CHI - VPS

$52 Find Cheap Flights from Chicago to Valparaiso - 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 Chicago to Valparaiso departing on 6/26. 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 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
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Everything you should know

Cheapest round-trip
$106
Typical prices: $123-$96
Allegiant Air
Fri 7/24Mon 7/27
MDW - VPS • Non-stop
Cheapest one-way
$52
Allegiant Air
Fri 6/26
MDW - VPS • Non-stop
Nonstop flights
You can fly direct with American Airlines and Allegiant Air. Average duration is 2h 19m
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
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Insights
Top layover airports
Cheapest • Avg $332 (round-trip)
Shortest trip • 4h 12m (one-way)
Insights
Insights
Insights
Insights
When to book
in advance
Our data shows that travelers who book at least 2 weeks in advance save around 25% compared to booking last minute.
Insights
Insights
Insights
Insights
When to travel
Cheapest • 60% price drop
Most popular
Good to know
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Flight Deals
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Expert advice
Flight Deals

Cheap Flights from Chicago to Valparaiso (CHI-VPS)

 
Here are some of the best deals found on KAYAK recently from the most popular airlines for round-trip flights from Chicago 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 for you by selecting your travel dates on KAYAK.

Recent round-trip flight deals from Chicago to Valparaiso

Fri, Jul 24 - Mon, Jul 27
Allegiant Air Logo
9:21 pm - 11:35 pm
MDW
-
VPS
2h 14mnonstop
Allegiant Air Logo
6:10 pm - 8:30 pm
VPS
-
MDW
2h 20mnonstop
$106Allegiant Air
Fri, Jul 3 - Fri, Jul 24
Allegiant Air Logo
9:15 pm - 11:29 pm
MDW
-
VPS
2h 14mnonstop
Allegiant Air Logo
6:11 pm - 8:31 pm
VPS
-
MDW
2h 20mnonstop
$118Allegiant Air
Fri, Oct 16 - Mon, Oct 19
Allegiant Air Logo
9:20 pm - 11:31 pm
MDW
-
VPS
2h 11mnonstop
Allegiant Air Logo
3:07 pm - 5:25 pm
VPS
-
MDW
2h 18mnonstop
$125Allegiant Air
Fri, Oct 2 - Mon, Oct 12
Allegiant Air Logo
9:24 pm - 11:35 pm
MDW
-
VPS
2h 11mnonstop
Allegiant Air Logo
5:39 pm - 7:57 pm
VPS
-
MDW
2h 18mnonstop
$127Allegiant Air
Sat, Aug 8 - Wed, Aug 12
Delta Logo
1:50 pm - 6:42 pm
ORD
-
VPS
4h 52m
1 stop
Delta Logo
5:06 pm - 11:57 pm
VPS
-
ORD
6h 51m
1 stop
$303Delta
Fri, Aug 7 - Tue, Aug 11
Delta Logo
9:54 am - 4:01 pm
ORD
-
VPS
6h 07m
1 stop
Delta Logo
2:45 pm - 8:55 pm
VPS
-
ORD
6h 10m
1 stop
$333Delta
Thu, Aug 20 - Sun, Aug 23
Sun Country Air Logo
6:32 pm - 4:59 pm
ORD
-
VPS
22h 27m
1 stop
Sun Country Air Logo
6:09 pm - 9:11 am
VPS
-
ORD
15h 02m
1 stop
$334Sun Country Air
Thu, Jul 23 - Fri, Jul 31
Multiple Airlines Logo
7:25 am - 5:03 pm
ORD
-
VPS
9h 38m
1 stop
Multiple Airlines Logo
6:25 am - 12:15 pm
VPS
-
ORD
29h 50m
2 stops
$343Multiple Airlines
Thu, Aug 20 - Thu, Aug 27
Sun Country Air Logo
6:32 pm - 4:59 pm
ORD
-
VPS
22h 27m
1 stop
Sun Country Air Logo
6:00 pm - 12:23 pm
VPS
-
ORD
18h 23m
1 stop
$364Sun Country Air
Wed, Jul 15 - Wed, Jul 22
American Airlines Logo
8:29 am - 11:01 am
ORD
-
VPS
2h 32mnonstop
American Airlines Logo
11:32 am - 2:14 pm
VPS
-
ORD
2h 42mnonstop
$376American Airlines
Booking Insights

KAYAK's insights & trends for Chicago to Valparaiso flights

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

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

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

What is the cheapest Chicago to Valparaiso flight route?

