$176+ Cheap flights from Kaua'i to Chicago (CHI)
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 4/15. Fares are subject to change and may not be available on all flights or dates of travel.
LIH — CHI
Mar 16 — Mar 231
1 adult, Economy
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Find cheap flights from Kaua'i to Chicago 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 Kaua'i to ChicagoExplore the most affordable flight options available from Kaua'i to Chicago. Find the lowest fares from popular airlines and budget airlines, with prices last updated on February 14, 2026.
Explore the most affordable flight options available from Kaua'i to Chicago. Find the lowest fares from popular airlines and budget airlines, with prices last updated on February 14, 2026.
This Kiwi.com deal was found by Cheapflights users on 2/11. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 2/277:45 pm
LIH
- ORD
2 stops13h 26m
Multiple Airlines
Tue 3/37:00 am
ORD
- LIH
1 stop12h 50m
Multiple Airlines
Deal found 2/11![Multiple Airlines logo]()
$438
This United Airlines deal was found by Cheapflights users on 2/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 2/248:40 pm
LIH
- ORD
1 stop10h 39m
United Airlines
Sat 2/282:35 pm
ORD
- LIH
1 stop12h 09m
United Airlines
Deal found 2/9![United Airlines logo]()
$454
This American Airlines deal was found by Cheapflights users on 2/11. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 2/2710:30 pm
LIH
- ORD
1 stop12h 23m
American Airlines
Tue 3/37:00 am
ORD
- LIH
1 stop14h 14m
American Airlines
Deal found 2/11![American Airlines logo]()
$464
This American Airlines deal was found by Cheapflights users on 2/11. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 6/312:56 pm
LIH
- ORD
1 stop13h 19m
American Airlines
Mon 6/156:00 am
ORD
- LIH
1 stop19h 38m
American Airlines
Deal found 2/11![American Airlines logo]()
$492
This Alaska Airlines deal was found by Cheapflights users on 2/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 2/2611:19 pm
LIH
- ORD
1 stop10h 52m
Multiple Airlines
Mon 3/28:20 am
ORD
- LIH
2 stops27h 42m
Multiple Airlines
Deal found 2/9![Multiple Airlines logo]()
$495
This Alaska Airlines deal was found by Cheapflights users on 2/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 2/2611:19 pm
LIH
- ORD
1 stop10h 52m
Alaska Airlines
Mon 3/28:20 am
ORD
- LIH
1 stop32h 27m
Alaska Airlines
Deal found 2/9![Alaska Airlines logo]()
$503
This Expedia deal was found by Cheapflights users on 2/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 2/241:33 pm
LIH
- ORD
2 stops21h 25m
Multiple Airlines
Sat 2/282:07 pm
ORD
- LIH
2 stops20h 10m
Multiple Airlines
Deal found 2/9![Multiple Airlines logo]()
$510
This Delta deal was found by Cheapflights users on 2/12. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/229:40 pm
LIH
- ORD
1 stop10h 53m
Delta
Sun 5/3112:47 pm
ORD
- LIH
1 stop11h 19m
Delta
Deal found 2/12![Delta logo]()
$534
This Delta deal was found by Cheapflights users on 2/11. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 2/279:20 pm
LIH
- MDW
2 stops14h 54m
Delta
Tue 3/36:00 am
MDW
- LIH
2 stops18h 28m
Delta
Deal found 2/11![Delta logo]()
$638
This Southwest deal was found by Cheapflights users on 2/11. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 2/279:15 pm
LIH
- MDW
1 stop16h 05m
Southwest
Tue 3/35:05 am
MDW
- LIH
2 stops15h 20m
Southwest
Deal found 2/11![Southwest logo]()
$656
This Delta deal was found by Cheapflights users on 2/13. 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 5/228:31 pm
LIH
- MDW
2 stops16h 43m
Delta
Sun 5/319:23 am
MDW
- LIH
2 stops13h 17m
Delta
Deal found 2/13![Delta logo]()
$825
Best flights from Kaua'i to ChicagoDiscover carefully curated flight deals from Kaua'i to Chicago that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated February 14, 2026.
Discover carefully curated flight deals from Kaua'i to Chicago that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated February 14, 2026.
