$178 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 3/4. 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
$424
American Airlines
Thu 2/12Thu 2/19
LIH - ORD • 1 stop
Cheapest one-way
$178
Typical prices: $374-$597
Southwest
Wed 3/4
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

Thu, Feb 12 - Thu, Feb 19
American Airlines Logo
10:30 pm - 2:53 pm
LIH
-
ORD
12h 23m
1 stop
American Airlines Logo
7:00 am - 5:14 pm
ORD
-
LIH
14h 14m
1 stop
$424American Airlines
Wed, Mar 4 - Sun, Mar 15
Alaska Airlines Logo
11:19 pm - 2:11 pm
LIH
-
ORD
10h 52m
1 stop
Alaska Airlines Logo
7:40 am - 12:56 pm
ORD
-
LIH
34h 16m
1 stop
$468Alaska Airlines
Thu, Feb 12 - Thu, Feb 19
Multiple Airlines Logo
6:48 am - 11:59 pm
LIH
-
ORD
13h 11m
2 stops
Multiple Airlines Logo
3:07 pm - 1:56 pm
ORD
-
LIH
26h 49m
1 stop
$474Multiple Airlines
Thu, Feb 12 - Thu, Feb 19
Multiple Airlines Logo
6:48 am - 11:59 pm
LIH
-
ORD
13h 11m
2 stops
Multiple Airlines Logo
8:20 am - 6:17 am
ORD
-
LIH
25h 57m
2 stops
$500Multiple Airlines
Mon, Mar 2 - Sun, Mar 15
Multiple Airlines Logo
3:00 pm - 1:11 pm
LIH
-
ORD
18h 11m
2 stops
Multiple Airlines Logo
7:40 am - 12:56 pm
ORD
-
LIH
34h 16m
1 stop
$538Multiple Airlines
Thu, Feb 12 - Thu, Feb 19
Southwest Logo
6:15 am - 10:15 pm
LIH
-
MDW
12h 00m
2 stops
Southwest Logo
8:10 am - 4:25 pm
MDW
-
LIH
12h 15m
1 stop
$575Southwest
Mon, Mar 2 - Sun, Mar 15
Alaska Airlines Logo
2:56 pm - 11:59 pm
LIH
-
ORD
29h 03m
1 stop
Alaska Airlines Logo
7:40 am - 12:56 pm
ORD
-
LIH
34h 16m
1 stop
$577Alaska Airlines
Wed, Mar 4 - Sun, Mar 15
United Airlines Logo
8:40 pm - 11:19 am
LIH
-
ORD
10h 39m
1 stop
United Airlines Logo
12:52 pm - 9:57 pm
ORD
-
LIH
14h 05m
1 stop
$584United Airlines
Thu, Feb 12 - Thu, Feb 19
Southwest Logo
6:15 am - 10:15 pm
LIH
-
MDW
12h 00m
2 stops
Southwest Logo
8:10 am - 6:15 pm
MDW
-
LIH
14h 05m
2 stops
$605Southwest
Fri, May 22 - Sun, May 31
Delta Logo
9:26 pm - 6:31 pm
LIH
-
MDW
16h 05m
2 stops
Delta Logo
9:30 am - 7:20 pm
MDW
-
LIH
14h 50m
2 stops
$1,175Delta
Useful Info

Good to know

Cheapest flight$178
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 9215 reviews
7.1Entertainment
7.3Comfort
7.7Boarding
8.1Crew
6.6Food
Airline reviews

Seated dude next to me even though lots of empty rows. But main thing was we sat on the tarmac after landing for 30 minutes because of, in the words of the dude who sat next to me, “operational incompetence”. We got changing directions about where to pick up gate checked bags. Pilot and flight attendant were awesome though.

4.0 OkaySean, Jan 2026
BOS - ORD
Read more United Airlines reviews

Seated dude next to me even though lots of empty rows. But main thing was we sat on the tarmac after landing for 30 minutes because of, in the words of the dude who sat next to me, “operational incompetence”. We got changing directions about where to pick up gate checked bags. Pilot and flight attendant were awesome though.

It was a pretty standard flight... until the almost hour and a half spent on the taxi way. I get that the weather has been poor but the delay had nothing to do with the weather and more to do with a plane with several issues tying up the gate. I get that that happens from time to time but this has been EVERY flight I've been on for the past 5 years and I fly 3 to 5 times a year. This isn't just United... it's American, it's Delta. It's an issue with the entire industry. I work for UPS and packages on a cargo plane get better service than people do these days. Anymore I HATE flying.

Perfect flight. Smooth flight. Arrived 20 minutes early at destination. Excellent service.

The flights were on time which was great give. It was holiday travel season and there’d been some weather issues. The only complaint and this is every time with United is the terrible seat design. The head rest is not built for comfort and having my neck bent forward for a cross country trip reminded me while I try not to take United flights as a rule.

Everything was absolutely wonderful from check in to baggage claim. Staff was very professional and sweet. Will definitely recommend United to family and friends.

They did the one thing that really matters - got to Chicago early.

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.

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.