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

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

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

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

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

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

To calculate monthly average prices, KAYAK takes all prices for each month over the last year for round-trip flights from Chicago to Valparaiso, 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 to Valparaiso is October, where tickets cost $52 (return) on average. On the other hand, the most expensive months are January and September, where the average cost of round-trip tickets is $250 and $235 respectively.

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

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 1 stop layover the cheapest option at $425 on average.

How far in advance should I book a flight from Chicago to Valparaiso?

To calculate weekly average prices, KAYAK takes all prices for each week before departure over the last year for round-trip flights from Chicago to Valparaiso, removes the top 0.1% to account for outliers, and then takes the average of all the values for each week.

To get a below average price on the flight from Chicago to Valparaiso, you should book around 2 weeks before departure, which saves you about 25% compared to booking last minute. For the absolute cheapest price, our data suggests you should book 24 weeks before departure.

Expert advice

Expert advice for your flight from Chicago to Valparaiso

 
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 seasonJanuary
Cheapest flight$52
Best time to beat the crowds but there is an average 2% increase in price.
Most popular time to fly with an average 11% increase in price.
Flight from Chicago Midway Airport to Valparaiso

When to book flights from Chicago to Valparaiso

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

  • What is the cheapest flight from Chicago to Valparaiso?

    In the last 5 days, the lowest price for a flight from Chicago to Valparaiso was $54 for a one-way ticket and $106 for a round-trip.

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

    No, a passport isn't needed to fly from Chicago to Valparaiso. However, local authorities might ask for an official ID.

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

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

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

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

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

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

  • Which airline alliances offer flights from Chicago to Valparaiso?

    SkyTeam, and oneworld are the airline alliances operating flights between Chicago and Valparaiso, with SkyTeam being the most commonly used for this route.

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

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

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

    The two airlines most popular with KAYAK users for flights from Chicago to Valparaiso are Southwest and Delta. With an average price for the route of $413 and an overall rating of 7.9, Southwest is the most popular choice. Delta is also a great choice for the route, with an average price of $445 and an overall rating of 7.9.

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

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

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight to Valparaiso from Chicago 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 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 with another airline.

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

  • Looking for a cheap flight? 25% of our users found flights on this route for $50 or less one-way and $330 or less round-trip.

Prefer to fly direct from Chicago to Valparaiso?

 
Direct data is based off flight results for the next 60 days. Find direct flights from all airlines flying direct from Chicago to Valparaiso Destin-Ft Walton Beach.
Find which airlines fly direct from Chicago to Valparaiso Destin-Ft Walton Beach Airport, which days they fly and book direct flights.

Direct departures

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

Direct returns

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

Reviews of the top 4 airlines serving from Chicago 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 Chicago 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.
7.9
SouthwestOverall score based on 4235 reviews
8.0Comfort
8.6Crew
7.5Entertainment
7.0Food
8.1Boarding
Airline reviews

OKay. I sat in the back of the plane and it was really loud between babies and little kids, and adults who.like to talk a lot and loudly most of the flight.

6.0 GoodAnonymous, Jun 2026
MDW - BDL
Read more Southwest reviews

OKay. I sat in the back of the plane and it was really loud between babies and little kids, and adults who.like to talk a lot and loudly most of the flight.

The first time I flew in the extra legroom section. It was difficult to notice a difference. I had bad luck with my neighbors. The crew was okay. Southwest has reduced the live TV options.

The flight was okay. The pilots did an amazing job and kept us updated on the flight. The flight attendants were okay. They found time to be chatty with each other rather than focus on the guests. One of the attendants was a little less warm when asking about my bag I had on my lap that I was using during latter part of the mid- flight. Mind you, it was not the departure descent. I’m respectful to each and every attendant, it was the tone in her voice reminding me to place my carryon bag on the floor. I hope to have a better experience next time.

