$212+ 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 5/1. Fares are subject to change and may not be available on all flights or dates of travel.
LIH — CHI
May 2 — May 91
Round-trip
1 adult, Economy
We work with more than 300 partners to bring you better travel deals
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
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 Kaua'i to Chicago
Cheapest
Best
Last-minute
One-way
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 April 2, 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 April 2, 2026.
This United 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 4/1512:55 pm
LIH
- ORD
1 stop11h 20m
United Airlines
Sun 4/197:00 am
ORD
- LIH
1 stop13h 47m
United Airlines
Deal found 3/30![United Airlines logo]()
$424
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.
Wed 4/158:20 pm
LIH
- ORD
2 stops17h 32m
Delta
Sun 4/197:15 am
ORD
- LIH
1 stop15h 25m
Delta
Deal found 3/30![Delta logo]()
$430
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.
Wed 4/157:10 pm
LIH
- MDW
2 stops12h 55m
Southwest
Sun 4/195:10 am
MDW
- LIH
2 stops16h 00m
Southwest
Deal found 3/31![Southwest 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 4/168:10 pm
LIH
- ORD
1 stop17h 25m
Southwest
Mon 4/206:15 am
ORD
- LIH
2 stops14h 55m
Southwest
Deal found 4/1![Southwest logo]()
$470
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 4/168:10 pm
LIH
- MDW
1 stop12h 00m
Southwest
Mon 4/2010:05 am
MDW
- LIH
1 stop11h 05m
Southwest
Deal found 4/1![Southwest logo]()
$504
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.
Wed 4/159:10 pm
LIH
- ORD
2 stops16h 25m
Southwest
Sun 4/196:15 am
ORD
- LIH
2 stops14h 55m
Southwest
Deal found 3/30![Southwest logo]()
$520
This Alaska Airlines 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 Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 4/2310:26 pm
LIH
- ORD
1 stop13h 30m
Alaska Airlines
Mon 4/278:50 am
ORD
- LIH
1 stop34h 14m
Alaska Airlines
Deal found 4/1![Alaska Airlines logo]()
$530
This Alaska Airlines 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 Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 4/2310:26 pm
LIH
- ORD
1 stop13h 30m
Multiple Airlines
Mon 4/278:50 am
ORD
- LIH
2 stops18h 31m
Multiple Airlines
Deal found 4/1![Multiple Airlines logo]()
$538
This United 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 4/2312:40 pm
LIH
- ORD
1 stop13h 27m
United Airlines
Mon 4/277:00 am
ORD
- LIH
2 stops17h 53m
United Airlines
Deal found 3/31![United Airlines logo]()
$580
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.
Fri 5/229:51 pm
LIH
- ORD
1 stop18h 54m
American Airlines
Sun 5/3110:27 pm
ORD
- LIH
1 stop18h 00m
American Airlines
Deal found 3/30![American Airlines logo]()
$607
This Delta 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/229:55 pm
LIH
- MDW
2 stops15h 01m
Delta
Sun 5/319:22 am
MDW
- LIH
2 stops14h 44m
Delta
Deal found 4/2![Delta logo]()
$703
This Southwest 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 4/128:10 pm
LIH
- MDW
2 stops13h 10m
Southwest
Thu 4/165:25 am
MDW
- LIH
2 stops13h 50m
Southwest
Deal found 3/28![Southwest logo]()
$784
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 April 2, 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 April 2, 2026.
This American Airlines 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 4/162:12 pm
LIH
- ORD
1 stop10h 35m
American Airlines
Mon 4/206:00 am
ORD
- LIH
1 stop11h 22m
American Airlines
Deal found 4/1![American Airlines logo]()
$424
This United 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 4/1512:55 pm
LIH
- ORD
1 stop11h 20m
United Airlines
Sun 4/197:00 am
ORD
- LIH
1 stop13h 47m
United Airlines
Deal found 3/30![United Airlines logo]()
$424
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.
