$205 Find Cheap Flights from Kaua'i 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 to Chicago departing on 9/10. 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
1 adult, Economy

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Cheap Flights from Kaua'i to Chicago

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

Wed, Nov 5 - Wed, Nov 12
Alaska Airlines Logo
6:49 am - 11:59 pmLIH-ORD
13h 10m2 stops
Alaska Airlines Logo
10:00 am - 10:25 pmORD-LIH
16h 25m1 stop
$414Alaska Airlines
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Wed, Nov 5 - Wed, Nov 12
Alaska Airlines Logo
6:02 am - 5:01 amLIH-ORD
18h 59m2 stops
Alaska Airlines Logo
9:20 am - 6:19 amORD-LIH
24h 59m2 stops
$419Alaska Airlines
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Wed, Nov 5 - Wed, Nov 12
American Airlines Logo
10:44 pm - 2:13 pmLIH-ORD
11h 29m1 stop
American Airlines Logo
6:03 pm - 1:18 pmORD-LIH
23h 15m1 stop
$466American Airlines
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Thu, Aug 14 - Mon, Aug 18
American Airlines Logo
9:16 pm - 10:43 pmLIH-ORD
20h 27m1 stop
American Airlines Logo
6:00 am - 12:12 pmORD-LIH
11h 12m1 stop
$501American Airlines
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Mon, Nov 17 - Mon, Nov 24
Delta Logo
10:45 pm - 5:48 pmLIH-ORD
15h 03m1 stop
Delta Logo
7:30 am - 8:22 pmORD-LIH
16h 52m1 stop
$503Delta
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Mon, Nov 17 - Mon, Nov 24
Delta Logo
10:45 pm - 1:28 pmLIH-ORD
10h 43m1 stop
Delta Logo
8:55 am - 8:22 pmORD-LIH
15h 27m2 stops
$509Delta
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Sat, Aug 16 - Wed, Aug 20
United Airlines Logo
7:40 pm - 11:25 amLIH-ORD
10h 45m1 stop
United Airlines Logo
7:15 am - 3:36 pmORD-LIH
13h 21m1 stop
$662United Airlines
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Mon, Nov 17 - Sun, Nov 23
United Airlines Logo
2:15 pm - 10:56 amLIH-ORD
16h 41m2 stops
United Airlines Logo
8:00 pm - 12:58 pmORD-LIH
20h 58m2 stops
$689United Airlines
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Thu, Nov 20 - Sun, Nov 30
Southwest Logo
9:10 pm - 1:05 pmLIH-MDW
11h 55m1 stop
Southwest Logo
5:35 am - 1:15 pmMDW-LIH
11h 40m1 stop
$728Southwest
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Thu, Nov 20 - Sun, Nov 30
Southwest Logo
7:05 pm - 12:30 pmLIH-MDW
13h 25m2 stops
Southwest Logo
5:35 am - 1:15 pmMDW-LIH
11h 40m1 stop
$733Southwest
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Good to know

Low seasonJanuary
Cheapest flight$205
Best time to beat the crowds with an average 11% drop in price.
Most popular time to fly and prices are also 11% lower on average.
Flight from Lihue to Chicago Midway Airport

FAQs for booking flights from Kaua'i to Chicago

  • How does KAYAK find such low prices on flights from Kaua'i 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 Kaua'i to Chicago.

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

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

  • What is KAYAK's "flexible dates" feature and why should I care when looking for a flight from Kaua'i 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 Kaua'i up to 3 days before/after your preferred dates. You can then pick the flights that suit you best.

Reviews of the top airlines flying from Kaua'i to Chicago

 
Need help choosing which airline to fly with from Kaua'i 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.
7.4
United AirlinesOverall score based on 8900 reviews
7.1Entertainment
7.3Comfort
8.1Crew
7.7Boarding
6.6Food
Airline reviews

Weather delay in Chicago?. No sense of urgency to make connection in Chicago for our connecting flight that wasn't delayed. Connection was missed.

4.0 OkayGary, Jul 2025PIA - ORD
Read more United Airlines reviews

Weather delay in Chicago?. No sense of urgency to make connection in Chicago for our connecting flight that wasn't delayed. Connection was missed.

Overall it was good. I missed my connection but I was put on another flight.

Overall a very poor experience - booked premium economy tickets but due to last minute flight delays , all my itinery went for a toss and had to fly economy class with no access to lounge or any compensation by united airlines to make up for the flight delays . i had expected better experience than that from united.

