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Kaua'i

$201+ 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 10/27. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — LIH
Oct 16 — Oct 231
Thu 10/16
Thu 10/23
1 adult, Economy
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Cheap 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 September 16, 2025.

Round-trip from

$421
(Alaska Airlines)

One-way from

$201
(KAYAK)

Popular in

December

Cheapest in

October

Average price

$561
From Chicago (CHI) to Kaua'i
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One-way flight from Chicago (CHI) to Kaua'i
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Highest demand for flights based on searches. 2% potential increase in price ($13 potential increase over avg. RT price).
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Cheapest flight prices on average. 3% potential price decrease ($20 potential savings vs. average RT price).
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Average for round-trip flights in September 2025
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Find 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 September 16, 2025.

This American Airlines deal was found by Cheapflights users on 9/15. 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.
Thu 11/66:00 amORD - LIH
1 stop11h 18mAmerican Airlines
Thu 11/62:49 pmLIH - ORD
1 stop11h 08mAmerican Airlines
Deal found 9/15$418
This Alaska Airlines deal was found by Cheapflights users on 9/15. 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 Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/47:59 pmORD - LIH
1 stop21h 54mAlaska Airlines
Tue 12/92:53 pmLIH - ORD
1 stop24h 01mAlaska Airlines
Deal found 9/15$421
This Delta deal was found by Cheapflights users on 9/14. 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 10/217:37 amORD - LIH
1 stop16h 28mDelta
Mon 11/310:40 pmLIH - ORD
1 stop10h 50mDelta
Deal found 9/14$423
This American Airlines deal was found by Cheapflights users on 9/15. 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.
Mon 11/107:00 amORD - LIH
1 stop12h 59mAmerican Airlines
Fri 11/212:49 pmLIH - ORD
1 stop11h 07mAmerican Airlines
Deal found 9/15$425
This Delta deal was found by Cheapflights users on 9/15. 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 10/217:37 amORD - LIH
1 stop16h 28mDelta
Fri 10/319:40 pmLIH - ORD
2 stops14h 10mDelta
Deal found 9/15$428
This American Airlines deal was found by Cheapflights users on 9/14. 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.
Sun 10/265:00 amORD - LIH
2 stops14h 30mAmerican Airlines
Sun 11/22:49 pmLIH - ORD
1 stop11h 08mAmerican Airlines
Deal found 9/14$429
This Alaska Airlines deal was found by Cheapflights users on 9/15. 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 Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/278:20 amORD - LIH
2 stops16h 10mAlaska Airlines
Fri 12/57:59 pmLIH - ORD
2 stops14h 10mAlaska Airlines
Deal found 9/15$433
This Alaska Airlines deal was found by Cheapflights users on 9/15. 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 Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/48:00 amORD - LIH
2 stops18h 23mAlaska Airlines
Mon 12/82:53 pmLIH - ORD
1 stop24h 01mAlaska Airlines
Deal found 9/15$436
This Alaska Airlines deal was found by Cheapflights users on 9/14. 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 Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/33:05 pmORD - LIH
2 stops26h 44mAlaska Airlines
Sun 12/142:53 pmLIH - ORD
1 stop24h 01mAlaska Airlines
Deal found 9/14$438
This Delta deal was found by Cheapflights users on 9/15. 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 10/237:37 amORD - LIH
1 stop16h 28mDelta
Tue 10/289:40 pmLIH - ORD
1 stop14h 30mDelta
Deal found 9/15$444
This Southwest deal was found by Cheapflights users on 9/14. 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.
Sun 12/77:45 amMDW - LIH
1 stop12h 30mSouthwest
Sat 12/139:10 pmLIH - MDW
2 stops15h 10mSouthwest
Deal found 9/14$528
This Delta deal was found by Cheapflights users on 9/15. 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.
Sun 10/269:35 amMDW - LIH
2 stops14h 30mDelta
Sun 11/29:30 pmLIH - MDW
2 stops16h 13mDelta
Deal found 9/15$564

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 September 16, 2025.
Use the filters below to find and compare flights from Chicago to Kaua'i that are best for you.

