$183+ 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 4/20. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — LIH
Mar 15 — Mar 221
1 adult, Economy
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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
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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 February 13, 2026.
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 February 13, 2026.
This Alaska Airlines deal was found by Cheapflights users on 2/10. 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.
Tue 3/37:00 am
ORD
- LIH
1 stop12h 50m
Alaska Airlines
Tue 3/311:19 pm
LIH
- ORD
1 stop10h 52m
Alaska Airlines
Deal found 2/10![Alaska Airlines logo]()
$417
This Alaska Airlines deal was found by Cheapflights users on 2/10. 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.
Tue 3/33:07 pm
ORD
- LIH
1 stop25h 40m
Alaska Airlines
Thu 3/511:19 pm
LIH
- ORD
1 stop13h 14m
Alaska Airlines
Deal found 2/10![Alaska Airlines logo]()
$418
This Alaska Airlines deal was found by Cheapflights users on 2/10. 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.
Tue 2/248:20 am
ORD
- LIH
1 stop32h 27m
Alaska Airlines
Tue 3/34:50 pm
LIH
- ORD
1 stop27h 09m
Alaska Airlines
Deal found 2/10![Alaska Airlines logo]()
$419
This American Airlines deal was found by Cheapflights users on 2/10. 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.
Sun 5/36:00 am
ORD
- LIH
1 stop11h 22m
American Airlines
Thu 5/72:12 pm
LIH
- ORD
1 stop10h 35m
American Airlines
Deal found 2/10![American Airlines logo]()
$422
This American Airlines deal was found by Cheapflights users on 2/10. 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.
Tue 2/247:00 am
ORD
- LIH
1 stop14h 14m
American Airlines
Tue 3/109:30 pm
LIH
- ORD
1 stop12h 23m
American Airlines
Deal found 2/10![American Airlines logo]()
$423
This Delta deal was found by Cheapflights users on 2/12. 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.
Tue 8/187:00 am
ORD
- LIH
1 stop15h 12m
Delta
Thu 8/279:26 pm
LIH
- ORD
1 stop11h 34m
Delta
Deal found 2/12![Delta logo]()
$424
This Alaska Airlines deal was found by Cheapflights users on 2/10. 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.
Tue 2/247:00 am
ORD
- LIH
2 stops16h 11m
Multiple Airlines
Tue 3/34:50 pm
LIH
- ORD
1 stop27h 09m
Multiple Airlines
Deal found 2/10![Multiple Airlines logo]()
$425
This Kiwi.com deal was found by Cheapflights users on 2/12. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 8/186:00 am
ORD
- LIH
1 stop11h 33m
Multiple Airlines
Thu 8/276:00 am
LIH
- ORD
2 stops12h 59m
Multiple Airlines
Deal found 2/12![Multiple Airlines logo]()
$427
This Alaska Airlines deal was found by Cheapflights users on 2/10. 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.
Tue 2/243:07 pm
ORD
- LIH
1 stop25h 40m
Multiple Airlines
Wed 3/47:45 pm
LIH
- ORD
2 stops15h 13m
Multiple Airlines
Deal found 2/10![Multiple Airlines logo]()
$428
This American Airlines deal was found by Cheapflights users on 2/9. 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 3/56:10 am
ORD
- LIH
2 stops15h 04m
American Airlines
Tue 3/109:30 pm
LIH
- ORD
1 stop12h 23m
American Airlines
Deal found 2/9![American Airlines logo]()
$429
This Delta deal was found by Cheapflights users on 2/12. 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 8/196:00 am
ORD
- LIH
2 stops16h 12m
Delta
Tue 9/19:45 pm
LIH
- ORD
1 stop14h 37m
Delta
Deal found 2/12![Delta logo]()
$430
This Delta deal was found by Cheapflights users on 2/12. 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.
Tue 2/249:34 am
MDW
- LIH
2 stops14h 15m
Delta
Wed 3/410:40 pm
LIH
- MDW
2 stops14h 57m
Delta
Deal found 2/12![Delta logo]()
$465
Best flights from Chicago to Kaua'iDiscover 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 February 13, 2026.
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 February 13, 2026.
This Alaska Airlines deal was found by Cheapflights users on 2/10. 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.
Tue 2/248:20 am
ORD
- LIH
1 stop32h 27m
Alaska Airlines
Tue 3/34:50 pm
LIH
- ORD
1 stop27h 09m
Alaska Airlines
Deal found 2/10![Alaska Airlines logo]()
$419
This American Airlines deal was found by Cheapflights users on 2/12. 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.
