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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 2/7. Fares are subject to change and may not be available on all flights or dates of travel.
LIH — CHI
Jan 25 — Feb 11
Sun 1/25
Sun 2/1
1 adult, Economy
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Cheap flight deals from Kaua'i to Chicago

Best flights from Kaua'i to Chicago
Discover carefully curated flight deals from Kaua'i to Chicago that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated December 26, 2025.

This Alaska Airlines deal was found by Cheapflights users on 12/23. 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 1/2910:20 pmLIH - ORD
1 stop21h 30mAlaska Airlines
Mon 2/23:44 pmORD - LIH
1 stop25h 19mAlaska Airlines
Deal found 12/23$424
This Alaska Airlines deal was found by Cheapflights users on 12/24. 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 Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 1/296:00 amLIH - ORD
2 stops13h 50mMultiple Airlines
Mon 2/23:44 pmORD - LIH
1 stop25h 19mMultiple Airlines
Deal found 12/24$433
This American Airlines deal was found by Cheapflights users on 12/25. 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 6/110:35 pmLIH - ORD
1 stop10h 40mAmerican Airlines
Mon 6/156:45 pmORD - LIH
1 stop22h 19mAmerican Airlines
Deal found 12/25$581
This Delta deal was found by Cheapflights users on 12/24. 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.
Fri 2/610:39 pmLIH - MDW
2 stops19h 43mDelta
Mon 2/99:33 amMDW - LIH
2 stops14h 21mDelta
Deal found 12/24$608
This Alaska Airlines deal was found by Cheapflights users on 12/24. 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 Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 2/67:49 pmLIH - ORD
2 stops14h 40mMultiple Airlines
Mon 2/93:44 pmORD - LIH
1 stop25h 19mMultiple Airlines
Deal found 12/24$438
This Delta deal was found by Cheapflights users on 12/24. 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.
Fri 1/911:38 amLIH - MDW
2 stops18h 54mDelta
Tue 1/139:32 amMDW - LIH
2 stops14h 23mDelta
Deal found 12/24$816
This Delta deal was found by Cheapflights users on 12/24. 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.
Fri 5/229:26 pmLIH - MDW
2 stops15h 39mDelta
Sun 5/319:30 amMDW - LIH
2 stops14h 50mDelta
Deal found 12/24$1,464

Find 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 December 26, 2025.

Most accurate provider

eDreams
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$423
(American Airlines)

One-way from

$212
(United Airlines)
Provider with most accurate pricing for Lihue-Chicago (CHI) flight deals.
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Provider most trusted by Cheapflights users for Lihue-Chicago (CHI) flights.
Search Deals
From Kaua'i to Chicago (CHI)
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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 December 26, 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 1/29

10:20 pm-11:50 pm

1 stop21h 30m

Chicago O'Hare Intl

Mon 2/2

3:44 pm-1:03 pm

1 stop25h 19m

$424

LihueChicago

LIH - ORD

LIHORD

Lihue

Thu 1/29

6:00 am-11:50 pm

2 stops13h 50m

Chicago O'Hare Intl

Mon 2/2

3:44 pm-1:03 pm

1 stop25h 19m

$433

LihueChicago

LIH - ORD

LIHORD

Lihue

Fri 2/6

7:49 pm-2:29 pm

2 stops14h 40m

Chicago O'Hare Intl

Mon 2/9

3:44 pm-1:03 pm

1 stop25h 19m

$438

LihueChicago

LIH - ORD

LIHORD

Lihue

Mon 6/1

10:35 pm-2:15 pm

1 stop10h 40m

Chicago O'Hare Intl

Mon 6/15

6:45 pm-12:04 pm

1 stop22h 19m

$581

LihueChicago

LIH - MDW

LIHMDW

Lihue

Fri 2/6

10:39 pm-10:22 pm

2 stops19h 43m

Chicago Midway

Mon 2/9

9:33 am-7:54 pm

2 stops14h 21m

$608

LihueChicago

LIH - MDW

LIHMDW

Lihue

Fri 1/9

11:38 am-10:32 am

2 stops18h 54m

Chicago Midway

Tue 1/13

9:32 am-7:55 pm

2 stops14h 23m

$816

LihueChicago

LIH - MDW

LIHMDW

Lihue

Fri 5/22

9:26 pm-6:05 pm

2 stops15h 39m

Chicago Midway

Sun 5/31

9:30 am-7:20 pm

2 stops14h 50m

$1,464

LihueChicago

LIH - ORD

LIHORD

Lihue

Sat 2/7

1:55 pm-6:30 am

1 stop12h 35m

$212

LihueChicago

LIH - ORD

LIHORD

Lihue

Thu 3/19

9:40 pm-9:34 pm

2 stops18h 54m

$217

LihueChicago

LIH - ORD

LIHORD

Lihue

Fri 5/1

1:36 pm-2:41 pm

1 stop20h 05m

$217

Flights are sorted by cheapest round-trip flights first.

Deals found on 12/25

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 December 26, 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
9,115 reviews

Boarding

7.7

Comfort

7.3

Entertainment

7.1

Crew

8.1

Overall

7.4

Food

6.6

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
9,115 reviews
United Airlines
7.4
Good
9,115 reviews

Boarding

7.7

Comfort

7.3

Entertainment

7.1

Crew

8.1

Overall

7.4

Food

6.6

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.
American Airlines
7.2
Good
11,061 reviews
United Airlines
7.4
Good
9,115 reviews

Boarding

7.7

Comfort

7.3

Entertainment

7.1

Crew

8.1

Overall

7.4

Food

6.6

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 $608, Alaska Airlines can have you in Chicago from Kaua'i in 19h 43m. The distance from Kaua'i to Chicago is about 4289 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 $211. Users have also found prices from $211 and $231 on Delta and United Airlines, 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?

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Lansing
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Hammond
Porter
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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 December 26, 2025.
AirlineCheapestAverageFlexibilityOn-time
United AirlinesCheapest$463Average$666FlexibilityNo cancel feeOn-time69%

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