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Kaua'i

$205+ 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 8/18. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — LIH
Jul 30 — Aug 61
Wed 7/30
Wed 8/6
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 July 25, 2025.

Round-trip from

$409
(United Airlines)

One-way from

$205
(American Airlines)

Popular in

December

Cheapest in

October

Average price

$692
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. 3% potential increase in price ($25 potential increase over avg. RT price).
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Cheapest flight prices on average. 3% potential price decrease ($24 potential savings vs. average RT price).
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Average for round-trip flights in July 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 July 25, 2025.

This American Airlines deal was found by Cheapflights users on 7/22. 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.
Fri 9/196:00 amORD - LIH
1 stop11h 14mAmerican Airlines
Thu 9/259:40 pmLIH - ORD
1 stop13h 18mAmerican Airlines
Deal found 7/22$409
This Alaska Airlines deal was found by Cheapflights users on 7/22. 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.
Tue 9/910:00 amORD - LIH
2 stops17h 12mAlaska Airlines
Tue 12/911:00 amLIH - ORD
1 stop27h 55mAlaska Airlines
Deal found 7/22$412
This Delta deal was found by Cheapflights users on 7/24. 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 12/47:30 amORD - LIH
1 stop16h 52mDelta
Thu 12/1110:45 pmLIH - ORD
1 stop10h 43mDelta
Deal found 7/24$423
This Southwest deal was found by Cheapflights users on 7/22. 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.
Thu 11/65:25 amMDW - LIH
1 stop11h 50mSouthwest
Thu 12/119:10 pmLIH - MDW
1 stop11h 55mSouthwest
Deal found 7/22$479
This Delta deal was found by Cheapflights users on 7/22. 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 9/109:30 amMDW - LIH
2 stops14h 33mDelta
Wed 9/178:32 pmLIH - MDW
2 stops17h 03mDelta
Deal found 7/22$605

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 July 25, 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

Fri 9/19

6:00 am-12:14 pm

1 stop11h 14m

Lihue

Thu 9/25

9:40 pm-3:58 pm

1 stop13h 18m

$409

ChicagoLihue

ORD - LIH

ORDLIH

Chicago O'Hare Intl

Tue 9/9

10:00 am-10:12 pm

2 stops17h 12m

Lihue

Tue 12/9

11:00 am-6:55 pm

1 stop27h 55m

$412

ChicagoLihue

ORD - LIH

ORDLIH

Chicago O'Hare Intl

Tue 8/26

7:15 am-5:18 pm

2 stops15h 03m

Lihue

Wed 9/3

9:40 pm-1:17 pm

1 stop10h 37m

$476

ChicagoLihue

MDW - LIH

MDWLIH

Chicago Midway

Tue 9/2

6:10 am-12:50 pm

1 stop11h 40m

Lihue

Mon 9/8

8:40 pm-3:45 pm

1 stop14h 05m

$556

ChicagoLihue

MDW - LIH

MDWLIH

Chicago Midway

Wed 9/10

9:30 am-7:03 pm

2 stops14h 33m

Lihue

Wed 9/17

8:32 pm-6:35 pm

2 stops17h 03m

$605

ChicagoLihue

ORD - LIH

ORDLIH

Chicago O'Hare Intl

Mon 8/18

6:00 am-12:12 pm

1 stop11h 12m

$205

ChicagoLihue

ORD - LIH

ORDLIH

Chicago O'Hare Intl

Wed 9/3

10:00 am-10:12 pm

2 stops17h 12m

$210

ChicagoLihue

ORD - LIH

ORDLIH

Chicago O'Hare Intl

Thu 9/4

7:15 am-7:03 pm

1 stop16h 48m

$274

ChicagoLihue

ORD - LIH

ORDLIH

Chicago O'Hare Intl

Fri 9/5

10:56 am-7:58 pm

2 stops14h 02m

$280

ChicagoLihue

MDW - LIH

MDWLIH

Chicago Midway

Sat 9/13

6:15 am-4:00 pm

2 stops14h 45m

$307

Flights are sorted by cheapest round-trip flights first.

