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$227+ 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 5/2. Fares are subject to change and may not be available on all flights or dates of travel.
LIH — CHI
Apr 9 — Apr 161
Wed 4/9
Wed 4/16
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 April 4, 2025.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$434
(Alaska Airlines)

One-way from

$227
(Alaska 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.
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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 April 4, 2025.

This Alaska Airlines deal was found by Cheapflights users on 4/4. 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.
Thu 5/17:42 pmLIH - ORD
2 stops17h 19mAlaska Airlines
Mon 5/56:58 pmORD - LIH
2 stops23h 40mAlaska Airlines
Deal found 4/4$434
This United Airlines deal was found by Cheapflights users on 4/3. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 4/301:12 pmLIH - ORD
1 stop11h 56mUnited Airlines
Mon 5/57:10 amORD - LIH
1 stop13h 36mUnited Airlines
Deal found 4/3$441
This Delta deal was found by Cheapflights users on 4/4. 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.
Mon 8/259:45 pmLIH - ORD
1 stop10h 39mDelta
Fri 8/297:15 amORD - LIH
2 stops17h 01mDelta
Deal found 4/4$449
This American Airlines deal was found by Cheapflights users on 4/4. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 5/12:12 pmLIH - ORD
1 stop10h 54mAmerican Airlines
Mon 5/57:13 pmORD - LIH
1 stop22h 19mAmerican Airlines
Deal found 4/4$481
This Southwest deal was found by Cheapflights users on 4/4. 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 8/258:40 pmLIH - MDW
1 stop11h 35mSouthwest
Fri 8/297:55 amMDW - LIH
2 stops15h 15mSouthwest
Deal found 4/4$733
This Delta deal was found by Cheapflights users on 4/3. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 4/1910:00 pmLIH - MDW
2 stops14h 19mDelta
Wed 4/239:20 amMDW - LIH
2 stops14h 24mDelta
Deal found 4/3$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 April 4, 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 5/1

7:42 pm-6:01 pm

2 stops17h 19m

Chicago O'Hare Intl

Mon 5/5

6:58 pm-1:38 pm

2 stops23h 40m

$434

LihueChicago

LIH - ORD

LIHORD

Lihue

Wed 4/30

1:12 pm-6:08 am

1 stop11h 56m

Chicago O'Hare Intl

Mon 5/5

7:10 am-3:46 pm

1 stop13h 36m

$441

LihueChicago

LIH - ORD

LIHORD

Lihue

Mon 8/25

9:45 pm-1:24 pm

1 stop10h 39m

Chicago O'Hare Intl

Fri 8/29

7:15 am-7:16 pm

2 stops17h 01m

$449

LihueChicago

LIH - ORD

LIHORD

Lihue

Thu 5/1

2:12 pm-6:06 am

1 stop10h 54m

Chicago O'Hare Intl

Mon 5/5

7:13 pm-12:32 pm

1 stop22h 19m

$481

LihueChicago

LIH - MDW

LIHMDW

Lihue

Mon 8/25

8:40 pm-1:15 pm

1 stop11h 35m

Chicago Midway

Fri 8/29

7:55 am-6:10 pm

2 stops15h 15m

$733

LihueChicago

LIH - MDW

LIHMDW

Lihue

Sat 4/19

10:00 pm-5:19 pm

2 stops14h 19m

Chicago Midway

Wed 4/23

9:20 am-6:44 pm

2 stops14h 24m

$1,014

LihueChicago

LIH - ORD

LIHORD

Lihue

Fri 5/2

4:50 pm-2:48 pm

2 stops16h 58m

$227

LihueChicago

LIH - ORD

LIHORD

Lihue

Fri 5/2

10:00 pm-4:11 pm

2 stops13h 11m

$237

LihueChicago

LIH - ORD

LIHORD

Lihue

Fri 5/2

12:48 pm-6:08 am

1 stop12h 20m

$282

LihueChicago

LIH - ORD

LIHORD

Lihue

Sat 8/2

9:46 pm-10:33 pm

1 stop19h 47m

$300

Flights are sorted by cheapest round-trip flights first.

Deals found on 4/4

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 April 4, 2025.
To help decide which airline to fly from Kaua'i to Chicago, see what other customers have to say about Alaska Airlines, Southwest and Delta. Users have also rated airlines in terms of entertainment options, comfort, food, crew/service, and boarding process.
Alaska Airlines
8.0
Very good
9,837 reviews

Crew

8.5

Food

7.1

Entertainment

7.1

Overall

8.0

Boarding

8.2

Comfort

7.9

Reviews

1 / 20
10.0
Excellent

Cheri,Jan 2025

FAT - SEA

Very friendly. I really liked that they had water for us in cartons not plastic. Impressed with Alaska Airlines, First time I had flown them
Alaska Airlines
8.0
Very good
9,837 reviews
Alaska Airlines
8.0
Very good
9,837 reviews

Crew

8.5

Food

7.1

Entertainment

7.1

Overall

8.0

Boarding

8.2

Comfort

7.9

Reviews

1 / 20
10.0
Excellent

Cheri,Jan 2025

FAT - SEA

Very friendly. I really liked that they had water for us in cartons not plastic. Impressed with Alaska Airlines, First time I had flown them
Southwest
8.0
Very good
4,276 reviews
Alaska Airlines
8.0
Very good
9,837 reviews

Crew

8.5

Food

7.1

Entertainment

7.1

Overall

8.0

Boarding

8.2

Comfort

7.9

Reviews

1 / 20
10.0
Excellent

Cheri,Jan 2025

FAT - SEA

Very friendly. I really liked that they had water for us in cartons not plastic. Impressed with Alaska Airlines, First time I had flown them
Delta
8.0
Very good
7,899 reviews
Alaska Airlines
8.0
Very good
9,837 reviews

Crew

8.5

Food

7.1

Entertainment

7.1

Overall

8.0

Boarding

8.2

Comfort

7.9

Reviews

1 / 20
10.0
Excellent

Cheri,Jan 2025

FAT - SEA

Very friendly. I really liked that they had water for us in cartons not plastic. Impressed with Alaska Airlines, First time I had flown them
United Airlines
7.4
Good
8,618 reviews
Alaska Airlines
8.0
Very good
9,837 reviews

Crew

8.5

Food

7.1

Entertainment

7.1

Overall

8.0

Boarding

8.2

Comfort

7.9

Reviews

1 / 20
10.0
Excellent

Cheri,Jan 2025

FAT - SEA

Very friendly. I really liked that they had water for us in cartons not plastic. Impressed with Alaska Airlines, First time I had flown them
American Airlines
7.2
Good
10,000 reviews
Alaska Airlines
8.0
Very good
9,837 reviews

Crew

8.5

Food

7.1

Entertainment

7.1

Overall

8.0

Boarding

8.2

Comfort

7.9

Reviews

1 / 20
10.0
Excellent

Cheri,Jan 2025

FAT - SEA

Very friendly. I really liked that they had water for us in cartons not plastic. Impressed with Alaska Airlines, First time I had flown them

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 Alaska Airlines. According to our data, you can fly for as low as $227. Users have also found prices from $237 and $282 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.

  • 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
New Buffalo
Hammond
Benton Harbor
Porter
Lansing
Valparaiso
Chesterton

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Top 2 airlines flying from Kaua'i to Chicago

Discover the top 2 airlines 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 April 4, 2025.
AirlineCheapestAverageFlexibilityOn-time
American AirlinesCheapest$379Average$461FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$463Average$666FlexibilityNo cancel feeOn-time69%

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