MDW - VPS

$84 Find Cheap Flights from Chicago Midway Airport to Valparaiso - Compare and Save

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Everything you should know

Cheapest round-trip
$84
Typical prices: $167-$417
Allegiant Air
Fri 11/16Mon 11/19
MDW - VPS • Non-stop
Cheapest one-way
$149
Typical prices: $98-$231
Allegiant Air
Thu 11/22
MDW - VPS • Non-stop
Nonstop flights
There are currently no direct flights between Chicago Midway Airport and Valparaiso. You'll need to take a connecting flight to reach the destination.
Insights
Insights
When to book
in advance
Our data shows that travelers who book at least 14 weeks in advance save around 72% compared to booking last minute.
Insights
Insights
When to travel
Cheapest • 57% price drop
Most popular
Good to know
+1
Good to know
+1
Top layover airports
Cheapest • Avg $334 (round-trip)
Shortest trip • 4h 19m (one-way)
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Insights
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We hope you love your trip to Valparaiso!
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Booking Insights
Flight Deals

Cheap Flights from Midway to Valparaiso (MDW-VPS)

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

Recent round-trip flight deals from Midway to Valparaiso

Mon, Nov 16 - Thu, Nov 19
Allegiant Air Logo
1:08 pm - 3:19 pmMDW  Chicago Midway-VPS Valparaiso Destin-Ft Walton Beach
2h 11mnonstop
Allegiant Air Logo
6:30 am - 8:54 amVPS  Valparaiso Destin-Ft Walton Beach-MDW Chicago Midway
2h 24mnonstop
$84Allegiant Air
Mon, Nov 16 - Thu, Nov 19
Allegiant Air Logo
1:08 pm - 3:19 pmMDW  Chicago Midway-VPS Valparaiso Destin-Ft Walton Beach
2h 11mnonstop
Allegiant Air Logo
6:30 am - 8:54 amVPS  Valparaiso Destin-Ft Walton Beach-MDW Chicago Midway
2h 24mnonstop
$89Allegiant Air
Mon, Nov 16 - Thu, Nov 19
Allegiant Air Logo
1:08 pm - 3:19 pmMDW  Chicago Midway-VPS Valparaiso Destin-Ft Walton Beach
2h 11mnonstop
Allegiant Air Logo
6:30 am - 8:54 amVPS  Valparaiso Destin-Ft Walton Beach-MDW Chicago Midway
2h 24mnonstop
$91Allegiant Air
Mon, Nov 16 - Thu, Nov 19
Allegiant Air Logo
1:08 pm - 3:19 pmMDW  Chicago Midway-VPS Valparaiso Destin-Ft Walton Beach
2h 11mnonstop
Allegiant Air Logo
6:30 am - 8:54 amVPS  Valparaiso Destin-Ft Walton Beach-MDW Chicago Midway
2h 24mnonstop
$94Allegiant Air
Mon, Nov 16 - Fri, Nov 20
Multiple Airlines Logo
1:08 pm - 3:19 pmMDW  Chicago Midway-VPS Valparaiso Destin-Ft Walton Beach
2h 11mnonstop
Multiple Airlines Logo
7:00 am - 7:33 amVPS  Valparaiso Destin-Ft Walton Beach-MDW Chicago Midway
24h 33m2 stops Washington, D.C. Dulles Intl Atlanta Hartsfield-Jackson
$265Multiple Airlines
Mon, Nov 16 - Thu, Nov 19
Multiple Airlines Logo
1:08 pm - 3:19 pmMDW  Chicago Midway-VPS Valparaiso Destin-Ft Walton Beach
2h 11mnonstop
Multiple Airlines Logo
1:49 pm - 7:33 amVPS  Valparaiso Destin-Ft Walton Beach-MDW Chicago Midway
41h 44m3 stops Indianapolis Orlando Atlanta Hartsfield-Jackson
$291Multiple Airlines
Mon, Nov 16 - Thu, Nov 19
Multiple Airlines Logo
1:08 pm - 3:19 pmMDW  Chicago Midway-VPS Valparaiso Destin-Ft Walton Beach
2h 11mnonstop
Multiple Airlines Logo
1:49 pm - 7:33 amVPS  Valparaiso Destin-Ft Walton Beach-MDW Chicago Midway
41h 44m3 stops Indianapolis Orlando Atlanta Hartsfield-Jackson
$321Multiple Airlines
Tue, Dec 15 - Thu, Dec 24
Southwest Logo
7:05 am - 1:25 pmMDW  Chicago Midway-VPS Valparaiso Destin-Ft Walton Beach
6h 20m1 stop Dallas Love Field
Southwest Logo
11:10 am - 7:55 pmVPS  Valparaiso Destin-Ft Walton Beach-MDW Chicago Midway
8h 45m1 stop Dallas Love Field
$336Southwest
Tue, Dec 15 - Thu, Dec 24
Southwest Logo
7:05 am - 1:25 pmMDW  Chicago Midway-VPS Valparaiso Destin-Ft Walton Beach
6h 20m1 stop Dallas Love Field
Southwest Logo
7:00 am - 3:30 pmVPS  Valparaiso Destin-Ft Walton Beach-MDW Chicago Midway
8h 30m2 stops Nashville Intl Lambert-St Louis
$336Southwest
Tue, Dec 15 - Thu, Dec 24
Southwest Logo
1:20 pm - 9:15 pmMDW  Chicago Midway-VPS Valparaiso Destin-Ft Walton Beach
7h 55m2 stops Tampa Nashville Intl
Southwest Logo
2:05 pm - 11:10 pmVPS  Valparaiso Destin-Ft Walton Beach-MDW Chicago Midway
9h 05m2 stops Nashville Intl Houston Hobby
$341Southwest
Booking Insights