Wed 5/66:00 am
ORD
- LIH
1 stop11h 22m
American Airlines
Wed 5/132:12 pm
LIH
- ORD
1 stop10h 35m
American Airlines
Deal found 2/12![American Airlines logo]()
$422
This Delta deal was found by Cheapflights users on 2/12. 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 5/1112:47 pm
ORD
- LIH
1 stop11h 19m
Delta
Mon 5/189:40 pm
LIH
- ORD
1 stop14h 24m
Delta
Deal found 2/12![Delta logo]()
$424
This Alaska Airlines deal was found by Cheapflights users on 2/10. 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.
Tue 2/247:00 am
ORD
- LIH
2 stops16h 11m
Multiple Airlines
Tue 3/34:50 pm
LIH
- ORD
1 stop27h 09m
Multiple Airlines
Deal found 2/10![Multiple Airlines logo]()
$425
This Southwest deal was found by Cheapflights users on 2/10. 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.
Tue 3/35:05 am
MDW
- LIH
2 stops15h 20m
Southwest
Sat 3/77:15 am
LIH
- MDW
2 stops12h 55m
Southwest
Deal found 2/10![Southwest logo]()
$604
This Alaska Airlines deal was found by Cheapflights users on 2/10. 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.
Tue 2/243:07 pm
ORD
- LIH
1 stop25h 40m
Multiple Airlines
Wed 3/47:45 pm
LIH
- ORD
2 stops15h 13m
Multiple Airlines
Deal found 2/10![Multiple Airlines logo]()
$428
This Delta deal was found by Cheapflights users on 2/12. 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.
Tue 4/287:15 am
ORD
- LIH
1 stop15h 25m
Delta
Sun 5/39:25 pm
LIH
- ORD
2 stops15h 48m
Delta
Deal found 2/12![Delta logo]()
$430
This Delta deal was found by Cheapflights users on 2/11. 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 5/67:15 am
ORD
- LIH
1 stop15h 25m
Delta
Wed 5/138:31 pm
LIH
- ORD
2 stops17h 49m
Delta
Deal found 2/11![Delta logo]()
$430
This Alaska Airlines deal was found by Cheapflights users on 2/10. 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.
Tue 2/248:20 am
ORD
- LIH
2 stops18h 02m
Multiple Airlines
Tue 3/101:33 pm
LIH
- ORD
2 stops20h 25m
Multiple Airlines
Deal found 2/10![Multiple Airlines logo]()
$434
This Alaska Airlines deal was found by Cheapflights users on 2/9. 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 3/28:20 am
ORD
- LIH
2 stops27h 42m
Multiple Airlines
Wed 3/47:45 pm
LIH
- ORD
2 stops15h 13m
Multiple Airlines
Deal found 2/9![Multiple Airlines logo]()
$440
This Delta deal was found by Cheapflights users on 2/10. 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.
Tue 2/249:34 am
MDW
- LIH
2 stops14h 15m
Delta
Tue 3/1010:05 pm
LIH
- MDW
2 stops14h 49m
Delta
Deal found 2/10![Delta logo]()
$475
This Southwest deal was found by Cheapflights users on 2/12. 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.
Tue 2/178:10 am
MDW
- LIH
1 stop12h 15m
Southwest
Thu 2/2610:00 am
LIH
- MDW
2 stops15h 05m
Southwest
Deal found 2/12![Southwest logo]()
$611
This Delta deal was found by Cheapflights users on 2/12. 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.
Tue 2/249:34 am
MDW
- LIH
2 stops14h 15m
Delta
Tue 3/39:20 pm
LIH
- MDW
2 stops16h 17m
Delta
Deal found 2/12![Delta logo]()
$495
This Southwest deal was found by Cheapflights users on 2/10. 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.
Wed 4/297:55 am
MDW
- LIH
2 stops13h 15m
Southwest
Sun 5/37:10 pm
LIH
- MDW
2 stops13h 35m
Southwest
Deal found 2/10![Southwest logo]()
$612
This Delta deal was found by Cheapflights users on 2/11. 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.