Fly from

Chicago

Fly to

Kaua'i

Route

Depart

Return

Price

ChicagoLihue

ORD - LIH

ORDLIH

Chicago O'Hare Intl

Tue 10/21

7:37 am-7:05 pm

1 stop16h 28m

Lihue

Fri 10/31

9:40 pm-5:18 pm

1 stop14h 38m

$423

ChicagoLihue

ORD - LIH

ORDLIH

Chicago O'Hare Intl

Wed 10/22

7:37 am-7:05 pm

1 stop16h 28m

Lihue

Fri 10/31

9:40 pm-5:18 pm

1 stop14h 38m

$423

ChicagoLihue

ORD - LIH

ORDLIH

Chicago O'Hare Intl

Thu 12/4

3:05 pm-1:53 pm

1 stop26h 48m

Lihue

Tue 12/9

6:54 pm-6:54 pm

2 stops20h 00m

$427

ChicagoLihue

ORD - LIH

ORDLIH

Chicago O'Hare Intl

Thu 12/4

3:05 pm-1:53 pm

1 stop26h 48m

Lihue

Thu 12/11

9:59 am-6:21 am

2 stops16h 22m

$428

ChicagoLihue

ORD - LIH

ORDLIH

Chicago O'Hare Intl

Wed 10/22

7:37 am-7:05 pm

1 stop16h 28m

Lihue

Sun 11/2

10:40 pm-1:34 pm

1 stop10h 54m

$444

ChicagoLihue

ORD - LIH

ORDLIH

Chicago O'Hare Intl

Tue 10/21

7:37 am-7:05 pm

1 stop16h 28m

Lihue

Sun 11/2

10:40 pm-1:34 pm

1 stop10h 54m

$444

ChicagoLihue

ORD - LIH

ORDLIH

Chicago O'Hare Intl

Thu 10/23

7:37 am-7:05 pm

1 stop16h 28m

Lihue

Tue 10/28

9:40 pm-5:10 pm

1 stop14h 30m

$444

ChicagoLihue

ORD - LIH

ORDLIH

Chicago O'Hare Intl

Thu 10/23

7:37 am-7:05 pm

1 stop16h 28m

Lihue

Fri 10/31

9:40 pm-4:50 pm

2 stops14h 10m

$449

ChicagoLihue

ORD - LIH

ORDLIH

Chicago O'Hare Intl

Fri 10/24

7:37 am-7:05 pm

1 stop16h 28m

Lihue

Fri 10/31

9:40 pm-4:50 pm

2 stops14h 10m

$449

ChicagoLihue

ORD - LIH

ORDLIH

Chicago O'Hare Intl

Fri 10/24

7:37 am-7:05 pm

1 stop16h 28m

Lihue

Tue 10/28

9:40 pm-6:41 pm

2 stops16h 01m

$450

Flights are sorted by cheapest round-trip flights first.

Deals found on 9/14

Showing 1-10 of 37 results
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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 $440). Flying from Chicago to Kaua'i in June is currently the most expensive (average of $689). 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.

What is the cheapest time of day to fly from CHI to FUS?

Find hourly flight availability from Chicago to Kaua'i. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated September 16, 2025.

When flying from Chicago to Kaua'i, the time of day you decide to fly out makes little to no difference towards the overall price you’ll pay on tickets.

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 September 16, 2025.
Read reviews from past customers who have flown Alaska Airlines, Southwest, and Delta 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.
Alaska Airlines
8.0
Very good
10,000 reviews

Entertainment

7.0

Boarding

8.1

Crew

8.5

Food

7.1

Overall

8.0

Comfort

7.8

Reviews

1 / 20
6.0
Good

Hannah,Aug 2025

SFO - SAN

Ticket said TSA pre check, but then the TSA agent said that Alaska Airlines has not actually entered the pre check information for the ticket, so I had to use regular security. During boarding, I have a disability and need to board early. The Alaska Airlines employee announced disability boarding, but then immediately announced 2 other groups to board, so I still had to fight the crowds. On the plane, the stewardess was brusk and rude. Seats were very uncomfortable, especially on lower back.
Alaska Airlines
8.0
Very good
10,000 reviews
Alaska Airlines
8.0
Very good
10,000 reviews

