VPS - CHI

$73 Find Cheap Flights from Valparaiso to Chicago

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 Chicago departing on 5/29. 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

 
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
$118
Allegiant Air
Fri 5/22Mon 5/25
VPS - MDW • Non-stop
Cheapest one-way
$73
Allegiant Air
Fri 5/29
VPS - MDW • Non-stop
Advice from real travelers
AI-powered summary based on content written by travel experts. AI can make mistakes.
American Airlines' Main Cabin Extra offers early boarding.
Allegiant's Bonus bundle includes carry-on and seat selection.
Expert advice
Expert advice
Expert advice
Expert advice
Nonstop flights
Every day
You can fly direct with American Airlines and Allegiant Air. Average duration is 2h 29m
Direct flights
Direct flights
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Direct flights
Direct flights
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Top routes
Cheapest • 59% average savings
Most popular
Insights
Insights
Insights
Insights
Top layover airports
Cheapest • Avg $386 (round-trip)
Shortest trip • 4h 36m (one-way)
Insights
Insights
Insights
Insights
When to travel
Cheapest • 73% price drop
Most popular
Good to know
Good to know
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Flight Deals
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Expert advice
Flight Deals

Cheap Flights from Valparaiso to Chicago (VPS-CHI)

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

Fri, May 22 - Mon, May 25
Allegiant Air Logo
1:19 pm - 3:38 pm
VPS
-
MDW
2h 19mnonstop
Allegiant Air Logo
9:30 pm - 11:37 pm
MDW
-
VPS
2h 07mnonstop
$118Allegiant Air
Mon, Jun 15 - Mon, Jun 29
Allegiant Air Logo
6:12 pm - 8:33 pm
VPS
-
MDW
2h 21mnonstop
Allegiant Air Logo
9:23 pm - 11:36 pm
MDW
-
VPS
2h 13mnonstop
$131Allegiant Air
Mon, Jun 22 - Mon, Jun 29
Allegiant Air Logo
6:12 pm - 8:33 pm
VPS
-
MDW
2h 21mnonstop
Allegiant Air Logo
9:23 pm - 11:36 pm
MDW
-
VPS
2h 13mnonstop
$146Allegiant Air
Mon, Jun 22 - Mon, Jun 29
Multiple Airlines Logo
8:23 pm - 11:09 am
VPS
-
MDW
38h 46m
2 stops
Multiple Airlines Logo
9:23 pm - 11:36 pm
MDW
-
VPS
2h 13mnonstop
$197Multiple Airlines
Thu, May 28 - Mon, Jun 1
Multiple Airlines Logo
6:40 pm - 10:02 pm
VPS
-
MDW
27h 22m
2 stops
Multiple Airlines Logo
9:30 pm - 11:37 pm
MDW
-
VPS
2h 07mnonstop
$217Multiple Airlines
Tue, May 26 - Tue, Jun 2
American Airlines Logo
6:37 pm - 11:59 pm
VPS
-
ORD
5h 22m
1 stop
American Airlines Logo
8:15 am - 10:50 am
ORD
-
VPS
2h 35mnonstop
$366American Airlines
Fri, May 29 - Wed, Jun 3
Delta Logo
2:55 pm - 9:53 pm
VPS
-
ORD
6h 58m
1 stop
Delta Logo
8:10 am - 2:00 pm
ORD
-
VPS
5h 50m
1 stop
$375Delta
Tue, May 26 - Tue, Jun 2
Delta Logo
1:17 pm - 8:26 pm
VPS
-
ORD
7h 09m
1 stop
Delta Logo
9:49 am - 2:00 pm
ORD
-
VPS
4h 11m
1 stop
$384Delta
Wed, Jul 1 - Thu, Jul 9
American Airlines Logo
11:16 am - 1:57 pm
VPS
-
ORD
2h 41mnonstop
American Airlines Logo
12:00 pm - 6:04 pm
ORD
-
VPS
6h 04m
1 stop
$385American Airlines
Thu, May 28 - Mon, Jun 1
Southwest Logo
7:20 am - 12:50 pm
VPS
-
ORD
5h 30m
1 stop
Southwest Logo
2:40 pm - 9:05 pm
ORD
-
VPS
6h 25m
1 stop
$389Southwest
Booking Insights

KAYAK's insights & trends for Valparaiso to Chicago flights

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

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

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

What is the cheapest Valparaiso to Chicago flight route?

Data is based on round-trip flight searches on KAYAK over the past month.

