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MDW - VPS

Find cheap flights from Chicago Midway Airport to Valparaiso from $104

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 5/9. 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
0 bags
Thu 5/16
Thu 5/23

Search 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
In the last 7 days travelers have searched 43,990,755 times on KAYAK, and here is why:

Save 22% or moreCompare multiple travel sites with one search.

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Cheap flight deals 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 and deals for you by selecting your travel dates.
Choose your dates
12:08 pm - 2:11 pmMDW-VPS
2h 03mnonstop
8:59 am - 11:18 amVPS-MDW
2h 19mnonstop
$120Allegiant Air
Find Deal
Mon, Jul 8 - Mon, Jul 15
12:08 pm - 2:11 pmMDW-VPS
2h 03mnonstop
8:59 am - 11:18 amVPS-MDW
2h 19mnonstop
$130Allegiant Air
Find Deal
Fri, May 31 - Mon, Jun 3
9:23 pm - 11:38 pmMDW-VPS
2h 15mnonstop
10:48 am - 4:01 pmVPS-MDW
29h 13m2 stops
Sun, Apr 28 - Tue, Apr 30
9:23 pm - 11:38 pmMDW-VPS
2h 15mnonstop
6:13 pm - 8:33 pmVPS-MDW
2h 20mnonstop
$182Allegiant Air
Find Deal
Thu, May 9 - Sun, May 12
12:28 pm - 2:42 pmMDW-VPS
26h 14m1 stop
6:13 pm - 8:33 pmVPS-MDW
2h 20mnonstop
Fri, May 10 - Sun, May 12
6:55 am - 7:51 pmMDW-VPS
12h 56m2 stops
6:13 pm - 8:33 pmVPS-MDW
2h 20mnonstop
Mon, May 6 - Sun, May 12
6:00 am - 11:02 amMDW-VPS
5h 02m1 stop
7:45 am - 11:55 amVPS-MDW
4h 10m1 stop
$254Delta
Find Deal
Sun, Apr 28 - Thu, May 2
8:33 pm - 3:41 pmMDW-VPS
19h 08m1 stop
8:59 am - 11:18 amVPS-MDW
2h 19mnonstop
$255Allegiant Air
Find Deal
Fri, May 31 - Mon, Jun 3
6:00 am - 11:02 amMDW-VPS
5h 02m1 stop
4:30 pm - 10:50 pmVPS-MDW
6h 20m1 stop
$264Delta
Find Deal
Sun, Apr 28 - Thu, May 2
9:46 am - 5:06 pmMDW-VPS
7h 20m1 stop
6:00 am - 11:52 amVPS-MDW
5h 52m1 stop
$310Delta
Find Deal
Tue, May 7 - Tue, May 14

Flights from Midway to Valparaiso - Travel Insights & Trends

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.

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

The average price of all flights from Chicago Midway Airport to Valparaiso, Florida clicked on KAYAK for each day over the last 12 months.
If you are looking for a flight deal from Chicago Midway Airport to Valparaiso, look for departures on Thursdays and avoid leaving on a Wednesday, as it's usually the priciest day. When flying back from Valparaiso, Monday is the cheapest day to fly and Wednesday is the most expensive.

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

To calculate monthly average prices, KAYAK takes all prices for each month over the last year for flights from Chicago Midway Airport to Valparaiso, Florida, 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, Florida is January, where tickets cost $176 on average. On the other hand, the most expensive months are March and December, where the average cost of tickets is $435 and $434 respectively.

How far in advance should I book a flight from Chicago Midway Airport to Valparaiso, Florida?

To calculate daily average prices, KAYAK takes all prices for each day before departure over the last year for flights from Chicago Midway Airport to Valparaiso, Florida, removes the top 0.1% to account for outliers, and then takes the average of all the values for each month.
To get a below average price on the flight from Chicago Midway Airport to Valparaiso, Florida, you should book around 1 day before departure. For the absolute cheapest price, our data suggests you should book 66 days before departure.

