VPS - MDW

$52 Find Cheap Flights from Valparaiso to Chicago Midway Airport - Compare and Save

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Everything you should know

Cheapest round-trip
$299
Typical prices: $138-$265
Southwest
Sat 12/8Mon 12/10
VPS - MDW • 1 stop
Cheapest one-way
$52
Typical prices: $74-$202
Allegiant Air
Mon 11/19
VPS - MDW • Non-stop
Nonstop flights
There are currently no direct flights between Valparaiso and Chicago Midway Airport. You'll need to take a connecting flight to reach the destination.
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Insights
When to travel
Cheapest • 48% price drop
Most popular
Good to know
+1
Good to know
+1
Top layover airports
Cheapest • Avg $392 (round-trip)
Shortest trip • 3h 47m (one-way)
Insights
Insights
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We hope you love your trip to Chicago Midway Airport!
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Flight Deals

Cheap Flights from Valparaiso to Midway (VPS-MDW)

 
Discover the best prices for you by selecting your travel dates on KAYAK.

Recent round-trip flight deals from Valparaiso to Midway

Tue, Dec 8 - Thu, Dec 10
Southwest Logo
11:10 am - 5:10 pmVPS  Valparaiso Destin-Ft Walton Beach-MDW Chicago Midway
6h 00m1 stop Dallas Love Field
Southwest Logo
7:05 am - 1:25 pmMDW  Chicago Midway-VPS Valparaiso Destin-Ft Walton Beach
6h 20m1 stop Dallas Love Field
$299Southwest
Fri, Nov 13 - Tue, Nov 17
Multiple Airlines Logo
7:30 am - 9:48 amVPS  Valparaiso Destin-Ft Walton Beach-MDW Chicago Midway
2h 18mnonstop
Multiple Airlines Logo
6:08 am - 12:59 pmMDW  Chicago Midway-VPS Valparaiso Destin-Ft Walton Beach
54h 51m3 stops Atlanta Hartsfield-Jackson Fort Lauderdale Indianapolis
$300Multiple Airlines
Tue, Dec 8 - Thu, Dec 10
Southwest Logo
7:00 am - 12:55 pmVPS  Valparaiso Destin-Ft Walton Beach-MDW Chicago Midway
5h 55m1 stop Nashville Intl
Southwest Logo
11:30 am - 9:15 pmMDW  Chicago Midway-VPS Valparaiso Destin-Ft Walton Beach
9h 45m2 stops Lambert-St Louis Nashville Intl
$305Southwest
Mon, Dec 7 - Thu, Dec 10
Southwest Logo
2:05 pm - 10:45 pmVPS  Valparaiso Destin-Ft Walton Beach-MDW Chicago Midway
8h 40m1 stop Nashville Intl
Southwest Logo
7:05 am - 1:25 pmMDW  Chicago Midway-VPS Valparaiso Destin-Ft Walton Beach
6h 20m1 stop Dallas Love Field
$305Southwest
Tue, Dec 8 - Thu, Dec 10
Southwest Logo
2:05 pm - 7:55 pmVPS  Valparaiso Destin-Ft Walton Beach-MDW Chicago Midway
5h 50m2 stops Nashville Intl Pittsburgh
Southwest Logo
11:30 am - 9:15 pmMDW  Chicago Midway-VPS Valparaiso Destin-Ft Walton Beach
9h 45m2 stops Lambert-St Louis Nashville Intl
$310Southwest
Mon, Dec 7 - Thu, Dec 10
Southwest Logo
2:05 pm - 10:45 pmVPS  Valparaiso Destin-Ft Walton Beach-MDW Chicago Midway
8h 40m1 stop Nashville Intl
Southwest Logo
11:30 am - 9:15 pmMDW  Chicago Midway-VPS Valparaiso Destin-Ft Walton Beach
9h 45m2 stops Lambert-St Louis Nashville Intl
$310Southwest
Fri, Nov 13 - Tue, Nov 17
Multiple Airlines Logo
7:30 am - 9:48 amVPS  Valparaiso Destin-Ft Walton Beach-MDW Chicago Midway
2h 18mnonstop
Multiple Airlines Logo
6:42 pm - 12:59 pmMDW  Chicago Midway-VPS Valparaiso Destin-Ft Walton Beach
42h 17m2 stops Atlanta Hartsfield-Jackson Indianapolis
$337Multiple Airlines
Wed, Nov 25 - Mon, Nov 30
Multiple Airlines Logo
11:37 am - 8:14 amVPS  Valparaiso Destin-Ft Walton Beach-MDW Chicago Midway
20h 37m2 stops Washington, D.C. Dulles Intl Atlanta Hartsfield-Jackson
Multiple Airlines Logo
6:51 pm - 8:56 pmMDW  Chicago Midway-VPS Valparaiso Destin-Ft Walton Beach
2h 05mnonstop
$345Multiple Airlines
Wed, Nov 25 - Mon, Nov 30
Multiple Airlines Logo
11:37 am - 8:14 amVPS  Valparaiso Destin-Ft Walton Beach-MDW Chicago Midway
20h 37m2 stops Washington, D.C. Dulles Intl Atlanta Hartsfield-Jackson
Multiple Airlines Logo
6:51 pm - 8:56 pmMDW  Chicago Midway-VPS Valparaiso Destin-Ft Walton Beach
2h 05mnonstop
$347Multiple Airlines
Thu, Dec 3 - Sun, Dec 6
Southwest Logo
2:05 pm - 10:45 pmVPS  Valparaiso Destin-Ft Walton Beach-MDW Chicago Midway
8h 40m1 stop Nashville Intl
Southwest Logo
5:20 am - 1:25 pmMDW  Chicago Midway-VPS Valparaiso Destin-Ft Walton Beach
8h 05m1 stop Dallas Love Field
$356Southwest
Booking Insights

