$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 10/5. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — LIH
Sep 25 — Oct 21
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
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 August 26, 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 August 26, 2026.
This American Airlines deal was found by Cheapflights users on 8/22. 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 10/196:00 am -
1 stop11h 25m
Wed 10/289:35 pm -
1 stop13h 34m
Deal found 8/22![American Airlines logo]()
$423
This Delta deal was found by Cheapflights users on 8/24. 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 -
1 stop11h 20m
Wed 9/239:54 pm -
1 stop10h 35m
Deal found 8/24![Delta logo]()
$424
This American Airlines deal was found by Cheapflights users on 8/22. 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 11/265:30 am -
1 stop11h 58m
Thu 12/310:35 pm -
1 stop13h 34m
Deal found 8/22![American Airlines logo]()
$425
This United Airlines deal was found by Cheapflights users on 8/25. 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 11/72:30 pm -
1 stop12h 00m
Thu 11/122:03 pm -
1 stop11h 56m
Deal found 8/25![United Airlines logo]()
$434
This Delta deal was found by Cheapflights users on 8/24. 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 10/207:35 am -
2 stops15h 01m
Wed 10/289:53 pm -
2 stops15h 17m
Deal found 8/24![Delta logo]()
$435
This Travelocity deal was found by Cheapflights users on 8/25. 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 Travelocity is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/72:15 pm -
1 stop27h 32m
Thu 11/128:03 pm -
2 stops18h 56m
Deal found 8/25![Multiple Airlines logo]()
$439
This Delta deal was found by Cheapflights users on 8/25. 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 10/2212:50 pm -
1 stop11h 24m
Wed 10/289:53 pm -
2 stops15h 17m
Deal found 8/25![Delta logo]()
$440
This Delta deal was found by Cheapflights users on 8/25. 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 9/912:50 pm -
1 stop11h 20m
Sun 9/139:54 pm -
1 stop10h 35m
Deal found 8/25![Delta logo]()
$444
This Alaska Airlines deal was found by Cheapflights users on 8/25. 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 11/47:20 am -
2 stops14h 38m
Wed 11/118:03 pm -
2 stops18h 56m
Deal found 8/25![Multiple Airlines logo]()
$445
This Southwest deal was found by Cheapflights users on 8/23. 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 11/35:50 am -
2 stops14h 25m
Sun 11/89:05 pm -
1 stop10h 45m
Deal found 8/23![Southwest logo]()
$490
This Delta deal was found by Cheapflights users on 8/24. 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 12/79:37 am -
2 stops14h 43m
Fri 12/1110:59 pm -
2 stops13h 51m
Deal found 8/24![Delta logo]()
$505
This Delta deal was found by Cheapflights users on 8/21. 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 10/229:29 am -
2 stops14h 45m
Mon 10/268:48 pm -
2 stops14h 59m
Deal found 8/21![Delta logo]()
$515
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 August 26, 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 August 26, 2026.
This Delta deal was found by Cheapflights users on 8/24. 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 9/119:45 am -
1 stop12h 54m
Fri 9/189:54 pm -
1 stop10h 35m
Deal found 8/24![Delta logo]()
$434
This United Airlines deal was found by Cheapflights users on 8/22. 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.
Mon 9/215:00 am -
1 stop11h 59m
Mon 9/287:35 pm -
1 stop10h 53m
Deal found 8/22![United Airlines logo]()
$434
This Alaska Airlines deal was found by Cheapflights users on 8/24. 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 11/117:20 am -
2 stops16h 10m
Sun 11/1511:45 am -
1 stop21h 32m
Deal found 8/24![Multiple Airlines logo]()
$470
This Southwest deal was found by Cheapflights users on 8/24. 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 10/239:50 am -
2 stops13h 20m
Wed 10/2812:15 pm -
1 stop12h 40m
Deal found 8/24![Southwest logo]()
$550
This Delta deal was found by Cheapflights users on 8/23. 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 9/1012:50 pm -
1 stop11h 20m
Thu 9/179:54 pm -
1 stop15h 07m
Deal found 8/23![Delta logo]()
$434
This United Airlines deal was found by Cheapflights users on 8/25. 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.
