Find flights
Deals
Insights
When to book
FAQs & Tips
Direct Flights
Airlines

MDW - VPS

$102 Find cheap flights from Chicago Midway Airport to Valparaiso

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 7/10. 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
Sat 6/15
Sat 6/22

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 42,211,976 times on KAYAK, and here is why:

Save 21% or moreCompare multiple travel sites with one search.

Track pricesNot ready to book? Create a price alert for when prices drop.

Filter your dealsChoose cabin class, free Wi-Fi and more.

Bundle and saveSave money when you bundle your flight + hotel.

Cheap flight deals from Midway to Valparaiso (MDW-VPS)

 
These are the cheapest deals for flights from Midway to Valparaiso currently on KAYAK along with options from the most popular airlines KAYAK users selected for this route. While these flights were available on KAYAK in the last 72 hours, prices and availability are subject to change and deals may expire.

Recent round-trip flight deals from Midway to Valparaiso

Recommended round-trip deals departing in the coming months from the most popular airlines that fly from Midway to Valparaiso.

Recent one-way flight deals from Midway to Valparaiso

Only flying one-way? Below are some of the best one-way flight deals from Midway to Valparaiso found on KAYAK recently.

Recent last minute flight deals from Midway to Valparaiso

Leaving soon but still want a bargain? Check out these latest deals for last minute flights from Midway to Valparaiso.

Recent direct flight deals from Midway to Valparaiso

The latest deals for direct flights from Midway to Valparaiso so you can sit back and relax without the need for a layover.

Cheap bus & train deals from Midway to Valparaiso

Find recent round-trip train or bus tickets from Midway to Valparaiso.