Tue 2/249:34 am
MDW
- LIH
2 stops14h 15m
Delta
Wed 3/410:40 pm
LIH
- MDW
2 stops14h 57m
Delta
Deal found 2/11![Delta logo]()
$539
This Delta deal was found by Cheapflights users on 2/11. 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 2/189:34 am
MDW
- LIH
2 stops14h 15m
Delta
Tue 2/249:20 pm
LIH
- MDW
2 stops16h 17m
Delta
Deal found 2/11![Delta logo]()
$585
This Delta deal was found by Cheapflights users on 2/9. 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.
Thu 5/79:23 am
MDW
- LIH
2 stops13h 17m
Delta
Wed 5/138:31 pm
LIH
- MDW
2 stops16h 43m
Delta
Deal found 2/9![Delta logo]()
$605
Last-minute flights from Chicago to Kaua'iDiscover last-minute flight deals from Chicago to Kaua'i. Data last updated February 13, 2026 and is based on user searches.
Discover last-minute flight deals from Chicago to Kaua'i. Data last updated February 13, 2026 and is based on user searches.
This Alaska Airlines deal was found by Cheapflights users on 2/10. 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.
Tue 2/248:20 am
ORD
- LIH
1 stop32h 27m
Alaska Airlines
Tue 3/34:50 pm
LIH
- ORD
1 stop27h 09m
Alaska Airlines
Deal found 2/10![Alaska Airlines logo]()
$419
This American Airlines deal was found by Cheapflights users on 2/10. 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.
Tue 2/247:00 am
ORD
- LIH
1 stop14h 14m
American Airlines
Wed 3/410:30 pm
LIH
- ORD
1 stop12h 23m
American Airlines
Deal found 2/10![American Airlines logo]()
$423
This Alaska Airlines deal was found by Cheapflights users on 2/10. 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.
Tue 2/247:00 am
ORD
- LIH
2 stops15h 02m
Multiple Airlines
Tue 3/34:50 pm
LIH
- ORD
1 stop27h 09m
Multiple Airlines
Deal found 2/10![Multiple Airlines logo]()
$425
This Alaska Airlines deal was found by Cheapflights users on 2/10. 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.
Tue 2/243:07 pm
ORD
- LIH
1 stop25h 40m
Multiple Airlines
Wed 3/47:45 pm
LIH
- ORD
2 stops15h 13m
Multiple Airlines
Deal found 2/10![Multiple Airlines logo]()
$428
This Delta deal was found by Cheapflights users on 2/12. 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.
Tue 2/249:34 am
MDW
- LIH
2 stops14h 15m
Delta
Wed 3/410:40 pm
LIH
- MDW
2 stops14h 57m
Delta
Deal found 2/12![Delta logo]()
$465
This Delta deal was found by Cheapflights users on 2/10. 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.
Tue 2/249:34 am
MDW
- LIH
2 stops14h 15m
Delta
Tue 3/1010:05 pm
LIH
- MDW
2 stops14h 49m
Delta
Deal found 2/10![Delta logo]()
$475
This Expedia deal was found by Cheapflights users on 2/10. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 3/18:20 am
ORD
- LIH
1 stop33h 36m
Multiple Airlines
Fri 3/63:00 pm
LIH
- ORD
2 stops19h 11m
Multiple Airlines
Deal found 2/10![Multiple Airlines logo]()
$433
This Alaska Airlines deal was found by Cheapflights users on 2/9. 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 3/28:20 am
ORD
- LIH
2 stops27h 42m
Multiple Airlines
Wed 3/44:50 pm
LIH
- ORD
1 stop27h 09m
Multiple Airlines
Deal found 2/9![Multiple Airlines logo]()
$440
This Alaska Airlines deal was found by Cheapflights users on 2/10. 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.
Tue 3/37:00 am
ORD
- LIH
1 stop12h 50m
Alaska Airlines
Tue 3/311:19 pm
LIH
- ORD
1 stop10h 52m
Alaska Airlines
Deal found 2/10![Alaska Airlines logo]()
$417
This Alaska Airlines deal was found by Cheapflights users on 2/10. 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.
Tue 3/33:07 pm
ORD
- LIH
1 stop25h 40m
Alaska Airlines
Thu 3/511:19 pm
LIH
- ORD
1 stop13h 14m
Alaska Airlines
Deal found 2/10![Alaska Airlines logo]()
$418
This Alaska Airlines deal was found by Cheapflights users on 2/10. 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.