Which airlines provide the cheapest flights from Chicago Midway Airport to Valparaiso?

The cheapest price for the route for each airline clicked by KAYAK users in the last 72 hours.
The cheapest return flight ticket from Chicago Midway Airport to Valparaiso found by KAYAK users in the last 72 hours was for $120 on Allegiant Air, followed by Delta ($254). One-way flight deals have also been found from as low as $104 on Allegiant Air and from $133 on Delta.

Which airlines fly non-stop between Chicago Midway Airport and Valparaiso, Florida?

Airline and price data is aggregated from results in KAYAK’s search results from the last 2 weeks for flights from Chicago Midway Airport to Valparaiso, Florida.
There is just one airline that flies from Chicago Midway Airport to Valparaiso, Florida direct and that is Allegiant Air. The best one-way deal found from Allegiant Air for the route is $82.

How many flights are there between Chicago Midway Airport and Valparaiso, Florida per day?

There is a maximum of 1 nonstop flight a day that takes off from Chicago Midway Airport and lands in Valparaiso, Florida, with an average flight time of 2h 11m. The most common departure time is 9:00 pm and most flights take off in the evening. Each week, there are 3 flights.

Which cabin class options are there for flights between Chicago Midway Airport and Valparaiso, Florida?

The average price of flights for each cabin class for the route found by users searching on KAYAK over the last 2 weeks.
There is only one cabin class option available for the route, which is Economy. Perform a search on KAYAK to find the latest prices and availability for all cabin fares, which differ across airlines.

How long does a flight from Chicago Midway Airport to Valparaiso take?

The duration of a nonstop flight to Valparaiso from Chicago Midway Airport is typically 2h 03m. The journey crosses a distance of 783 miles.

What’s the earliest departure time from Chicago Midway Airport to Valparaiso?

Early birds can take the earliest flight from Chicago Midway Airport at 1:08 pm and will be landing in Valparaiso, Florida at 3:11 pm.

What’s the latest departure time from Chicago Midway Airport to Valparaiso?

If you prefer to fly at night, the latest flight from Chicago Midway Airport to Valparaiso, Florida jets off at 9:23 pm and lands at 11:38 pm.

Good to know

Low season

September

High season

April

Cheapest flight

$104
Best time to beat the crowds but there is an average 82% increase in price.
Most popular time to fly and prices are also 18% lower on average.
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, Florida?

    In the last 3 days, the lowest price for a flight from Chicago Midway Airport to Valparaiso, Florida was $104 for a one-way ticket and $120 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 A319 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, Thursday, Friday, and Sunday.

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

    The two airlines most popular with KAYAK users for flights from Chicago to Valparaiso are Delta and Allegiant Air. With an average price for the route of $419 and an overall rating of 8.0, Delta is the most popular choice. Allegiant Air is also a great choice for the route, with an average price of $168 and an overall rating of 7.4.

  • 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.

See more FAQs

Top tips for finding a cheap flight from MDW to Valparaiso

  • Looking for a cheap flight? 25% of our users found flights on this route for $51 or less one-way and $132 or less round-trip.

Prefer to fly non-stop from Chicago Midway Airport to Valparaiso?

Find which airlines fly direct from Midway to Destin-Ft Walton Beach, which days they fly and book direct flights.

Nonstop departures

Chicago Midway to Valparaiso Destin-Ft Walton Beach

Monday

Allegiant Air

Allegiant Air

Thursday

Allegiant Air

Allegiant Air

Friday

Allegiant Air

Allegiant Air

Sunday

Allegiant Air

Allegiant Air

See more direct flights

Nonstop returns

Valparaiso Destin-Ft Walton Beach to Chicago Midway

Monday

Allegiant Air

Allegiant Air

Thursday

Allegiant Air

Allegiant Air

Friday

Allegiant Air

Allegiant Air

Sunday

Allegiant Air

Allegiant Air

See more direct flights
See more direct flights

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.
8.0
DeltaOverall score based on 11123 reviews
7.9comfort
8.0entertainment
8.2boarding
7.5food
8.6crew
Airline reviews