Fri 9/185:00 am -
1 stop11h 59m
Thu 9/241:05 pm -
1 stop11h 10m
Deal found 8/25![United Airlines logo]()
$434
This Delta deal was found by Cheapflights users on 8/22. 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 9/1312:50 pm -
1 stop11h 20m
Sun 9/208:45 pm -
1 stop11h 59m
Deal found 8/22![Delta logo]()
$434
This Delta deal was found by Cheapflights users on 8/25. 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 9/97:45 am -
2 stops16h 25m
Sun 9/209:54 pm -
2 stops15h 10m
Deal found 8/25![Delta logo]()
$455
This Southwest deal was found by Cheapflights users on 8/25. 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 10/216:05 am -
1 stop11h 30m
Wed 10/2812:15 pm -
1 stop12h 40m
Deal found 8/25![Southwest logo]()
$594
This Delta deal was found by Cheapflights users on 8/25. 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 9/66:00 am -
2 stops18h 16m
Tue 9/159:54 pm -
1 stop10h 35m
Deal found 8/25![Delta logo]()
$460
This Southwest deal was found by Cheapflights users on 8/22. 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 10/146:05 am -
2 stops13h 15m
Mon 10/1911:50 am -
2 stops13h 05m
Deal found 8/22![Southwest logo]()
$606
This Delta deal was found by Cheapflights users on 8/23. 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 10/206:20 am -
2 stops16h 16m
Mon 10/269:53 pm -
2 stops17h 37m
Deal found 8/23![Delta logo]()
$474
This Southwest deal was found by Cheapflights users on 8/22. 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 10/66:25 am -
2 stops12h 55m
Tue 10/1312:15 pm -
1 stop12h 40m
Deal found 8/22![Southwest logo]()
$641
This Delta deal was found by Cheapflights users on 8/21. 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 10/229:29 am -
2 stops14h 45m
Mon 10/268:48 pm -
2 stops14h 59m
Deal found 8/21![Delta logo]()
$515
This Southwest deal was found by Cheapflights users on 8/25. 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 11/65:45 am -
1 stop11h 30m
Wed 11/114:05 pm -
1 stop15h 30m
Deal found 8/25![Southwest logo]()
$654
This Southwest deal was found by Cheapflights users on 8/21. 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 10/55:25 am -
2 stops13h 55m
Mon 10/1211:50 am -
2 stops13h 05m
Deal found 8/21![Southwest logo]()
$675
This Southwest deal was found by Cheapflights users on 8/23. 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 10/76:25 am -
2 stops16h 45m
Wed 10/1412:15 pm -
1 stop12h 40m
Deal found 8/23![Southwest logo]()
$741
This Delta deal was found by Cheapflights users on 8/24. 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 11/119:30 am -
2 stops14h 37m
Sun 11/159:45 pm -
2 stops16h 19m
Deal found 8/24![Delta logo]()
$775
This Southwest deal was found by Cheapflights users on 8/21. 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 9/46:15 am -
2 stops13h 00m
Tue 9/88:25 pm -
1 stop10h 30m
Deal found 8/21![Southwest logo]()
$836
Last-minute flights from Chicago to Kaua'iDiscover last-minute flight deals from Chicago to Kaua'i. Data last updated August 26, 2026 and is based on user searches.
Discover last-minute flight deals from Chicago to Kaua'i. Data last updated August 26, 2026 and is based on user searches.
This Delta deal was found by Cheapflights users on 8/25. 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 8/279:24 am -
2 stops14h 52m
Thu 9/39:55 pm -
2 stops15h 38m
Deal found 8/25![Delta logo]()
$575
This Delta deal was found by Cheapflights users on 8/21. 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 9/19:30 am -
1 stop13h 11m
Tue 9/159:54 pm -
1 stop10h 35m
Deal found 8/21![Delta logo]()
$454
This Delta deal was found by Cheapflights users on 8/25. 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 9/912:50 pm -
1 stop11h 20m
Sun 9/139:54 pm -
1 stop10h 35m
Deal found 8/25![Delta logo]()
$444
This Delta deal was found by Cheapflights users on 8/24. 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 9/912:50 pm -
1 stop11h 20m
Sun 9/209:54 pm -
2 stops15h 10m
Deal found 8/24![Delta logo]()
$450
This Delta deal was found by Cheapflights users on 8/23. 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 9/108:55 am -
2 stops15h 15m
Thu 9/178:45 pm -
2 stops15h 14m
Deal found 8/23![Delta logo]()
$445
This Delta deal was found by Cheapflights users on 8/21. 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 9/136:10 am -
2 stops16h 29m
Sun 9/208:45 pm -
1 stop11h 59m
Deal found 8/21![Delta logo]()
$440
This Delta deal was found by Cheapflights users on 8/25. 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 9/157:45 am -
2 stops16h 25m
Tue 9/298:45 pm -
2 stops14h 28m
Deal found 8/25![Delta logo]()
$435
This Delta deal was found by Cheapflights users on 8/23. 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 9/159:29 am -
2 stops14h 41m
Tue 9/298:45 pm -
2 stops16h 34m
Deal found 8/23![Delta logo]()
$535
This Delta deal was found by Cheapflights users on 8/24. 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 -
1 stop11h 20m
Wed 9/239:54 pm -
1 stop10h 35m
Deal found 8/24![Delta logo]()
$424
This United Airlines deal was found by Cheapflights users on 8/22. 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.
