MDW - VPS

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

This is the cheapest one-way flight price found by a KAYAK user in the last 72 hours by searching for a flight from Midway to Valparaiso departing on 6/26. 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 Valparaiso

 
These are the airlines KAYAK users have selected most often from within our search results in flight searches from Chicago to Valparaiso, 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 Chicago to Valparaiso, as well as popular online travel agencies
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Everything you should know

Cheapest round-trip
$106
Typical prices: $123-$96
Allegiant Air
Fri 7/24Mon 7/27
MDW - VPS • Non-stop
Cheapest one-way
$52
Allegiant Air
Fri 6/26
MDW - VPS • Non-stop
Nonstop flights
Mon, Fri
You can fly direct with Allegiant Air. Average duration is 2h 13m
Direct flights
Direct flights
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+1
Direct flights
Direct flights
+1
When to travel
Cheapest • 68% price drop
Most popular
Good to know
Good to know
+1
+1
Good to know
Good to know
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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 Valparaiso!
Flight Deals
Booking Insights
Flight Deals

Cheap Flights from Midway to Valparaiso (MDW-VPS)

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

Fri, Jul 24 - Mon, Jul 27
Allegiant Air Logo
9:21 pm - 11:35 pm
MDW
-
VPS
2h 14mnonstop
Allegiant Air Logo
6:10 pm - 8:30 pm
VPS
-
MDW
2h 20mnonstop
$106Allegiant Air
Fri, Jul 3 - Fri, Jul 24
Allegiant Air Logo
9:15 pm - 11:29 pm
MDW
-
VPS
2h 14mnonstop
Allegiant Air Logo
6:11 pm - 8:31 pm
VPS
-
MDW
2h 20mnonstop
$118Allegiant Air
Fri, Oct 16 - Mon, Oct 19
Allegiant Air Logo
9:20 pm - 11:31 pm
MDW
-
VPS
2h 11mnonstop
Allegiant Air Logo
3:07 pm - 5:25 pm
VPS
-
MDW
2h 18mnonstop
$125Allegiant Air
Fri, Oct 2 - Mon, Oct 12
Allegiant Air Logo
9:24 pm - 11:35 pm
MDW
-
VPS
2h 11mnonstop
Allegiant Air Logo
5:39 pm - 7:57 pm
VPS
-
MDW
2h 18mnonstop
$127Allegiant Air
Mon, Jul 6 - Mon, Jul 20
Allegiant Air Logo
9:20 pm - 11:34 pm
MDW
-
VPS
2h 14mnonstop
Allegiant Air Logo
6:10 pm - 8:30 pm
VPS
-
MDW
2h 20mnonstop
$131Allegiant Air
Fri, Jul 3 - Fri, Jul 24
Allegiant Air Logo
9:15 pm - 11:29 pm
MDW
-
VPS
2h 14mnonstop
Allegiant Air Logo
6:11 pm - 8:31 pm
VPS
-
MDW
2h 20mnonstop
$137Allegiant Air
Mon, Jul 20 - Fri, Jul 24
Allegiant Air Logo
9:20 pm - 11:34 pm
MDW
-
VPS
2h 14mnonstop
Allegiant Air Logo
6:11 pm - 8:31 pm
VPS
-
MDW
2h 20mnonstop
$146Allegiant Air
Mon, Jul 20 - Fri, Jul 24
Allegiant Air Logo
9:20 pm - 11:34 pm
MDW
-
VPS
2h 14mnonstop
Allegiant Air Logo
6:11 pm - 8:31 pm
VPS
-
MDW
2h 20mnonstop
$147Allegiant Air
Mon, Jul 20 - Fri, Jul 24
Allegiant Air Logo
9:20 pm - 11:34 pm
MDW
-
VPS
2h 14mnonstop
Allegiant Air Logo
6:11 pm - 8:31 pm
VPS
-
MDW
2h 20mnonstop
$151Allegiant Air
Mon, Jul 20 - Fri, Jul 24
Allegiant Air Logo
9:20 pm - 11:34 pm
MDW
-
VPS
2h 14mnonstop
Allegiant Air Logo
6:11 pm - 8:31 pm
VPS
-
MDW
2h 20mnonstop
$152Allegiant Air
Booking Insights

KAYAK's insights & trends for Midway to Valparaiso flights

Get data-powered insights and trends into flights from Midway to Valparaiso to help you find the cheapest flights, the best time to fly and much more.

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

This analysis is based on the cheapest round-trip price found on KAYAK in the last 12 months by searching for a flight from Chicago Midway Airport to Valparaiso, Florida departing in July.

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

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

When flying from Chicago Midway Airport to Valparaiso, you should consider leaving on a Wednesday and avoid Fridays if you are looking for the best rates. For your return to Chicago Midway Airport, you’ll find the best rates on Thursdays and the most expensive ones on Fridays.