This Kiwi.com deal was found by Cheapflights users on 2/11. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 2/277:45 pm
LIH
- ORD
2 stops13h 26m
Multiple Airlines
Tue 3/37:00 am
ORD
- LIH
1 stop12h 50m
Multiple Airlines
Deal found 2/11![Multiple Airlines logo]()
$438
This United Airlines deal was found by Cheapflights users on 2/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 2/248:40 pm
LIH
- ORD
1 stop10h 39m
United Airlines
Sat 2/282:35 pm
ORD
- LIH
1 stop12h 09m
United Airlines
Deal found 2/9![United Airlines logo]()
$454
This American Airlines deal was found by Cheapflights users on 2/11. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 2/2710:30 pm
LIH
- ORD
1 stop12h 23m
American Airlines
Tue 3/37:00 am
ORD
- LIH
1 stop14h 14m
American Airlines
Deal found 2/11![American Airlines logo]()
$464
This Alaska Airlines deal was found by Cheapflights users on 2/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 2/2611:19 pm
LIH
- ORD
1 stop10h 52m
Alaska Airlines
Mon 3/28:20 am
ORD
- LIH
1 stop32h 27m
Alaska Airlines
Deal found 2/9![Alaska Airlines logo]()
$503
This Delta deal was found by Cheapflights users on 2/12. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/229:40 pm
LIH
- ORD
1 stop10h 53m
Delta
Sun 5/3112:47 pm
ORD
- LIH
1 stop11h 19m
Delta
Deal found 2/12![Delta logo]()
$534
This Southwest deal was found by Cheapflights users on 2/11. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 2/279:15 pm
LIH
- MDW
1 stop16h 05m
Southwest
Tue 3/35:05 am
MDW
- LIH
2 stops15h 20m
Southwest
Deal found 2/11![Southwest logo]()
$656
This American Airlines deal was found by Cheapflights users on 2/11. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 6/312:56 pm
LIH
- ORD
1 stop13h 19m
American Airlines
Mon 6/156:00 am
ORD
- LIH
1 stop19h 38m
American Airlines
Deal found 2/11![American Airlines logo]()
$492
This Alaska Airlines deal was found by Cheapflights users on 2/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 2/2611:19 pm
LIH
- ORD
1 stop10h 52m
Multiple Airlines
Mon 3/28:20 am
ORD
- LIH
2 stops27h 42m
Multiple Airlines
Deal found 2/9![Multiple Airlines logo]()
$495
This Expedia deal was found by Cheapflights users on 2/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 2/241:33 pm
LIH
- ORD
2 stops21h 25m
Multiple Airlines
Sat 2/282:07 pm
ORD
- LIH
2 stops20h 10m
Multiple Airlines
Deal found 2/9![Multiple Airlines logo]()
$510
This Delta deal was found by Cheapflights users on 2/11. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 2/279:20 pm
LIH
- MDW
2 stops14h 54m
Delta
Tue 3/36:00 am
MDW
- LIH
2 stops18h 28m
Delta
Deal found 2/11![Delta logo]()
$638
This Delta deal was found by Cheapflights users on 2/12. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/228:31 pm
LIH
- MDW
2 stops16h 43m
Delta
Sun 5/319:23 am
MDW
- LIH
2 stops13h 17m
Delta
Deal found 2/12![Delta logo]()
$825
Last-minute flights from Kaua'i to ChicagoDiscover last-minute flight deals from Kaua'i to Chicago. Data last updated February 14, 2026 and is based on user searches.
Discover last-minute flight deals from Kaua'i to Chicago. Data last updated February 14, 2026 and is based on user searches.
This United Airlines deal was found by Cheapflights users on 2/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 2/248:40 pm
LIH
- ORD
1 stop10h 39m
United Airlines
Sat 2/282:35 pm
ORD
- LIH
1 stop12h 09m
United Airlines
Deal found 2/9![United Airlines logo]()
$454
This Expedia deal was found by Cheapflights users on 2/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 2/241:33 pm
LIH
- ORD
2 stops21h 25m
Multiple Airlines
Sat 2/282:07 pm
ORD
- LIH
2 stops20h 10m
Multiple Airlines
Deal found 2/9![Multiple Airlines logo]()
$510
This Alaska Airlines deal was found by Cheapflights users on 2/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 2/2611:19 pm
LIH
- ORD
1 stop10h 52m
Multiple Airlines
Mon 3/28:20 am
ORD
- LIH
2 stops27h 42m
Multiple Airlines
Deal found 2/9![Multiple Airlines logo]()
$495
This Alaska Airlines deal was found by Cheapflights users on 2/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 2/2611:19 pm
LIH
- ORD
1 stop10h 52m
Alaska Airlines
Mon 3/28:20 am
ORD
- LIH
1 stop32h 27m
Alaska Airlines
Deal found 2/9![Alaska Airlines logo]()
$503
This United Airlines deal was found by Cheapflights users on 2/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 2/268:40 pm
LIH
- ORD
1 stop10h 39m
United Airlines
Mon 3/27:10 am
ORD
- LIH
1 stop13h 54m
United Airlines
Deal found 2/10![United Airlines logo]()
