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Kaua'i

$212+ Cheap flights from Chicago (CHI) to Kaua'i

This is the cheapest one-way flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 9/27. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — LIH
Jun 28 — Jul 51
Sun 6/28
Sun 7/5
1 adult, Economy
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Cheap flight deals from Chicago to Kaua'i

Cheapest flights from Chicago to Kaua'i
Explore the most affordable flight options available from Chicago to Kaua'i. Find the lowest fares from popular airlines and budget airlines, with prices last updated on May 29, 2026.

This United Airlines deal was found by Cheapflights users on 5/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/156:00 am
ORD
-
LIH
1 stop11h 04m
United Airlines
Tue 9/227:35 pm
LIH
-
ORD
1 stop10h 53m
United Airlines
Deal found 5/28$424
This Delta deal was found by Cheapflights users on 5/29. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 8/188:28 am
ORD
-
LIH
2 stops14h 13m
Delta
Thu 8/279:38 pm
LIH
-
ORD
1 stop14h 05m
Delta
Deal found 5/29$430
This American Airlines deal was found by Cheapflights users on 5/27. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/206:00 am
ORD
-
LIH
1 stop11h 15m
American Airlines
Mon 10/261:45 pm
LIH
-
ORD
1 stop11h 16m
American Airlines
Deal found 5/27$431
This Delta deal was found by Cheapflights users on 5/25. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/2012:40 pm
ORD
-
LIH
1 stop11h 42m
Delta
Mon 10/269:45 pm
LIH
-
ORD
1 stop14h 29m
Delta
Deal found 5/25$438
This Delta deal was found by Cheapflights users on 5/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/2012:40 pm
ORD
-
LIH
1 stop11h 42m
Delta
Thu 10/299:45 pm
LIH
-
ORD
1 stop14h 29m
Delta
Deal found 5/28$444
This American Airlines deal was found by Cheapflights users on 5/27. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/2211:00 am
ORD
-
LIH
1 stop14h 09m
American Airlines
Thu 8/2710:00 pm
LIH
-
ORD
1 stop12h 54m
American Airlines
Deal found 5/27$445
This Delta deal was found by Cheapflights users on 5/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/112:50 pm
ORD
-
LIH
1 stop11h 11m
Delta
Wed 10/79:26 pm
LIH
-
ORD
2 stops17h 08m
Delta
Deal found 5/28$447
This Delta deal was found by Cheapflights users on 5/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/1512:50 pm
ORD
-
LIH
1 stop11h 11m
Delta
Tue 9/299:50 pm
LIH
-
ORD
2 stops17h 32m
Delta
Deal found 5/28$450
This Delta deal was found by Cheapflights users on 5/26. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/226:25 am
ORD
-
LIH
2 stops17h 42m
Delta
Thu 8/279:38 pm
LIH
-
ORD
1 stop10h 45m
Delta
Deal found 5/26$451
This Delta deal was found by Cheapflights users on 5/26. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/1712:50 pm
ORD
-
LIH
1 stop11h 11m
Delta
Sun 9/279:50 pm
LIH
-
ORD
1 stop10h 41m
Delta
Deal found 5/26$452
This Southwest deal was found by Cheapflights users on 5/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 8/186:50 am
MDW
-
LIH
2 stops14h 20m
Southwest
Mon 8/248:25 pm
LIH
-
MDW
1 stop10h 30m
Southwest
Deal found 5/28$482
This Delta deal was found by Cheapflights users on 5/26. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 5/279:22 am
MDW
-
LIH
2 stops14h 44m
Delta
Tue 6/29:55 pm
LIH
-
MDW
2 stops15h 38m
Delta
Deal found 5/26$495

Find flight deals from Chicago to Kaua'i

Keep the following information in mind while searching for Chicago to Kaua'i flight deals. Data was last updated May 29, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$424
(United Airlines)

One-way from

$212
(United Airlines)

Popular in

December

Cheapest in

February

Average price

$517
Provider with most accurate pricing for Chicago (CHI)-Lihue flight deals.
Search Deals
Provider most trusted by Cheapflights users for Chicago (CHI)-Lihue flights.
Search Deals
From Chicago (CHI) to Kaua'i
Search Deals
One-way flight from Chicago (CHI) to Kaua'i
Search Deals
Highest demand for flights based on searches. 7% potential increase in price ($51 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 5% potential price decrease ($32 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in May 2026
Search Deals

Cheapflights Fare Finder

 
Customize your flight search to find flights from Chicago to Kaua'i that fit within your specific budget. Explore options based on user searches and filter the results based on your desired price range. Find flights that match your budget for a cost-effective journey. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated May 29, 2026.
Use the filters below to find and compare flights from Chicago to Kaua'i that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip

