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$201+ Cheap flights from Kaua'i to Chicago (CHI)

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 10/31. Fares are subject to change and may not be available on all flights or dates of travel.
LIH — CHI
Oct 15 — Oct 221
Wed 10/15
Wed 10/22
1 adult, Economy
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Cheap flight deals from Kaua'i to Chicago

Keep the following information in mind while searching for Kaua'i to Chicago flight deals. Data was last updated September 15, 2025.

Round-trip from

$423
(United Airlines)

One-way from

$201
(KAYAK)
From Kaua'i to Chicago (CHI)
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One-way flight from Kaua'i to Chicago (CHI)
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Find flight deals from Kaua'i to Chicago

Cheapest flights from Kaua'i to Chicago
Explore the most affordable flight options available from Kaua'i to Chicago. Find the lowest fares from popular airlines and budget airlines, with prices last updated on September 15, 2025.

This United Airlines deal was found by Cheapflights users on 9/13. 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.
Thu 10/27:40 pmLIH - ORD
1 stop10h 48mUnited Airlines
Mon 10/2012:53 pmORD - LIH
1 stop12h 02mUnited Airlines
Deal found 9/13$423
This American Airlines deal was found by Cheapflights users on 9/13. 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 12/203:55 pmLIH - ORD
1 stop11h 06mAmerican Airlines
Sun 1/410:40 amORD - LIH
1 stop11h 59mAmerican Airlines
Deal found 9/13$451
This Alaska Airlines deal was found by Cheapflights users on 9/13. 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 11/179:00 pmLIH - ORD
2 stops15h 30mAlaska Airlines
Mon 11/2412:59 pmORD - LIH
2 stops21h 18mAlaska Airlines
Deal found 9/13$503
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.
Mon 11/179:29 pmLIH - ORD
2 stops14h 59mDelta
Mon 11/247:47 amORD - LIH
1 stop16h 17mDelta
Deal found 9/14$509
This American Airlines deal was found by Cheapflights users on 9/13. 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 10/269:40 pmLIH - ORD
1 stop11h 35mAmerican Airlines
Sat 11/17:01 pmORD - LIH
1 stop23h 17mAmerican Airlines
Deal found 9/13$550
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 9/309:40 pmLIH - ORD
1 stop10h 40mDelta
Thu 10/26:15 amORD - LIH
2 stops16h 06mDelta
Deal found 9/14$574
This American Airlines deal was found by Cheapflights users on 9/13. 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 10/21:44 pmLIH - ORD
1 stop11h 17mAmerican Airlines
Mon 10/136:03 amORD - LIH
1 stop11h 12mAmerican Airlines
Deal found 9/13$581
This United 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/3012:50 pmLIH - ORD
1 stop11h 23mUnited Airlines
Thu 10/27:10 amORD - LIH
1 stop13h 26mUnited Airlines
Deal found 9/14$593
This Delta deal was found by Cheapflights users on 9/13. 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 10/38:32 pmLIH - ORD
2 stops15h 29mDelta
Mon 10/137:37 amORD - LIH
1 stop16h 28mDelta
Deal found 9/13$600
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 9/308:32 pmLIH - MDW
2 stops16h 03mDelta
Thu 10/26:00 amMDW - LIH
2 stops18h 27mDelta
Deal found 9/15$826
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.
Tue 9/307:05 pmLIH - MDW
2 stops12h 10mSouthwest
Thu 10/27:45 amMDW - LIH
2 stops15h 35mSouthwest
Deal found 9/14$849
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 10/261:33 pmLIH - MDW
2 stops14h 22mDelta
Fri 11/79:35 amMDW - LIH
2 stops14h 30mDelta
Deal found 9/15$1,014

Cheapflights Fare Finder

 
Customize your flight search to find flights from Kaua'i to Chicago 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 15, 2025.
Use the filters below to find and compare flights from Kaua'i to Chicago that are best for you.

