$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 4/28. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — LIH
May 2 — May 91
Round-trip
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
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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 April 2, 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 April 2, 2026.
This American Airlines deal was found by Cheapflights users on 3/29. 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 9/186:00 am
ORD
- LIH
1 stop11h 14m
American Airlines
Fri 9/181:44 pm
LIH
- ORD
1 stop10h 16m
American Airlines
Deal found 3/29![American Airlines logo]()
$419
This American Airlines deal was found by Cheapflights users on 3/31. 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 4/286:00 am
ORD
- LIH
1 stop11h 22m
American Airlines
Tue 5/52:12 pm
LIH
- ORD
1 stop10h 35m
American Airlines
Deal found 3/31![American Airlines logo]()
$424
This Delta deal was found by Cheapflights users on 3/31. 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
Tue 5/58:20 pm
LIH
- ORD
2 stops19h 20m
Delta
Deal found 3/31![Delta logo]()
$430
This Delta deal was found by Cheapflights users on 3/31. 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 4/287:35 am
ORD
- LIH
2 stops15h 05m
Delta
Sun 5/39:25 pm
LIH
- ORD
2 stops16h 27m
Delta
Deal found 3/31![Delta logo]()
$435
This Delta deal was found by Cheapflights users on 3/31. 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 5/139:55 pm
LIH
- ORD
2 stops15h 10m
Delta
Deal found 3/31![Delta logo]()
$444
This American Airlines deal was found by Cheapflights users on 3/28. 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.
Mon 4/207:04 am
ORD
- LIH
1 stop13h 11m
American Airlines
Mon 4/279:30 pm
LIH
- ORD
2 stops12h 48m
American Airlines
Deal found 3/28![American Airlines logo]()
$447
This American Airlines deal was found by Cheapflights users on 3/29. 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 4/267:04 am
ORD
- LIH
1 stop13h 11m
American Airlines
Sun 5/32:12 pm
LIH
- ORD
1 stop10h 35m
American Airlines
Deal found 3/29![American Airlines logo]()
$448
This Delta deal was found by Cheapflights users on 3/29. 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 4/167:15 am
ORD
- LIH
1 stop15h 25m
Delta
Tue 4/219:25 pm
LIH
- ORD
2 stops15h 39m
Delta
Deal found 3/29![Delta logo]()
$449
This Delta deal was found by Cheapflights users on 3/28. 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 4/307:15 am
ORD
- LIH
1 stop15h 25m
Delta
Thu 5/79:55 pm
LIH
- ORD
1 stop13h 54m
Delta
Deal found 3/28![Delta logo]()
$450
This Alaska Airlines deal was found by Cheapflights users on 3/30. 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 5/37:59 pm
ORD
- LIH
1 stop23h 25m
Multiple Airlines
Thu 5/76:40 pm
LIH
- ORD
2 stops19h 23m
Multiple Airlines
Deal found 3/30![Multiple Airlines logo]()
$453
This American Airlines deal was found by Cheapflights users on 3/31. 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 4/176:00 am
ORD
- LIH
1 stop11h 22m
American Airlines
Tue 4/282:12 pm
LIH
- ORD
1 stop10h 35m
American Airlines
Deal found 3/31![American Airlines logo]()
$454
This Delta deal was found by Cheapflights users on 3/30. 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 5/159:22 am
MDW
- LIH
2 stops14h 44m
Delta
Fri 5/229:55 pm
LIH
- MDW
2 stops15h 01m
Delta
Deal found 3/30![Delta logo]()
$459
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 April 2, 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 April 2, 2026.