$574
This Kiwi.com deal was found by Cheapflights users on 2/11. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 2/277:45 pm
LIH
- ORD
2 stops13h 26m
Multiple Airlines
Tue 3/37:00 am
ORD
- LIH
1 stop12h 50m
Multiple Airlines
Deal found 2/11![Multiple Airlines logo]()
$438
This American Airlines deal was found by Cheapflights users on 2/11. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 2/2710:30 pm
LIH
- ORD
1 stop12h 23m
American Airlines
Tue 3/37:00 am
ORD
- LIH
1 stop14h 14m
American Airlines
Deal found 2/11![American Airlines logo]()
$464
This Delta deal was found by Cheapflights users on 2/11. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 2/279:20 pm
LIH
- MDW
2 stops14h 54m
Delta
Tue 3/36:00 am
MDW
- LIH
2 stops18h 28m
Delta
Deal found 2/11![Delta logo]()
$638
This Southwest deal was found by Cheapflights users on 2/11. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 2/279:15 pm
LIH
- MDW
1 stop16h 05m
Southwest
Tue 3/35:05 am
MDW
- LIH
2 stops15h 20m
Southwest
Deal found 2/11![Southwest logo]()
$656
One-way flights from Kaua'i to ChicagoSearch for one-way flight options from Kaua'i to Chicago. Find affordable one-way fares based on user searches. Data last updated February 14, 2026.
Search for one-way flight options from Kaua'i to Chicago. Find affordable one-way fares based on user searches. Data last updated February 14, 2026.
This Kiwi.com deal was found by Cheapflights users on 2/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 4/156:00 am
LIH
- ORD
2 stops18h 50m
Multiple Airlines
Deal found 2/10![Multiple Airlines logo]()
$176
This Kiwi.com deal was found by Cheapflights users on 2/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 4/159:00 pm
LIH
- MDW
3 stops36h 49m
Multiple Airlines
Deal found 2/10![Multiple Airlines logo]()
$184
This American Airlines deal was found by Cheapflights users on 2/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 4/152:12 pm
LIH
- ORD
1 stop10h 35m
American Airlines
Deal found 2/10![American Airlines logo]()
$211
This American Airlines deal was found by Cheapflights users on 2/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 3/169:30 pm
LIH
- ORD
1 stop10h 42m
American Airlines
Deal found 2/10![American Airlines logo]()
$212
This Kiwi.com deal was found by Cheapflights users on 2/11. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 3/166:32 pm
LIH
- ORD
2 stops29h 17m
Multiple Airlines
Deal found 2/11![Multiple Airlines logo]()
$221
This Expedia deal was found by Cheapflights users on 2/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 3/123:50 pm
LIH
- ORD
1 stop27h 09m
Alaska Airlines
Deal found 2/10![Alaska Airlines logo]()
$223
This Delta deal was found by Cheapflights users on 2/11. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 3/1210:05 pm
LIH
- ORD
2 stops18h 29m
Delta
Deal found 2/11![Delta logo]()
$228
This American Airlines deal was found by Cheapflights users on 2/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/12:12 pm
LIH
- ORD
1 stop10h 35m
American Airlines
Deal found 2/10![American Airlines logo]()
$240
This Delta deal was found by Cheapflights users on 2/12. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/18:20 pm
LIH
- ORD
1 stop12h 03m
Delta
Deal found 2/12![Delta logo]()
$242
This Alaska Airlines deal was found by Cheapflights users on 2/11. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 3/163:50 pm
LIH
- ORD
2 stops19h 43m
Alaska Airlines
Deal found 2/11![Alaska Airlines logo]()
$243
This Delta deal was found by Cheapflights users on 2/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 7/89:26 pm
LIH
- ORD
1 stop11h 34m
Delta
Deal found 2/10![Delta logo]()
$244
This Kiwi.com deal was found by Cheapflights users on 2/11. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 3/166:32 pm
LIH
- MDW
3 stops46h 47m
Multiple Airlines
Deal found 2/11![Multiple Airlines logo]()
$259
Find flight deals from Kaua'i to Chicago
Keep the following information in mind while searching for Kaua'i to Chicago flight deals. Data was last updated February 14, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $438 (Kiwi.com) |
One-way from | $176 (Kiwi.com) |
Cheapflights Fare Finder
Customize your flight search to find flights from Kaua'i to Chicago that fit within your specific budget. Explore options based on user searches and filter the results based on your desired price range. Find flights that match your budget for a cost-effective journey. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated February 14, 2026.
