VPS - MDW

$48 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 10/30. 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 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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Flights 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, Aug 28 - Mon, Sep 1
Southwest Logo
4:10 pm - 10:50 pmVPS-MDW
6h 40m1 stop
Southwest Logo
5:10 am - 11:15 amMDW-VPS
6h 05m1 stop
$235Southwest
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Thu, Aug 28 - Mon, Sep 1
Southwest Logo
12:00 pm - 7:30 pmVPS-MDW
7h 30m2 stops
Southwest Logo
5:10 am - 11:15 amMDW-VPS
6h 05m1 stop
$240Southwest
Find Deal
Fri, Aug 22 - Mon, Aug 25
Southwest Logo
2:00 pm - 8:50 pmVPS-MDW
6h 50m1 stop
Southwest Logo
5:10 am - 11:15 amMDW-VPS
6h 05m1 stop
$258Southwest
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Fri, Aug 22 - Mon, Aug 25
Southwest Logo
12:00 pm - 7:30 pmVPS-MDW
7h 30m2 stops
Southwest Logo
5:10 am - 11:15 amMDW-VPS
6h 05m1 stop
$263Southwest
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Sat, Sep 13 - Tue, Sep 16
Southwest Logo
11:30 am - 4:40 pmVPS-MDW
5h 10m1 stop
Southwest Logo
10:45 am - 7:00 pmMDW-VPS
8h 15m2 stops
$365Southwest
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Thu, Sep 4 - Mon, Sep 8
Southwest Logo
12:00 pm - 7:30 pmVPS-MDW
7h 30m2 stops
Southwest Logo
12:25 pm - 9:05 pmMDW-VPS
8h 40m2 stops
$370Southwest
Find Deal
Sat, Aug 30 - Mon, Sep 1
Southwest Logo
11:30 am - 6:55 pmVPS-MDW
7h 25m2 stops
Southwest Logo
5:25 am - 1:15 pmMDW-VPS
7h 50m1 stop
$376Southwest
Find Deal
Sat, Sep 20 - Thu, Sep 25
Delta Logo
6:00 am - 6:35 pmVPS-MDW
12h 35m2 stops
Delta Logo
6:00 am - 10:36 amMDW-VPS
4h 36m1 stop
$377Delta
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Thu, Aug 28 - Mon, Sep 1
Southwest Logo
12:00 pm - 7:30 pmVPS-MDW
7h 30m2 stops
Southwest Logo
6:30 am - 3:25 pmMDW-VPS
8h 55m2 stops
$382Southwest
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Sat, Sep 20 - Thu, Sep 25
Delta Logo
12:55 pm - 8:49 amVPS-MDW
19h 54m1 stop
Delta Logo
6:00 am - 10:36 amMDW-VPS
4h 36m1 stop
$392Delta
Find Deal
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.

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

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 Friday, 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 Monday 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 $258, prices are generally cheapest when you fly direct.

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Good to know

Low seasonFebruary
Cheapest flight$48
Best time to beat the crowds with an average 74% drop in price.
Most popular time to fly and prices are also 45% lower on average.
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

  • 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 $48 for a one-way ticket and $235 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 Monday, and Friday.

  • 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 $86 or less one-way.

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

Monday

Allegiant Air

Allegiant Air

Wednesday

Allegiant Air

Allegiant Air

Friday

Allegiant Air

Allegiant Air

See more direct flights

Direct returns

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

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

Information on your arrival and departure airports

Valparaiso (VPS)
Midway (MDW)

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