This Delta deal was found by Cheapflights users on 4/1. 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 4/287:35 am
ORD
- LIH
2 stops16h 05m
Delta
Sun 5/38:20 pm
LIH
- ORD
1 stop12h 03m
Delta
Deal found 4/1![Delta logo]()
$430
This Southwest deal was found by Cheapflights users on 3/29. 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 4/265:10 am
MDW
- LIH
2 stops16h 00m
Southwest
Sun 5/37:10 pm
LIH
- MDW
2 stops12h 35m
Southwest
Deal found 3/29![Southwest logo]()
$516
This Delta deal was found by Cheapflights users on 3/29. 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 4/267:15 am
ORD
- LIH
1 stop15h 25m
Delta
Sun 5/39:25 pm
LIH
- ORD
2 stops16h 27m
Delta
Deal found 3/29![Delta logo]()
$430
This Delta deal was found by Cheapflights users on 3/28. 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 4/278:52 am
ORD
- LIH
2 stops14h 48m
Delta
Mon 5/48:20 pm
LIH
- ORD
2 stops16h 53m
Delta
Deal found 3/28![Delta logo]()
$435
This Southwest deal was found by Cheapflights users on 4/1. 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 4/1610:05 am
MDW
- LIH
1 stop11h 05m
Southwest
Mon 4/208:10 pm
LIH
- MDW
1 stop10h 50m
Southwest
Deal found 4/1![Southwest logo]()
$537
This Delta deal was found by Cheapflights users on 3/30. 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 5/159:22 am
MDW
- LIH
2 stops14h 44m
Delta
Fri 5/229:55 pm
LIH
- MDW
2 stops15h 01m
Delta
Deal found 3/30![Delta logo]()
$459
This Delta deal was found by Cheapflights users on 3/28. 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 4/137:35 am
ORD
- LIH
2 stops16h 05m
Delta
Thu 4/168:20 pm
LIH
- ORD
2 stops17h 32m
Delta
Deal found 3/28![Delta logo]()
$459
This Southwest deal was found by Cheapflights users on 3/29. 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 4/157:55 am
MDW
- LIH
2 stops13h 15m
Southwest
Sun 4/198:10 pm
LIH
- MDW
1 stop15h 05m
Southwest
Deal found 3/29![Southwest logo]()
$590
This Delta deal was found by Cheapflights users on 3/31. 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 5/116:24 am
ORD
- LIH
2 stops16h 16m
Delta
Mon 5/188:40 pm
LIH
- ORD
2 stops17h 40m
Delta
Deal found 3/31![Delta logo]()
$468
This Delta deal was found by Cheapflights users on 3/29. 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 4/177:35 am
ORD
- LIH
2 stops16h 05m
Delta
Tue 4/288:20 pm
LIH
- ORD
1 stop12h 03m
Delta
Deal found 3/29![Delta logo]()
$479
This Delta deal was found by Cheapflights users on 3/31. 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 5/1512:47 pm
ORD
- LIH
1 stop11h 19m
Delta
Fri 5/229:55 pm
LIH
- ORD
2 stops18h 25m
Delta
Deal found 3/31![Delta logo]()
$490
This Southwest deal was found by Cheapflights users on 3/31. 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.
Fri 5/156:55 am
MDW
- LIH
2 stops14h 15m
Southwest
Fri 5/228:10 pm
LIH
- MDW
1 stop13h 15m
Southwest
Deal found 3/31![Southwest logo]()
$785
This Delta deal was found by Cheapflights users on 4/1. 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 5/68:50 am
ORD
- LIH
2 stops14h 50m
Delta
Wed 5/139:55 pm
LIH
- ORD
1 stop13h 54m
Delta
Deal found 4/1![Delta logo]()
$490
This Delta deal was found by Cheapflights users on 3/31. 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 5/301:22 pm
MDW
- LIH
2 stops34h 44m
Delta
Tue 6/99:55 pm
LIH
- MDW
2 stops29h 42m
Delta
Deal found 3/31![Delta logo]()
$559
This Southwest deal was found by Cheapflights users on 3/30. 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 6/297:30 am
MDW
- LIH
2 stops13h 40m
Southwest
Thu 7/98:10 pm
LIH
- MDW
1 stop10h 35m
Southwest
Deal found 3/30![Southwest logo]()
$1,010
This Southwest deal was found by Cheapflights users on 3/31. 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 6/155:10 am
MDW
- LIH
2 stops14h 05m
Southwest
Wed 6/248:10 pm
LIH
- MDW
1 stop10h 35m
Southwest
Deal found 3/31![Southwest logo]()
