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

One-way options have recently been found by users for as low as $212 on United Airlines. Other airlines that offer cheap prices include Delta from $257 and Alaska Airlines from $296 one-way.

What are the most popular airlines that fly from Chicago to Kaua'i?

Consider American Airlines, Alaska Airlines or Delta when booking your flight. These represent the most popular airlines when flying from Chicago to Kaua'i.

How far in advance should I book a flight from Chicago to Kaua'i?

Find a great deal and save up to 21% by booking at least 23 days prior to your desired departure date, rather than waiting until the week of travel. According to our data, there are a number of flights available from Chicago to Kaua'i within the next two weeks, with the cheapest ticket starting at $415.

What is the cheapest month to fly from Chicago to Kaua'i?

The best pricing can be found in the month of November. Prices to Kaua'i from Chicago average $676. You can even find prices in November for less than $676, as users have found deals to Kaua'i from as low as $364. The month of December appears to be one of the more expensive times to travel to Kaua'i from Chicago. Flying in the targeted month can save you up to 42%.

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

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

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

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

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

Yes. Cheapflights offers flight deals from Chicago to Kaua'i by cabin class. In addition to browsing deals, you can also filter by cabin class on the search results page after making a search.

$212+ Flights from Chicago to Kaua'i

Home Search by date Vacation packages Hotels Flight deals Car rental Travel tips & news

Find cheap flights from Chicago to Kaua'i with Cheapflights

1. Tell us where you want to go

Enter your travel information like dates, passengers, trip type (one-way or round trip), and preferred cabin class then click “Find deals”

2. Select your favorite providers

We find the providers serving your travel needs. Choose up to four travel providers to compare side-by-side for flights, hotels, or car rentals.

3. Compare prices and book

Review each provider’s pricing and select the best option for you! Book through your favorite provider’s website for a seamless experience.

Cheap flight deals from Chicago to Kaua'i

Most accurate provider	FlightHub 3 stars
Most trusted provider	eDreams 3 stars
Round-trip from	$543 (Southwest)
One-way from	$212 (United Airlines)
Popular in	December
Cheapest in	November
Average price	$648

Provider with most accurate pricing for Chicago (CHI)-Lihue flight deals.

Search Deals

Provider most trusted by Cheapflights users for Chicago (CHI)-Lihue flights.

Search Deals

From Chicago (CHI) to Kaua'i

Search Deals

One-way flight from Chicago (CHI) to Kaua'i

Search Deals

Highest demand for flights based on searches. 4% potential increase in price ($29 potential increase over avg. RT price).

Search Deals

Cheapest flight prices on average. 4% potential price decrease ($27 potential savings vs. average RT price).

Search Deals

Average for round-trip flights in May 2025

Search Deals

Find flight deals from Chicago to Kaua'i

Cheapest flights from Chicago to Kaua'i
Explore the most affordable flight options available from Chicago to Kaua'i. Find the lowest fares from popular airlines and budget airlines, with prices last updated on May 1, 2025.