Tue 3/33:07 pm
ORD
- LIH
1 stop25h 40m
Multiple Airlines
Wed 3/49:00 pm
LIH
- ORD
2 stops15h 33m
Multiple Airlines
Deal found 2/10![Multiple Airlines logo]()
$424
This American Airlines deal was found by Cheapflights users on 2/9. 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 3/56:10 am
ORD
- LIH
2 stops15h 04m
American Airlines
Tue 3/109:30 pm
LIH
- ORD
1 stop12h 23m
American Airlines
Deal found 2/9![American Airlines logo]()
$429
One-way flights from Chicago to Kaua'iSearch for one-way flight options from Chicago to Kaua'i. Find affordable one-way fares based on user searches. Data last updated February 13, 2026.
Search for one-way flight options from Chicago to Kaua'i. Find affordable one-way fares based on user searches. Data last updated February 13, 2026.
This Kiwi.com deal was found by Cheapflights users on 2/11. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 4/207:43 am
ORD
- LIH
3 stops27h 34m
Multiple Airlines
Deal found 2/11![Multiple Airlines logo]()
$183
This Kiwi.com deal was found by Cheapflights users on 2/11. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 4/137:55 am
ORD
- LIH
3 stops35h 13m
Multiple Airlines
Deal found 2/11![Multiple Airlines logo]()
$209
This American Airlines deal was found by Cheapflights users on 2/11. 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.
Tue 4/216:00 am
ORD
- LIH
1 stop11h 22m
American Airlines
Deal found 2/11![American Airlines logo]()
$211
This American Airlines deal was found by Cheapflights users on 2/11. 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.
Sun 4/266:00 am
ORD
- LIH
1 stop11h 22m
American Airlines
Deal found 2/11![American Airlines logo]()
$216
This American Airlines deal was found by Cheapflights users on 2/12. 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.
Wed 2/259:25 am
ORD
- LIH
1 stop11h 49m
American Airlines
Deal found 2/12![American Airlines logo]()
$217
This Expedia deal was found by Cheapflights users on 2/11. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 4/216:00 am
ORD
- LIH
2 stops14h 46m
Multiple Airlines
Deal found 2/11![Multiple Airlines logo]()
$222
This Kiwi.com deal was found by Cheapflights users on 2/11. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 3/77:39 pm
ORD
- LIH
2 stops23h 35m
Multiple Airlines
Deal found 2/11![Multiple Airlines logo]()
$243
This Southwest deal was found by Cheapflights users on 2/11. 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.
Tue 4/216:10 am
MDW
- LIH
1 stop12h 00m
Southwest
Deal found 2/11![Southwest logo]()
$244
This Southwest deal was found by Cheapflights users on 2/12. 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.
Wed 2/258:25 am
MDW
- LIH
2 stops13h 50m
Southwest
Deal found 2/12![Southwest logo]()
$253
This Kiwi.com deal was found by Cheapflights users on 2/11. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 3/79:16 pm
MDW
- LIH
3 stops38h 46m
Multiple Airlines
Deal found 2/11![Multiple Airlines logo]()
$283
This Southwest deal was found by Cheapflights users on 2/11. 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 4/2010:05 am
MDW
- LIH
1 stop11h 05m
Southwest
Deal found 2/11![Southwest logo]()
$292
This Southwest deal was found by Cheapflights users on 2/9. 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.
Sun 5/35:10 am
MDW
- LIH
2 stops16h 00m
Southwest
Deal found 2/9![Southwest logo]()
$293
Find 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 February 13, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $417 (Alaska Airlines) |
One-way from | $183 (Kiwi.com) |
Popular in | December |
Cheapest in | February |
Average price | $468 |
Cheapflights Fare Finder
Customize your flight search to find flights from Chicago to Kaua'i 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 February 13, 2026.
Use the filters below to find and compare flights from Chicago to Kaua'i that are best for you.
