VPS - MDW

$114 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 6/22. 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
$125
Allegiant Air
Mon 7/20Fri 7/24
VPS - MDW • Non-stop
Cheapest one-way
$114
Allegiant Air
Mon 6/22
VPS - MDW • Non-stop
Nonstop flights
2 days a week
Mon, Fri
You can fly direct with Allegiant Air. Average duration is 2h 20m
Direct flights
Direct flights
+1
+1
Direct flights
Direct flights
+1
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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

Mon, Jul 20 - Fri, Jul 24
Allegiant Air Logo
6:10 pm - 8:30 pm
VPS
-
MDW
2h 20mnonstop
Allegiant Air Logo
9:21 pm - 11:35 pm
MDW
-
VPS
2h 14mnonstop
$125Allegiant Air
Mon, Jul 20 - Fri, Jul 24
Allegiant Air Logo
6:10 pm - 8:30 pm
VPS
-
MDW
2h 20mnonstop
Allegiant Air Logo
9:21 pm - 11:35 pm
MDW
-
VPS
2h 14mnonstop
$130Allegiant Air
Fri, Jul 3 - Mon, Jul 6
Allegiant Air Logo
6:05 pm - 8:25 pm
VPS
-
MDW
2h 20mnonstop
Allegiant Air Logo
9:20 pm - 11:34 pm
MDW
-
VPS
2h 14mnonstop
$166Allegiant Air
Mon, Jun 29 - Fri, Aug 7
Allegiant Air Logo
6:12 pm - 8:33 pm
VPS
-
MDW
2h 21mnonstop
Allegiant Air Logo
9:25 pm - 11:39 pm
MDW
-
VPS
2h 14mnonstop
$178Allegiant Air
Mon, Jun 29 - Mon, Aug 10
Allegiant Air Logo
6:12 pm - 8:33 pm
VPS
-
MDW
2h 21mnonstop
Allegiant Air Logo
9:25 pm - 11:39 pm
MDW
-
VPS
2h 14mnonstop
$181Allegiant Air
Sun, Jun 28 - Fri, Aug 7
Allegiant Air Logo
3:12 pm - 5:48 pm
VPS
-
MDW
26h 36m
1 stop
Allegiant Air Logo
9:25 pm - 11:39 pm
MDW
-
VPS
2h 14mnonstop
$255Allegiant Air
Sun, Jun 28 - Mon, Aug 10
Allegiant Air Logo
3:12 pm - 5:48 pm
VPS
-
MDW
26h 36m
1 stop
Allegiant Air Logo
9:25 pm - 11:39 pm
MDW
-
VPS
2h 14mnonstop
$258Allegiant Air
Thu, Jul 2 - Fri, Aug 7
Allegiant Air Logo
8:30 pm - 2:38 pm
VPS
-
MDW
18h 08m
1 stop
Allegiant Air Logo
9:25 pm - 11:39 pm
MDW
-
VPS
2h 14mnonstop
$264Allegiant Air
Mon, Jun 29 - Wed, Aug 12
Multiple Airlines Logo
6:12 pm - 8:33 pm
VPS
-
MDW
2h 21mnonstop
Multiple Airlines Logo
4:45 pm - 11:38 pm
MDW
-
VPS
30h 53m
2 stops
$267Multiple Airlines
Mon, Jul 20 - Fri, Jul 24
Multiple Airlines Logo
8:39 am - 10:03 pm
VPS
-
MDW
13h 24m
2 stops
Multiple Airlines Logo
9:21 pm - 11:35 pm
MDW
-
VPS
2h 14mnonstop
$289Multiple Airlines
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, Friday 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 Fridays 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 $312, prices are generally cheapest when you fly direct.

Find deals

Good to know

Cheapest flight$114
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 5 days, the lowest price for a flight from Valparaiso to Chicago Midway Airport was $114 for a one-way ticket and $125 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 Embraer 175 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 $57 or less one-way and $154 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

Monday

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

Friday

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.
7.3
Allegiant AirOverall score based on 694 reviews
5.8Food
8.1Crew
7.6Boarding
6.9Comfort
5.4Entertainment
Airline reviews

Seats were very uncomfortable and being charged for snacks and water.........

4.0 OkayDennis, May 2026
ICT - LAS
Read more Allegiant Air reviews

Seats were very uncomfortable and being charged for snacks and water.........

Allegiant actually impressed me, original inbound flight from PBG was so late they gave us a bird inbound from Des Moines and only left 1h late and gained 40 minutes back in the air. Comfortable flight with no frills but no complaints.

Flight was delayed. Crew was good but hot coffee was not available.

Great. No choice for n/a. No food or entertainment options

No food is available without purchasing it and there is no in-flight entertainment. Both of these are OK because we got an inexpensive flight from Allegiant and, otherwise, our experience was excellent.

just had water and there was plenty of leg & seat room. But then i don't weight 220#s!!

Not totally their fault- screaming kids that had zero parent intervention.

It was cold on the flight. The crew was very pleasant. I didn't order any food. We were delayed due to Captain waiting on maintenance log. He kept us informed though. The flight itself was smooth. I would definitely fly with Allegiant again!

I had a fantastic experience with Allegiant. I had wheelchair assistance and they helped me find my luggage and brought me to my car. Even loaded my luggage. Wonderful service!! Thank you Allegiant!

Superb. Staff great. Great flight. As with other airlines, seating too tight and restrictive.

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

Information on your arrival and departure airports

Valparaiso (VPS)
Midway (MDW)