MDW - VPS

$55 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 12/1. 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

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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Flights 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

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, Aug 23 - Wed, Aug 27
Southwest Logo
9:35 am - 3:15 pmMDW-VPS
5h 40m1 stop
Southwest Logo
2:00 pm - 7:45 pmVPS-MDW
5h 45m1 stop
$235Southwest
Find Deal
Sat, Aug 23 - Wed, Aug 27
Southwest Logo
11:25 am - 6:45 pmMDW-VPS
7h 20m2 stops
Southwest Logo
7:00 am - 10:45 amVPS-MDW
3h 45m1 stop
$240Southwest
Find Deal
Sat, Aug 23 - Wed, Aug 27
Southwest Logo
7:00 am - 5:00 pmMDW-VPS
10h 00m2 stops
Southwest Logo
7:00 am - 3:10 pmVPS-MDW
8h 10m2 stops
$245Southwest
Find Deal
Thu, Oct 2 - Sun, Oct 5
Allegiant Air Logo
11:07 am - 1:12 pmMDW-VPS
2h 05mnonstop
Allegiant Air Logo
8:00 am - 10:17 amVPS-MDW
2h 17mnonstop
$248Allegiant Air
Find Deal
Mon, Sep 8 - Wed, Sep 17
Southwest Logo
5:10 am - 11:15 amMDW-VPS
6h 05m1 stop
Southwest Logo
10:35 am - 4:25 pmVPS-MDW
5h 50m1 stop
$258Southwest
Find Deal
Mon, Sep 8 - Wed, Sep 17
Southwest Logo
7:45 am - 3:25 pmMDW-VPS
7h 40m2 stops
Southwest Logo
12:40 pm - 7:15 pmVPS-MDW
6h 35m1 stop
$263Southwest
Find Deal
Tue, Sep 9 - Wed, Sep 17
Delta Logo
9:30 am - 9:54 pmMDW-VPS
12h 24m2 stops
Delta Logo
6:00 am - 6:35 pmVPS-MDW
12h 35m2 stops
$330Delta
Find Deal
Sat, Sep 27 - Fri, Oct 3
Delta Logo
9:35 am - 9:49 pmMDW-VPS
12h 14m2 stops
Delta Logo
7:06 pm - 8:40 amVPS-MDW
13h 34m2 stops
$333Delta
Find Deal
Sat, Aug 23 - Sat, Aug 30
Delta Logo
1:43 pm - 12:00 pmMDW-VPS
22h 17m1 stop
Delta Logo
6:00 am - 6:37 pmVPS-MDW
12h 37m2 stops
$337Delta
Find Deal
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 Monday 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 Fridays and the most expensive ones on Wednesdays.

Good to know

Low seasonJuly
Cheapest flight$55
Best time to beat the crowds with an average 60% drop in price.
Most popular time to fly and prices are also 60% 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

  • 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 $55 for a one-way ticket and $210 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 A320-100/200 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 Monday, and Friday.

  • 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 $388 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 $162 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 $64 or less one-way and $86 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

Monday

Allegiant Air

Allegiant Air

Wednesday

Allegiant Air

Allegiant Air

Friday

Allegiant Air

Allegiant Air

See more direct flights

Direct returns

Valparaiso Destin-Ft Walton Beach to Chicago Midway

Monday

Allegiant Air

Allegiant Air

Wednesday

Allegiant Air

Allegiant Air

Friday

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 4241 reviews
7.5Entertainment
8.1Boarding
7.0Food
8.6Crew
8.0Comfort
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

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 Midway to Valparaiso

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