Tue 8/196:10 amMDW - LIH

2 stops14h 50mSouthwest

Tue 8/268:40 pmLIH - MDW

1 stop11h 35mSouthwest

Deal found 4/30

$543

Tue 6/37:30 amORD - LIH

2 stops16h 30mDelta

Tue 6/108:35 pmLIH - ORD

2 stops16h 28mDelta

Deal found 5/1

$544

Fri 8/296:00 amORD - LIH

1 stop11h 12mAmerican Airlines

Sun 9/711:03 pmLIH - ORD

1 stop18h 30mAmerican Airlines

Deal found 4/30

$551

Fri 11/72:00 pmORD - LIH

1 stop12h 15mAlaska Airlines

Sun 11/96:00 amLIH - ORD

2 stops13h 10mAlaska Airlines

Deal found 5/1

$556

Wed 6/47:25 pmMDW - LIH

2 stops28h 35mDelta

Tue 6/108:35 pmLIH - MDW

2 stops17h 06mDelta

Deal found 4/30

$561

Sun 12/79:10 pmORD - LIH

2 stops19h 40mUnited Airlines

Sun 12/212:15 pmLIH - ORD

2 stops13h 11mUnited Airlines

Deal found 4/30

$636

Sat 8/26:15 amORD - LIH

2 stops16h 45mSouthwest

Sun 8/108:40 pmLIH - ORD

2 stops13h 40mSouthwest

Deal found 4/29

$814

Best flights from Chicago to Kaua'i
Discover carefully curated flight deals from Chicago to Kaua'i that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated May 1, 2025.

Tue 8/196:10 amMDW - LIH

2 stops14h 50mSouthwest

Tue 8/268:40 pmLIH - MDW

1 stop11h 35mSouthwest

Deal found 4/30

$543

Sat 6/76:59 pmORD - LIH

1 stop29h 11mDelta

Mon 6/169:40 pmLIH - ORD

1 stop14h 40mDelta

Deal found 4/30

$545

Fri 8/296:00 amORD - LIH

1 stop11h 12mAmerican Airlines

Sun 9/711:03 pmLIH - ORD

1 stop18h 30mAmerican Airlines

Deal found 4/30

$551

Fri 10/38:00 amORD - LIH

1 stop18h 30mAlaska Airlines

Sun 10/126:00 amLIH - ORD

2 stops12h 10mAlaska Airlines

Deal found 4/30

$557

Wed 7/97:20 amORD - LIH

2 stops18h 05mUnited Airlines

Wed 7/1612:30 pmLIH - ORD

2 stops12h 15mUnited Airlines

Deal found 4/30

$737

Sun 6/151:56 pmORD - LIH

2 stops26h 23mMultiple Airlines

Sun 6/2210:54 pmLIH - ORD

1 stop19h 02mMultiple Airlines

Deal found 5/1

$880

Wed 6/47:25 pmMDW - LIH

2 stops28h 35mDelta

Tue 6/108:35 pmLIH - MDW

2 stops17h 06mDelta

Deal found 4/30

$561

Sat 8/26:15 amORD - LIH

2 stops16h 45mSouthwest

Sun 8/108:40 pmLIH - ORD

2 stops13h 40mSouthwest

Deal found 4/29

$814

Last-minute flights from Chicago to Kaua'i
Discover last-minute flight deals from Chicago to Kaua'i. Data last updated May 1, 2025 and is based on user searches.

Mon 5/58:00 amMDW - LIH

2 stops15h 10mSouthwest

Mon 5/199:00 amLIH - MDW

1 stop15h 20mSouthwest

Deal found 5/1

$668

Tue 5/69:20 amMDW - LIH

2 stops14h 24mDelta

Wed 5/149:45 pmLIH - MDW

2 stops16h 00mDelta

Deal found 4/30

$679

Sat 5/107:30 amORD - LIH

2 stops15h 19mDelta

Fri 5/169:45 pmLIH - ORD

1 stop14h 44mDelta

Deal found 4/30

$548

Sat 5/107:13 pmORD - LIH

2 stops23h 25mAlaska Airlines

Fri 5/166:00 amLIH - ORD

2 stops12h 59mAlaska Airlines

Deal found 4/30

$634

Sat 5/103:55 pmORD - LIH

1 stop24h 37mUnited Airlines

Fri 5/161:20 pmLIH - ORD

1 stop10h 51mUnited Airlines

Deal found 4/30

$644

Thu 5/292:09 pmORD - LIH

1 stop25h 12mAlaska Airlines

Thu 6/510:21 amLIH - ORD

2 stops14h 19mAlaska Airlines

Deal found 4/29

$587

Thu 5/297:13 pmORD - LIH

1 stop22h 19mAmerican Airlines

Thu 6/59:25 pmLIH - ORD

1 stop20h 06mAmerican Airlines

Deal found 4/29

$609

One-way flights from Chicago to Kaua'i
Search for one-way flight options from Chicago to Kaua'i. Find affordable one-way fares based on user searches. Data last updated May 1, 2025.

