$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 10/16. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — LIH
Aug 11 — Aug 181
Round-trip
1 adult, Economy
We work with more than 300 partners to bring you better travel deals
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
Cheapest
Best
Last-minute
One-way
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 July 12, 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 July 12, 2026.
This Delta deal was found by Cheapflights users on 7/8. 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 8/299:30 am
ORD
- LIH
1 stop13h 11m
Delta
Sat 8/299:55 pm
LIH
- ORD
1 stop10h 28m
Delta
Deal found 7/8![Delta logo]()
$419
This Southwest deal was found by Cheapflights users on 7/7. 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 8/176:40 am
MDW
- LIH
1 stop10h 55m
Southwest
Mon 8/248:25 pm
LIH
- MDW
1 stop12h 05m
Southwest
Deal found 7/7![Southwest logo]()
$424
This Delta deal was found by Cheapflights users on 7/8. 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 8/229:30 am
ORD
- LIH
1 stop13h 11m
Delta
Sat 8/298:41 pm
LIH
- ORD
1 stop12h 00m
Delta
Deal found 7/8![Delta logo]()
$424
This American Airlines deal was found by Cheapflights users on 7/11. 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.
Thu 8/1311:49 am
ORD
- LIH
1 stop13h 20m
American Airlines
Wed 8/2612:59 pm
LIH
- ORD
1 stop13h 07m
American Airlines
Deal found 7/11![American Airlines logo]()
$426
This Expedia deal was found by Cheapflights users on 7/11. 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.
Mon 8/172:20 pm
ORD
- LIH
1 stop26h 08m
Multiple Airlines
Mon 8/248:45 pm
LIH
- ORD
2 stops17h 36m
Multiple Airlines
Deal found 7/11![Multiple Airlines logo]()
$428
This Southwest deal was found by Cheapflights users on 7/11. 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.
Thu 11/125:45 am
MDW
- LIH
1 stop11h 30m
Southwest
Wed 11/189:05 pm
LIH
- MDW
1 stop13h 00m
Southwest
Deal found 7/11![Southwest logo]()
$429
This Alaska Airlines deal was found by Cheapflights users on 7/10. 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.
Mon 8/242:18 pm
ORD
- LIH
1 stop26h 18m
Multiple Airlines
Mon 8/318:45 pm
LIH
- ORD
2 stops17h 36m
Multiple Airlines
Deal found 7/10![Multiple Airlines logo]()
$429
This Delta deal was found by Cheapflights users on 7/8. 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 10/206:30 am
ORD
- LIH
2 stops17h 44m
Delta
Mon 10/269:50 pm
LIH
- ORD
1 stop14h 09m
Delta
Deal found 7/8![Delta logo]()
$430
This American Airlines deal was found by Cheapflights users on 7/11. 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 8/255:00 am
ORD
- LIH
2 stops14h 55m
American Airlines
Tue 9/112:59 pm
LIH
- ORD
1 stop11h 01m
American Airlines
Deal found 7/11![American Airlines logo]()
$433
This Delta deal was found by Cheapflights users on 7/10. 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.
Wed 10/289:29 am
MDW
- LIH
2 stops14h 45m
Delta
Sun 11/18:39 pm
LIH
- MDW
2 stops16h 00m
Delta
Deal found 7/10![Delta logo]()
$435
This Delta deal was found by Cheapflights users on 7/10. 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.
Fri 11/277:35 am
ORD
- LIH
1 stop14h 45m
Delta
Fri 12/1110:45 pm
LIH
- ORD
1 stop10h 46m
Delta
Deal found 7/10![Delta logo]()
$441
This Delta deal was found by Cheapflights users on 7/8. 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 8/319:30 am
ORD
- LIH
1 stop13h 11m
Delta
Mon 8/319:55 pm
LIH
- ORD
1 stop10h 28m
Delta
Deal found 7/8![Delta logo]()
$443
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 July 12, 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 July 12, 2026.
This United Airlines deal was found by Cheapflights users on 7/8. 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 9/166:00 am
ORD
- LIH
1 stop11h 04m
United Airlines
Wed 9/237:35 pm
LIH
- ORD
1 stop12h 01m
United Airlines
Deal found 7/8![United Airlines logo]()
$424
This Delta deal was found by Cheapflights users on 7/11. 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 9/1612:50 pm
ORD
- LIH
1 stop11h 20m
Delta
Wed 9/239:54 pm
LIH
- ORD
1 stop15h 07m
Delta
Deal found 7/11![Delta logo]()
$424
This Alaska Airlines deal was found by Cheapflights users on 7/9. 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.
