VPS - MDW

$113 Find Cheap Flights from Valparaiso to Chicago Midway Airport

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 Midway departing on 5/25. 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 Midway Airport

 
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
$299
Multiple Airlines
Thu 4/23Mon 4/27
VPS - MDW • Non-stop
Cheapest non-stop
$311
Allegiant Air
Thu 3/26Sun 3/29
VPS - MDW • Non-stop
Top airlines
Southwest
Cheapest • from $307 (round-trip)
Allegiant Air
Best reviews • 7.2 score
Airline reviews
Airline reviews
+1
+1
Airline reviews
Airline reviews
+1
Nonstop flights
2 days a week
There are direct flights from Valparaiso to Midway 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 Midway!
Flight Deals
Booking Insights
Flight Deals

Cheap Flights from Valparaiso to Midway (VPS-MDW)

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

Thu, Apr 23 - Mon, Apr 27
Multiple Airlines Logo
2:40 pm - 4:57 pm
VPS
-
MDW
2h 17mnonstop
Multiple Airlines Logo
9:14 am - 8:48 am
MDW
-
VPS
23h 34m
3 stops
$299Multiple Airlines
Thu, Apr 23 - Mon, Apr 27
Multiple Airlines Logo
2:40 pm - 4:57 pm
VPS
-
MDW
2h 17mnonstop
Multiple Airlines Logo
9:14 am - 8:48 am
MDW
-
VPS
23h 34m
2 stops
$305Multiple Airlines
Wed, Jul 1 - Sat, Jul 11
Southwest Logo
2:30 pm - 7:35 pm
VPS
-
MDW
5h 05m
1 stop
Southwest Logo
5:25 am - 2:35 pm
MDW
-
VPS
9h 10m
1 stop
$307Southwest
Thu, Mar 26 - Sun, Mar 29
Allegiant Air Logo
5:37 pm - 7:53 pm
VPS
-
MDW
2h 16mnonstop
Allegiant Air Logo
8:43 pm - 10:51 pm
MDW
-
VPS
2h 08mnonstop
$311Allegiant Air
Wed, Jul 1 - Sat, Jul 11
Southwest Logo
7:15 am - 3:10 pm
VPS
-
MDW
7h 55m
2 stops
Southwest Logo
5:25 am - 2:35 pm
MDW
-
VPS
9h 10m
1 stop
$312Southwest
Thu, Jul 2 - Sat, Jul 11
Southwest Logo
6:05 pm - 12:15 am
VPS
-
MDW
6h 10m
1 stop
Southwest Logo
5:25 am - 2:35 pm
MDW
-
VPS
9h 10m
1 stop
$326Southwest
Wed, Jul 1 - Wed, Jul 8
Southwest Logo
1:35 pm - 7:05 pm
VPS
-
MDW
5h 30m
1 stop
Southwest Logo
6:30 am - 11:25 am
MDW
-
VPS
4h 55m
1 stop
$331Southwest
Wed, Jul 1 - Wed, Jul 8
Southwest Logo
7:15 am - 3:10 pm
VPS
-
MDW
7h 55m
2 stops
Southwest Logo
6:30 am - 11:25 am
MDW
-
VPS
4h 55m
1 stop
$336Southwest
Wed, Jul 1 - Wed, Jul 8
Southwest Logo
10:30 am - 7:05 pm
VPS
-
MDW
8h 35m
2 stops
Southwest Logo
7:45 am - 3:20 pm
MDW
-
VPS
7h 35m
2 stops
$346Southwest
Thu, May 21 - Wed, Jun 10
Southwest Logo
6:15 pm - 11:30 pm
VPS
-
MDW
5h 15m
1 stop
Southwest Logo
6:30 am - 11:25 am
MDW
-
VPS
4h 55m
1 stop
$350Southwest
Booking Insights

KAYAK's insights & trends for Valparaiso to Midway flights

Get data-powered insights and trends into flights from Valparaiso to Midway 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 Valparaiso to Chicago Midway Airport?

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

If your flying dates are flexible, you should consider flying to Chicago Midway Airport on a Thursday, as we generally find the cheapest rates on that day for this route. On the other hand, Wednesday is the most expensive day to fly from Valparaiso to Chicago Midway Airport. For your return ticket, we recommend flying on a Wednesday and avoiding Saturdays for the best deals.

Can I save money by flying with a layover from Valparaiso to Chicago Midway Airport?

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 $104, prices are generally cheapest when you fly direct.

Find deals

Good to know

Cheapest flight$113
Flight from Valparaiso to Chicago Midway Airport

When to book flights from Valparaiso to Midway

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

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

    There is a maximum of 1 nonstop flight a day that takes off from Valparaiso and lands in Chicago Midway Airport, with an average flight time of 2h 19m. The most common departure time is 12:00 pm and most flights take off in the morning. Each week, there are 2 flights.

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

    In the last 3 days, the lowest price for a flight from Valparaiso to Chicago Midway Airport was $113 for a one-way ticket and $299 for a round-trip.

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

    No, a passport isn't needed to fly from Valparaiso to Chicago Midway Airport. However, local authorities might ask for an official ID.

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

    On your way to Chicago Midway Airport, you’ll fly out from Valparaiso Destin-Ft Walton Beach. You’ll be landing at Chicago Midway.

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

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

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

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

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

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

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

    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 Midway Airport.

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

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight to Chicago Midway Airport 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 Midway Airport?

    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 Midway Airport with an airline and back to Valparaiso with another airline. Booking your flights between Valparaiso and MDW 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 Valparaiso to Chicago Midway Airport?

    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 Midway Airport 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 Midway Airport

  • Looking for a cheap flight? 25% of our users found flights on this route for $102 or less round-trip.

Prefer to fly direct from Valparaiso to Chicago Midway Airport?

 
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 Midway.
Find which airlines fly direct from Valparaiso Destin-Ft Walton Beach Airport to Chicago Midway Airport, which days they fly and book direct flights.

Direct departures

Valparaiso Destin-Ft Walton Beach to Chicago Midway

Thursday

Allegiant Air

Allegiant Air

Sunday

Allegiant Air

Allegiant Air

See more direct flights

Direct returns

Chicago Midway to Valparaiso Destin-Ft Walton Beach

Thursday

Allegiant Air

Allegiant Air

Sunday

Allegiant Air

Allegiant Air

See more direct flights

Reviews of the top airline flying from Valparaiso to Midway

 
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 Midway? 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.
7.2
Allegiant AirOverall score based on 706 reviews
5.9Food
8.1Crew
6.8Comfort
5.5Entertainment
7.6Boarding
Airline reviews

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

8.0 ExcellentBreanna, Dec 2025
SFB - GRR
Read more Allegiant Air reviews

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 Valparaiso to Midway

Information on your arrival and departure airports

Valparaiso (VPS)
Midway (MDW)