Deals found on 7/22

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 July 25, 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 July 25, 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

Food

7.1

Overall

8.0

Boarding

8.1

Comfort

7.8

Crew

8.5

Entertainment

7.1

Reviews

1 / 20
10.0
Excellent

Jonathan,Jul 2025

SEA - BOS

Fantastic Check-in with easy baggage drop. While it took a while to find out which was the gate, the boarding was a dream, the stewards were simply incredible and the flight fantastic.
Alaska Airlines
8.0
Very good
10,000 reviews
Alaska Airlines
8.0
Very good
10,000 reviews

Food

7.1

Overall

8.0

Boarding

8.1

Comfort

7.8

Crew

8.5

Entertainment

7.1

Reviews

1 / 20
10.0
Excellent

Jonathan,Jul 2025

SEA - BOS

Fantastic Check-in with easy baggage drop. While it took a while to find out which was the gate, the boarding was a dream, the stewards were simply incredible and the flight fantastic.
Southwest
8.0
Very good
4,235 reviews
Alaska Airlines
8.0
Very good
10,000 reviews

Food

7.1

Overall

8.0

Boarding

8.1

Comfort

7.8

Crew

8.5

Entertainment

7.1

Reviews

1 / 20
10.0
Excellent

Jonathan,Jul 2025

SEA - BOS

Fantastic Check-in with easy baggage drop. While it took a while to find out which was the gate, the boarding was a dream, the stewards were simply incredible and the flight fantastic.
Delta
8.0
Very good
7,967 reviews
Alaska Airlines
8.0
Very good
10,000 reviews

Food

7.1

Overall

8.0

Boarding

8.1

Comfort

7.8

Crew

8.5

Entertainment

7.1

Reviews

1 / 20
10.0
Excellent

Jonathan,Jul 2025

SEA - BOS

Fantastic Check-in with easy baggage drop. While it took a while to find out which was the gate, the boarding was a dream, the stewards were simply incredible and the flight fantastic.
United Airlines
7.4
Good
8,880 reviews
Alaska Airlines
8.0
Very good
10,000 reviews

Food

7.1

Overall

8.0

Boarding

8.1

Comfort

7.8

Crew

8.5

Entertainment

7.1

Reviews

1 / 20
10.0
Excellent

Jonathan,Jul 2025

SEA - BOS

Fantastic Check-in with easy baggage drop. While it took a while to find out which was the gate, the boarding was a dream, the stewards were simply incredible and the flight fantastic.
American Airlines
7.2
Good
10,000 reviews
Alaska Airlines
8.0
Very good
10,000 reviews

Food

7.1

Overall

8.0

Boarding

8.1

Comfort

7.8

Crew

8.5

Entertainment

7.1

Reviews

1 / 20
10.0
Excellent

Jonathan,Jul 2025

SEA - BOS

Fantastic Check-in with easy baggage drop. While it took a while to find out which was the gate, the boarding was a dream, the stewards were simply incredible and the flight fantastic.

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.

  • 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 $205 on American Airlines. Other airlines that offer cheap prices include Alaska Airlines from $210 and Delta from $212 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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Top 5 airlines flying from Chicago to Kaua'i

Discover the top 5 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 July 25, 2025.
AirlineCheapestAverageFlexibilityOn-time
DeltaCheapest$316Average$551FlexibilityNo cancel feeOn-timeN/A
American AirlinesCheapest$379Average$593FlexibilityNo cancel feeOn-time71%
Alaska AirlinesCheapest$421Average$682FlexibilityNo cancel feeOn-time75%
United AirlinesCheapest$424Average$759FlexibilityNo cancel feeOn-time69%
SouthwestCheapest$424Average$883FlexibilityNo cancel feeOn-time63%

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