The experience was good and the flight departed on time and landed early

10.0 ExcellentFoster, Apr 2024ATL - JAX
Read more about Delta reviews

The experience was good and the flight departed on time and landed early

The flight was delayed but we got to our final destination.

public website still broken for years randomly blocking browsers with privacy options active after loading a page maybe once. check-in on laptop was almost impossible but eventually randomly worked. had to print pass at airport since couldn't get back in to load digital pass on mobile firefox or chrome. red eye flight so smooth onboarding, plenty of room to spread out, easy offboarding. onboard wifi instructions mention vpn can cause problems connecting but fails to also mention private dns. no printed or built in menu list, seems weird to require personal device to point at qr code link for menu which does not even allow direct ordering. people with health condition risk related dietary restrictions trying to avoid for example cholesterol and sugar are left guessing what they can order either way without nutritional info highlights (cranberry juice was minute maid cocktail with as much suger as typical can of soda). tap to pay wasn't working and always seems sketchy to manually enter card info. good movie variety, so limited tv was okay.

Horrible. Flight ORD to CGH was okay, but Paris was a nightmare. Old planes, delays, involuntary downgrades, broken planes, terrible communication. CGH to CPT was my worst flight ever.

Boarding super slow with people allowed to linger in aisles

There were choices for the snacks. Good choices and tasty lunch and breakfast as well.

First time travel in economy and the worst experience I ever had ! Shame on paying 600 dollars to be in a tuna can ! Service was terrible no even water no even class no even matters your flight attendants were lazy and sloppy very bad experience! After all these years traveling in first and once I try this cause I need to go to a destination for an emergency wow shame on you !

Everything was smooth and easy to fly. No complains and a lot of thanks!

More space in the cabin. The guy in front of me leaned his seat back and I felt he was sitting in my lap.

The boarding process was terrible especially with an indirect flight Chicago to Seattle to San Diego was terrible talking about we overbooked a flight idk if I’d take this airline ever again we got off our flight from Chicago to Seattle and we traveled for business and they told us our connecting flight was over booked and their was no seats asking people to take a delayed next flight and they don’t tell anyone coughing to wear masks seats 30A-B were terrible during the flight no one wants to sit next to people coughing all around I don’t want to be sick traveling for work or get sick anytime it’s very upsetting the staff doesn’t take this stuff serious to tell them to wear masks when they see people coughing and sneezing

The net issue I had was with the gate agent. We had added a carryon to our boarding pass when we checked bags. When I got to the boarding gate the agent was rude asking why I had a backpack - I said I added it - even had an orange tag on it. She ripped my tag off and swung her monitor around to show me how she was right- saying it isn’t wasn’t listed - only a checked bag. I explained again that I wasn’t sure what the issue was but I wouldn’t have an orange tag if I hadn’t added it. Then she finally checked my husband’s boarding pass and found that the agent at checkin had added my carryon to his boarding pass instead of mine. She sent me on my way without my orange tag. Was a bit embarrassing for me the tone she used with me assuming I was trying to get away with something.

Gate agent asked if I could switch seats so a family could sit together. Agent moved me to a seat in the front of the plane, no charge. It was easy. The agent did a great job.

Great seat space. However food and drink prices outrageous. Jabbing to pay for a carry on bag or stuck paying at the gate too much.

Every Allegiant Air flight I've ever taken has been delayed. This flight was delayed a full 2 hours. It was excuse after excuse after excuse. It was a flight from southern Florida. They made us board the plane on time, but made us wait for 2 hours on the tarmac. Because the engines were kept shut off, so was the air conditioning. One can only imagine how hot the air was in the cabin over those 2 hours on the tarmac, while in the hot Florida sun. Just terrible.

Actually, for the price, I'm willing to put up with a little discomfort (upright chairs) and at times inconveniences (like any airline), lack of entertainment (I can bring my own). My flight was non stop and smooth. I would fly this route again.

