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

VPS - MDW

$126 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 7/24. 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
Wed 6/5
Wed 6/12

Search 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
In the last 7 days travelers have searched 42,573,820 times on KAYAK, and here is why:

Save 22% 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 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 and deals for you by selecting your travel dates.
Choose your dates
8:59 am - 11:18 amVPS-MDW
2h 19mnonstop
12:08 pm - 2:11 pmMDW-VPS
2h 03mnonstop
$129Allegiant Air
Find Deal
Mon, Aug 5 - Fri, Aug 9
8:59 am - 11:18 amVPS-MDW
2h 19mnonstop
12:03 pm - 2:06 pmMDW-VPS
2h 03mnonstop
$134Allegiant Air
Find Deal
Mon, Jun 3 - Mon, Jun 10
10:00 am - 12:18 pmVPS-MDW
2h 18mnonstop
12:08 pm - 2:11 pmMDW-VPS
2h 03mnonstop
$200Allegiant Air
Find Deal
Fri, May 24 - Fri, May 31
4:20 pm - 9:47 pmVPS-MDW
5h 27m1 stop
6:50 pm - 11:19 pmMDW-VPS
4h 29m1 stop
$244Delta
Find Deal
Mon, Aug 5 - Fri, Aug 9
6:00 am - 10:11 amVPS-MDW
4h 11m1 stop
4:41 pm - 11:16 pmMDW-VPS
6h 35m1 stop
$281Delta
Find Deal
Sat, Jun 1 - Wed, Jun 5
7:10 am - 11:55 amVPS-MDW
4h 45m1 stop
6:49 pm - 11:16 pmMDW-VPS
4h 27m1 stop
$318Delta
Find Deal
Thu, Jun 20 - Mon, Jun 24
4:24 pm - 6:42 pmVPS-MDW
2h 18mnonstop
1:08 pm - 3:11 pmMDW-VPS
2h 03mnonstop
$344Allegiant Air
Find Deal
Mon, May 20 - Fri, May 24
4:45 pm - 10:01 pmVPS-MDW
5h 16m1 stop
6:00 am - 9:55 amMDW-VPS
3h 55m1 stop
$356Delta
Find Deal
Mon, Jun 3 - Mon, Jun 10
4:45 pm - 10:01 pmVPS-MDW
5h 16m1 stop
6:00 am - 12:00 pmMDW-VPS
6h 00m1 stop
$379Delta
Find Deal
Thu, Jun 6 - Sun, Jun 9
7:16 am - 11:52 amVPS-MDW
4h 36m1 stop
6:48 pm - 11:16 pmMDW-VPS
4h 28m1 stop
$476Delta
Find Deal
Fri, May 24 - Fri, May 31

Flights from Valparaiso to Midway - Travel Insights & Trends

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 flights from Valparaiso, Florida to Chicago Midway Airport clicked on KAYAK for each day over the last 12 months.
For Valparaiso to Chicago Midway Airport, Tuesday is the cheapest day to fly on average and Monday is the most expensive. Flying from Chicago Midway Airport back to Valparaiso, the best deals are generally found on Wednesday, with Tuesday being the most expensive.

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

Airline and price data is aggregated from results in KAYAK’s search results from the last 2 weeks for flights from Valparaiso, Florida to Chicago Midway Airport.
There is just one airline that flies from Valparaiso, Florida to Chicago Midway Airport direct and that is Allegiant Air. The best one-way deal found from Allegiant Air for the route is $77.

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

Each day, there are between 2 and 3 nonstop flights that take off from Valparaiso, Florida and land in Chicago Midway Airport, with an average flight time of 2h 18m. The most common departure time is 4:00 pm and most flights take off in the morning. Each week, there are 5 flights. The most frequent day of departure is Friday, when 60% of all weekly flights depart. The fewest flights depart on a Monday.

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

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 Valparaiso to Chicago Midway Airport take?

Direct flights cover the 783 miles separating Valparaiso to Chicago Midway Airport in about 2h 18m.

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

Early birds can take the earliest flight from Valparaiso, Florida at 8:55 am and will be landing in Chicago Midway Airport at 11:13 am.

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

If you prefer to fly at night, the latest flight from Valparaiso, Florida to Chicago Midway Airport jets off at 4:24 pm and lands at 6:42 pm.

Good to know

Low season

February

High season

May

Cheapest flight

$126
Best time to beat the crowds with an average 73% drop in price.
Most popular time to fly and prices are also 33% lower on average.
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, Florida to Chicago Midway Airport?

    In the last 3 days, the lowest price for a flight from Valparaiso, Florida to Chicago Midway Airport was $126 for a one-way ticket and $129 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 Airbus A320-100/200 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.

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

    The two airlines most popular with KAYAK users for flights from Valparaiso to Chicago are Delta and Allegiant Air. With an average price for the route of $539 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 $138 and an overall rating of 7.4.

  • 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.

See more FAQs

Top tips for finding a cheap flight from VPS to Chicago Midway Airport

  • Looking for a cheap flight? 25% of our users found flights on this route for $69 or less one-way and $89 or less round-trip.