All round-trip flight deals to Valparaiso

The cheapest plane tickets to Valparaiso found on KAYAK recently.
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
$117Allegiant 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
$124Allegiant 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
$141Allegiant Air
Find Deal
Fri, Jul 12 - Mon, Jul 15
12:08 pm - 2:11 pmMDW-VPS
2h 03mnonstop
8:55 am - 11:13 amVPS-MDW
2h 18mnonstop
$161Allegiant Air
Find Deal
Mon, Jun 3 - Fri, Jun 7
12:08 pm - 2:11 pmMDW-VPS
2h 03mnonstop
8:59 am - 11:18 amVPS-MDW
2h 19mnonstop
$182Allegiant Air
Find Deal
Mon, Jul 22 - Mon, Jul 29
12:08 pm - 2:11 pmMDW-VPS
2h 03mnonstop
9:00 am - 11:18 amVPS-MDW
2h 18mnonstop
$184Allegiant Air
Find Deal
Fri, Aug 2 - Fri, Aug 9
6:55 pm - 11:25 pmMDW-VPS
4h 30m1 stop
3:59 pm - 9:46 pmVPS-MDW
5h 47m1 stop
$222Delta
Find Deal
Tue, Jul 23 - Fri, Aug 2
9:46 am - 5:05 pmMDW-VPS
7h 19m1 stop
4:44 pm - 9:46 pmVPS-MDW
5h 02m1 stop
$224Delta
Find Deal
Wed, Jun 5 - Tue, Jun 11
6:15 pm - 11:16 pmMDW-VPS
5h 01m1 stop
7:45 am - 1:11 pmVPS-MDW
5h 26m1 stop
$239Delta
Find Deal
Mon, Nov 4 - Sat, Nov 9
7:46 pm - 7:48 pmMDW-VPS
24h 02m2 stops
6:05 pm - 8:18 pmVPS-MDW
26h 13m2 stops
Sun, Jun 2 - Sun, Jun 16
6:00 am - 9:59 amMDW-VPS
3h 59m1 stop
$102Delta
Find Deal
Wed, Jul 10
6:49 pm - 11:16 pmMDW-VPS
4h 27m1 stop
$122Delta
Find Deal
Thu, Jun 20
3:45 pm - 9:12 pmMDW-VPS
5h 27m1 stop
$169Delta
Find Deal
Sat, Jun 29
10:12 am - 6:48 amMDW-VPS
20h 36m2 stops
$230Allegiant Air
Find Deal
Thu, Jun 20
9:46 am - 5:06 pmMDW-VPS
7h 20m1 stop
$349Delta
Find Deal
Wed, May 22
5:15 pm - 2:40 pmMDW-VPS
21h 25m2 stops
Wed, Jul 10
2:24 pm - 11:25 pmMDW-VPS
9h 01m2 stops
$492Delta
Find Deal
Wed, Jul 10
5:15 pm - 5:18 pmMDW-VPS
24h 03m3 stops
Wed, Jul 10
12:07 pm - 11:16 pmMDW-VPS
11h 09m2 stops
$543Delta
Find Deal
Sat, Jun 29
1:21 pm - 8:59 pmMDW-VPS
7h 38m2 stops
$623Delta
Find Deal
Wed, May 22
7:32 pm - 9:35 pmMDW-VPS
2h 03mnonstop
10:00 am - 12:18 pmVPS-MDW
2h 18mnonstop
$152Allegiant Air
Find Deal
Mon, May 20 - Fri, May 24
11:59 am - 5:06 pmMDW-VPS
5h 07m1 stop
5:05 pm - 10:01 pmVPS-MDW
4h 56m1 stop
$645Delta
Find Deal
Sat, May 18 - Thu, May 23
11:59 am - 11:16 pmMDW-VPS
11h 17m2 stops
11:40 am - 5:58 pmVPS-MDW
6h 18m1 stop
$846Delta
Find Deal
Sat, May 18 - Thu, May 23
6:00 am - 12:15 pmMDW-VPS
6h 15m1 stop
5:05 pm - 10:01 pmVPS-MDW
4h 56m1 stop
$865Delta
Find Deal
Mon, May 20 - Fri, May 24
6:00 am - 10:35 amMDW-VPS
4h 35m1 stop
5:05 pm - 10:01 pmVPS-MDW
4h 56m1 stop
$1,105Delta
Find Deal
Fri, May 17 - Sun, May 19
12:08 pm - 2:11 pmMDW-VPS
2h 03mnonstop
8:59 am - 11:18 amVPS-MDW
2h 19mnonstop
$117Allegiant 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
$124Allegiant 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
$141Allegiant Air
Find Deal
Fri, Jul 12 - Mon, Jul 15
12:08 pm - 2:11 pmMDW-VPS
2h 03mnonstop
8:55 am - 11:13 amVPS-MDW
2h 18mnonstop
$161Allegiant Air
Find Deal
Mon, Jun 3 - Fri, Jun 7
12:08 pm - 2:11 pmMDW-VPS
2h 03mnonstop
8:59 am - 11:18 amVPS-MDW
2h 19mnonstop
$182Allegiant Air
Find Deal
Mon, Jul 22 - Mon, Jul 29
12:08 pm - 2:11 pmMDW-VPS
2h 03mnonstop
9:00 am - 11:18 amVPS-MDW
2h 18mnonstop
$184Allegiant Air
Find Deal
Fri, Aug 2 - Fri, Aug 9
12:08 pm - 2:11 pmMDW-VPS
2h 03mnonstop
9:00 am - 11:18 amVPS-MDW
2h 18mnonstop
$200Allegiant Air
Find Deal
Mon, Jul 22 - Fri, Aug 2

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 Wednesdays and avoid leaving on a Tuesday, as it's usually the priciest day. When flying back from Valparaiso, Tuesday is the cheapest day to fly and Monday 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 $98 on average. On the other hand, the most expensive months are March and August, where the average cost of tickets is $449 and $380 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 21 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 $117 on Allegiant Air, followed by Delta ($222). One-way flight deals have also been found from as low as $102 on Delta and from $230 on Allegiant Air.

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?

Each day, there are 3 nonstop flights that take off from Chicago Midway Airport and land in Valparaiso, Florida, with an average flight time of 2h 03m. The most common departure time is 12:00 pm and most flights take off in the morning. Each week, there are 6 flights and there are the same amount of flights each day 3.

