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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 1/31. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — LIH
Dec 5 — Dec 121
Fri 12/5
Fri 12/12
1 adult, Economy
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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 November 5, 2025.

This Alaska Airlines deal was found by Cheapflights users on 11/4. 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 12/98:55 amORD - LIH
1 stop32h 58mAlaska Airlines
Tue 12/233:25 pmLIH - ORD
1 stop24h 37mAlaska Airlines
Deal found 11/4$363
This Alaska Airlines deal was found by Cheapflights users on 11/3. 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.
Mon 12/88:55 amORD - LIH
1 stop32h 58mAlaska Airlines
Wed 12/243:25 pmLIH - ORD
1 stop24h 37mAlaska Airlines
Deal found 11/3$391
This Alaska Airlines deal was found by Cheapflights users on 11/4. 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
Wed 12/106:00 amLIH - ORD
2 stops13h 50mAlaska Airlines
Deal found 11/4$395
This Delta deal was found by Cheapflights users on 11/4. 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 12/27:50 amORD - LIH
1 stop16h 20mDelta
Mon 12/89:50 pmLIH - ORD
1 stop11h 43mDelta
Deal found 11/4$404
This Delta deal was found by Cheapflights users on 11/4. 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 12/29:34 amMDW - LIH
2 stops14h 36mDelta
Mon 12/810:55 pmLIH - MDW
2 stops15h 23mDelta
Deal found 11/4$564
This Delta deal was found by Cheapflights users on 11/4. 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 11/276:00 amMDW - LIH
2 stops18h 30mDelta
Fri 12/510:55 pmLIH - MDW
2 stops15h 23mDelta
Deal found 11/4$596
This Southwest deal was found by Cheapflights users on 11/4. 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 11/167:45 amMDW - LIH
1 stop12h 30mSouthwest
Sat 11/227:05 pmLIH - MDW
2 stops13h 35mSouthwest
Deal found 11/4$738
This Southwest deal was found by Cheapflights users on 11/4. 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.
Sat 11/85:15 amMDW - LIH
2 stops17h 00mSouthwest
Mon 11/179:10 pmLIH - MDW
1 stop10h 25mSouthwest
Deal found 11/4$803
This Southwest deal was found by Cheapflights users on 11/3. 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.
Fri 11/215:30 amMDW - LIH
2 stops16h 45mSouthwest
Sat 12/67:05 pmLIH - MDW
2 stops13h 35mSouthwest
Deal found 11/3$859
This Southwest deal was found by Cheapflights users on 11/4. 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.
Mon 12/225:10 amMDW - LIH
1 stop12h 05mSouthwest
Fri 12/269:10 pmLIH - MDW
1 stop10h 00mSouthwest
Deal found 11/4$923
This Delta deal was found by Cheapflights users on 11/4. 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.
Fri 11/79:35 amMDW - LIH
2 stops14h 30mDelta
Thu 11/203:20 pmLIH - MDW
2 stops13h 41mDelta
Deal found 11/4$934

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 November 5, 2025.

Most accurate provider

eDreams
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$363
(Alaska Airlines)

One-way from

$212
(American Airlines)

Popular in

December

Cheapest in

January

Average price

$563
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. 3% potential increase in price ($26 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 4% potential price decrease ($29 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in November 2025
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 November 5, 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 1/27