ChicagoLihue

ORD - LIH

ORDLIH

Chicago O'Hare Intl

Tue 8/18

6:25 am-5:41 pm

2 stops16h 16m

Lihue

Thu 8/27

9:38 pm-4:43 pm

1 stop14h 05m

$430

ChicagoLihue

ORD - LIH

ORDLIH

Chicago O'Hare Intl

Mon 10/19

7:35 am-5:20 pm

1 stop14h 45m

Lihue

Sun 10/25

9:45 pm-1:31 pm

1 stop10h 46m

$438

ChicagoLihue

ORD - LIH

ORDLIH

Chicago O'Hare Intl

Thu 10/1

12:50 pm-7:01 pm

1 stop11h 11m

Lihue

Wed 10/7

9:26 pm-7:34 pm

2 stops17h 08m

$447

ChicagoLihue

ORD - LIH

ORDLIH

Chicago O'Hare Intl

Tue 10/20

7:30 am-7:22 pm

2 stops16h 52m

Lihue

Mon 10/26

9:45 pm-5:57 pm

2 stops15h 12m

$449

ChicagoLihue

ORD - LIH

ORDLIH

Chicago O'Hare Intl

Sun 9/13

7:30 am-7:20 pm

2 stops16h 50m

Lihue

Sun 9/20

8:32 pm-1:44 pm

1 stop12h 12m

$451

ChicagoLihue

ORD - LIH

ORDLIH

Chicago O'Hare Intl

Tue 9/15

8:27 am-5:40 pm

2 stops14h 13m

Lihue

Tue 9/22

9:50 pm-6:19 pm

2 stops15h 29m

$455

ChicagoLihue

ORD - LIH

ORDLIH

Chicago O'Hare Intl

Wed 10/28

6:00 am-5:20 pm

2 stops16h 20m

Lihue

Mon 11/9

10:45 pm-5:57 pm

2 stops15h 12m

$462

ChicagoLihue

ORD - LIH

ORDLIH

Chicago O'Hare Intl

Tue 9/22

7:45 am-7:01 pm

2 stops16h 16m

Lihue

Mon 9/28

9:50 pm-6:19 pm

2 stops15h 29m

$462

ChicagoLihue

MDW - LIH

MDWLIH

Chicago Midway

Tue 10/20

9:30 am-7:22 pm

2 stops14h 52m

Lihue

Fri 10/30

9:45 pm-4:50 pm

2 stops14h 05m

$545

ChicagoLihue

MDW - LIH

MDWLIH

Chicago Midway

Tue 9/22

6:50 am-4:10 pm

2 stops14h 20m

Lihue

Mon 9/28

7:10 pm-11:55 am

2 stops11h 45m

$575

Flights are sorted by cheapest round-trip flights first.

Deals found on 5/25

Showing 1-10 of 34 resultsSorted by cheapest first
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Best time to book a flight from Chicago to Kaua'i

Have a flexible travel schedule? Discover the best time to fly to Kaua'i from Chicago with our price prediction graph.
Estimated round-trip price
Rates are based on past data. Find the cheapest month and day to book your flight based on your travel requirements, then search for cheap deals.

Cheapflights Insights

Everything you need to know about your flight from Chicago to Kaua'i

What is the cheapest month to book a flight from Chicago to Kaua'i?

Currently, January is the cheapest month in which you can book a flight from Chicago to Kaua'i (average of $211). Flying from Chicago to Kaua'i in October is currently the most expensive (average of $423). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

How far ahead should I book a flight from Chicago to Kaua'i?

Booking 85 days in advance of your planned departure date is, on average, the best time to get cheap flights from Chicago to Kaua'i. The general trend is that the closer you book to the departure date, the more expensive your flight will be.

Reviews of airlines servicing Kaua'i

Get insights into the airlines that provide service to Kaua'i. Read reviews, discover amenities, and learn about the overall travel experience offered by airlines. Use this information to make informed decisions when choosing an airline for your flight to Kaua'i. Reviews last updated May 29, 2026.
Read reviews from past customers who have flown Southwest,Alaska Airlines, andDelta from Chicago to Kaua'i. You can also see how each airline compares in terms of entertainment options, comfort, food, crew/service, and boarding process.
Southwest
8.0
Very good
4,264 reviews

Crew

8.6

Overall

8.0

Boarding

8.1

Food

7.0

Entertainment

7.5

Comfort

8.0

Reviews

1 / 20
2.0
Mediocre

Dominic,Mar 2026

MCO - SMF

I had to try and sleep on the floor of the Austin airport. I spent 12 hours there. The airline policies were so poor, that a near violent argument broke out between the people in front of me and the flight attendants - making for a super stressful situation at 30,000 feet. Garbage airline choice by Kayak Garbage idea to book a flight with a layover. Next time I will pay for a quality booking myself, and somehow force the company to reimburse it.
Southwest
8.0
Very good
4,264 reviews
Southwest
8.0
Very good
4,264 reviews

Crew

8.6

Overall

8.0

Boarding

8.1

Food

7.0

Entertainment

7.5

Comfort

8.0

Reviews

1 / 20
2.0
Mediocre

Dominic,Mar 2026

MCO - SMF

I had to try and sleep on the floor of the Austin airport. I spent 12 hours there. The airline policies were so poor, that a near violent argument broke out between the people in front of me and the flight attendants - making for a super stressful situation at 30,000 feet. Garbage airline choice by Kayak Garbage idea to book a flight with a layover. Next time I will pay for a quality booking myself, and somehow force the company to reimburse it.
Alaska Airlines
7.9
Good
12,429 reviews
Southwest
8.0
Very good
4,264 reviews