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

Round-trip flights from Chicago Midway Airport to Valparaiso typically range from $167 to $417. The lowest price found in the past 5 days was $84, on Allegiant Air.

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

Based on deals KAYAK users found in the last 12 months, Monday is the cheapest day of the week to fly from Chicago Midway Airport to Valparaiso. It’s 56% cheaper than the average day, while Saturday is the most expensive, with prices 30% higher.

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

•October is the cheapest month to fly from Chicago Midway Airport to Valparaiso at $119 round-trip.
•May ($534) and September ($413) are the most expensive months.
•The price difference between flying in the cheapest and most expensive months is 348% on average.
This is based on KAYAK aggregated and averaged internal data over the past 12 months.

When are flights from Chicago Midway Airport to Valparaiso the cheapest?

Flights from Chicago Midway Airport to Valparaiso are cheapest 14 weeks before departure. Booking in this window typically costs about 72% less than the average last-minute fare (within 2 weeks of the flight), based on KAYAK data.

Key details for Chicago Midway Airport to Valparaiso flights

Low season

January

Cheapest flight

$84
Beat the crowds with an average 25% drop in travelers.
The most popular month to fly with an average 55% increase in travelers.
Round-trip 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

Your Chicago Midway Airport to Valparaiso 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 Chicago Midway Airport to Valparaiso?

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

    • Earliest: departs at 9:41 am and lands at 11:48 am
    • Latest: departs at 9:22 pm and lands at 11:29 pm.

    The flight takes about 2h 07m.

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

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

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

    A nonstop flight from Chicago Midway Airport to Valparaiso takes 2h 07m, covering 783 miles.

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

    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 Chicago Midway Airport to Valparaiso flight?

    Round-trip flights from Chicago Midway Airport to Valparaiso range from $167 to $417, with an average of $279 over the past 12 months. Anything below $167 counts as a good deal.

  • How expensive are last-minute Chicago Midway Airport to Valparaiso flights?

    Last-minute fares on this route (booked within two weeks of departure) run 47% above the $279 route average. Book 14 weeks before departure for the lowest fares.

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

    On this route, nonstop flights are cheaper than layover options on average. Nonstop fares average $218 round-trip, compared to $334 via a layover through Dallas Love Field (DAL).

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

    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 Chicago Midway Airport to Valparaiso?

    The Airbus A319 family is used most often on this route, operated mainly by Allegiant Air and United Airlines. Other aircraft seen on the route include Embraer 175 variants.

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

    One-way fares from Chicago Midway Airport to Valparaiso are currently higher than usual. Average one-way flight prices are about $207, which is 40% above the typical average for this route.

  • What car rental options are available at Valparaiso Destin-Ft Walton Beach Airport (VPS)?

    Valparaiso Destin-Ft Walton Beach Airport (VPS) hosts 5 major car rental companies, with daily rates averaging $66 for economy cars. Top options include:

    • Dollar
    • Hertz
    • Budget
    • Alamo
    • Avis

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

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

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

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

    • Nashville Intl (BNA) - 52% of one-stop connections
    • Atlanta Hartsfield-Jackson (ATL) - 33% of one-stop connections
    • Baltimore/Washington (BWI) - 4% of one-stop connections
    • Dallas Love Field (DAL) - 4% of one-stop connections

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

    Yes. Flexible dates can save you up to 66% on flights from Chicago Midway Airport to Valparaiso. Monday is the cheapest departure day at $125 round-trip on average, while Saturday is the most expensive at $365, a difference of $240.

    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 Chicago Midway Airport to Valparaiso?

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

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

    Flying via Lambert-St Louis (STL) gives the shortest average 1-stop total travel time at 4h 19m, compared with 4h 37m via Nashville Intl (BNA) and 5h 12m via Atlanta Hartsfield-Jackson (ATL).

Your guide to booking Chicago Midway Airport to Valparaiso 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 Monday departure and avoid flying on Saturday. On this route, Monday flights average $125, about $240 less than Saturday fares (66% savings) based on the last 12 months.
  • For the best chance at a low fare, aim to book around 14 weeks before you fly. On this route, that window historically saves about 72% versus last-minute pricing (KAYAK booking data, last 12 months).
  • If you can choose when to travel, plan your Chicago Midway Airport to Valparaiso trip for October. Fares historically average $119 round-trip in that month - typically $415 less than the most expensive month, which is May (based on the last 12 months).

Prefer to fly direct from Chicago Midway Airport to Valparaiso?

 
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

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

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

More options for your flight from Midway to Valparaiso

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