3:49 pm-1:03 pm

1 stop25h 14m

Lihue

Mon 2/2

10:25 am-11:37 pm

1 stop33h 12m

$363

ChicagoLihue

ORD - LIH

ORDLIH

Chicago O'Hare Intl

Mon 1/26

3:49 pm-1:03 pm

1 stop25h 14m

Lihue

Mon 2/2

7:49 pm-11:37 pm

2 stops23h 48m

$379

ChicagoLihue

ORD - LIH

ORDLIH

Chicago O'Hare Intl

Sun 2/1

9:00 am-1:45 pm

1 stop32h 45m

Lihue

Tue 2/3

6:00 am-11:37 pm

2 stops13h 37m

$379

ChicagoLihue

ORD - LIH

ORDLIH

Chicago O'Hare Intl

Mon 2/2

9:00 am-1:03 pm

1 stop32h 03m

Lihue

Wed 2/4

6:00 am-11:37 pm

2 stops13h 37m

$379

ChicagoLihue

ORD - LIH

ORDLIH

Chicago O'Hare Intl

Sun 2/1

9:00 am-1:45 pm

1 stop32h 45m

Lihue

Mon 2/2

7:49 pm-11:37 pm

2 stops23h 48m

$379

ChicagoLihue

ORD - LIH

ORDLIH

Chicago O'Hare Intl

Mon 2/2

3:49 pm-1:03 pm

1 stop25h 14m

Lihue

Thu 2/5

6:47 am-11:37 pm

2 stops12h 50m

$389

ChicagoLihue

ORD - LIH

ORDLIH

Chicago O'Hare Intl

Wed 1/21

3:49 pm-1:03 pm

1 stop25h 14m

Lihue

Wed 4/15

11:55 am-5:07 am

1 stop12h 12m

$393

ChicagoLihue

ORD - LIH

ORDLIH

Chicago O'Hare Intl

Wed 12/3

3:05 pm-1:49 pm

2 stops26h 44m

Lihue

Wed 12/10

6:00 am-11:50 pm

2 stops13h 50m

$395

ChicagoLihue

ORD - LIH

ORDLIH

Chicago O'Hare Intl

Wed 1/28

3:49 pm-4:54 pm

2 stops29h 05m

Lihue

Mon 2/2

10:25 am-2:29 pm

1 stop24h 04m

$398

ChicagoLihue

MDW - LIH

MDWLIH

Chicago Midway

Thu 1/29

9:50 am-7:55 pm

2 stops14h 05m

Lihue

Tue 2/3

10:45 pm-6:36 pm

2 stops15h 51m

$497

Flights are sorted by cheapest round-trip flights first.

Deals found on 11/4

Showing 1-10 of 35 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, September is the cheapest month in which you can book a flight from Chicago to Kaua'i (average of $231). Flying from Chicago to Kaua'i in July is currently the most expensive (average of $545). 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 November 5, 2025.

It’s optimal to fly from Chicago to Kaua'i in the afternoon. By choosing this option you can save up to 36% on the cost of your flight, compared to a flight in the morning.

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 November 5, 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
11,242 reviews

Boarding

8.1

Food

7.1

Comfort

7.8

Entertainment

7.0

Overall

8.0

Crew

8.5

Reviews

1 / 20
10.0
Excellent

Anonymous,Sep 2025

BOS - HNL

The flight was awesome but a little long. I would prefer a flight with a layover. The amount of space available was minimal and a little uncomfortable for that long of a flight.
Alaska Airlines
8.0
Very good
11,242 reviews
Alaska Airlines
8.0
Very good
11,242 reviews

Boarding

8.1

Food

7.1

Comfort

7.8

Entertainment

7.0

Overall

8.0

Crew

8.5

Reviews

1 / 20
10.0
Excellent

Anonymous,Sep 2025

BOS - HNL

The flight was awesome but a little long. I would prefer a flight with a layover. The amount of space available was minimal and a little uncomfortable for that long of a flight.
Southwest
8.0
Very good
4,240 reviews
Alaska Airlines
8.0
Very good
11,242 reviews

Boarding

8.1

Food

7.1

Comfort

7.8

Entertainment

7.0

Overall

8.0

Crew

8.5

Reviews

1 / 20
10.0
Excellent

Anonymous,Sep 2025

BOS - HNL

The flight was awesome but a little long. I would prefer a flight with a layover. The amount of space available was minimal and a little uncomfortable for that long of a flight.
Delta
7.9
Good
8,004 reviews
Alaska Airlines
8.0
Very good
11,242 reviews

Boarding

8.1

Food

7.1

Comfort

7.8

Entertainment

7.0

Overall

8.0

Crew

8.5

Reviews

1 / 20
10.0
Excellent

Anonymous,Sep 2025

BOS - HNL

The flight was awesome but a little long. I would prefer a flight with a layover. The amount of space available was minimal and a little uncomfortable for that long of a flight.
United Airlines
7.4
Good
9,002 reviews
Alaska Airlines
8.0
Very good
11,242 reviews

Boarding

8.1

Food

7.1

Comfort

7.8

Entertainment

7.0

Overall

8.0

Crew

8.5

Reviews

1 / 20
10.0
Excellent

Anonymous,Sep 2025

BOS - HNL

The flight was awesome but a little long. I would prefer a flight with a layover. The amount of space available was minimal and a little uncomfortable for that long of a flight.
American Airlines
7.2
Good
11,042 reviews
Alaska Airlines
8.0
Very good
11,242 reviews

Boarding

8.1

Food

7.1

Comfort

7.8

Entertainment

7.0

Overall

8.0

Crew

8.5

Reviews

1 / 20
10.0
Excellent

Anonymous,Sep 2025

BOS - HNL

The flight was awesome but a little long. I would prefer a flight with a layover. The amount of space available was minimal and a little uncomfortable for that long of a flight.

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?

    Alaska Airlines and Delta can get you from Chicago to Kaua'i in just under 14h 05m. Your travel time can differ by up to 11h 09m. 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 $212 on American Airlines. Other airlines that offer cheap prices include Delta from $217 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, September is the cheapest month in which you can book a flight from Chicago to Kaua'i (average of $231). Flying from Chicago to Kaua'i in July is currently the most expensive (average of $545). 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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See prices for flight routes from nearby airports that may be better suited for you.
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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 November 5, 2025.
AirlineCheapestAverageFlexibilityOn-time
Hawaiian AirlinesCheapest$231Average$471FlexibilityNo cancel feeOn-time85%
DeltaCheapest$343Average$549FlexibilityNo cancel feeOn-timeN/A
American AirlinesCheapest$380Average$637FlexibilityNo cancel feeOn-time71%
Alaska AirlinesCheapest$423Average$660FlexibilityNo cancel feeOn-time75%
SouthwestCheapest$424Average$883FlexibilityNo cancel feeOn-time63%
United AirlinesCheapest$443Average$756FlexibilityNo cancel feeOn-time69%

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