Wed 4/158:20 pm
LIH
- ORD
2 stops17h 32m
Delta
Sun 4/197:15 am
ORD
- LIH
1 stop15h 25m
Delta
Deal found 3/30![Delta logo]()
$430
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 4/168:10 pm
LIH
- ORD
2 stops13h 50m
Southwest
Mon 4/206:15 am
ORD
- LIH
2 stops14h 55m
Southwest
Deal found 4/1![Southwest logo]()
$475
This Alaska Airlines 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 Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 4/2310:26 pm
LIH
- ORD
1 stop13h 30m
Alaska Airlines
Mon 4/278:50 am
ORD
- LIH
1 stop34h 14m
Alaska Airlines
Deal found 4/1![Alaska Airlines logo]()
$530
This Alaska 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 Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 4/2310:26 pm
LIH
- ORD
1 stop13h 30m
Multiple Airlines
Mon 4/278:50 am
ORD
- LIH
2 stops16h 39m
Multiple Airlines
Deal found 3/28![Multiple Airlines logo]()
$560
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.
Wed 4/157:10 pm
LIH
- MDW
2 stops12h 55m
Southwest
Sun 4/199:55 am
MDW
- LIH
1 stop11h 15m
Southwest
Deal found 3/31![Southwest logo]()
$490
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 4/168:10 pm
LIH
- MDW
2 stops12h 35m
Southwest
Mon 4/206:55 am
MDW
- LIH
2 stops14h 15m
Southwest
Deal found 4/1![Southwest logo]()
$515
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 5/229:51 pm
LIH
- ORD
1 stop18h 54m
American Airlines
Sun 5/3110:27 pm
ORD
- LIH
1 stop18h 00m
American Airlines
Deal found 3/29![American Airlines logo]()
$607
This United 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 4/2312:55 pm
LIH
- ORD
1 stop12h 25m
United Airlines
Mon 4/2710:45 pm
ORD
- LIH
1 stop17h 38m
United Airlines
Deal found 3/30![United Airlines logo]()
$636
This Delta 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/229:55 pm
LIH
- MDW
2 stops15h 01m
Delta
Sun 5/319:22 am
MDW
- LIH
2 stops14h 44m
Delta
Deal found 4/2![Delta logo]()
$703
This Southwest 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 4/128:10 pm
LIH
- MDW
2 stops13h 10m
Southwest
Thu 4/165:25 am
MDW
- LIH
2 stops13h 50m
Southwest
Deal found 3/28![Southwest logo]()
$784
Last-minute flights from Kaua'i to ChicagoDiscover last-minute flight deals from Kaua'i to Chicago. Data last updated April 2, 2026 and is based on user searches.
Discover last-minute flight deals from Kaua'i to Chicago. Data last updated April 2, 2026 and is based on user searches.
This Southwest 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 4/128:10 pm
LIH
- MDW
2 stops13h 10m
Southwest
Thu 4/165:25 am
MDW
- LIH
2 stops13h 50m
Southwest
Deal found 3/28![Southwest logo]()
$784
This United 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 4/1512:55 pm
LIH
- ORD
1 stop11h 20m
United Airlines
Sun 4/197:00 am
ORD
- LIH
1 stop13h 47m
United Airlines
Deal found 3/30![United Airlines logo]()
$424
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.
Wed 4/158:20 pm
LIH
- ORD
2 stops17h 32m
Delta
Sun 4/197:15 am
ORD
- LIH
1 stop15h 25m
Delta
Deal found 3/30![Delta logo]()
$430
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.
Wed 4/157:10 pm
LIH
- MDW
2 stops12h 55m
Southwest
Sun 4/195:10 am
MDW
- LIH
2 stops16h 00m
Southwest
Deal found 3/31![Southwest logo]()
$435
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.