Mon 9/215:00 am -
1 stop11h 59m
Mon 9/287:35 pm -
1 stop10h 53m
Deal found 8/22![United Airlines logo]()
$434
This Delta deal was found by Cheapflights users on 8/22. 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 9/2112:50 pm -
1 stop11h 20m
Mon 9/289:54 pm -
2 stops15h 10m
Deal found 8/22![Delta logo]()
$460
This Southwest deal was found by Cheapflights users on 8/22. 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 9/226:50 am -
2 stops12h 20m
Fri 10/212:15 pm -
1 stop12h 40m
Deal found 8/22![Southwest logo]()
$601
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 August 26, 2026.
Search for one-way flight options from Chicago to Kaua'i. Find affordable one-way fares based on user searches. Data last updated August 26, 2026.
This American Airlines deal was found by Cheapflights users on 8/21. 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 10/55:59 am -
1 stop13h 52m
Deal found 8/21![American Airlines logo]()
$212
This Delta deal was found by Cheapflights users on 8/24. 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 1/1812:40 pm -
1 stop11h 42m
Deal found 8/24![Delta logo]()
$213
This Delta deal was found by Cheapflights users on 8/22. 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 10/66:20 am -
2 stops17h 59m
Deal found 8/22![Delta logo]()
$218
This Delta deal was found by Cheapflights users on 8/25. 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 10/1612:50 pm -
1 stop11h 24m
Deal found 8/25![Delta logo]()
$222
This Delta deal was found by Cheapflights users on 8/25. 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 10/169:29 am -
2 stops14h 45m
Deal found 8/25![Delta logo]()
$228
This Alaska Airlines deal was found by Cheapflights users on 8/21. 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 10/57:16 pm -
2 stops23h 21m
Deal found 8/21![Multiple Airlines logo]()
$238
This United Airlines deal was found by Cheapflights users on 8/25. 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 9/51:58 pm -
1 stop11h 16m
Deal found 8/25![United Airlines logo]()
$242
This Alaska Airlines deal was found by Cheapflights users on 8/24. 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 2/97:40 am -
1 stop11h 55m
Deal found 8/24![Alaska Airlines logo]()
$247
This Delta deal was found by Cheapflights users on 8/24. 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 9/58:28 am -
2 stops14h 13m
Deal found 8/24![Delta logo]()
$248
This Trip.com deal was found by Cheapflights users on 8/22. 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/241:03 pm -
1 stop12h 11m
Deal found 8/22![Alaska Airlines logo]()
$252
This Alaska Airlines deal was found by Cheapflights users on 8/24. 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 2/87:40 am -
2 stops15h 48m
Deal found 8/24![Multiple Airlines logo]()
$253
This Alaska Airlines deal was found by Cheapflights users on 8/23. 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 10/11:03 pm -
2 stops22h 37m
Deal found 8/23![Multiple Airlines logo]()
$265
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 August 26, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $423 (American Airlines) |
One-way from | $212 (American Airlines) |
Popular in | June |
Cheapest in | February |
Average price | $504 |
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 7,457,451 searches. Data last updated August 26, 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 Chicago O'Hare Intl - LIH Lihue
