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$212+ 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 11/23. Fares are subject to change and may not be available on all flights or dates of travel.
LIH — CHI
Dec 3 — Dec 101
Wed 12/3
Wed 12/10
1 adult, Economy
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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 November 3, 2025.

This American Airlines deal was found by Cheapflights users on 11/2. 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 12/193:55 pmLIH - ORD
1 stop11h 04mAmerican Airlines
Fri 1/96:00 amORD - LIH
1 stop14h 37mAmerican Airlines
Deal found 11/2$453
This Delta deal was found by Cheapflights users on 11/1. 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 11/59:30 pmLIH - ORD
2 stops17h 11mDelta
Sun 11/167:47 amORD - LIH
1 stop16h 17mDelta
Deal found 11/1$458
This United Airlines deal was found by Cheapflights users on 11/1. 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.
Wed 11/52:31 pmLIH - ORD
1 stop10h 29mUnited Airlines
Sun 11/167:10 amORD - LIH
1 stop13h 48mUnited Airlines
Deal found 11/1$460
This Alaska Airlines deal was found by Cheapflights users on 11/2. 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.
Fri 12/193:25 pmLIH - ORD
1 stop24h 37mAlaska Airlines
Fri 1/99:00 amORD - LIH
2 stops25h 57mAlaska Airlines
Deal found 11/2$470
This American Airlines deal was found by Cheapflights users on 11/1. 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 11/310:39 pmLIH - ORD
1 stop11h 34mAmerican Airlines
Thu 11/137:00 amORD - LIH
1 stop12h 59mAmerican Airlines
Deal found 11/1$483
This KAYAK deal was found by Cheapflights users on 11/1. 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 KAYAK is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/39:00 pmLIH - ORD
2 stops12h 54mAlaska Airlines
Thu 11/1310:00 amORD - LIH
2 stops16h 15mAlaska Airlines
Deal found 11/1$484
This Delta deal was found by Cheapflights users on 11/1. 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 11/39:30 pmLIH - ORD
2 stops17h 11mDelta
Thu 11/137:47 amORD - LIH
1 stop16h 17mDelta
Deal found 11/1$488
This Delta deal was found by Cheapflights users on 11/2. 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 12/1910:55 pmLIH - ORD
2 stops18h 41mDelta
Fri 1/97:20 amORD - LIH
2 stops15h 01mDelta
Deal found 11/2$524
This American Airlines deal was found by Cheapflights users on 11/2. 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 11/1710:39 pmLIH - ORD
1 stop13h 03mAmerican Airlines
Mon 11/246:00 amORD - LIH
1 stop11h 18mAmerican Airlines
Deal found 11/2$582
This Alaska Airlines deal was found by Cheapflights users on 11/1. 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 11/1712:31 pmLIH - ORD
2 stops13h 51mAlaska Airlines
Mon 11/246:02 pmORD - LIH
1 stop32h 30mAlaska Airlines
Deal found 11/1$607
This Delta deal was found by Cheapflights users on 11/1. 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 11/292:01 pmLIH - MDW
2 stops14h 53mDelta
Sat 12/66:00 amMDW - LIH
2 stops15h 27mDelta
Deal found 11/1$2,129

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 November 3, 2025.

Most accurate provider

eDreams
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$453
(American Airlines)

One-way from

$212
(American Airlines)
Provider with most accurate pricing for Lihue-Chicago (CHI) flight deals.
Search Deals
Provider most trusted by Cheapflights users for Lihue-Chicago (CHI) flights.
Search Deals
From Kaua'i to Chicago (CHI)
Search Deals
One-way flight from Kaua'i to Chicago (CHI)
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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 November 3, 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

Fri 12/19

3:55 pm-6:59 am

1 stop11h 04m

Chicago O'Hare Intl

Fri 1/9

6:00 am-4:37 pm

1 stop14h 37m

$453

LihueChicago

LIH - ORD

LIHORD

Lihue

Fri 12/19

3:25 pm-8:02 pm

1 stop24h 37m

Chicago O'Hare Intl

Fri 1/9

9:00 am-6:57 am

2 stops25h 57m

$470

LihueChicago

LIH - ORD

LIHORD

Lihue

Fri 12/19

10:55 pm-9:36 pm

2 stops18h 41m

Chicago O'Hare Intl

Fri 1/9

7:20 am-6:21 pm

2 stops15h 01m

$524

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

$564

LihueChicago

LIH - ORD

LIHORD

Lihue

Mon 11/17

12:31 pm-6:22 am

2 stops13h 51m

Chicago O'Hare Intl

Mon 11/24

6:02 pm-10:32 pm

1 stop32h 30m

$607

LihueChicago

LIH - ORD

LIHORD

Lihue

Tue 3/10

12:10 pm-5:04 am

1 stop11h 54m

Chicago O'Hare Intl

Wed 3/11

2:00 pm-9:15 pm

1 stop12h 15m

$613

LihueChicago

LIH - MDW

LIHMDW

Lihue

Tue 3/10

2:12 pm-8:54 am

2 stops13h 42m

Chicago Midway

Wed 3/11

2:00 pm-8:25 pm

2 stops35h 25m

$946

LihueChicago

LIH - MDW

LIHMDW

Lihue

Sat 11/29

2:01 pm-8:54 am

2 stops14h 53m

Chicago Midway

Sat 12/6

6:00 am-5:27 pm

2 stops15h 27m

$2,129

LihueChicago

LIH - ORD

LIHORD

Lihue

Sun 11/23

2:49 pm-6:43 am

1 stop11h 54m

$212

LihueChicago

LIH - ORD

LIHORD

Lihue

Sat 2/7

1:55 pm-6:30 am

1 stop12h 35m

$216

Flights are sorted by cheapest round-trip flights first.

Deals found on 11/1

Showing 1-10 of 24 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 November 3, 2025.
Read reviews from past customers who have flown United 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
8,997 reviews

Comfort

7.3

Overall

7.4

Entertainment

7.1

Food

6.6

Boarding

7.7

Crew

8.1

Reviews

1 / 20
8.0
Excellent

Anonymous,Oct 2025

YUL - ORD

Crew and customer service are 5 stars. I had a lot of luggage for a very long trip and they were nothing but helpful and found solutions to every problem. It was my first time flying with United, and they really are the friendly skies. Leg room however, on 2/3 flights was terrible. Same for entertainment: There was only a seat-mounted screen on 1/3 flights. It would have been nice to have on the longest leg of the journey.
United Airlines
7.4
Good
8,997 reviews
United Airlines
7.4
Good
8,997 reviews

Comfort

7.3

Overall

7.4

Entertainment

7.1

Food

6.6

Boarding

7.7

Crew

8.1

Reviews

1 / 20
8.0
Excellent

Anonymous,Oct 2025

YUL - ORD

Crew and customer service are 5 stars. I had a lot of luggage for a very long trip and they were nothing but helpful and found solutions to every problem. It was my first time flying with United, and they really are the friendly skies. Leg room however, on 2/3 flights was terrible. Same for entertainment: There was only a seat-mounted screen on 1/3 flights. It would have been nice to have on the longest leg of the journey.

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 $453, American Airlines can have you in Chicago from Kaua'i in 11h 04m. 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 American Airlines. According to our data, you can fly for as low as $212. Users have also found prices from $216 and $217 on United 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.

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
Porter
Benton Harbor

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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 November 3, 2025.
AirlineCheapestAverageFlexibilityOn-time
United AirlinesCheapest$463Average$666FlexibilityNo cancel feeOn-time69%

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