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

To calculate monthly average prices, KAYAK takes all prices for each month over the last year for round-trip flights from Chicago Midway Airport to Valparaiso, removes the top 0.1% to account for outliers, and then takes the median of all values for each month.

The cheapest month for flights from Chicago Midway Airport to Valparaiso is July, where tickets cost $97 (return) on average. On the other hand, the most expensive months are May and June, where the average cost of round-trip tickets is $534 and $498 respectively.

Good to know

Low seasonJanuary
Cheapest flight$52
Best time to beat the crowds with an average 17% drop in price.
Most popular time to fly with an average 77% increase in price.
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
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 Chicago Midway Airport to Valparaiso flights

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

    In the last 5 days, the lowest price for a flight from Chicago Midway Airport to Valparaiso was $54 for a one-way ticket and $106 for a round-trip.

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

    No

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

    Chicago Midway Airport and Valparaiso are both served by 1 main airport. You will leave Chicago Midway Airport from Chicago Midway and will be arriving at Valparaiso Destin-Ft Walton Beach.

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

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

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

    The Airbus A320-100/200 is the aircraft model that flies most regularly on the Chicago Midway Airport to Valparaiso flight route.

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

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

  • Which is the best airline for flights from Chicago to Valparaiso, Southwest or Allegiant Air?

    The two airlines most popular with KAYAK users for flights from Chicago to Valparaiso are Southwest and Allegiant Air. With an average price for the route of $413 and an overall rating of 7.9, Southwest is the most popular choice. Allegiant Air is also a great choice for the route, with an average price of $347 and an overall rating of 7.3.

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

    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 Chicago Midway Airport to Valparaiso.

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

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

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

    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 Valparaiso from Chicago Midway Airport 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 Chicago Midway Airport to Valparaiso

  • Looking for a cheap flight? 25% of our users found flights on this route for $50 or less one-way and $188 or less round-trip.

Prefer to fly direct from Chicago Midway Airport to Valparaiso?

 
Direct data is based off flight results for the next 60 days. Find direct flights from all airlines flying direct from Chicago Midway to Valparaiso Destin-Ft Walton Beach.
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

Friday

Allegiant Air

Allegiant Air

See more direct flights

Direct returns

Valparaiso Destin-Ft Walton Beach to Chicago Midway

Monday

Allegiant Air

Allegiant Air

Friday

Allegiant Air

Allegiant Air

See more direct flights

Reviews of the top airlines flying from Midway to Valparaiso

 
See real verified KAYAK customer reviews for airlines flying from Chicago to Valparaiso. 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 Midway to Valparaiso? 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.
7.9
SouthwestOverall score based on 4235 reviews
8.6Crew
8.0Comfort
7.0Food
7.5Entertainment
8.1Boarding
Airline reviews

OKay. I sat in the back of the plane and it was really loud between babies and little kids, and adults who.like to talk a lot and loudly most of the flight.

6.0 GoodAnonymous, Jun 2026
MDW - BDL
Read more Southwest reviews

OKay. I sat in the back of the plane and it was really loud between babies and little kids, and adults who.like to talk a lot and loudly most of the flight.

The first time I flew in the extra legroom section. It was difficult to notice a difference. I had bad luck with my neighbors. The crew was okay. Southwest has reduced the live TV options.

The flight was okay. The pilots did an amazing job and kept us updated on the flight. The flight attendants were okay. They found time to be chatty with each other rather than focus on the guests. One of the attendants was a little less warm when asking about my bag I had on my lap that I was using during latter part of the mid- flight. Mind you, it was not the departure descent. I’m respectful to each and every attendant, it was the tone in her voice reminding me to place my carryon bag on the floor. I hope to have a better experience next time.

Terrible. Even though there’s assigned seating now, they are still the slowest boarding airline of anyone.

I flew twice this week on Southwest, was delayed over 2 hours both ways. From Pittsburgh to Chicago it was due to weather but the gate agents, pilot etc were great at updating everyone. Today from Midway to Pittsburgh the plane had come from an international location, kept getting delayed, no information was given until we were delayed for the third time. It was ridiculous, whoever scheduled that plane to fly to Pittsburgh after didn’t consider a lot of things.

It was canceled. Supposedly weather. But there was no snow in Baltimore. At least we found out before driving to airport

The staff was very friendly, professional, and courteous. The overall flight was a great experience.

Okay, not wonderful. Short flight. Wi-fi didn't work properly. Stuck waiting for a gate to open upon arrival for 20 or so minutes.

They sent a notice that they were boarding an hour early. We had to leave the club and run to the gate. They said sorry, that came from corporate and was a mistake. They did not have enough seating because the flight before it had not taken off on time. They moved our gate and delayed it for an hour.

Plane crashed into a bus or some other vehicle on the ground while pulling out of the gate. No injuries, but wing tip was damaged and returned to gate for “maintenance issues” and we departed 5 hours later because the plane went out of service and new plane was flown in from a nearby airport, Midway.

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 Midway to Valparaiso

Information on your arrival and departure airports