ORDLIH
Chicago O'Hare Intl
Fri 9/11
9:45 am-5:39 pm
1 stop12h 54m
Lihue
Fri 9/18
9:54 pm-1:29 pm
1 stop10h 35m
$434
Quickest round-trip
ChicagoLihue
ORD Chicago O'Hare Intl - LIH Lihue
ORDLIH
Chicago O'Hare Intl
Mon 9/21
5:00 am-11:59 am
1 stop11h 59m
Lihue
Mon 9/28
7:35 pm-11:28 am
1 stop10h 53m
$434
ChicagoLihue
ORD Chicago O'Hare Intl - LIH Lihue
ORDLIH
Chicago O'Hare Intl
Thu 9/10
12:50 pm-7:10 pm
1 stop11h 20m
Lihue
Thu 9/17
9:54 pm-6:01 pm
1 stop15h 07m
$434
ChicagoLihue
ORD Chicago O'Hare Intl - LIH Lihue
ORDLIH
Chicago O'Hare Intl
Fri 9/18
5:00 am-11:59 am
1 stop11h 59m
Lihue
Thu 9/24
1:05 pm-5:15 am
1 stop11h 10m
$434
ChicagoLihue
ORD Chicago O'Hare Intl - LIH Lihue
ORDLIH
Chicago O'Hare Intl
Sun 9/13
12:50 pm-7:10 pm
1 stop11h 20m
Lihue
Sun 9/20
8:45 pm-1:44 pm
1 stop11h 59m
$434
ChicagoLihue
ORD Chicago O'Hare Intl - LIH Lihue
ORDLIH
Chicago O'Hare Intl
Wed 9/9
7:45 am-7:10 pm
2 stops16h 25m
Lihue
Sun 9/20
9:54 pm-6:04 pm
2 stops15h 10m
$455
ChicagoLihue
ORD Chicago O'Hare Intl - LIH Lihue
ORDLIH
Chicago O'Hare Intl
Sun 9/6
6:00 am-7:16 pm
2 stops18h 16m
Lihue
Tue 9/15
9:54 pm-1:29 pm
1 stop10h 35m
$460
ChicagoLihue
ORD Chicago O'Hare Intl - LIH Lihue
ORDLIH
Chicago O'Hare Intl
Wed 11/11
7:20 am-7:30 pm
2 stops16h 10m
Lihue
Sun 11/15
11:45 am-1:17 pm
1 stop21h 32m
$470
ChicagoLihue
ORD Chicago O'Hare Intl - LIH Lihue
ORDLIH
Chicago O'Hare Intl
Tue 10/20
6:20 am-5:36 pm
2 stops16h 16m
Lihue
Mon 10/26
9:53 pm-8:30 pm
2 stops17h 37m
$474
ChicagoLihue
MDW Chicago Midway - LIH Lihue
MDWLIH
Chicago Midway
Thu 10/22
9:29 am-7:14 pm
2 stops14h 45m
Lihue
Mon 10/26
8:48 pm-4:47 pm
2 stops14h 59m
$515
Showing 1-10 of 36 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, October is the cheapest month in which you can book a flight from Chicago to Kaua'i (average of $492). Flying from Chicago to Kaua'i in December is currently the most expensive (average of $928). 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 August 26, 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.
Boarding
8.1
Comfort
8.0
Entertainment
7.5
Food
7.0
Overall
8.0
Crew
8.6
Reviews
1 / 20
10.0
ExcellentAnonymous,Mar 2026
KOA - HNL
Boarding
8.1
Comfort
8.0
Entertainment
7.5
Food
7.0
Overall
8.0
Crew
8.6
Reviews
1 / 20
10.0
ExcellentAnonymous,Mar 2026
KOA - HNL
Boarding
8.1
Comfort
8.0
Entertainment
7.5
Food
7.0
Overall
8.0
Crew
8.6
Reviews
1 / 20
10.0
ExcellentAnonymous,Mar 2026
KOA - HNL
Boarding
8.1
Comfort
8.0
Entertainment
7.5
Food
7.0
Overall
8.0
Crew
8.6
Reviews
1 / 20
10.0
ExcellentAnonymous,Mar 2026
KOA - HNL
Boarding
8.1
Comfort
8.0
Entertainment
7.5
Food
7.0
Overall
8.0
Crew
8.6
Reviews
1 / 20
10.0
ExcellentAnonymous,Mar 2026
KOA - HNL
Boarding
8.1
Comfort
8.0
Entertainment
7.5
Food
7.0
Overall
8.0
Crew
8.6
Reviews
1 / 20
10.0
ExcellentAnonymous,Mar 2026
KOA - HNL
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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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 August 26, 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 7,457,451 searches. Data last updated August 26, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$382 | Average$573 | FlexibilityNo cancel fee | On-time75% | |
| Cheapest$423 | Average$604 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$424 | Average$617 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$424 | Average$552 | FlexibilityNo cancel fee | On-timeN/A |