$1,010
This Delta deal was found by Cheapflights users on 3/28. 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 4/139:27 am
MDW
- LIH
2 stops14h 13m
Delta
Thu 4/168:20 pm
LIH
- MDW
2 stops16h 38m
Delta
Deal found 3/28![Delta logo]()
$699
This Delta deal was found by Cheapflights users on 3/28. 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 5/279:23 am
MDW
- LIH
2 stops13h 17m
Delta
Tue 6/29:55 pm
LIH
- MDW
2 stops15h 01m
Delta
Deal found 3/28![Delta logo]()
$1,080
This Delta deal was found by Cheapflights users on 3/31. 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 5/239:22 am
MDW
- LIH
2 stops14h 44m
Delta
Fri 5/298:40 pm
LIH
- MDW
2 stops16h 53m
Delta
Deal found 3/31![Delta logo]()
$1,290
This Delta deal was found by Cheapflights users on 3/29. 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 5/249:22 am
MDW
- LIH
2 stops14h 44m
Delta
Sat 5/308:40 pm
LIH
- MDW
2 stops16h 16m
Delta
Deal found 3/29![Delta logo]()
$1,303
Last-minute flights from Chicago to Kaua'iDiscover last-minute flight deals from Chicago to Kaua'i. Data last updated April 2, 2026 and is based on user searches.
Discover last-minute flight deals from Chicago to Kaua'i. Data last updated April 2, 2026 and is based on user searches.
This Delta deal was found by Cheapflights users on 3/28. 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 4/137:35 am
ORD
- LIH
2 stops16h 05m
Delta
Thu 4/168:20 pm
LIH
- ORD
2 stops17h 32m
Delta
Deal found 3/28![Delta logo]()
$459
This Delta deal was found by Cheapflights users on 3/30. 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 4/167:15 am
ORD
- LIH
1 stop15h 25m
Delta
Mon 4/209:25 pm
LIH
- ORD
2 stops15h 39m
Delta
Deal found 3/30![Delta logo]()
$449
This American Airlines deal was found by Cheapflights users on 3/31. 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 4/176:00 am
ORD
- LIH
1 stop11h 22m
American Airlines
Tue 4/282:12 pm
LIH
- ORD
1 stop10h 35m
American Airlines
Deal found 3/31![American Airlines logo]()
$454
This American Airlines deal was found by Cheapflights users on 3/29. 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 4/267:04 am
ORD
- LIH
1 stop13h 11m
American Airlines
Sun 5/32:12 pm
LIH
- ORD
1 stop10h 35m
American Airlines
Deal found 3/29![American Airlines logo]()
$448
This Southwest deal was found by Cheapflights users on 3/29. 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 4/276:55 am
MDW
- LIH
2 stops14h 15m
Southwest
Thu 4/307:10 pm
LIH
- MDW
2 stops12h 35m
Southwest
Deal found 3/29![Southwest logo]()
$491
This American Airlines deal was found by Cheapflights users on 3/31. 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 4/286:00 am
ORD
- LIH
1 stop11h 22m
American Airlines
Tue 5/52:12 pm
LIH
- ORD
1 stop10h 35m
American Airlines
Deal found 3/31![American Airlines logo]()
$424
This Delta deal was found by Cheapflights users on 3/31. 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
Tue 5/58:20 pm
LIH
- ORD
2 stops19h 20m
Delta
Deal found 3/31![Delta logo]()
$430
This Delta deal was found by Cheapflights users on 3/31. 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 4/287:35 am
ORD
- LIH
2 stops15h 05m
Delta
Sun 5/39:25 pm
LIH
- ORD
2 stops16h 27m
Delta
Deal found 3/31![Delta logo]()
$435
This Alaska Airlines deal was found by Cheapflights users on 3/30. 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 5/37:59 pm
ORD
- LIH
1 stop23h 25m
Multiple Airlines
Thu 5/76:40 pm
LIH
- ORD
2 stops19h 23m
Multiple Airlines
Deal found 3/30![Multiple Airlines logo]()
$453
This Delta deal was found by Cheapflights users on 3/31. 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 5/139:55 pm
LIH
- ORD
2 stops15h 10m
Delta
Deal found 3/31![Delta logo]()
$444
This American Airlines deal was found by Cheapflights users on 3/30. 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.