Wed 5/286:00 amORD - LIH

1 stop10h 59mUnited Airlines

Deal found 4/29

$212

Wed 5/286:24 amORD - LIH

2 stops16h 25mDelta

Deal found 4/29

$257

Mon 5/266:00 amORD - LIH

2 stops14h 15mAlaska Airlines

Deal found 4/29

$296

Wed 5/289:16 amMDW - LIH

2 stops14h 44mDelta

Deal found 4/29

$377

Tue 7/227:00 amMDW - LIH

2 stops14h 00mSouthwest

Deal found 4/29

$397

Sat 6/1410:18 pmORD - LIH

1 stop20h 58mAmerican Airlines

Deal found 4/30

$428

Wed 7/233:09 pmORD - LIH

1 stop11h 45mHawaiian Airlines

Deal found 4/30

$1,021

Cheapflights Fare Finder

Use the filters below to find and compare flights from Chicago to Kaua'i that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

ChicagoLihue

MDW - LIH

MDWLIH

Chicago Midway

Tue 8/19

6:10 am-4:00 pm

2 stops14h 50m

Lihue

Tue 8/26

8:40 pm-1:15 pm

1 stop11h 35m

$543

ChicagoLihue

ORD - LIH

ORDLIH

Chicago O'Hare Intl

Tue 6/3

7:30 am-7:00 pm

2 stops16h 30m

Lihue

Tue 6/10

8:35 pm-6:03 pm

2 stops16h 28m

$544

ChicagoLihue

ORD - LIH

ORDLIH

Chicago O'Hare Intl

Fri 8/29

6:00 am-12:12 pm

1 stop11h 12m

Lihue

Sun 9/7

11:03 pm-10:33 pm

1 stop18h 30m

$551

ChicagoLihue

ORD - LIH

ORDLIH

Chicago O'Hare Intl

Fri 10/3

8:00 am-9:30 pm

1 stop18h 30m

Lihue

Sun 10/12

6:00 am-11:10 pm

2 stops12h 10m

$557

ChicagoLihue

MDW - LIH

MDWLIH

Chicago Midway

Wed 6/4

7:25 pm-7:00 pm

2 stops28h 35m

Lihue

Tue 6/10

8:35 pm-6:41 pm

2 stops17h 06m

$561

ChicagoLihue

ORD - LIH

ORDLIH

Chicago O'Hare Intl

Thu 7/31

6:00 am-11:58 am

1 stop10h 58m

Lihue

Sun 8/3

1:13 pm-5:45 am

1 stop11h 32m

$654

ChicagoLihue

ORD - LIH

ORDLIH

Chicago O'Hare Intl

Sat 8/2

6:15 am-6:00 pm

2 stops16h 45m

Lihue

Sun 8/10

8:40 pm-3:20 pm

2 stops13h 40m

$814

ChicagoLihue

ORD - LIH

ORDLIH

Chicago O'Hare Intl

Wed 5/28

6:00 am-11:59 am

1 stop10h 59m

$212

ChicagoLihue

ORD - LIH

ORDLIH

Chicago O'Hare Intl

Wed 5/28

6:24 am-5:49 pm

2 stops16h 25m

$257

ChicagoLihue

ORD - LIH

ORDLIH

Chicago O'Hare Intl

Mon 5/26

6:00 am-3:15 pm

2 stops14h 15m

$296

Flights are sorted by cheapest round-trip flights first.

Deals found on 4/29

Showing 1-10 of 14 results

Best time to book a flight from Chicago to Kaua'i

Have a flexible travel schedule? Discover the best time to fly to Kaua'i from Chicago 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 Chicago to Kaua'i

What is the cheapest month to book a flight from Chicago to Kaua'i?

Currently, January is the cheapest month in which you can book a flight from Chicago to Kaua'i (average of $440). Flying from Chicago to Kaua'i in June is currently the most expensive (average of $678). 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.