Sun 9/138:17 pm
ORD
- LIH
1 stop20h 19m
Multiple Airlines
Sun 9/208:03 pm
LIH
- ORD
2 stops18h 18m
Multiple Airlines
Deal found 7/9![Multiple Airlines logo]()
$454
This Southwest deal was found by Cheapflights users on 7/11. 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 8/176:40 am
MDW
- LIH
1 stop10h 55m
Southwest
Mon 8/248:25 pm
LIH
- MDW
1 stop12h 05m
Southwest
Deal found 7/11![Southwest logo]()
$474
This Delta deal was found by Cheapflights users on 7/9. 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.
Mon 8/176:59 am
ORD
- LIH
2 stops17h 17m
Delta
Mon 8/248:41 pm
LIH
- ORD
1 stop12h 00m
Delta
Deal found 7/9![Delta logo]()
$430
This United Airlines deal was found by Cheapflights users on 7/11. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 9/135:00 am
ORD
- LIH
1 stop12h 04m
United Airlines
Fri 9/1810:48 pm
LIH
- ORD
1 stop11h 02m
United Airlines
Deal found 7/11![United Airlines logo]()
$445
This Alaska Airlines deal was found by Cheapflights users on 7/11. 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 Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 8/256:01 am
ORD
- LIH
2 stops14h 12m
Multiple Airlines
Tue 9/13:42 pm
LIH
- ORD
2 stops22h 39m
Multiple Airlines
Deal found 7/11![Multiple Airlines logo]()
$484
This Delta deal was found by Cheapflights users on 7/9. 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.
Sun 9/136:00 am
ORD
- LIH
2 stops18h 10m
Delta
Sun 9/209:54 pm
LIH
- ORD
2 stops15h 07m
Delta
Deal found 7/9![Delta logo]()
$459
This Alaska Airlines deal was found by Cheapflights users on 7/11. 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 Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/92:18 pm
ORD
- LIH
2 stops24h 24m
Multiple Airlines
Sun 9/208:45 pm
LIH
- ORD
2 stops17h 36m
Multiple Airlines
Deal found 7/11![Multiple Airlines logo]()
$484
This Southwest deal was found by Cheapflights users on 7/12. 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.
Mon 10/59:50 am
MDW
- LIH
2 stops16h 40m
Southwest
Mon 10/1212:15 pm
LIH
- MDW
1 stop12h 40m
Southwest
Deal found 7/12![Southwest logo]()
$540
This Delta deal was found by Cheapflights users on 7/9. 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.
Wed 9/96:00 am
ORD
- LIH
2 stops16h 40m
Delta
Sun 9/209:54 pm
LIH
- ORD
2 stops15h 07m
Delta
Deal found 7/9![Delta logo]()
$469
This Southwest deal was found by Cheapflights users on 7/10. 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.
Mon 8/246:15 am
MDW
- LIH
2 stops13h 00m
Southwest
Mon 8/318:25 pm
LIH
- MDW
2 stops12h 55m
Southwest
Deal found 7/10![Southwest logo]()
$555
This Delta deal was found by Cheapflights users on 7/10. 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 7/286:30 am
ORD
- LIH
2 stops17h 28m
Delta
Tue 8/49:55 pm
LIH
- ORD
1 stop14h 05m
Delta
Deal found 7/10![Delta logo]()
$480
This Southwest deal was found by Cheapflights users on 7/10. 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 8/266:40 am
MDW
- LIH
2 stops14h 30m
Southwest
Thu 9/38:25 pm
LIH
- MDW
1 stop10h 40m
Southwest
Deal found 7/10![Southwest logo]()
$580
This Delta deal was found by Cheapflights users on 7/7. 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 7/167:05 am
ORD
- LIH
2 stops16h 53m
Delta
Sun 7/199:55 pm
LIH
- ORD
1 stop10h 33m
Delta
Deal found 7/7![Delta logo]()
$490
This Southwest deal was found by Cheapflights users on 7/11. 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.
Sun 9/135:25 am
MDW
- LIH
1 stop12h 10m
Southwest
Fri 9/188:25 pm
LIH
- MDW
1 stop10h 40m
Southwest
Deal found 7/11![Southwest logo]()
$606
This Delta deal was found by Cheapflights users on 7/9. 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.
Sat 8/158:28 am
ORD
- LIH
2 stops14h 13m
Delta
Sat 8/228:41 pm
LIH
- ORD
1 stop12h 00m
Delta
Deal found 7/9![Delta logo]()
$510
This Southwest deal was found by Cheapflights users on 7/11. 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 8/2510:15 am
MDW
- LIH
1 stop10h 55m
Southwest
Tue 9/18:25 pm
LIH
- MDW
1 stop12h 05m
Southwest
Deal found 7/11![Southwest logo]()
$616
This Delta deal was found by Cheapflights users on 7/9. 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.