The cheapest return flight from Valparaiso to Chicago costs $96 on the route between Valparaiso (VPS) and Chicago Midway Airport (MDW). Over the past month, this route was, on average, 59% cheaper than other Valparaiso-Chicago routes. The most popular route is between Valparaiso (VPS) and Chicago O'Hare Intl Airport (ORD).

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

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

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

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

To calculate monthly average prices, KAYAK takes all prices for each month over the last year for round-trip flights from Valparaiso to Chicago, 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 Valparaiso to Chicago is May, where tickets cost $48 (return) on average. On the other hand, the most expensive months are December and January, where the average cost of round-trip tickets is $376 and $343 respectively.

Can I save money by flying with a layover from Valparaiso to Chicago?

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 $288, prices are generally cheapest when you fly direct.

Expert advice

Expert advice for your flight from Valparaiso to Chicago

 
AI-powered summary based on content written by travel experts. AI can make mistakes.
KAYAK teamed up with top travel experts to share the best tips for your journey.
Our travel experts
Harriet Baskas

Harriet Baskas

Expert on American Airlines

Harriet is an award-winning journalist who is happiest in an airport or an unusual museum. Her stories about airports, air travel, and the business of travel have appeared on NBC News, CNBC, USA TODAY, The Points Guy and other outlets. She is the creator of the StuckatTheAirport.com blog and the author of nine books. When not out on the road or exploring the latest airport amenities, she’s home in Seattle getting ready for the next adventure.

Daniel Scheffler

Daniel Scheffler

Expert on Allegiant Air

Daniel Scheffler is a travel writer, podcaster, and producer. Born in Africa, bred in Europe and now living in America he has traveled to 140 countries (and all 50 U.S. states). Plus he has stayed at over 2500 hotels across the globe. His original shows Everywhere and Without Maps (available on Spotify) showcase his beliefs, travel is about humanity and sharing that beauty. And thus it reminds you that you shouldn’t believe everything you think.

Good to know

Low seasonAugust
Cheapest flight$73
Best time to beat the crowds with an average 10% drop in price.
Most popular time to fly and prices are also 61% lower on average.
Flight from Valparaiso to Chicago Midway Airport

When to book flights from Valparaiso to Chicago

Are your dates flexible? Find out the best times to travel from Valparaiso to Chicago 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 flights from Valparaiso to Chicago

  • What is the cheapest flight from Valparaiso to Chicago?

    In the last 3 days, the lowest price for a flight from Valparaiso to Chicago was $73 for a one-way ticket and $118 for a round-trip.

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

    Even though you are not required to have a passport, keep in mind that an official ID is needed to board the airplane.

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

    When flying out of Valparaiso you will be using Valparaiso Destin-Ft Walton Beach. You will be landing at one of these airports: Chicago Midway or Chicago O'Hare Intl.

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

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

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

    The Embraer 175 is the aircraft model that flies most regularly on the Valparaiso to Chicago flight route.

  • Which airline alliances offer flights from Valparaiso to Chicago?

    oneworld is the only airline alliance operating flights between Valparaiso and Chicago.

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

    There are nonstop flights from Valparaiso to Chicago on a daily basis.

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

    The two airlines most popular with KAYAK users for flights from Valparaiso to Chicago are Southwest and Allegiant Air. With an average price for the route of $280 and an overall rating of 8.0, Southwest is the most popular choice. Allegiant Air is also a great choice for the route, with an average price of $118 and an overall rating of 7.3.

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

    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.

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

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

    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 with an airline and back to Valparaiso with another airline.

  • What is KAYAK's "flexible dates" feature and why should I care when looking for a flight from Valparaiso to Chicago?

    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 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

  • Looking for a cheap flight? 25% of our users found flights on this route for $246 or less one-way and $270 or less round-trip.

Prefer to fly direct from Valparaiso to Chicago?

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

Direct departures

Valparaiso Destin-Ft Walton Beach to Chicago

Monday

Allegiant Air,American Airlines

Allegiant Air,American Airlines

Tuesday

American Airlines

American Airlines

Wednesday

American Airlines

American Airlines

Thursday

Allegiant Air,American Airlines

Allegiant Air,American Airlines

Friday

Allegiant Air,American Airlines

Allegiant Air,American Airlines

Saturday

American Airlines

American Airlines

Sunday

Allegiant Air,American Airlines

Allegiant Air,American Airlines

See more direct flights

Direct returns

Chicago to Valparaiso Destin-Ft Walton Beach

Monday

Allegiant Air,American Airlines

Allegiant Air,American Airlines

Tuesday

American Airlines

American Airlines

Wednesday

American Airlines

American Airlines

Thursday

Allegiant Air,American Airlines

Allegiant Air,American Airlines

Friday

Allegiant Air,American Airlines

Allegiant Air,American Airlines

Saturday

American Airlines

American Airlines

Sunday

Allegiant Air,American Airlines

Allegiant Air,American Airlines

See more direct flights

Reviews of the top 3 airlines serving from Valparaiso to Chicago

 
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 Chicago? 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
SouthwestOverall score based on 4314 reviews
8.1Boarding
7.0Food
7.5Entertainment
8.6Crew
8.0Comfort
Airline reviews

no service at all due to turbulence. they should've at least given us snacks, there were only 10 people on the entire flight.