Crew

8.6

Overall

8.0

Boarding

8.1

Food

7.0

Entertainment

7.5

Comfort

8.0

Reviews

1 / 20
2.0
Mediocre

Dominic,Mar 2026

MCO - SMF

I had to try and sleep on the floor of the Austin airport. I spent 12 hours there. The airline policies were so poor, that a near violent argument broke out between the people in front of me and the flight attendants - making for a super stressful situation at 30,000 feet. Garbage airline choice by Kayak Garbage idea to book a flight with a layover. Next time I will pay for a quality booking myself, and somehow force the company to reimburse it.
Delta
7.9
Good
8,419 reviews
Southwest
8.0
Very good
4,264 reviews

Crew

8.6

Overall

8.0

Boarding

8.1

Food

7.0

Entertainment

7.5

Comfort

8.0

Reviews

1 / 20
2.0
Mediocre

Dominic,Mar 2026

MCO - SMF

I had to try and sleep on the floor of the Austin airport. I spent 12 hours there. The airline policies were so poor, that a near violent argument broke out between the people in front of me and the flight attendants - making for a super stressful situation at 30,000 feet. Garbage airline choice by Kayak Garbage idea to book a flight with a layover. Next time I will pay for a quality booking myself, and somehow force the company to reimburse it.
United Airlines
7.4
Good
9,762 reviews
Southwest
8.0
Very good
4,264 reviews

Crew

8.6

Overall

8.0

Boarding

8.1

Food

7.0

Entertainment

7.5

Comfort

8.0

Reviews

1 / 20
2.0
Mediocre

Dominic,Mar 2026

MCO - SMF

I had to try and sleep on the floor of the Austin airport. I spent 12 hours there. The airline policies were so poor, that a near violent argument broke out between the people in front of me and the flight attendants - making for a super stressful situation at 30,000 feet. Garbage airline choice by Kayak Garbage idea to book a flight with a layover. Next time I will pay for a quality booking myself, and somehow force the company to reimburse it.
American Airlines
7.1
Good
11,643 reviews
Southwest
8.0
Very good
4,264 reviews

Crew

8.6

Overall

8.0

Boarding

8.1

Food

7.0

Entertainment

7.5

Comfort

8.0

Reviews

1 / 20
2.0
Mediocre

Dominic,Mar 2026

MCO - SMF

I had to try and sleep on the floor of the Austin airport. I spent 12 hours there. The airline policies were so poor, that a near violent argument broke out between the people in front of me and the flight attendants - making for a super stressful situation at 30,000 feet. Garbage airline choice by Kayak Garbage idea to book a flight with a layover. Next time I will pay for a quality booking myself, and somehow force the company to reimburse it.

Related info for your journey

Find useful and relevant information for your journey from Chicago to Kaua'i. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.

  • How long is the flight from Chicago to Kaua'i?

    Delta and Southwest can get you from Chicago to Kaua'i in just under 14h 20m. Your travel time can differ by up to 1h 56m. The distance from Chicago to Kaua'i is about 4289 mi. Both multi-stop and nonstop flights can be found to your destination and back.

  • What are the cheapest airlines to fly from Chicago to Kaua'i one-way?

    One-way options have recently been found by users for as low as $211 on American Airlines. Other airlines that offer cheap prices include United Airlines from $211 and Alaska Airlines from $217 one-way.

  • Can I find deals for flights from Chicago to Kaua'i that include hotel bookings?

    Yes. In addition to deals on Chicago to Kaua'i flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from Chicago to Kaua'i?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Chicago to Kaua'i.

  • Can I find deals for business class flights from Chicago to Kaua'i?

    Yes. Cheapflights offers flight deals from Chicago to Kaua'i by cabin class. In addition to browsing deals, you can also filter by cabin class on the search results page after making a search.

  • What is the cheapest month to book a flight from Chicago to Kaua'i?

    Currently, January is the cheapest month in which you can book a flight from Chicago to Kaua'i (average of $211). Flying from Chicago to Kaua'i in October is currently the most expensive (average of $423). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

See more FAQs

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Top 4 airlines flying from Chicago to Kaua'i

Discover the top 4 airlines that operate flights from Chicago to Kaua'i. Compare their services, reliability, and customer satisfaction ratings to choose the airline that best suits your travel preferences and needs. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated May 29, 2026.
AirlineCheapestAverageFlexibilityOn-time
Alaska AirlinesCheapest$382Average$688FlexibilityNo cancel feeOn-time75%
American AirlinesCheapest$423Average$602FlexibilityNo cancel feeOn-time71%
DeltaCheapest$424Average$577FlexibilityNo cancel feeOn-timeN/A
United AirlinesCheapest$424Average$647FlexibilityNo cancel feeOn-time69%

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