Terrible. Even though there’s assigned seating now, they are still the slowest boarding airline of anyone.

I flew twice this week on Southwest, was delayed over 2 hours both ways. From Pittsburgh to Chicago it was due to weather but the gate agents, pilot etc were great at updating everyone. Today from Midway to Pittsburgh the plane had come from an international location, kept getting delayed, no information was given until we were delayed for the third time. It was ridiculous, whoever scheduled that plane to fly to Pittsburgh after didn’t consider a lot of things.

It was canceled. Supposedly weather. But there was no snow in Baltimore. At least we found out before driving to airport

The staff was very friendly, professional, and courteous. The overall flight was a great experience.

Okay, not wonderful. Short flight. Wi-fi didn't work properly. Stuck waiting for a gate to open upon arrival for 20 or so minutes.

They sent a notice that they were boarding an hour early. We had to leave the club and run to the gate. They said sorry, that came from corporate and was a mistake. They did not have enough seating because the flight before it had not taken off on time. They moved our gate and delayed it for an hour.

Plane crashed into a bus or some other vehicle on the ground while pulling out of the gate. No injuries, but wing tip was damaged and returned to gate for “maintenance issues” and we departed 5 hours later because the plane went out of service and new plane was flown in from a nearby airport, Midway.

Definitely a southern flavor. Cordiality was evident even though no drinks or snacks were served.

No service flight that took 5 hrs and a stop at an unscheduled airport. Crew and pilots did their jobs

I continue to be satisfied with Delta’s excellent service out of LGA. The digit id works well and gets me through security in no time. Whenever possible, I choose Delta.

Was revoked with Jet Blue due to delay from Kenya Air

Very easy to use and convenient, you can perform any action within the same portal

Overall Good! The weather delayed our takeoff from Atlanta and our arrival in Miami! If Mother Nature can mess up a flight she will do it every time!

Okay considering we had weather delays which the Pilot notified us of immediately!

N Everything was perfect from boarding to assistance to baggage in Tampa

The boarding was organized and informative but the plane was tight meaning that you were sitting on one another and extremely uncomfortable. It’s disappointing that can’t have common seating comfort on the plane.

Everything could have benn better. Short fly, no food, no entertainment and no wifi.

Seats were very uncomfortable and being charged for snacks and water.........

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.

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.

I’ve got 31F seat and window seat . My 2 co passengers was AA crew members and they were very rude attitude and when I was going to use bathroom their gestures was very different and awkward and the guy beside me completely occupied the hand rest and I was really uncomfortable

It was so much better than expected, Ohare is not such a pleasant experience but American Airlines with the new, clean aeroplane and free Wi-Fi was outstanding and the crew so pleasant and helpful.

It wa sort of on time; the cab was left with some trash

American Airlines II: Delay Boogaloo. Multiple gate changes, delays, boarded and then MORE delays. I hate to say this won’t matter, but posting stuff about major corporations in 2026 is a post-modern “scream into the void.” Was multiple hours late coming home, so there you go.

The airplane was an old model, the overhead didn’t have enough room for people’s items and made boarding and boarding disappointing and stressful. Crew allowed passengers to bring more than the permitted baggage sizes.

Original flight was on time, then late, then changed gates...4 times. Once our newest plane came in, it was fine.

I almost missed my flight and they helped me out enormously

Delays experienced in boarding/take off due to incoming plane delayed. However, the boarding time/depart time in the app was significantly delayed in providing these updates. Usually not updated until an hour after we should have already boarded. Poorly managed.

Moved to earlier flight which unexpectedly had maintenance issues initially indicated as quick fix to ultimately plane changes. Moved back to original flight, also delayed. In all cases customer updates and communication very unclear, no updates on drivers for delays.

Typical AA - late by 90+ mn. Gate changed twice... Changed the departure time 6 times No explanation, no communication on reasons for delay I travel with AA twice a year... and it is consistently very poor.. I will continue to use AA only when i have to.

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

Information on your arrival and departure airports