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 12:03 pm and will be landing in Valparaiso, Florida at 2:06 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 1:08 pm and lands at 3:11 pm.

Good to know

Low season

February

High season

March

Cheapest flight

$102
Best time to beat the crowds with an average 66% drop in price.
Most popular time to fly with an average 10% 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, Florida?

    In the last 3 days, the lowest price for a flight from Chicago Midway Airport to Valparaiso, Florida was $102 for a one-way ticket and $117 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, 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 $424 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 $166 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

KAYAK’s top tips for finding a cheap flight from Chicago Midway Airport to Valparaiso, Florida

  • Looking for a cheap flight? 25% of our users found flights on this route for $50 or less one-way and $116 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

Friday

Allegiant Air

Allegiant Air

See more direct flights

Nonstop returns

Valparaiso Destin-Ft Walton Beach to Chicago Midway

Monday

Allegiant Air

Allegiant Air

Friday

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 10673 reviews
8.6Crew
7.9Comfort
7.4Food
8.0Entertainment
8.2Boarding
Airline reviews

5-hour delay due to storms in Tanoa and airspace restricted by Miami traffic controllers.

6.0 GoodGary, May 2024MSP - TPA
Read more about Delta reviews

5-hour delay due to storms in Tanoa and airspace restricted by Miami traffic controllers.

I would fly again the whole experience was great. The only feed back I can give that they don't do that American Airlines does is the crew there is more humorous with boarding and thank their passengers. It makes it more fun to fly with them. I would however fly Delta again.

Horrible. This was not first class. This was a connecting flight whi h was late. My original flight never came. I hated the fact that delta gave me a connecting flight from New York to Orlando Florida. No meals and the television screens were not working. There wasn't even any power to charge your phones. This is NOT FIRST CLASS DELTA!!! Do better next time!

They did a fine job. Can't wait to use Delta in the future.

Seat back monitors and outlets were dead and not working.

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

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.
7/10Wed
1 stopDelta
3h 59mMDW-VPS
$102
6/20Thu
1 stopDelta
4h 27mMDW-VPS
$122
6/29Sat
1 stopDelta
5h 27mMDW-VPS
$169
6/20Thu
2 stopsAllegiant Air
20h 36mMDW-VPS
$230
5/22Wed
1 stopDelta
7h 20mMDW-VPS
$349
7/10Wed
2 stops
21h 25mMDW-VPS
$387
7/10Wed
2 stopsDelta
9h 01mMDW-VPS
$492
7/10Wed
3 stops
24h 03mMDW-VPS
$497
6/29Sat
2 stopsDelta
11h 09mMDW-VPS
$543
5/22Wed
2 stopsDelta
7h 38mMDW-VPS
$623

Search by stops

Search by airline

Search by price

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.
5/20Mon
nonstopAllegiant Air
2h 03mMDW-VPS
5/24Fri
nonstopAllegiant Air
2h 18mVPS-MDW
$152
5/18Sat
multi-stopDelta
5h 07mMDW-VPS
5/23Thu
multi-stopDelta
4h 56mVPS-MDW
$645
5/18Sat
multi-stopDelta
11h 17mMDW-VPS
5/23Thu
multi-stopDelta
6h 18mVPS-MDW
$846
5/20Mon
multi-stopDelta
6h 15mMDW-VPS
5/24Fri
multi-stopDelta
4h 56mVPS-MDW
$865
5/17Fri
multi-stopDelta
4h 35mMDW-VPS
5/19Sun
multi-stopDelta
4h 56mVPS-MDW
$1,105

Search by stops

Search by airline

Search by price

Chicago Midway Airport - Valparaiso Flights

Departure:

Chicago Midway Airport (undefined)United States

Destination:

Valparaiso (VPS)United States

Return flight deals:

Valparaiso - Chicago Midway Airport

Cabin classes:

$108