VPS - CHI

$58 Find Cheap Flights from Valparaiso to Chicago - 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 Valparaiso to Chicago departing on 10/5. 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.
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Everything you should know

Cheapest round-trip
$134
Allegiant Air
Fri 8/14Mon 8/17
VPS - MDW • Non-stop
Cheapest one-way
$58
Allegiant Air
Mon 10/5
VPS - MDW • Non-stop
Top airlines
Cheapest • from $134 (round-trip)
Best reviews • 7.3 score
Airline reviews
Airline reviews
+1
+1
Airline reviews
Airline reviews
+1
Nonstop flights
Every day
You can fly direct with American Airlines and Allegiant Air. Average duration is 2h 29m
Direct flights
Direct flights
+1
+1
Direct flights
Direct flights
+1
Top routes
Cheapest • 52% average savings
Most popular
Insights
Insights
Insights
Insights
When to travel
Cheapest • 26% price drop
Most popular
Good to know
Good to know
+1
+1
Good to know
Good to know
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Flight Deals
Booking Insights
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, Aug 14 - Mon, Aug 17
Allegiant Air Logo
6:14 pm - 8:35 pm
VPS
-
MDW
2h 21mnonstop
Allegiant Air Logo
9:25 pm - 11:39 pm
MDW
-
VPS
2h 14mnonstop
$134Allegiant Air
Fri, Oct 2 - Mon, Oct 5
Allegiant Air Logo
6:16 pm - 8:34 pm
VPS
-
MDW
2h 18mnonstop
Allegiant Air Logo
9:02 pm - 11:13 pm
MDW
-
VPS
2h 11mnonstop
$135Allegiant Air
Fri, Aug 14 - Mon, Aug 17
Allegiant Air Logo
6:14 pm - 8:35 pm
VPS
-
MDW
2h 21mnonstop
Allegiant Air Logo
9:25 pm - 11:39 pm
MDW
-
VPS
2h 14mnonstop
$148Allegiant Air
Fri, Oct 2 - Fri, Oct 9
Allegiant Air Logo
6:16 pm - 8:34 pm
VPS
-
MDW
2h 18mnonstop
Allegiant Air Logo
9:25 pm - 11:36 pm
MDW
-
VPS
2h 11mnonstop
$168Allegiant Air
Fri, Oct 2 - Mon, Oct 5
Multiple Airlines Logo
6:16 pm - 8:34 pm
VPS
-
MDW
2h 18mnonstop
Multiple Airlines Logo
6:25 am - 8:17 pm
MDW
-
VPS
13h 52m
2 stops
$232Multiple Airlines
Fri, Oct 2 - Sun, Oct 4
Multiple Airlines Logo
6:16 pm - 8:34 pm
VPS
-
MDW
2h 18mnonstop
Multiple Airlines Logo
6:46 pm - 8:17 pm
MDW
-
VPS
25h 31m
2 stops
$261Multiple Airlines
Fri, Oct 2 - Sun, Oct 4
Multiple Airlines Logo
12:09 pm - 11:51 am
VPS
-
ORD
23h 42m
2 stops
Multiple Airlines Logo
6:30 am - 11:37 pm
ORD
-
VPS
17h 07m
1 stop
$331Multiple Airlines
Tue, Nov 24 - Tue, Dec 1
American Airlines Logo
11:44 am - 2:39 pm
VPS
-
ORD
2h 55mnonstop
American Airlines Logo
8:34 am - 11:10 am
ORD
-
VPS
2h 36mnonstop
$386American Airlines
Tue, Nov 24 - Wed, Dec 2
American Airlines Logo
11:44 am - 2:39 pm
VPS
-
ORD
2h 55mnonstop
American Airlines Logo
8:33 am - 10:59 am
ORD
-
VPS
2h 26mnonstop
$386American Airlines
Tue, Aug 25 - Tue, Sep 1
American Airlines Logo
11:28 am - 2:13 pm
VPS
-
ORD
2h 45mnonstop
American Airlines Logo
8:25 am - 10:53 am
ORD
-
VPS
2h 28mnonstop
$386American Airlines
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.

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 $126 on the route between Valparaiso (VPS) and Chicago Midway Airport (MDW). Over the past month, this route was, on average, 52% 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 Tuesdays if you are looking for the best rates. For your return to Valparaiso, you’ll find the best rates on Tuesdays 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 February, where tickets cost $295 (return) on average. On the other hand, the most expensive months are August and July, where the average cost of round-trip tickets is $517 and $497 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.