Entertainment

7.0

Boarding

8.1

Crew

8.5

Food

7.1

Overall

8.0

Comfort

7.8

Reviews

1 / 20
6.0
Good

Hannah,Aug 2025

SFO - SAN

Ticket said TSA pre check, but then the TSA agent said that Alaska Airlines has not actually entered the pre check information for the ticket, so I had to use regular security. During boarding, I have a disability and need to board early. The Alaska Airlines employee announced disability boarding, but then immediately announced 2 other groups to board, so I still had to fight the crowds. On the plane, the stewardess was brusk and rude. Seats were very uncomfortable, especially on lower back.
Southwest
8.0
Very good
4,242 reviews
Alaska Airlines
8.0
Very good
10,000 reviews

Entertainment

7.0

Boarding

8.1

Crew

8.5

Food

7.1

Overall

8.0

Comfort

7.8

Reviews

1 / 20
6.0
Good

Hannah,Aug 2025

SFO - SAN

Ticket said TSA pre check, but then the TSA agent said that Alaska Airlines has not actually entered the pre check information for the ticket, so I had to use regular security. During boarding, I have a disability and need to board early. The Alaska Airlines employee announced disability boarding, but then immediately announced 2 other groups to board, so I still had to fight the crowds. On the plane, the stewardess was brusk and rude. Seats were very uncomfortable, especially on lower back.
Delta
8.0
Very good
7,954 reviews
Alaska Airlines
8.0
Very good
10,000 reviews

Entertainment

7.0

Boarding

8.1

Crew

8.5

Food

7.1

Overall

8.0

Comfort

7.8

Reviews

1 / 20
6.0
Good

Hannah,Aug 2025

SFO - SAN

Ticket said TSA pre check, but then the TSA agent said that Alaska Airlines has not actually entered the pre check information for the ticket, so I had to use regular security. During boarding, I have a disability and need to board early. The Alaska Airlines employee announced disability boarding, but then immediately announced 2 other groups to board, so I still had to fight the crowds. On the plane, the stewardess was brusk and rude. Seats were very uncomfortable, especially on lower back.
United Airlines
7.4
Good
8,929 reviews
Alaska Airlines
8.0
Very good
10,000 reviews

Entertainment

7.0

Boarding

8.1

Crew

8.5

Food

7.1

Overall

8.0

Comfort

7.8

Reviews

1 / 20
6.0
Good

Hannah,Aug 2025

SFO - SAN

Ticket said TSA pre check, but then the TSA agent said that Alaska Airlines has not actually entered the pre check information for the ticket, so I had to use regular security. During boarding, I have a disability and need to board early. The Alaska Airlines employee announced disability boarding, but then immediately announced 2 other groups to board, so I still had to fight the crowds. On the plane, the stewardess was brusk and rude. Seats were very uncomfortable, especially on lower back.
American Airlines
7.2
Good
10,000 reviews
Alaska Airlines
8.0
Very good
10,000 reviews

Entertainment

7.0

Boarding

8.1

Crew

8.5

Food

7.1

Overall

8.0

Comfort

7.8

Reviews

1 / 20
6.0
Good

Hannah,Aug 2025

SFO - SAN

Ticket said TSA pre check, but then the TSA agent said that Alaska Airlines has not actually entered the pre check information for the ticket, so I had to use regular security. During boarding, I have a disability and need to board early. The Alaska Airlines employee announced disability boarding, but then immediately announced 2 other groups to board, so I still had to fight the crowds. On the plane, the stewardess was brusk and rude. Seats were very uncomfortable, especially on lower back.

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, Alaska Airlines, and Southwest can get you from Chicago to Kaua'i in just under 12h 30m. Your travel time can differ by up to 14h 18m. 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 $201 on Alaska Airlines. Other airlines that offer cheap prices include American Airlines from $212 and Delta from $247 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 $440). Flying from Chicago to Kaua'i in June is currently the most expensive (average of $689). 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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Alternative routes for Chicago to Kaua'i

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Top 6 airlines flying from Chicago to Kaua'i

Discover the top 6 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 September 16, 2025.
AirlineCheapestAverageFlexibilityOn-time
Hawaiian AirlinesCheapest$231Average$471FlexibilityNo cancel feeOn-time85%
DeltaCheapest$343Average$557FlexibilityNo cancel feeOn-timeN/A
American AirlinesCheapest$379Average$620FlexibilityNo cancel feeOn-time71%
Alaska AirlinesCheapest$421Average$680FlexibilityNo cancel feeOn-time75%
SouthwestCheapest$424Average$873FlexibilityNo cancel feeOn-time63%
United AirlinesCheapest$441Average$762FlexibilityNo cancel feeOn-time69%

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