$204 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 11/19. 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

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Flight Deals

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 12 - Tue, Nov 18
Delta Logo
9:40 pm - 1:34 pmLIH-ORD
11h 54m1 stop
Delta Logo
7:20 am - 8:04 pmORD-LIH
16h 44m2 stops
$436Delta
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Wed, Nov 12 - Tue, Nov 18
Delta Logo
10:55 pm - 6:45 pmLIH-ORD
15h 50m2 stops
Delta Logo
7:20 am - 8:04 pmORD-LIH
16h 44m2 stops
$442Delta
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Wed, Nov 12 - Sun, Nov 16
United Airlines Logo
2:15 pm - 6:29 amLIH-ORD
12h 14m1 stop
United Airlines Logo
8:47 am - 4:58 pmORD-LIH
12h 11m1 stop
$443United Airlines
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Fri, Dec 19 - Sat, Jan 10
Alaska Airlines Logo
3:25 pm - 11:59 pmLIH-ORD
28h 34m1 stop
Alaska Airlines Logo
8:00 am - 10:42 pmORD-LIH
18h 42m1 stop
$464Alaska Airlines
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Fri, Dec 19 - Sat, Jan 10
United Airlines Logo
8:30 pm - 11:25 amLIH-ORD
10h 55m1 stop
United Airlines Logo
12:53 pm - 10:34 pmORD-LIH
13h 41m2 stops
$495United Airlines
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Fri, Dec 19 - Sat, Jan 10
Alaska Airlines Logo
3:25 pm - 11:59 pmLIH-ORD
28h 34m1 stop
Alaska Airlines Logo
8:00 am - 10:23 pmORD-LIH
18h 23m2 stops
$510Alaska Airlines
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Mon, Nov 17 - Mon, Nov 24
American Airlines Logo
2:49 pm - 6:43 amLIH-ORD
11h 54m1 stop
American Airlines Logo
6:00 am - 1:18 pmORD-LIH
11h 18m1 stop
$533American Airlines
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Fri, Nov 14 - Tue, Nov 18
American Airlines Logo
2:49 pm - 5:57 amLIH-ORD
11h 08m1 stop
American Airlines Logo
7:00 am - 3:59 pmORD-LIH
12h 59m1 stop
$546American Airlines
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Wed, Nov 12 - Tue, Nov 18
Southwest Logo
7:05 pm - 12:40 pmLIH-MDW
13h 35m2 stops
Southwest Logo
5:15 am - 1:15 pmMDW-LIH
12h 00m1 stop
$588Southwest
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Wed, Nov 12 - Tue, Nov 18
Southwest Logo
9:10 pm - 1:05 pmLIH-MDW
11h 55m1 stop
Southwest Logo
5:15 am - 1:15 pmMDW-LIH
12h 00m1 stop
$628Southwest
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Everything you should know

Cheapest round-trip
$436
Delta
Wed 11/12Tue 11/18
LIH - ORD • 1 stop
Cheapest one-way
$204
Typical prices: $255-$321
Multiple Airlines
Wed 11/19
LIH - ORD • 1 stop
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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$204
Best time to beat the crowds with an average 11% drop in price.
Most popular time to fly with an average 1% increase in price.
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 airline 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 8999 reviews
7.3Comfort
7.7Boarding
6.6Food
7.1Entertainment
8.1Crew
Airline reviews

Flight was delayed only slightly before takeoff due to traffic control. However, the flight arrived early to ORD. Good flight. United has been very reliable for me.

10.0 ExcellentDr. Joseph, Oct 2025STL - ORD
Read more United Airlines reviews

Flight was delayed only slightly before takeoff due to traffic control. However, the flight arrived early to ORD. Good flight. United has been very reliable for me.

Another delayed flight. When the delays exceed the duration of the flight, it’s a problem.

After boarding the plane in Chicago, the passengers were told that there was a technical problem with the plane. Passengers remained on the plane as they tried to fix the problem. After what was probably an hour passengers were told that there was a need to change planes as the problem was not solved. Passengers disembarked and boarded another plane. After taxing to the runway and waiting for takeoff, passengers were told that owing to the thunderstorm the flight was unable to take off but would try and reroute. After some time passengers were told there wasn't enough fuel for the new route and the plane had to return to the gate for additional fuel. after another log delay the flight got underway. On the plane there was food, drinks, ice or entertainment. We were a glass of water, which appeared rationed. Flight arrived about 5 hours late. The pilot was fantastic and communicated with the passengers throughout the ordeal.

Better WiFi. I cannot understand that in 2025, United is so behind on a technology that is now a necessity and still painfully unreliable, slow and keeps disconnecting.

Trip was great. A wild landing in Ottawa with the wind and rain, but the pilot did a great job. Always love flying United.👍

Excellent experience. Starting with the agent at the Premier bag drop who noticed I was very early for my scheduled flight and offered to rebook me on an earlier flight with my seat preference. She would not let me leave the counter until she knew that all of the changes and new boarding pass showed up on my United app. At the gate, the flight boarded quickly such that we departed early and the flight was smooth. We arrived 20 minutes early at ORD and I was able to be home in time for dinner. One of the best flights I've had.

Salina to travers city was great! But the sept 24 Tranverse city was not! Traverse city to chichago was cancelled, i went to Denver & got to Salina 6 hours later!

See previous note about the passenger in Denver who threw my husband's bag out of the overhead bin in order to maker room for his own. And the flight attendant back up the new passenger.

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.

Traveling to a place near Chicago?

Book flights to Chicago if you plan to visit one of these locations
Merrillville
Saint Joseph
Hammond
Portage
Lansing
Valparaiso
Chesterton
Schererville
Munster
Porter
Monticello
Saint John
Griffith

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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