Fly from

Kaua'i

Fly to

Chicago

Route

Depart

Return

Price

LihueChicago

LIH - ORD

LIHORD

Lihue

Thu 10/2

7:40 pm-11:28 am

1 stop10h 48m

Chicago O'Hare Intl

Mon 10/20

12:53 pm-7:55 pm

1 stop12h 02m

$423

LihueChicago

LIH - ORD

LIHORD

Lihue

Sat 12/20

3:55 pm-7:01 am

1 stop11h 06m

Chicago O'Hare Intl

Sun 1/4

10:40 am-6:39 pm

1 stop11h 59m

$451

LihueChicago

LIH - ORD

LIHORD

Lihue

Mon 11/17

9:29 pm-5:18 pm

1 stop15h 49m

Chicago O'Hare Intl

Mon 11/24

7:47 am-8:04 pm

1 stop16h 17m

$503

LihueChicago

LIH - ORD

LIHORD

Lihue

Mon 11/17

9:00 pm-4:30 pm

2 stops15h 30m

Chicago O'Hare Intl

Mon 11/24

12:59 pm-6:17 am

2 stops21h 18m

$503

LihueChicago

LIH - ORD

LIHORD

Lihue

Sun 10/26

9:40 pm-2:15 pm

1 stop11h 35m

Chicago O'Hare Intl

Sat 11/1

7:01 pm-1:18 pm

1 stop23h 17m

$550

LihueChicago

LIH - ORD

LIHORD

Lihue

Tue 3/10

1:30 pm-5:10 am

1 stop10h 40m

Chicago O'Hare Intl

Wed 3/11

12:45 pm-9:22 pm

1 stop13h 37m

$563

LihueChicago

LIH - ORD

LIHORD

Lihue

Tue 3/10

11:14 am-5:04 am

2 stops12h 50m

Chicago O'Hare Intl

Wed 3/11

2:00 pm-9:15 pm

1 stop12h 15m

$566

LihueChicago

LIH - MDW

LIHMDW

Lihue

Tue 9/30

8:32 pm-5:35 pm

2 stops16h 03m

Chicago Midway

Thu 10/2

6:00 am-7:27 pm

2 stops18h 27m

$826

LihueChicago

LIH - MDW

LIHMDW

Lihue

Tue 9/30

7:05 pm-12:15 pm

2 stops12h 10m

Chicago Midway

Thu 10/2

7:45 am-6:20 pm

2 stops15h 35m

$849

LihueChicago

LIH - MDW

LIHMDW

Lihue

Sun 10/26

1:33 pm-8:55 am

2 stops14h 22m

Chicago Midway

Fri 11/7

9:35 am-8:05 pm

2 stops14h 30m

$1,014

Flights are sorted by cheapest round-trip flights first.

Deals found on 9/14

Showing 1-10 of 21 results
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Best time to book a flight from Kaua'i to Chicago

Have a flexible travel schedule? Discover the best time to fly to Chicago from Kaua'i 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 Kaua'i to Chicago
No data available for this route at this time. Please check back soon.

Reviews of airlines servicing Chicago

Get insights into the airlines that provide service to Chicago. 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 Chicago. Reviews last updated September 15, 2025.
Read reviews from past customers who have flown United Airlines and American Airlines from Kaua'i to Chicago. You can also see how each airline compares in terms of entertainment options, comfort, food, crew/service, and boarding process.
United Airlines
7.4
Good
8,929 reviews

Comfort

7.3

Overall

7.4

Food

6.6

Boarding

7.7

Crew

8.1

Entertainment

7.1

Reviews

1 / 20
2.0
Mediocre

Deb,Jan 2025

MKE - ORD

It was terrible! So much to say, but in a nutshell we used vouchers from United because our last trip with them was awful with many mishaps and errors made. Unfortunately, this trip was even worse!
United Airlines
7.4
Good
8,929 reviews
United Airlines
7.4
Good
8,929 reviews

Comfort

7.3

Overall

7.4

Food

6.6

Boarding

7.7

Crew

8.1

Entertainment

7.1

Reviews

1 / 20
2.0
Mediocre

Deb,Jan 2025

MKE - ORD

It was terrible! So much to say, but in a nutshell we used vouchers from United because our last trip with them was awful with many mishaps and errors made. Unfortunately, this trip was even worse!
American Airlines
7.2
Good
10,000 reviews
United Airlines
7.4
Good
8,929 reviews

Comfort

7.3

Overall

7.4

Food

6.6

Boarding

7.7

Crew

8.1

Entertainment

7.1

Reviews

1 / 20
2.0
Mediocre

Deb,Jan 2025

MKE - ORD

It was terrible! So much to say, but in a nutshell we used vouchers from United because our last trip with them was awful with many mishaps and errors made. Unfortunately, this trip was even worse!

Related info for your journey

Find useful and relevant information for your journey from Kaua'i to Chicago. 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 Kaua'i to Chicago?

    For as low as $423, United Airlines can have you in Chicago from Kaua'i in 10h 48m. The distance from Kaua'i to Chicago is about 4280 mi. When browsing for deals, the options you’ll see will be for both nonstop flights and flights with stops.

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

    For one-way options, check prices for Alaska Airlines. According to our data, you can fly for as low as $201. Users have also found prices from $212 and $327 on American Airlines and Delta, respectively.

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

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

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

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

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

    Yes. Cheapflights offers flight deals from Kaua'i to Chicago 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 Kaua'i to Chicago?

    Currently, August is the cheapest month in which you can book a flight from Kaua'i to Chicago (average of $245). Flying from Kaua'i to Chicago in March is currently the most expensive (average of $321). 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

Traveling to a place near Chicago?

Book flights to Chicago if you plan to visit one of these locations
Merrillville
Lansing
Hammond
Benton Harbor
Porter
Chesterton

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Top airline flying from Kaua'i to Chicago

Discover the top airline that operate flights from Kaua'i to Chicago. 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 15, 2025.
AirlineCheapestAverageFlexibilityOn-time
United AirlinesCheapest$463Average$666FlexibilityNo cancel feeOn-time69%

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