Use the filters below to find and compare flights from Kaua'i to Chicago that are best for you.
Fly from
Kaua'i
Fly to
Chicago
Route
Depart
Return
Price
LihueChicago
LIH - ORD
LIHORD
Lihue
Fri 2/27
7:45 pm-1:11 pm
2 stops13h 26m
Chicago O'Hare Intl
Tue 3/3
7:00 am-3:50 pm
1 stop12h 50m
$438
LihueChicago
LIH - ORD
LIHORD
Lihue
Tue 2/24
8:40 pm-11:19 am
1 stop10h 39m
Chicago O'Hare Intl
Sat 2/28
2:35 pm-10:44 pm
1 stop12h 09m
$454
LihueChicago
LIH - ORD
LIHORD
Lihue
Fri 2/27
10:30 pm-2:53 pm
1 stop12h 23m
Chicago O'Hare Intl
Tue 3/3
7:00 am-5:14 pm
1 stop14h 14m
$464
LihueChicago
LIH - ORD
LIHORD
Lihue
Wed 6/3
12:56 pm-7:15 am
1 stop13h 19m
Chicago O'Hare Intl
Mon 6/15
6:00 am-8:38 pm
1 stop19h 38m
$492
LihueChicago
LIH - ORD
LIHORD
Lihue
Thu 2/26
11:19 pm-2:11 pm
1 stop10h 52m
Chicago O'Hare Intl
Mon 3/2
8:20 am-8:02 am
2 stops27h 42m
$495
LihueChicago
LIH - ORD
LIHORD
Lihue
Thu 2/26
11:19 pm-2:11 pm
1 stop10h 52m
Chicago O'Hare Intl
Mon 3/2
8:20 am-12:47 pm
1 stop32h 27m
$503
LihueChicago
LIH - ORD
LIHORD
Lihue
Tue 2/24
1:33 pm-2:58 pm
2 stops21h 25m
Chicago O'Hare Intl
Sat 2/28
2:07 pm-6:17 am
2 stops20h 10m
$510
LihueChicago
LIH - ORD
LIHORD
Lihue
Fri 5/22
9:40 pm-1:33 pm
1 stop10h 53m
Chicago O'Hare Intl
Sun 5/31
12:47 pm-7:06 pm
1 stop11h 19m
$534
LihueChicago
LIH - MDW
LIHMDW
Lihue
Fri 2/27
9:20 pm-4:14 pm
2 stops14h 54m
Chicago Midway
Tue 3/3
6:00 am-8:28 pm
2 stops18h 28m
$638
LihueChicago
LIH - MDW
LIHMDW
Lihue
Fri 2/27
9:15 pm-5:20 pm
1 stop16h 05m
Chicago Midway
Tue 3/3
5:05 am-4:25 pm
2 stops15h 20m
$656
Showing 1-10 of 31 results
Best time to book a flight from Kaua'i to Chicago
Have a flexible travel schedule? Discover the best time to fly to Chicago from Kaua'i with our price prediction graph.
LIH-ORD
LIH-MDW
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 Kaua'i to Chicago
zzFUS-CHI
LIH-ORD
LIH-MDW
No data available for this route at this time. Please check back soon.
Reviews of airlines servicing Chicago
Get insights into the airlines that provide service to Chicago. 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 Chicago. Reviews last updated February 14, 2026.
Read reviews from past customers who have flown United Airlines from Kaua'i to Chicago. You can also see how each airline compares in terms of entertainment options, comfort, food, crew/service, and boarding process.
Overall
7.4
Entertainment
7.1
Boarding
7.7
Crew
8.1
Comfort
7.3
Food
6.6
Reviews
1 / 20
8.0
ExcellentAnonymous,Oct 2025
YUL - ORD
Overall
7.4
Entertainment
7.1
Boarding
7.7
Crew
8.1
Comfort
7.3
Food
6.6
Reviews
1 / 20
8.0
ExcellentAnonymous,Oct 2025
YUL - ORD
Related info for your journey
Find useful and relevant information for your journey from Kaua'i to Chicago. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.
Traveling to a place near Chicago?
Book flights to Chicago if you plan to visit one of these locationsLansing
Merrillville
Hammond
Porter
Benton Harbor
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Top airline flying from Kaua'i to Chicago
Discover the top airline that operate flights from Kaua'i to Chicago. Compare their services, reliability, and customer satisfaction ratings to choose the airline that best suits your travel preferences and needs. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated February 14, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$410 | Average$651 | FlexibilityNo cancel fee | On-time69% |