$201 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 10/31. 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

Thu, Oct 2 - Mon, Oct 20
United Airlines Logo
7:40 pm - 11:28 amLIH-ORD
10h 48m1 stop
United Airlines Logo
12:53 pm - 7:55 pmORD-LIH
12h 02m1 stop
$423United Airlines
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Mon, Nov 17 - Mon, Nov 24
Delta Logo
9:29 pm - 5:18 pmLIH-ORD
15h 49m1 stop
Delta Logo
7:47 am - 8:04 pmORD-LIH
16h 17m1 stop
$473Delta
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Mon, Nov 17 - Mon, Nov 24
Delta Logo
9:29 pm - 3:02 pmLIH-ORD
13h 33m2 stops
Delta Logo
7:47 am - 8:04 pmORD-LIH
16h 17m1 stop
$478Delta
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Sun, Oct 26 - Fri, Nov 7
American Airlines Logo
9:40 pm - 2:15 pmLIH-ORD
11h 35m1 stop
American Airlines Logo
6:00 am - 1:18 pmORD-LIH
11h 18m1 stop
$493American Airlines
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Mon, Nov 17 - Mon, Nov 24
Alaska Airlines Logo
6:20 pm - 4:30 pmLIH-ORD
18h 10m2 stops
Alaska Airlines Logo
12:59 pm - 6:17 amORD-LIH
21h 18m2 stops
$503Alaska Airlines
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Mon, Nov 17 - Mon, Nov 24
Delta Logo
9:29 pm - 4:28 pmLIH-ORD
14h 59m2 stops
Delta Logo
7:47 am - 8:04 pmORD-LIH
16h 17m1 stop
$509Delta
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Tue, Mar 10 - Wed, Mar 11
Alaska Airlines Logo
11:14 am - 5:04 amLIH-ORD
12h 50m2 stops
Alaska Airlines Logo
2:00 pm - 9:15 pmORD-LIH
12h 15m1 stop
$566Alaska Airlines
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Thu, Oct 2 - Mon, Oct 13
American Airlines Logo
1:44 pm - 6:01 amLIH-ORD
11h 17m1 stop
American Airlines Logo
6:03 am - 12:15 pmORD-LIH
11h 12m1 stop
$583American Airlines
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Tue, Sep 30 - Thu, Oct 2
Southwest Logo
7:05 pm - 12:15 pmLIH-MDW
12h 10m2 stops
Southwest Logo
7:45 am - 6:20 pmMDW-LIH
15h 35m2 stops
$849Southwest
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Tue, Sep 30 - Thu, Oct 2
Southwest Logo
7:05 pm - 12:15 pmLIH-MDW
12h 10m2 stops
Southwest Logo
7:45 am - 4:00 pmMDW-LIH
13h 15m1 stop
$853Southwest
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Everything you should know

Cheapest round-trip
$423
United Airlines
Thu 10/2Mon 10/20
LIH - ORD • 1 stop
Cheapest one-way
$201
Typical prices: $237-332
Alaska Airlines
Fri 10/31
LIH - ORD • 2 stops
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KAYAK searches 100s of sites at once to find you the best travel deals.
We hope you love your trip to Chicago!
Useful Info

Good to know

Low seasonJanuary
Cheapest flight$201
Best time to beat the crowds with an average 12% drop in price.
Most popular time to fly and prices are also 4% lower on average.
Flight from Lihue to Chicago O'Hare 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 8929 reviews
6.6Food
7.3Comfort
7.1Entertainment
7.7Boarding
8.1Crew
Airline reviews

Flight attendant in first class gave poor service (like he didn't want to be there) and food was awful. We sat waiting for gate upon arrival over 45 mins.

2.0 MediocreAnonymous, Aug 2025RSW - ORD
Read more United Airlines reviews

Flight attendant in first class gave poor service (like he didn't want to be there) and food was awful. We sat waiting for gate upon arrival over 45 mins.

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

Any flight to ORD after about 2pm this summer has been challenging. Flight was delayed getting in (coming from ORD) and that led to it not leaving before a ground stop due to lightening before they could fuel the plane, and so forth. They made up some time but we were still late in arriving at ORD, and that led to missed connections.

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

Pretty good. The food was just mediocre, the boarding and crew were good.

My flight got switched and my prepaid bag didnt transfer over properly so I paid to check ANOTHER BAG. I was placed in a middle seat and it was just miserable. At least it was a bulkhead row so I had legroom. The flight just never seem3d to end

Was not able to watch most shows on the entertainment site. They would not load

On Wednesday, July 30 we were in mid flight from Manchester to Charlotte and we turned around because the right engine was malfunctioning. That was the last flight out of Manchester that night. I was rebooked for Thursday, which became a weather event Friday. There were no seats left on the flight from Manchester to Charlotte. Consequently I didn’t leave Manchester until Saturday morning and we flew to Chicago so to say the least my scheduled flight and return to Iowa was three days off and it messed with my business schedule. Consequently cash flow. I would like some sort of acknowledgment of this event.

Dreadful experience. Our flight was delayed more than 8 hours due to a maintenance issue and the assistance from rebooking was poor. I was travelling with a bad knee and needed assistance waited in one place more than 3 hours before someone came with a wheelchair. The woman next to me was a 91 year old great grandmother who had waited more than 4 hours. There were moments of support from the staff but it appeared as they were going against the direction of management. It was apathy, lack of ownership and dismissive responses with small moments of kindness and understanding typically from grey haired, female, veteran staff..

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.

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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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