chicago Midway Airport to Valparaiso?

    The Airbus A319 is the aircraft model that flies most regularly on the Chicago Midway Airport to Valparaiso flight route.

  • On which days can I fly direct from Chicago Midway Airport to Valparaiso?

    You can catch a nonstop flight from Chicago Midway Airport to Valparaiso on Thursday, and Sunday.

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

    The two airlines most popular with KAYAK users for flights from Chicago to Valparaiso are Southwest and Allegiant Air. With an average price for the route of $381 and an overall rating of 8.0, Southwest is the most popular choice. Allegiant Air is also a great choice for the route, with an average price of $169 and an overall rating of 7.2.

  • How does KAYAK find such low prices on flights from Chicago Midway Airport 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 Midway Airport to Valparaiso.

  • How does KAYAK's flight Price Forecast tool help me choose the right time to buy my flight ticket from Chicago Midway Airport to Valparaiso?

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight to Valparaiso from Chicago Midway Airport 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 Midway Airport 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 Midway Airport with another airline. Booking your flights between Chicago Midway Airport and VPS can sometimes prove cheaper using this method.

  • What is KAYAK's "flexible dates" feature and why should I care when looking for a flight from Chicago Midway Airport 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 Midway Airport 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 Midway Airport to Valparaiso

  • Looking for a cheap flight? 25% of our users found flights on this route for $138 or less one-way and $164 or less round-trip.

Prefer to fly direct from Chicago Midway Airport to Valparaiso?

 
Direct data is based off flight results for the next 60 days. Find direct flights from all airlines flying direct from Chicago Midway to Valparaiso Destin-Ft Walton Beach.
Find which airlines fly direct from Chicago Midway Airport to Valparaiso Destin-Ft Walton Beach Airport, which days they fly and book direct flights.

Direct departures

Chicago Midway to Valparaiso Destin-Ft Walton Beach

Thursday

Allegiant Air

Allegiant Air

Sunday

Allegiant Air

Allegiant Air

See more direct flights

Direct returns

Valparaiso Destin-Ft Walton Beach to Chicago Midway

Thursday

Allegiant Air

Allegiant Air

Sunday

Allegiant Air

Allegiant Air

See more direct flights

Reviews of the top airlines flying from Midway 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 Midway 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 4268 reviews
8.6Crew
7.5Entertainment
8.0Comfort
8.1Boarding
7.0Food
Airline reviews

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

10.0 ExcellentManetta, Jan 2026
MDW - CLT
Read more Southwest reviews

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

Okay, not wonderful. Short flight. Wi-fi didn't work properly. Stuck waiting for a gate to open upon arrival for 20 or so minutes.

They sent a notice that they were boarding an hour early. We had to leave the club and run to the gate. They said sorry, that came from corporate and was a mistake. They did not have enough seating because the flight before it had not taken off on time. They moved our gate and delayed it for an hour.

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.

All was good. I just had a hard time getting connected to the WiFi/internet during the flight

Better and more food and drinks. Put msnbc and free speech tv on the news channel selection list.

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

It was fine. Nobody was outstandingly friendly but no one was rude and everything was smooth . The captain thanked us for flying but no one greeted me as I walked on the plane or as I exited which is the least they could do lol

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.

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

Information on your arrival and departure airports