It was fine, definitely older planes with no charging or anything. There’s no entertainment set up on board, but it is nice that they allow you to access the in flight entertainment from your phone without having to pay for the Wi-Fi and they do offer free texting.

I liked that the flight was nonstop from ORD to CIU for $200 round trip.

While the staff was pleasant and helpful, the following observations are for your awareness. There was some delay on the tarmac on take off and landing. The paid lunch/food offerings were limited. Entertainment was only available on WiFi at a cost.

The first flight was better in terms of the aircraft.

Smooth flight. Boarding was chaotic. Could not hear the gate agent over the intercom. People were lined up in the wrong lines. Groups one and two were told to board through line one and group 3 through line 2. All very confusing. Once in the air, the flight was smooth. There was no entertainment option on this aircraft, even though it was a larger aircraft.

Overall poor for me I paid extra for seats with leg room and my regional flights exit row seats have less leg room then the others that's money that could have been saved and on my final flight home the flights air was not operating it was unbearably hot in the cabin I will be contacting United and filing a DOT complaint

There's just no way to sit fully upright and comfortably in these seats. There needs to be 2 more inches of room, and that's not something that only one person on the flight needs - the whole flight needs 2 more inches of room. If that means you sell 6 less seats, so be it. It's too close for anyone. Forcing people to pay for "premium" economy just to get "barely enough space to breathe" isn't really an answer to that.

Couldn’t get the door on the plane to close leading to a nearly 2 hour delay. But, hey at least they didn’t cancel the flight.

The flight was fine and the crew awesome. The problem is ORD and AA. Computers went down, ORD fell apart and a 40 min flight turned into a 3 hour trip. Guess the answer is to not try and fly to ORD after noon. But, as I said, crew was awesome and did everything they could to lesson the flight time.

The flight was fine but the 8 hour delay in Chicago was awful - 5 gate changes and repeated delays without an explanation. No vouchers. Nothing.

Most miserable flight ever. We waited almost 2 hours on the runway because the flight was oversold. American offered $1200 credit. Then there was some nonsense about weight distribution. Ridiculous. No food for 8 plus hours on the flight. I will be writing a letter.

The flight was 2 hour delayed, otherwise everything was excellent. The delay was due to the hourly limit requirement so given that as a reason, I'm happy with the flight!

Not sure the logic of the boarding in Groups. I was loaded first on the aisle. Then the guy in the middle. Then the guy by the window. Constantly holding up the other people boarding behind them with us blocking the aisle and this happened in most of the other rows

To start, I’d like to say that every American Airline personnel I interacted with on the ground, especially flight crew, was very friendly and did their best to help me out. Despite this, however, my experience with the airline was an entire mess. The 7:19 PM flight was heavily delayed due to weather, and pushed to 10:30 AM the next morning. Because of this, I had to spend the night inside of the airport. At some point later in the night, I got an email saying that the flight had been canceled. I called the support number, and the representative on the other line told me that the flight was still on and that I didn’t need to rebook. The next morning, no one came to the gate to open the door for the crew until almost 11 AM. By this time the flight crew had been waiting for over an hour, and they had called management to get someone to open the door for them multiple times. Around 11:30, the gate screen had changed to a different flight. I ended up buying a last minute ticket with Southwest airline just to get to Chicago, because the next flight with American wasn’t until 7:19 pm that day. Now, earlier that morning my suitcase had been sent ahead of me to ORD. I went to baggage claim to ask them if I could have my suitcase forwarded to where I was staying. The representative at SDF baggage claim said they could and put the claim in for me. As I was going back through TSA, I got an email that the airline had found my suitcase, but the next step was to send it BACK to SDF. I called the airline support number again, and I made it clear that my suitcase needed to stay in Chicago and to not come back to SDF. The representative told me that they would hold my suitcase at ORD and that it wasn’t going to be forwarded anywhere. Once I got there, I found that they had loaded my suitcase onto a plane to send it back to SDF. Thankfully, I had gotten to the baggage claim counter in time for them to put in a request to bring my suitcase back up. My refund with the airline is processing already, but because of this entire experience and miscommunication at every turn of the way, I will not book with American Airlines in the future.

The plane was late and then sat on the runway for almost 45 minutes before taking off.

Crew professional. Easy bag drop off. On time. Good entertainment.

Everything was great. Boarding, early departure, early arrival, and deplaning were smooth. Smooth flight.

Everything you need to know for your flight to Chicago

Cabin class types available on flights to Kaua'i

Cabin classes available on flights to Chicago. Prices are the lowest found on KAYAK over the last 7 days. Price and availability is not guaranteed.

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