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

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

Nonstop departures

Valparaiso Destin-Ft Walton Beach to Chicago Midway

Monday

Allegiant Air

Allegiant Air

Friday

Allegiant Air

Allegiant Air

See more direct flights

Nonstop returns

Chicago Midway to Valparaiso Destin-Ft Walton Beach

Monday

Allegiant Air

Allegiant Air

Friday

Allegiant Air

Allegiant Air

See more direct flights
See more direct flights

Top airlines 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.
8.0
DeltaOverall score based on 10818 reviews
8.0Entertainment
8.6Crew
8.2Boarding
7.4Food
7.9Comfort
Airline reviews

Delayed due to an ill passenger after loading. Not preventable on Delta's part. Was in first class. The seats are becoming worn and detaching from their velcro attachments. Only got snacks on flight. The attendant was not the friendliest.

6.0 GoodJames, Apr 2024TPA - RDU
Read more about Delta reviews

Delayed due to an ill passenger after loading. Not preventable on Delta's part. Was in first class. The seats are becoming worn and detaching from their velcro attachments. Only got snacks on flight. The attendant was not the friendliest.

I liked the ease of checking in, luggage check in, wheel chair assistance, boarding and flight.

I usually have a positive experience with Delta. Complimentary upgrades are always nice!

The main person that was coordinating everything was a short white/light skin Spanish man and he was very rude. It honestly made me feel like it was everyone’s First day at work. His announcements were very not reasonable and they did not make sense. The stewardess on the flight that made the announcements she didn’t even know what she was talking about she sounded inebriated. There were no snacks or drinks on our flight there wasn’t even much turbulence. This flight was not enjoyable nor was it what a Delta flight should be and just this past week I flew with Delta 3 times.

nothing Delta could do... the person sitting next to me was huge and overflowing into my seat

Crew was great! I need wheelchair assistance and they knew who I was and updated me that my chair was on its way and to just hang tight. There was some turbulence but the captain announced we would be going thru it and he handled the plane well. Landing was soft and his.

Aircraft very cramped. Check-in was great with an agent helping us. Food was almost non-existent. Pre-flight went well once I got the app reloaded on my phone since we don’t fly much anymore.

I like that it got us where we were going. Everything else needed work. It was 1/2 hour late and we took off an hour late. The plane had to be cleaned and the disabled loaded on board before we could take off which took forever and then we sat at the terminal FOREVER before we took off. The ride was so bumpy that they couldn’t serve drinks and snack but to about 1/2 the plane. Seriously we should have flown out of Fort Lauderdale. We probably would’ve gotten home several hours earlier.

Flight was on time, the staff was personable & professional, & the plane arrived on time.

Flight was great. DELTA did a fantastic job! FLL airport was chaotic!

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.

My daughter dropped her cell phone right through the crack between walkway and plane. Right in front of myself, the lead flight attendant and crew below. In slow motion we all watched. The crew was on it as they got her phone back to her. Surprisingly, not damaged! This same head flight attendant was hilarious on the speaker! Loved his humor! Pilots were very clear to hear. Sometimes there’s a lot of noise interference or they sound muffled, but this time I could understand everything that was spoken. One more positive experience was renting a car through Allegiant which was my first time. We got a great car deal through Alamo and the car was really nice too, 2024 Blazer.

We waited for our captain to arrive and she made our flight take off 20 minutes late.

Book cheap flights from Valparaiso to Chicago

Recent one-way flight deals

 
Only flying one-way? Below are some of the best one-way flight deals from Valparaiso to Chicago found on KAYAK in the last 72 hours.
7/24Wed
1 stopDelta
5h 28mVPS-MDW
$126
7/21Sun
2 stops
25h 57mVPS-MDW
$212
5/16Thu
1 stopDelta
4h 56mVPS-MDW
$218
7/24Wed
2 stopsDelta
8h 48mVPS-MDW
$480
5/16Thu
2 stopsDelta
6h 40mVPS-MDW
$567

Search by stops

Search by airline

Search by price

Last minute flights from Valparaiso to Midway

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 Valparaiso to Chicago that are departing in the next 10 days.
5/11Sat
multi-stopDelta
4h 59mVPS-MDW
5/14Tue
multi-stopDelta
6h 00mMDW-VPS
$519
5/11Sat
multi-stopDelta
5h 34mVPS-MDW
5/20Mon
multi-stopDelta
5h 58mMDW-VPS
$526
5/11Sat
multi-stopDelta
4h 59mVPS-MDW
5/14Tue
multi-stopDelta
4h 15mMDW-VPS
$559
5/11Sat
multi-stopDelta
9h 39mVPS-MDW
5/14Tue
multi-stopDelta
6h 00mMDW-VPS
$677
5/11Sat
multi-stopDelta
20h 01mVPS-MDW
5/14Tue
multi-stopDelta
6h 00mMDW-VPS
$687
5/11Sat
multi-stopDelta
5h 34mVPS-MDW
5/20Mon
multi-stopDelta
7h 35mMDW-VPS
$787

Search by stops

Search by airline

Search by price

Valparaiso - Chicago Midway Airport Flights

Departure:

Valparaiso (VPS)United States

Destination:

Chicago Midway Airport (MDW)United States

Return flight deals:

Chicago Midway Airport - Valparaiso

Cabin classes:

$80