Fly from
Chicago
Fly to
Kaua'i
Route
Depart
Return
Price
ChicagoLihue
ORD - LIH
ORDLIH
Chicago O'Hare Intl
Tue 2/24
8:20 am-12:47 pm
1 stop32h 27m
Lihue
Tue 3/3
4:50 pm-11:59 pm
1 stop27h 09m
$419
ChicagoLihue
ORD - LIH
ORDLIH
Chicago O'Hare Intl
Wed 5/6
6:00 am-12:22 pm
1 stop11h 22m
Lihue
Wed 5/13
2:12 pm-5:47 am
1 stop10h 35m
$422
ChicagoLihue
ORD - LIH
ORDLIH
Chicago O'Hare Intl
Mon 5/11
12:47 pm-7:06 pm
1 stop11h 19m
Lihue
Mon 5/18
9:40 pm-5:04 pm
1 stop14h 24m
$424
ChicagoLihue
ORD - LIH
ORDLIH
Chicago O'Hare Intl
Tue 2/24
7:00 am-7:11 pm
2 stops16h 11m
Lihue
Tue 3/3
4:50 pm-11:59 pm
1 stop27h 09m
$425
ChicagoLihue
ORD - LIH
ORDLIH
Chicago O'Hare Intl
Tue 2/24
3:07 pm-12:47 pm
1 stop25h 40m
Lihue
Wed 3/4
7:45 pm-2:58 pm
2 stops15h 13m
$428
ChicagoLihue
ORD - LIH
ORDLIH
Chicago O'Hare Intl
Tue 4/28
7:15 am-5:40 pm
1 stop15h 25m
Lihue
Sun 5/3
9:25 pm-6:13 pm
2 stops15h 48m
$430
ChicagoLihue
ORD - LIH
ORDLIH
Chicago O'Hare Intl
Wed 5/6
7:15 am-5:40 pm
1 stop15h 25m
Lihue
Wed 5/13
8:31 pm-7:20 pm
2 stops17h 49m
$430
ChicagoLihue
ORD - LIH
ORDLIH
Chicago O'Hare Intl
Tue 2/24
8:20 am-10:22 pm
2 stops18h 02m
Lihue
Tue 3/10
1:33 pm-2:58 pm
2 stops20h 25m
$434
ChicagoLihue
ORD - LIH
ORDLIH
Chicago O'Hare Intl
Mon 3/2
8:20 am-8:02 am
2 stops27h 42m
Lihue
Wed 3/4
7:45 pm-2:58 pm
2 stops15h 13m
$440
ChicagoLihue
MDW - LIH
MDWLIH
Chicago Midway
Tue 2/24
9:34 am-7:49 pm
2 stops14h 15m
Lihue
Tue 3/10
10:05 pm-5:54 pm
2 stops14h 49m
$475
Showing 1-10 of 36 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.
ORD-LIH
MDW-LIH
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
CHI-zzFUS
ORD-LIH
MDW-LIH
What is the cheapest month to book a flight from Chicago to Kaua'i?
Currently, September is the cheapest month in which you can book a flight from Chicago to Kaua'i (average of $231). Flying from Chicago to Kaua'i in July is currently the most expensive (average of $545). 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.
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 February 13, 2026.
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 compares in terms of entertainment options, comfort, food, crew/service, and boarding process.
Boarding
8.1
Entertainment
7.0
Comfort
7.8
Overall
8.0
Crew
8.5
Food
7.1
Reviews
1 / 20
10.0
Excellentrobert,Feb 2026
LAS - SAN
Boarding
8.1
Entertainment
7.0
Comfort
7.8
Overall
8.0
Crew
8.5
Food
7.1
Reviews
1 / 20
10.0
Excellentrobert,Feb 2026
LAS - SAN
Boarding
8.1
Entertainment
7.0
Comfort
7.8
Overall
8.0
Crew
8.5
Food
7.1
Reviews
1 / 20
10.0
Excellentrobert,Feb 2026
LAS - SAN
Boarding
8.1
Entertainment
7.0
Comfort
7.8
Overall
8.0
Crew
8.5
Food
7.1
Reviews
1 / 20
10.0
Excellentrobert,Feb 2026
LAS - SAN
Boarding
8.1
Entertainment
7.0
Comfort
7.8
Overall
8.0
Crew
8.5
Food
7.1
Reviews
1 / 20
10.0
Excellentrobert,Feb 2026
LAS - SAN
Boarding
8.1
Entertainment
7.0
Comfort
7.8
Overall
8.0
Crew
8.5
Food
7.1
Reviews
1 / 20
10.0
Excellentrobert,Feb 2026
LAS - SAN
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.
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Chicago and Kaua'i flights
Browse other Chicago and Kaua'i flight options. Last updated on February 13, 2026.
Popular flight searches
Check out other popular destinations found by fellow travelers in 2026
Top 5 airlines flying from Chicago to Kaua'i
Discover the top 5 airlines that operate flights from Chicago to Kaua'i. 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 February 13, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$293 | Average$551 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$405 | Average$686 | FlexibilityNo cancel fee | On-time75% | |
| Cheapest$423 | Average$614 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$443 | Average$725 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$468 | Average$911 | FlexibilityNo cancel fee | On-time63% |