What is the cheapest time of day to fly from CHI to FUS?

When flying from Chicago to Kaua'i, the time of day you decide to fly out makes little to no difference towards the overall price you’ll pay on tickets.

Rainfall in Kaua'i by month

In terms of precipitation, rainfall in Kaua'i ranges from 2.2 - 6.7 inches per month. January is typically the wettest month, when rainfall can reach 6.7 in. June is typically the driest time to visit Kaua'i when rainfall is around 2.2 in.

Temperature in Kaua'i by month

If weather is an important factor for your trip to Kaua'i, 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 77.0 F. Travelers looking to avoid the cold should look outside of January, when temperatures are typically at their lowest (around 69.8 F).

Reviews of airlines servicing Kaua'i

Read reviews from past customers who have flown Alaska Airlines, Southwest and Delta from Chicago to Kaua'i. You can also see how each airline stacks up in terms of entertainment options, comfort, food, crew/service, and boarding process.

Alaska Airlines

8.0

Very good

9,972 reviews

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

9,972 reviews

Alaska Airlines

8.0

Very good

9,972 reviews

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

4,293 reviews

Alaska Airlines

8.0

Very good

9,972 reviews

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

7,934 reviews

Alaska Airlines

8.0

Very good

9,972 reviews

Reviews

1 / 20

10.0

Excellent

James,Apr 2025

LAX - SFO

Good flight except the uncontrollable cold air from the ceiling.

Hawaiian Airlines

7.9

Good

2,409 reviews

Alaska Airlines

8.0

Very good

9,972 reviews

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

8,696 reviews

Alaska Airlines

8.0

Very good

9,972 reviews

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

What are the cheapest airlines to fly from Chicago to Kaua'i one-way?
One-way options have recently been found by users for as low as $212 on United Airlines. Other airlines that offer cheap prices include Delta from $257 and Alaska Airlines from $296 one-way.
Can I find deals for flights from Chicago to Kaua'i that include hotel bookings?
Yes. In addition to deals on Chicago to Kaua'i flights, Cheapflights offers vacation packages that include both flights and hotel.
How can I find direct flights from Chicago to Kaua'i?
After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Chicago to Kaua'i.
Can I find deals for business class flights from Chicago to Kaua'i?
Yes. Cheapflights offers flight deals from Chicago to Kaua'i 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 Chicago to Kaua'i?
Currently, January is the cheapest month in which you can book a flight from Chicago to Kaua'i (average of $440). Flying from Chicago to Kaua'i in June is currently the most expensive (average of $678). 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

