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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 9/17. Fares are subject to change and may not be available on all flights or dates of travel.
LIH — CHI
Jun 21 — Jun 281
Sat 6/21
Sat 6/28
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 June 16, 2025.

Round-trip from

$699
(United Airlines)

One-way from

$212
(American Airlines)
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 June 16, 2025.

This United Airlines deal was found by Cheapflights users on 6/14. 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.
Mon 6/3011:10 pmLIH - ORD
1 stop10h 42mUnited Airlines
Fri 7/47:10 amORD - LIH
1 stop13h 25mUnited Airlines
Deal found 6/14$699
This Delta deal was found by Cheapflights users on 6/14. 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 6/309:40 pmLIH - MDW
2 stops15h 00mDelta
Fri 7/46:00 amMDW - LIH
2 stops18h 27mDelta
Deal found 6/14$996
This Delta deal was found by Cheapflights users on 6/14. 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.
Sat 7/269:40 pmLIH - ORD
1 stop14h 40mDelta
Sun 8/36:00 amORD - LIH
2 stops18h 27mDelta
Deal found 6/14$1,001
This Alaska Airlines deal was found by Cheapflights users on 6/14. 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 Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 7/269:00 pmLIH - ORD
2 stops17h 42mAlaska Airlines
Sun 8/37:00 amORD - LIH
2 stops19h 54mAlaska Airlines
Deal found 6/14$1,159

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 June 16, 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

Mon 6/30

11:10 pm-2:52 pm

1 stop10h 42m

Chicago O'Hare Intl

Fri 7/4

7:10 am-3:35 pm

1 stop13h 25m

$699

LihueChicago

LIH - MDW

LIHMDW

Lihue

Mon 6/30

9:40 pm-5:40 pm

2 stops15h 00m

Chicago Midway

Fri 7/4

6:00 am-7:27 pm

2 stops18h 27m

$996

LihueChicago

LIH - ORD

LIHORD

Lihue

Sat 7/26

9:40 pm-5:20 pm

1 stop14h 40m

Chicago O'Hare Intl

Sun 8/3

6:00 am-7:27 pm

2 stops18h 27m

$1,001

LihueChicago

LIH - ORD

LIHORD

Lihue

Sat 7/26

9:00 pm-7:42 pm

2 stops17h 42m

Chicago O'Hare Intl

Sun 8/3

7:00 am-9:54 pm

2 stops19h 54m

$1,159

LihueChicago

LIH - ORD

LIHORD

Lihue

Wed 9/17

1:44 pm-6:01 am

1 stop11h 17m

$212

LihueChicago

LIH - ORD

LIHORD

Lihue

Tue 10/14

6:54 pm-2:50 pm

2 stops14h 56m

$217

LihueChicago

LIH - ORD

LIHORD

Lihue

Mon 8/4

9:40 pm-5:20 pm

1 stop14h 40m

$232

LihueChicago

LIH - ORD

LIHORD

Lihue

Thu 7/3

10:15 pm-2:42 pm

1 stop11h 27m

$282

LihueChicago

LIH - MDW

LIHMDW

Lihue

Thu 7/3

9:40 pm-5:40 pm

2 stops15h 00m

$322

LihueChicago

LIH - MDW

LIHMDW

Lihue

Fri 7/4

8:40 pm-6:05 pm

1 stop16h 25m

$382

Flights are sorted by cheapest round-trip flights first.

Deals found on 6/14

Showing 1-10 of 11 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

Rainfall in Chicago by month

Plan your trip to Chicago by taking into account the average rainfall totals by month.

In terms of precipitation, rainfall in Chicago ranges from 1.7 - 4.9 inches per month. August is typically the wettest month, when rainfall can reach 4.9 in. January is typically the driest time to visit Chicago when rainfall is around 1.7 in.

Temperature in Chicago by month

Plan your trip to Chicago by taking into account the average temperature totals by month.

If weather is an important factor for your trip to Chicago, use this chart to help with planning. For those seeking warmer temperatures, July is the ideal time of year to visit, when temperatures reach an average of 73.4 F. Travelers looking to avoid the cold should look outside of January, when temperatures are typically at their lowest (around 23.0 F).

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 June 16, 2025.
Alaska Airlines
8.0
Very good
10,000 reviews

Crew

8.5

Comfort

7.8

Boarding

8.1

Entertainment

7.1

Overall

8.0

Food

7.1

Reviews

1 / 20
10.0
Excellent

James,Apr 2025

LAX - SFO

Good flight except the uncontrollable cold air from the ceiling.
Alaska Airlines
8.0
Very good
10,000 reviews
Alaska Airlines
8.0
Very good
10,000 reviews

Crew

8.5

Comfort

7.8

Boarding

8.1

Entertainment

7.1

Overall

8.0

Food

7.1

Reviews

1 / 20
10.0
Excellent

James,Apr 2025

LAX - SFO

Good flight except the uncontrollable cold air from the ceiling.
Southwest
8.0
Very good
4,278 reviews
Alaska Airlines
8.0
Very good
10,000 reviews

Crew

8.5

Comfort

7.8

Boarding

8.1

Entertainment

7.1

Overall

8.0

Food

7.1

Reviews

1 / 20
10.0
Excellent

James,Apr 2025

LAX - SFO

Good flight except the uncontrollable cold air from the ceiling.
Delta
8.0
Very good
7,963 reviews
Alaska Airlines
8.0
Very good
10,000 reviews

Crew

8.5

Comfort

7.8

Boarding

8.1

Entertainment

7.1

Overall

8.0

Food

7.1

Reviews

1 / 20
10.0
Excellent

James,Apr 2025

LAX - SFO

Good flight except the uncontrollable cold air from the ceiling.
United Airlines
7.4
Good
8,801 reviews
Alaska Airlines
8.0
Very good
10,000 reviews

Crew

8.5

Comfort

7.8

Boarding

8.1

Entertainment

7.1

Overall

8.0

Food

7.1

Reviews

1 / 20
10.0
Excellent

James,Apr 2025

LAX - SFO

Good flight except the uncontrollable cold air from the ceiling.
American Airlines
7.2
Good
10,000 reviews
Alaska Airlines
8.0
Very good
10,000 reviews

Crew

8.5

Comfort

7.8

Boarding

8.1

Entertainment

7.1

Overall

8.0

Food

7.1

Reviews

1 / 20
10.0
Excellent

James,Apr 2025

LAX - SFO

Good flight except the uncontrollable cold air from the ceiling.

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.

  • 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 $217 and $232 on Alaska 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 Kaua'i?

Book flights to Kaua'i if you plan to visit one of these locations
Merrillville
Lansing
Benton Harbor
Porter
Hammond
Valparaiso
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 June 16, 2025.
AirlineCheapestAverageFlexibilityOn-time
United AirlinesCheapest$463Average$724FlexibilityNo cancel feeOn-time69%

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