Mon 8/179:24 am
MDW
- LIH
2 stops14h 52m
Delta
Mon 8/248:41 pm
LIH
- MDW
2 stops16h 20m
Delta
Deal found 7/9![Delta logo]()
$555
This Southwest deal was found by Cheapflights users on 7/9. 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 8/236:55 am
MDW
- LIH
2 stops14h 20m
Southwest
Sun 8/308:25 pm
LIH
- MDW
1 stop10h 40m
Southwest
Deal found 7/9![Southwest logo]()
$646
This Southwest deal was found by Cheapflights users on 7/11. 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.
Thu 8/136:40 am
MDW
- LIH
2 stops12h 30m
Southwest
Wed 8/268:25 pm
LIH
- MDW
1 stop10h 40m
Southwest
Deal found 7/11![Southwest logo]()
$671
This Southwest deal was found by Cheapflights users on 7/12. 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.
Sat 8/226:55 am
MDW
- LIH
2 stops14h 15m
Southwest
Sat 8/299:25 pm
LIH
- MDW
2 stops12h 00m
Southwest
Deal found 7/12![Southwest logo]()
$705
Last-minute flights from Chicago to Kaua'iDiscover last-minute flight deals from Chicago to Kaua'i. Data last updated July 12, 2026 and is based on user searches.
Discover last-minute flight deals from Chicago to Kaua'i. Data last updated July 12, 2026 and is based on user searches.
This American Airlines deal was found by Cheapflights users on 7/11. 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.
Thu 8/1311:49 am
ORD
- LIH
1 stop13h 20m
American Airlines
Wed 8/2612:59 pm
LIH
- ORD
1 stop13h 07m
American Airlines
Deal found 7/11![American Airlines logo]()
$426
This Southwest deal was found by Cheapflights users on 7/7. 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 8/176:40 am
MDW
- LIH
1 stop10h 55m
Southwest
Mon 8/248:25 pm
LIH
- MDW
1 stop12h 05m
Southwest
Deal found 7/7![Southwest logo]()
$424
This Expedia deal was found by Cheapflights users on 7/11. 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.
Mon 8/172:20 pm
ORD
- LIH
1 stop26h 08m
Multiple Airlines
Mon 8/248:45 pm
LIH
- ORD
2 stops17h 36m
Multiple Airlines
Deal found 7/11![Multiple Airlines logo]()
$428
This United Airlines deal was found by Cheapflights users on 7/9. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 8/187:00 am
ORD
- LIH
1 stop13h 40m
United Airlines
Mon 8/247:35 pm
LIH
- ORD
1 stop10h 52m
United Airlines
Deal found 7/9![United Airlines logo]()
$447
This Delta deal was found by Cheapflights users on 7/8. 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 8/229:30 am
ORD
- LIH
1 stop13h 11m
Delta
Sat 8/298:41 pm
LIH
- ORD
1 stop12h 00m
Delta
Deal found 7/8![Delta logo]()
$424
This Alaska Airlines deal was found by Cheapflights users on 7/10. 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.
Mon 8/242:18 pm
ORD
- LIH
1 stop26h 18m
Multiple Airlines
Mon 8/318:45 pm
LIH
- ORD
2 stops17h 36m
Multiple Airlines
Deal found 7/10![Multiple Airlines logo]()
$429
This Delta deal was found by Cheapflights users on 7/8. 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 8/258:28 am
ORD
- LIH
2 stops15h 48m
Delta
Mon 8/319:55 pm
LIH
- ORD
1 stop14h 05m
Delta
Deal found 7/8![Delta logo]()
$430
This American Airlines deal was found by Cheapflights users on 7/11. 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 8/255:00 am
ORD
- LIH
2 stops14h 55m
American Airlines
Tue 9/112:59 pm
LIH
- ORD
1 stop11h 01m
American Airlines
Deal found 7/11![American Airlines logo]()
$433
This Delta deal was found by Cheapflights users on 7/8. 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 8/299:30 am
ORD
- LIH
1 stop13h 11m
Delta
Sat 8/299:55 pm
LIH
- ORD
1 stop10h 28m
Delta
Deal found 7/8![Delta logo]()
$419
This American Airlines deal was found by Cheapflights users on 7/10. 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.