Mon 5/116:00 am
ORD
- LIH
1 stop11h 22m
American Airlines
Mon 5/182:12 pm
LIH
- ORD
1 stop10h 35m
American Airlines
Deal found 3/30![American Airlines logo]()
$450
This Delta deal was found by Cheapflights users on 3/30. 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 5/159:22 am
MDW
- LIH
2 stops14h 44m
Delta
Fri 5/229:55 pm
LIH
- MDW
2 stops15h 01m
Delta
Deal found 3/30![Delta logo]()
$459
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 April 2, 2026.
Search for one-way flight options from Chicago to Kaua'i. Find affordable one-way fares based on user searches. Data last updated April 2, 2026.
This American Airlines deal was found by Cheapflights users on 3/28. 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 4/286:00 am
ORD
- LIH
1 stop11h 22m
American Airlines
Deal found 3/28![American Airlines logo]()
$212
This Delta deal was found by Cheapflights users on 3/28. 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 4/286:25 am
ORD
- LIH
2 stops17h 15m
Delta
Deal found 3/28![Delta logo]()
$218
This Kiwi.com deal was found by Cheapflights users on 3/31. 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.
Thu 9/37:00 am
ORD
- LIH
2 stops13h 48m
Multiple Airlines
Deal found 3/31![Multiple Airlines logo]()
$284
This American Airlines deal was found by Cheapflights users on 3/31. 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 9/36:00 am
ORD
- LIH
1 stop11h 12m
American Airlines
Deal found 3/31![American Airlines logo]()
$286
This United Airlines deal was found by Cheapflights users on 4/2. 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 8/157:00 am
ORD
- LIH
2 stops17h 44m
United Airlines
Deal found 4/2![United Airlines logo]()
$293
This Delta deal was found by Cheapflights users on 3/28. 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 6/175:55 pm
ORD
- LIH
1 stop30h 06m
Delta
Deal found 3/28![Delta logo]()
$303
This American Airlines deal was found by Cheapflights users on 3/29. 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 6/96:51 am
ORD
- LIH
1 stop18h 30m
American Airlines
Deal found 3/29![American Airlines logo]()
$337
This Delta deal was found by Cheapflights users on 3/29. 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 6/96:30 am
ORD
- LIH
2 stops17h 31m
Delta
Deal found 3/29![Delta logo]()
$338
This Delta deal was found by Cheapflights users on 3/28. 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 6/135:55 pm
ORD
- LIH
1 stop30h 06m
Delta
Deal found 3/28![Delta logo]()
$339
This American Airlines deal was found by Cheapflights users on 3/29. 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.