4.0 OkayCrystal, Apr 2026
MSY - MDW
Read more Southwest reviews

no service at all due to turbulence. they should've at least given us snacks, there were only 10 people on the entire flight.

For the first time in a long time, the Wi-Fi actually worked the entire flight! The flight crew was amazing as usual.

Great flight. I didn't get a drink because I was asleep whole on the flight.

Communication about the delayed flight was poor. We were told to move gates three times but that was bad information. We went from gate 128 to gate 126 and then to gate 123 and back to gate 126. Communication about the delay was bad. Ended up being 1 1/2 hour late getting home.

Love them will get a Southwest card to track my points and keep flying with them. My family and I were pleased with the services.

Southwest continues to do less for more money. Flight attendants used to be fun and friendly. But now it’s like they don’t even see you. Such a shame.

I liked it better when you were truer to your roots Am paying more for less fun

I was supposed to be on a later flight. When I showed up at the gate, the woman working there was extremely helpful getting moved up to this earlier flight.

Long layover between flights to Long Island from BWI - need better coordination between flights

I realize they are still working out kinks with the new boarding process, but by the time I boarded in group 5, most of the bins were full. All airlines should better enforce small bags and jackets going under the seats until everyone has boarded.

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.

There is not one likable thing about this airline. It’s starts with the deceptive pricing and continues through the whole flight. The worst staff I’ve ever experienced way over priced bags absolutely no food or drink (unacceptable and you should be embarrassed) the seats are cramped and uncomfortable there is no entertainment there is nothing about this trash airline that constitutes any amount of money. It’s worse than spirit and way more expensive it is disgraceful. Do not travel with Allegiant I repeat do not bother no matter what they say the price is it is never ever going to be the right choice I’m mind blown at how awful the entire experience was I’m embarrassed that I chose so poorly I cannot reiterate enough how beyond horrible this company and its staff are, not one person on this flight or at the airport is qualified to sweep up trash on a city sidewalk they should certainly never be given any job that requires a brain or manners or communication with human beings, what a disgrace to the human race. Your criminal chiselers and should be put out to pasture

Great flight. Friendly staff. Free snacks and drinks would be nice. I would love fewer taxes and fees added on.

My 90 year old father flew with me. He needed wheel chair assistance and is nearly deaf. The staff was amazing with him.

It was good, the staff was great, and the food, was as usual, tea and biscuit. Bathroom was clean, and the plane was clean as well.

Very good I can’t complain one bit. Thank you American Airlines for making my flight enjoyable and safe!

The staff and service on American Airlines were truly outstanding. I had requested wheelchair assistance for my mother due to her knee issues, and the team went above and beyond every step of the way—from boarding in Boston to our arrival in Chicago. Their care, professionalism, and attentiveness made the entire experience smooth and stress-free. I’m very grateful for the support they provided.

The new planes (American Eagle) are beautiful and especially comfortable. The flight attendants are consistently professional and courteous. And, while it may seem inconsequential, the new liquid tube of coffee creamer—in contrast to the powdered coffee creamer—makes all the difference in a cup of coffee.

I'm not sure American is capable of on-time arrivals and departures. When you land at ORD, you almost always get held on the tarmac because your gate is still occupied. I may have missed my connection, but that ended up up being significantly delayed as well. Once again, I finally got home well after midnight.

Crew at the gate was very crabby and not at all polite. The plane was very hot the entire flight. And the seat cushion was very worn out.

The staff are very, very professional. It's what flying should feel like.

Flight was delayed half hour before boarding, but when I checked flight aware the plane that would Pick us up had a delay of more than an hour. AA should let us know in advance to avoid waiting several hours in the airport

Delays with no explanation. It could have been handled better.

Jill was the flight attendant in first class she was fabulous!! Best flight attendant I have had in years.!! And I fly every other week. Other can learn from her!!

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

Information on your arrival and departure airports