Yes, flying with a layover may cost you more time, but you can also save money on the route, with a 2 stops layover the cheapest option at $304 on average.

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 season

August

Cheapest flight

$58
Best time to beat the crowds but there is an average 114% increase in price.
Most popular time to fly with an average 31% increase in price.
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 5 days, the lowest price for a flight from Valparaiso to Chicago was $58 for a one-way ticket and $134 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, Allegiant Air or American Airlines?

    The two airlines most popular with KAYAK users for flights from Valparaiso to Chicago are Allegiant Air and American Airlines. With an average price for the route of $138 and an overall rating of 7.3, Allegiant Air is the most popular choice. American Airlines is also a great choice for the route, with an average price of $425 and an overall rating of 7.1.

  • 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 $72 or less one-way and $350 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

American Airlines

American Airlines

Friday

Allegiant Air,American Airlines

Allegiant Air,American Airlines

Saturday

American Airlines

American Airlines

Sunday

American Airlines

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

American Airlines

American Airlines

Friday

Allegiant Air,American Airlines

Allegiant Air,American Airlines

Saturday

American Airlines

American Airlines

Sunday

American Airlines

American Airlines

See more direct flights

Reviews of the top airlines flying 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.
7.3
Allegiant AirOverall score based on 678 reviews
8.1Crew
5.5Entertainment
5.8Food
6.9Comfort
7.6Boarding
Airline reviews

This is a no frills, get it done, efficient airline. The seat is a lawn chair. You better bring your own entertainment. If you want something other than water you need to pay for it. But they will get you to your destination quickly, on time, and then they will turn the flight around and go right back where they came from. Reliably. Couple times a week tops. If it fits into your schedule, you can’t get there cheaper or faster.

10.0 ExcellentChristina, Jun 2026
PGD - PIT
Read more Allegiant Air reviews

This is a no frills, get it done, efficient airline. The seat is a lawn chair. You better bring your own entertainment. If you want something other than water you need to pay for it. But they will get you to your destination quickly, on time, and then they will turn the flight around and go right back where they came from. Reliably. Couple times a week tops. If it fits into your schedule, you can’t get there cheaper or faster.

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.

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!

Superb. Staff great. Great flight. As with other airlines, seating too tight and restrictive.

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 fine. Nobody was outstandingly friendly but no one was rude and everything was smooth . The captain thanked us for flying but no one greeted me as I walked on the plane or as I exited which is the least they could do lol

Clean, friendly, roomy. But check-in from the phone link was terrible. Repeated attempts wouldn’t save at the final step. Just kept spinning! It was very frustrating. Finally, I used the app (vs website link) to check-in which worked very smoothly on the first attempt.

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.

Be just a little friendlier, instead of just doing their job and speaking because it’s their job. At least act they want to speak.

- flight was delayed several hours due to weather (understandable) - flight delayed further and we were told by attendants "we are not sure where the pilots are but they are on their way" as we have to find different pilots for the flight - announcements over the PA were somewhat unprofessional by the attendants, seems they need more training and were not reading off the script. They showed their young age and immaturity in their communications with the passengers. They were not clear and lacked professional communication language. - going from a hub to hub we were also parked at the tarmac at ohare for an additional hour and kept being told "few more minutes". Please just let the passengers know the real wait time instead of hiding the truth. We understand there is traffic and weather delays, but we just want transparency. There are several logistics of our lives that revolve around what the attendants and pilots are sharing with us but they are not being transparant.

Requested early boarding to disinfect seat, tray table, etc. before general boarding. Instructed to board after wheelchair passengers. Waited on jet bridge behind 12 wheelchair passengers. Stopped immediately after entering plane to wait for gate agent in rear of plane cleaning a seat that was wet, got to my row and found both seats adjacent to mine already occupied, with the lack of room making it impossible for me to clean my own space and defeating the purpose of my boarding early. Cleaned the armrests and tray table as best I could.

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.

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.

Waited for oxygen tanks for 30 minutes after boarding was complete.

Little warm on the plane and delayed for an hour

I enjoyed the extra leg room compared to other airlines. The first stewards made my daughter’s birthday special by giving her an extra snack. Then the last one coming home from Chicago to Appleton made our night really enjoyable Thanks for making our trip enjoyable

Lost bag and 2 days no word leaving for cruise no clothes or stuff

Food was ok, but not as good as I have had before on AA.

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

Information on your arrival and departure airports