Mon 6/296:00 am
ORD
- LIH
1 stop19h 21m
American Airlines
Deal found 3/29![American Airlines logo]()
$360
This Delta deal was found by Cheapflights users on 3/28. 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 6/126:55 am
ORD
- LIH
1 stop17h 06m
Delta
Deal found 3/28![Delta logo]()
$364
This Southwest deal was found by Cheapflights users on 3/30. 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 6/85:10 am
MDW
- LIH
2 stops14h 05m
Southwest
Deal found 3/30![Southwest logo]()
$508
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 April 2, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $419 (American Airlines) |
One-way from | $212 (American Airlines) |
Popular in | December |
Cheapest in | February |
Average price | $532 |
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 April 2, 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
Tue 4/28
7:35 am-6:40 pm
2 stops16h 05m
Lihue
Sun 5/3
8:20 pm-1:23 pm
1 stop12h 03m
$430
ChicagoLihue
ORD - LIH
ORDLIH
Chicago O'Hare Intl
Sun 4/26
7:15 am-5:40 pm
1 stop15h 25m
Lihue
Sun 5/3
9:25 pm-6:52 pm
2 stops16h 27m
$430
ChicagoLihue
ORD - LIH
ORDLIH
Chicago O'Hare Intl
Mon 4/27
8:52 am-6:40 pm
2 stops14h 48m
Lihue
Mon 5/4
8:20 pm-6:13 pm
2 stops16h 53m
$435
ChicagoLihue
MDW - LIH
MDWLIH
Chicago Midway
Fri 5/15
9:22 am-7:06 pm
2 stops14h 44m
Lihue
Fri 5/22
9:55 pm-5:56 pm
2 stops15h 01m
$459
ChicagoLihue
ORD - LIH
ORDLIH
Chicago O'Hare Intl
Mon 4/13
7:35 am-6:40 pm
2 stops16h 05m
Lihue
Thu 4/16
8:20 pm-6:52 pm
2 stops17h 32m
$459
ChicagoLihue
ORD - LIH
ORDLIH
Chicago O'Hare Intl
Mon 5/11
6:24 am-5:40 pm
2 stops16h 16m
Lihue
Mon 5/18
8:40 pm-7:20 pm
2 stops17h 40m
$468
ChicagoLihue
ORD - LIH
ORDLIH
Chicago O'Hare Intl
Fri 4/17
7:35 am-6:40 pm
2 stops16h 05m
Lihue
Tue 4/28
8:20 pm-1:23 pm
1 stop12h 03m
$479
ChicagoLihue
ORD - LIH
ORDLIH
Chicago O'Hare Intl
Fri 5/15
12:47 pm-7:06 pm
1 stop11h 19m
Lihue
Fri 5/22
9:55 pm-9:20 pm
2 stops18h 25m
$490
ChicagoLihue
ORD - LIH
ORDLIH
Chicago O'Hare Intl
Wed 5/6
8:50 am-6:40 pm
2 stops14h 50m
Lihue
Wed 5/13
9:55 pm-4:49 pm
1 stop13h 54m
$490
ChicagoLihue
MDW - LIH
MDWLIH
Chicago Midway
Sun 4/26
5:10 am-4:10 pm
2 stops16h 00m
Lihue
Sun 5/3
7:10 pm-12:45 pm
2 stops12h 35m
$516
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, 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 $557). 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 April 2, 2026.
Read reviews from past customers who have flown Southwest,Alaska Airlines, 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.
Food
7.0
Entertainment
7.5
Crew
8.6
Comfort
8.0
Boarding
8.1
Overall
8.0
Reviews
1 / 20
2.0
MediocreDominic,Mar 2026
MCO - SMF
Food
7.0
Entertainment
7.5
Crew
8.6
Comfort
8.0
Boarding
8.1
Overall
8.0
Reviews
1 / 20
2.0
MediocreDominic,Mar 2026
MCO - SMF
Food
7.0
Entertainment
7.5
Crew
8.6
Comfort
8.0
Boarding
8.1
Overall
8.0
Reviews
1 / 20
2.0
MediocreDominic,Mar 2026
MCO - SMF
Food
7.0
Entertainment
7.5
Crew
8.6
Comfort
8.0
Boarding
8.1
Overall
8.0
Reviews
1 / 20
2.0
MediocreDominic,Mar 2026
MCO - SMF
Food
7.0
Entertainment
7.5
Crew
8.6
Comfort
8.0
Boarding
8.1
Overall
8.0
Reviews
1 / 20
2.0
MediocreDominic,Mar 2026
MCO - SMF
Food
7.0
Entertainment
7.5
Crew
8.6
Comfort
8.0
Boarding
8.1
Overall
8.0
Reviews
1 / 20
2.0
MediocreDominic,Mar 2026
MCO - SMF
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 April 2, 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 April 2, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$382 | Average$688 | FlexibilityNo cancel fee | On-time75% | |
| Cheapest$408 | Average$603 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$423 | Average$601 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$429 | Average$694 | FlexibilityNo cancel fee | On-time69% |