Browse thousands of different options on Cheapflights for your next trip

Alternative routes for Chicago to Kaua'i

O'Hare Intl to Honolulu flights

O'Hare Intl to Kahului flights

Midway to Honolulu flights

O'Hare Intl to Kailua-Kona flights

St. Louis to Honolulu flights

O'Hare Intl to Lihue flights

Midway to Kahului flights

St. Louis to Kahului flights

Midway to Kailua-Kona flights

Midway to Lihue flights

St. Louis to Lihue flights

O'Hare Intl to Hilo flights

St. Louis to Kailua-Kona flights

Bloomington to Kahului flights

Peoria to Honolulu flights

St. Louis to Hilo flights

Peoria to Kahului flights

Moline to Honolulu flights

Bloomington to Honolulu flights

Midway to Hilo flights

St. Louis to Kapalua flights

Evansville to Honolulu flights

Springfield to Honolulu flights

O'Hare Intl to Waimea (Big Island) flights

Moline to Kahului flights

O'Hare Intl to Kapalua flights

Moline to Lihue flights

Peoria to Lihue flights

Evansville to Lihue flights

St. Louis to Waimea (Big Island) flights

O'Hare Intl to Hana flights

Evansville to Kahului flights

Dubuque to Honolulu flights

St. Louis to Hana flights

Decatur to Honolulu flights

Springfield to Kahului flights

Springfield to Lihue flights

Moline to Hilo flights

Bloomington to Lihue flights

Champaign to Honolulu flights

Moline to Kailua-Kona flights

Champaign to Kailua-Kona flights

Top 5 airlines flying from Chicago to Kaua'i

Airline	Cheapest	Average	Flexibility	On-time
Delta	Cheapest$343	Average$548	FlexibilityNo cancel fee	On-timeN/A
American Airlines	Cheapest$379	Average$605	FlexibilityNo cancel fee	On-time71%
Alaska Airlines	Cheapest$421	Average$677	FlexibilityNo cancel fee	On-time75%
United Airlines	Cheapest$421	Average$770	FlexibilityNo cancel fee	On-time69%
Southwest	Cheapest$424	Average$873	FlexibilityNo cancel fee	On-time63%

100% Free

Cheapflights is completely free to use, so you can start saving the moment you arrive.

Book with Flexibility

Our users can plan ahead with confidence and find flights with no change fees

Travel Smart

Millions of people come to us for their flight needs every year. We help make travel planning easy by providing useful insights and data-driven graphs that can inform your decisions.

$212+ Cheap flights from Chicago (CHI) to Kaua'i

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 5/28. Fares are subject to change and may not be available on all flights or dates of travel.

Find cheap flights from Chicago to Kaua'i with Cheapflights

1. Tell us where you want to go

2. Select your favorite providers

3. Compare prices and book

Cheap flight deals from Chicago to Kaua'i

Keep the following information in mind while searching for Chicago to Kaua'i flight deals. Data was last updated May 1, 2025.

Most accurate provider

Most trusted provider

Round-trip from

One-way from

Popular in

Cheapest in

Average price

Find flight deals from Chicago to Kaua'i

Cheapest flights from Chicago to Kaua'iExplore the most affordable flight options available from Chicago to Kaua'i. Find the lowest fares from popular airlines and budget airlines, with prices last updated on May 1, 2025.

Explore the most affordable flight options available from Chicago to Kaua'i. Find the lowest fares from popular airlines and budget airlines, with prices last updated on May 1, 2025.

Cheapflights Fare Finder

Use the filters below to find and compare flights from Chicago to Kaua'i that are best for you.

Best time to book a flight from Chicago to Kaua'i

Have a flexible travel schedule? Discover the best time to fly to Kaua'i from Chicago with our price prediction graph.

Cheapflights Insights

Everything you need to know about your flight from Chicago to Kaua'i

What is the cheapest month to book a flight from Chicago to Kaua'i?

What is the cheapest time of day to fly from CHI to FUS?

Find hourly flight availability from Chicago to Kaua'i. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated May 1, 2025.

Rainfall in Kaua'i by month

Plan your trip to Kaua'i by taking into account the average rainfall totals by month.

Temperature in Kaua'i by month

Plan your trip to Kaua'i by taking into account the average temperature totals by month.

Reviews of airlines servicing Kaua'i

Get insights into the airlines that provide service to Kaua'i. 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 Kaua'i. Reviews last updated May 1, 2025.

Read reviews from past customers who have flown Alaska Airlines, Southwest and Delta from Chicago to Kaua'i. You can also see how each airline stacks up in terms of entertainment options, comfort, food, crew/service, and boarding process.

Related info for your journey

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

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

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

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

What is the cheapest month to book a flight from Chicago to Kaua'i?

Browse thousands of different options on Cheapflights for your next trip

Toggle through the tabs below to find thousands of options on Cheapflights for your next trip.

Alternative routes for Chicago to Kaua'i

See prices for flight routes from nearby airports that may be better suited for you.

Top 5 airlines flying from Chicago to Kaua'i

100% Free

Book with Flexibility

Travel Smart

Cheapest flights from Chicago to Kaua'i
Explore the most affordable flight options available from Chicago to Kaua'i. Find the lowest fares from popular airlines and budget airlines, with prices last updated on May 1, 2025.