$187 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 3/3. 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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Everything you should know

Cheapest round-trip
$389
Multiple Airlines
pt. 2/6pon. 2/9
LIH - ORD • 2 stops
Cheapest one-way
$197
Typical prices: $488-$603
Alaska Airlines
wt. 3/3
LIH - ORD • 1 stop
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Flight Deals
Useful Info
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

pt., lut 6 - pon., lut 9
Multiple Airlines Logo
1:39 pm - 2:29 pm
LIH
-
ORD
20h 50m2 stops
Multiple Airlines Logo
3:44 pm - 1:03 pm
ORD
-
LIH
25h 19m1 stop
$389Multiple Airlines
pt., lut 6 - pon., lut 9
Alaska Airlines Logo
10:25 am - 2:29 pm
LIH
-
ORD
24h 04m1 stop
Alaska Airlines Logo
3:44 pm - 1:03 pm
ORD
-
LIH
25h 19m1 stop
$392Alaska Airlines
śr., sty 21 - ndz., sty 25
Multiple Airlines Logo
9:00 pm - 2:38 pm
LIH
-
ORD
13h 38m2 stops
Multiple Airlines Logo
3:44 pm - 1:45 pm
ORD
-
LIH
26h 01m1 stop
$397Multiple Airlines
pt., lut 6 - pon., lut 9
Alaska Airlines Logo
10:25 am - 2:29 pm
LIH
-
ORD
24h 04m1 stop
Alaska Airlines Logo
3:44 pm - 1:03 pm
ORD
-
LIH
25h 19m1 stop
$412Alaska Airlines
pt., lut 6 - pon., lut 9
Multiple Airlines Logo
1:39 pm - 2:29 pm
LIH
-
ORD
20h 50m2 stops
Multiple Airlines Logo
9:00 am - 6:17 am
ORD
-
LIH
25h 17m2 stops
$413Multiple Airlines
śr., sty 21 - ndz., sty 25
Multiple Airlines Logo
7:49 pm - 2:38 pm
LIH
-
ORD
14h 49m2 stops
Multiple Airlines Logo
9:00 am - 1:45 pm
ORD
-
LIH
32h 45m1 stop
$417Multiple Airlines
pt., lut 6 - pon., lut 9
Alaska Airlines Logo
10:25 am - 2:29 pm
LIH
-
ORD
24h 04m1 stop
Alaska Airlines Logo
9:00 am - 1:03 pm
ORD
-
LIH
32h 03m1 stop
$420Alaska Airlines
ndz., gru 28 - ndz., sty 4
American Airlines Logo
9:45 pm - 2:24 pm
LIH
-
ORD
12h 39m1 stop
American Airlines Logo
8:15 am - 6:39 pm
ORD
-
LIH
14h 24m1 stop
$423American Airlines
pt., lut 6 - pon., lut 9
Delta Logo
10:35 pm - 4:38 pm
LIH
-
ORD
14h 03m2 stops
Delta Logo
6:50 am - 7:54 pm
ORD
-
LIH
17h 04m2 stops
$434Delta
pt., lut 6 - pon., lut 9
Delta Logo
10:35 pm - 10:22 pm
LIH
-
MDW
19h 47m2 stops
Delta Logo
9:33 am - 7:54 pm
MDW
-
LIH
14h 21m2 stops
$580Delta
Useful Info

Good to know

Low seasonJanuary
Cheapest flight$197
Best time to beat the crowds with an average 16% drop in price.
Most popular time to fly with an average 2% 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 9092 reviews
7.7Boarding
6.6Food
7.3Comfort
8.1Crew
7.1Entertainment
Airline reviews

The flight was on time. I generally don’t drink or eat on short flights and the seats were good and the flight attendants were friendly. That’s all I expect

10.0 ExcellentRoger, Dec 2025
CAE - ORD
Read more United Airlines reviews

The flight was on time. I generally don’t drink or eat on short flights and the seats were good and the flight attendants were friendly. That’s all I expect

It was nice to have gotten up upgraded to first class with a meal on a three hour flight

Very bad! They kept delaying my flight and wouldn’t do anything about it

Door to door, the crew and staff were amazing. It was a stressful travel day with delays, but they were focused on customers and doing what they could to get us to our destinations.

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.

Traveling to a place near Chicago?

Book flights to Chicago if you plan to visit one of these locations
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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.