Sat 8/2911:00 am
ORD
- LIH
1 stop14h 09m
American Airlines
Sun 9/69:00 pm
LIH
- ORD
1 stop10h 44m
American Airlines
Deal found 7/10![American Airlines logo]()
$441
This Delta deal was found by Cheapflights users on 7/8. 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 8/319:30 am
ORD
- LIH
1 stop13h 11m
Delta
Mon 8/319:55 pm
LIH
- ORD
1 stop10h 28m
Delta
Deal found 7/8![Delta logo]()
$443
This Delta deal was found by Cheapflights users on 7/8. 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 8/319:30 am
ORD
- LIH
1 stop13h 11m
Delta
Fri 9/49:55 pm
LIH
- ORD
1 stop14h 05m
Delta
Deal found 7/8![Delta logo]()
$448
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 July 12, 2026.
Search for one-way flight options from Chicago to Kaua'i. Find affordable one-way fares based on user searches. Data last updated July 12, 2026.
This American Airlines deal was found by Cheapflights users on 7/11. 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.
Fri 10/165:57 am
ORD
- LIH
1 stop11h 28m
American Airlines
Deal found 7/11![American Airlines logo]()
$212
This Alaska Airlines deal was found by Cheapflights users on 7/10. 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.
Mon 8/248:17 pm
ORD
- LIH
2 stops23h 56m
Multiple Airlines
Deal found 7/10![Multiple Airlines logo]()
$218
This Delta deal was found by Cheapflights users on 7/10. 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.
Fri 10/166:30 am
ORD
- LIH
2 stops17h 44m
Delta
Deal found 7/10![Delta logo]()
$235
This American Airlines deal was found by Cheapflights users on 7/10. 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.
Wed 10/145:57 am
ORD
- LIH
1 stop11h 28m
American Airlines
Deal found 7/10![American Airlines logo]()
$242
This Delta deal was found by Cheapflights users on 7/11. 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.
Sat 7/187:45 am
ORD
- LIH
2 stops16h 13m
Delta
Deal found 7/11![Delta logo]()
$248
This Delta deal was found by Cheapflights users on 7/10. 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 9/812:50 pm
ORD
- LIH
1 stop11h 20m
Delta
Deal found 7/10![Delta logo]()
$262
This Delta deal was found by Cheapflights users on 7/7. 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 9/166:00 am
ORD
- LIH
2 stops18h 10m
Delta
Deal found 7/7![Delta logo]()
$263
This United Airlines deal was found by Cheapflights users on 7/11. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 7/186:59 am
ORD
- LIH
1 stop13h 38m
United Airlines
Deal found 7/11![United Airlines logo]()
$265
This Alaska Airlines deal was found by Cheapflights users on 7/10. 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.
Wed 10/142:21 pm
ORD
- LIH
2 stops24h 22m
Alaska Airlines
Deal found 7/10![Alaska Airlines logo]()
$266
This Southwest deal was found by Cheapflights users on 7/10. 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 10/1410:15 am
MDW
- LIH
2 stops16h 15m
Southwest
Deal found 7/10![Southwest logo]()
$268
This Alaska Airlines deal was found by Cheapflights users on 7/7. 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 8/135:42 pm
ORD
- LIH
2 stops17h 58m
Multiple Airlines
Deal found 7/7![Multiple Airlines logo]()
$268
This Southwest deal was found by Cheapflights users on 7/9. 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.
Thu 10/299:50 am
MDW
- LIH
2 stops13h 20m
Southwest
Deal found 7/9![Southwest logo]()
$271
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 July 12, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $419 (Delta) |
One-way from | $212 (American Airlines) |
Popular in | March |
Cheapest in | February |
Average price | $698 |
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 July 12, 2026.