Price, demand and travel trends for Valparaiso to Chicago Midway Airport flights

Use KAYAK data on prices, travel dates, airlines and seasonal trends to compare options and book flights with more confidence.

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

Round-trip flights from Valparaiso to Chicago Midway Airport typically range from $138 to $265. The lowest price found in the past 5 days was $299, on Southwest.

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

Based on deals KAYAK users found in the last 12 months, Wednesday is the cheapest day of the week to fly from Valparaiso to Chicago Midway Airport. It’s 49% cheaper than the average day, while Tuesday is the most expensive, with prices 139% higher.

Key details for Valparaiso to Chicago Midway Airport flights

Low season

February

Cheapest flight

$52
Beat the crowds with an average 46% drop in travelers.
The most popular month to fly with an average 29% increase in travelers.
One-way 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

Your Valparaiso to Chicago Midway Airport flight questions, answered

Find helpful answers about this route, including flight times, airports, airlines and booking tips.

  • What are the earliest and latest flights from Valparaiso to Chicago Midway Airport?

    These are the earliest and latest flight times available from Valparaiso to Chicago Midway Airport:

    • Earliest: departs at 6:30 am and lands at 8:51 am
    • Latest: departs at 6:08 pm and lands at 8:29 pm.

    The flight takes about 2h 21m.

  • What cabin classes can I book on flights from Valparaiso to Chicago Midway Airport?

    Only Economy Class is available on flights from Valparaiso to Chicago Midway Airport.

  • How long is a flight from Valparaiso to Chicago Midway Airport?

    A nonstop flight from Valparaiso to Chicago Midway Airport takes 2h 21m, covering 783 miles.

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

    No, a passport is not required for this domestic route, but you will need a real ID-compliant driver's license, a state ID or another TSA-accepted form of identification.

  • How much should I expect to pay for a Valparaiso to Chicago Midway Airport flight?

    Round-trip flights from Valparaiso to Chicago Midway Airport range from $138 to $265, with an average of $200 over the past 12 months. Anything below $138 counts as a good deal.

  • How much can I save by taking a layover when flying from Valparaiso to Chicago Midway Airport?

    On this route, nonstop flights are cheaper than layover options on average. Nonstop fares average $149 round-trip, compared to $392 via a layover through Atlanta Hartsfield-Jackson (ATL).

  • What is the standard checked-bag allowance on flights from Valparaiso to Chicago Midway Airport?

    There is no standard. Checked-bag policies vary by airline on this route. Most carriers charge $25–$100 for the first checked bag in economy. Premium fares and elite-status bookings typically include a free checked bag.

  • Which aircraft model is used most often on flights from Valparaiso to Chicago Midway Airport?

    The Airbus A319 family is used most often on this route, operated mainly by Allegiant Air and American Airlines. Other aircraft seen on the route include Boeing 737-700 variants.