The flight was delayed 6 hours and we were only offered an $8 food credit. My husband stood in line to get the credit for 45 minutes and when he got close to the end of the line the computers went down.

Worst ever! Flight cancelled supposedly for weather even though we k ow of many others who flew into Bangor same time no problem. At the airport there was no customer service at all just refund and no possibility of rebook for 3-4 days. Aweful won’t fly with them again!!

It’s a budget airline so adjust expectations accordingly. Nothing is without a fee but such is necessary for tickets to remain so affordable.

No complaints. It’s a budget airline so can’t expect any frills.

My TSA number was missing from my ticket which shouldn’t have happened since it’s in my file. The on board flight attendant who was a male, did not want to help me put my luggage in the overhead bin and made a very rude comment and was very unpleasant. The good… the woman who fixed my ticket with the TSA number was excellent and I had extra legroom which was perfect.

Book cheap flights from Chicago to Valparaiso

Recent one-way flight deals

 
Only flying one-way? Below are some of the best one-way flight deals from Chicago to Valparaiso found on KAYAK in the last 72 hours.
5/9Thu
nonstopAllegiant Air
2h 15mMDW-VPS
$104
5/28Tue
1 stopDelta
4h 35mMDW-VPS
$133
5/8Wed
1 stopDelta
7h 20mMDW-VPS
$239
6/29Sat
1 stopDelta
4h 20mMDW-VPS
$304
5/9Thu
2 stops
22h 07mMDW-VPS
$337
5/9Thu
3 stops
22h 07mMDW-VPS
$384
5/9Thu
1 stopDelta
4h 35mMDW-VPS
$434
5/28Tue
2 stopsDelta
11h 10mMDW-VPS
$466
6/29Sat
2 stopsDelta
11h 09mMDW-VPS
$551
8/15Thu
2 stopsDelta
10h 09mMDW-VPS
$626

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Last minute flights from Midway to Valparaiso

Last minute flight, train and bus deals

 
These last-minute flight deals are the cheapest flights found on KAYAK in the last 72 hours for flights from Chicago to Valparaiso that are departing in the next 10 days.
4/20Sat
multi-stopDelta
4h 31mMDW-VPS
4/23Tue
multi-stopDelta
5h 44mVPS-MDW
$279
4/20Sat
multi-stopDelta
4h 31mMDW-VPS
4/23Tue
multi-stopDelta
5h 44mVPS-MDW
$323
4/17Wed
multi-stopDelta
5h 55mMDW-VPS
4/18Thu
multi-stopDelta
5h 55mVPS-MDW
$348
4/18Thu
nonstopAllegiant Air
2h 15mMDW-VPS
4/21Sun
nonstopAllegiant Air
2h 20mVPS-MDW
$350
4/18Thu
nonstopAllegiant Air
2h 15mMDW-VPS
4/21Sun
nonstopAllegiant Air
2h 20mVPS-MDW
$370
4/18Thu
nonstopAllegiant Air
2h 15mMDW-VPS
4/21Sun
nonstopAllegiant Air
2h 20mVPS-MDW
$378
4/18Thu
multi-stopDelta
5h 02mMDW-VPS
4/18Thu
multi-stopDelta
5h 44mVPS-MDW
$585
4/19Fri
multi-stopDelta
4h 29mMDW-VPS
4/22Mon
multi-stopDelta
5h 44mVPS-MDW
$616
4/20Sat
multi-stopDelta
9h 01mMDW-VPS
4/23Tue
multi-stopDelta
5h 44mVPS-MDW
$710
4/18Thu
nonstop
2h 15mMDW-VPS
4/21Sun
multi-stop
27h 37mVPS-MDW
$733

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Chicago Midway Airport - Valparaiso Flights

Departure:

Chicago Midway Airport (MDW)United States

Destination:

Valparaiso (VPS)United States

Return flight deals:

Valparaiso - Chicago Midway Airport

Cabin classes:

$98