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
Cheapest round-trip
ChicagoLihue
ORD - LIH
ORDLIH
Chicago O'Hare Intl
Wed 9/16
6:00 am-12:04 pm
1 stop11h 04m
Lihue
Wed 9/23
7:35 pm-12:36 pm
1 stop12h 01m
$424
ChicagoLihue
ORD - LIH
ORDLIH
Chicago O'Hare Intl
Wed 9/16
12:50 pm-7:10 pm
1 stop11h 20m
Lihue
Wed 9/23
9:54 pm-6:01 pm
1 stop15h 07m
$424
ChicagoLihue
ORD - LIH
ORDLIH
Chicago O'Hare Intl
Mon 8/17
6:59 am-7:16 pm
2 stops17h 17m
Lihue
Mon 8/24
8:41 pm-1:41 pm
1 stop12h 00m
$430
ChicagoLihue
ORD - LIH
ORDLIH
Chicago O'Hare Intl
Sun 9/13
5:00 am-12:04 pm
1 stop12h 04m
Lihue
Fri 9/18
10:48 pm-2:50 pm
1 stop11h 02m
$445
ChicagoLihue
ORD - LIH
ORDLIH
Chicago O'Hare Intl
Sun 9/13
8:17 pm-11:36 am
1 stop20h 19m
Lihue
Sun 9/20
8:03 pm-7:21 pm
2 stops18h 18m
$454
ChicagoLihue
ORD - LIH
ORDLIH
Chicago O'Hare Intl
Sun 9/13
6:00 am-7:10 pm
2 stops18h 10m
Lihue
Sun 9/20
9:54 pm-6:01 pm
2 stops15h 07m
$459
ChicagoLihue
ORD - LIH
ORDLIH
Chicago O'Hare Intl
Wed 9/9
6:00 am-5:40 pm
2 stops16h 40m
Lihue
Sun 9/20
9:54 pm-6:01 pm
2 stops15h 07m
$469
ChicagoLihue
MDW - LIH
MDWLIH
Chicago Midway
Mon 8/17
6:40 am-12:35 pm
1 stop10h 55m
Lihue
Mon 8/24
8:25 pm-1:30 pm
1 stop12h 05m
$474
ChicagoLihue
ORD - LIH
ORDLIH
Chicago O'Hare Intl
Tue 7/28
6:30 am-6:58 pm
2 stops17h 28m
Lihue
Tue 8/4
9:55 pm-5:00 pm
1 stop14h 05m
$480
ChicagoLihue
ORD - LIH
ORDLIH
Chicago O'Hare Intl
Tue 8/25
6:01 am-3:13 pm
2 stops14h 12m
Lihue
Tue 9/1
3:42 pm-7:21 pm
2 stops22h 39m
$484
Showing 1-10 of 39 resultsSorted by cheapest first
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, January is the cheapest month in which you can book a flight from Chicago to Kaua'i (average of $211). Flying from Chicago to Kaua'i in July is currently the most expensive (average of $454). 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.
How far ahead should I book a flight from Chicago to Kaua'i?
Booking 42 days in advance of your planned departure date is, on average, the best time to get cheap flights from Chicago to Kaua'i. The general trend is that the closer you book to the departure date, the more expensive your flight will be.
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 July 12, 2026.
Read reviews from past customers who have flown Alaska Airlines,Southwest, andDelta 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.
Entertainment
7.0
Food
7.1
Comfort
7.8
Boarding
8.1
Crew
8.5
Overall
7.9
Reviews
1 / 20
4.0
OkayAnonymous,Jun 2026
SEA - RNO
Entertainment
7.0
Food
7.1
Comfort
7.8
Boarding
8.1
Crew
8.5
Overall
7.9
Reviews
1 / 20
4.0
OkayAnonymous,Jun 2026
SEA - RNO
Entertainment
7.0
Food
7.1
Comfort
7.8
Boarding
8.1
Crew
8.5
Overall
7.9
Reviews
1 / 20
4.0
OkayAnonymous,Jun 2026
SEA - RNO
Entertainment
7.0
Food
7.1
Comfort
7.8
Boarding
8.1
Crew
8.5
Overall
7.9
Reviews
1 / 20
4.0
OkayAnonymous,Jun 2026
SEA - RNO
Entertainment
7.0
Food
7.1
Comfort
7.8
Boarding
8.1
Crew
8.5
Overall
7.9
Reviews
1 / 20
4.0
OkayAnonymous,Jun 2026
SEA - RNO
Entertainment
7.0
Food
7.1
Comfort
7.8
Boarding
8.1
Crew
8.5
Overall
7.9
Reviews
1 / 20
4.0
OkayAnonymous,Jun 2026
SEA - RNO
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.
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
Complete your trip
Flights by cabin class
Other flight options
Popular flights
Alternative routes for Chicago to Kaua'i
See prices for flight routes from nearby airports that may be better suited for you.
Complete your trip
Complete your trip to Kaua'i by adding a car rental and/or hotel reservation to your travel itinerary.
Search flights from Chicago to Kaua'i by cabin class
Find flights from Chicago to Kaua'i, based on your preferred cabin class, be it economy, premium economy, business, or first class.
Chicago and Kaua'i flights
Browse other Chicago and Kaua'i flight options. Last updated on July 12, 2026.
Popular flight searches
Check out other popular destinations found by fellow travelers in 2026
Top 4 airlines flying from Chicago to Kaua'i
Discover the top 4 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 July 12, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$382 | Average$573 | FlexibilityNo cancel fee | On-time75% | |
| Cheapest$423 | Average$613 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$424 | Average$645 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$424 | Average$561 | FlexibilityNo cancel fee | On-timeN/A |