  • Have flight prices from Valparaiso to Chicago Midway Airport changed much recently?

    Yes. Based on fares seen in the past 5 days, round-trip prices on this route showed a wide range, from about $299 to $933. That means the highest observed fare was about 3x higher than the lowest one.

  • How are flight prices from Valparaiso to Chicago Midway Airport looking right now?

    One-way fares from Valparaiso to Chicago Midway Airport are currently higher than usual. Average one-way flight prices are about $188, which is 26% above the typical average for this route.

  • What car rental options are available at Chicago Midway Airport (MDW)?

    Chicago Midway Airport (MDW) hosts 5 major car rental companies, with daily rates averaging $84 for economy cars. Top options include:

    • Hertz
    • Dollar
    • Budget
    • Alamo
    • Rent-A-Wreck

  • Which airports can I use when flying from Valparaiso to Chicago Midway Airport?

    Flights from Valparaiso to Chicago Midway Airport usually depart from Valparaiso Destin-Ft Walton Beach (VPS) and arrive at Chicago Midway (MDW).

  • Which airports do connecting flights from Valparaiso to Chicago Midway Airport pass through?

    One-stop flights from Valparaiso to Chicago Midway Airport most commonly connect through:

    • Atlanta Hartsfield-Jackson (ATL) - 67% of one-stop connections
    • Nashville Intl (BNA) - 17% of one-stop connections
    • Dallas Love Field (DAL) - 8% of one-stop connections
    • Lambert-St Louis (STL) - 8% of one-stop connections

  • Can I save money by using flexible dates for flights from Valparaiso to Chicago Midway Airport?

    Yes. Flexible dates can save you up to 79% on flights from Valparaiso to Chicago Midway Airport. Wednesday is the cheapest departure day at $103 round-trip on average, while Tuesday is the most expensive at $479, a difference of $376.

    KAYAK's flexible dates feature shows options up to 3 days before and after your selected dates, making it easier to compare nearby fares.

  • What airlines fly from Valparaiso to Chicago Midway Airport?

    Only Allegiant Air operates flights between Valparaiso and Chicago Midway Airport.

  • How much time can I save by choosing a different layover airport from Valparaiso to Chicago Midway Airport?

    Flying via Lambert-St Louis (STL) gives the shortest average 1-stop total travel time at 3h 47m, compared with 4h 43m via Nashville Intl (BNA) and 4h 47m via Atlanta Hartsfield-Jackson (ATL).

  • What popular places can I visit in Chicago Midway Airport?

    Some of the most popular sights in Chicago Midway Airport are Magnificent Mile, Grant Park and Soldier Field. These are among the most viewed places in Chicago Midway Airport on KAYAK.

Your guide to booking Valparaiso to Chicago Midway Airport flights

Get tips on when to book, when to fly and what to know before your trip.
  • If your dates are flexible, aim for a Wednesday departure and avoid flying on Tuesday. On this route, Wednesday flights average $103, about $376 less than Tuesday fares (78% savings) based on the last 12 months.
  • If you can choose when to travel, plan your Valparaiso to Chicago Midway Airport trip for March. Fares historically average $103 round-trip in that month - typically $343 less than the most expensive month, which is August (based on the last 12 months).
  • If you're arriving late at night and need somewhere to stay, check out these hotels close to Chicago Midway Airport.

    • DoubleTree by Hilton Chicago Midway Airport
    • Holiday Inn Chicago - Midway Airport S by IHG
    • Skylark Motel Chicago Midway Airport

Prefer to fly direct from Valparaiso to Chicago Midway Airport?

 
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

Tuesday

Allegiant Air

Allegiant Air

Thursday

Allegiant Air

Allegiant Air

Friday

Allegiant Air

Allegiant Air

Saturday

Allegiant Air

Allegiant Air

Sunday

Allegiant Air

Allegiant Air

See more direct flights

Direct returns

Chicago Midway to Valparaiso Destin-Ft Walton Beach

Monday

Allegiant Air

Allegiant Air

Tuesday

Allegiant Air

Allegiant Air

Thursday

Allegiant Air

Allegiant Air

Friday

Allegiant Air

Allegiant Air

Saturday

Allegiant Air

Allegiant Air

Sunday

Allegiant Air

Allegiant Air

See more direct flights

More options for your flight from Valparaiso to Midway

Complete your trip to Chicago with a hotel stay or car rental