Wed 4/159:10 pm
LIH
- ORD
2 stops16h 25m
Southwest
Sun 4/196:15 am
ORD
- LIH
2 stops14h 55m
Southwest
Deal found 3/30![Southwest logo]()
$520
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 4/168:10 pm
LIH
- ORD
1 stop17h 25m
Southwest
Mon 4/206:15 am
ORD
- LIH
2 stops14h 55m
Southwest
Deal found 4/1![Southwest logo]()
$470
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 4/168:10 pm
LIH
- MDW
1 stop12h 00m
Southwest
Mon 4/2010:05 am
MDW
- LIH
1 stop11h 05m
Southwest
Deal found 4/1![Southwest logo]()
$504
This Alaska Airlines 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 Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 4/2310:26 pm
LIH
- ORD
1 stop13h 30m
Alaska Airlines
Mon 4/278:50 am
ORD
- LIH
1 stop34h 14m
Alaska Airlines
Deal found 4/1![Alaska Airlines logo]()
$530
This Alaska Airlines 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 Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 4/2310:26 pm
LIH
- ORD
1 stop13h 30m
Multiple Airlines
Mon 4/278:50 am
ORD
- LIH
2 stops18h 31m
Multiple Airlines
Deal found 4/1![Multiple Airlines logo]()
$538
This United 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 4/2312:40 pm
LIH
- ORD
1 stop13h 27m
United Airlines
Mon 4/277:00 am
ORD
- LIH
2 stops17h 53m
United Airlines
Deal found 3/31![United Airlines logo]()
$580
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.
Fri 5/229:51 pm
LIH
- ORD
1 stop18h 54m
American Airlines
Sun 5/3110:27 pm
ORD
- LIH
1 stop18h 00m
American Airlines
Deal found 3/30![American Airlines logo]()
$607
This Delta 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/229:55 pm
LIH
- MDW
2 stops15h 01m
Delta
Sun 5/319:22 am
MDW
- LIH
2 stops14h 44m
Delta
Deal found 4/2![Delta logo]()
$703
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 April 2, 2026.
Search for one-way flight options from Kaua'i to Chicago. Find affordable one-way fares based on user searches. Data last updated April 2, 2026.
This Alaska 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 Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/11:36 pm
LIH
- ORD
1 stop18h 37m
Alaska Airlines
Deal found 3/31![Alaska Airlines logo]()
$212
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 4/159:10 pm
LIH
- ORD
2 stops16h 25m
Southwest
Deal found 3/29![Southwest logo]()
$218
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.
Sun 7/199:55 pm
LIH
- ORD
2 stops16h 02m
Delta
Deal found 4/1![Delta logo]()
$223
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 5/12:12 pm
LIH
- ORD
1 stop10h 35m
American Airlines
Deal found 3/29![American Airlines logo]()
$236
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 5/19:25 pm
LIH
- MDW
2 stops15h 33m
Delta
Deal found 3/31![Delta logo]()
$239
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.
Wed 4/158:20 pm
LIH
- MDW
2 stops16h 38m
Delta
Deal found 3/29![Delta logo]()
$242
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 4/288:20 pm
LIH
- ORD
2 stops16h 44m
Delta
Deal found 3/28![Delta logo]()
$242
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 4/710:05 pm
LIH
- ORD
2 stops15h 00m
Delta
Deal found 3/29![Delta logo]()
$248
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 5/19:25 pm
LIH
- ORD
2 stops13h 53m
Delta
Deal found 3/31![Delta logo]()
$268
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.
Wed 6/249:40 pm
LIH
- ORD
1 stop19h 46m
American Airlines
Deal found 3/31![American Airlines logo]()
$270
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 4/79:30 pm
LIH
- ORD
1 stop10h 37m
American Airlines
Deal found 3/29![American Airlines logo]()
$286
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.
Sat 5/97:55 pm
LIH
- ORD
2 stops16h 01m
Multiple Airlines
Deal found 3/31![Multiple Airlines logo]()
$292
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 April 2, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $424 (United Airlines) |
One-way from | $212 (Alaska Airlines) |
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 April 2, 2026.
Use the filters below to find and compare flights from Kaua'i to Chicago that are best for you.
Fly from
Fly to
Route
Depart
Return
Cheapest round-trip
Quickest round-trip
LihueChicago
LIH - ORD
LIHORD
Lihue
Thu 4/16
2:12 pm-5:47 am
1 stop10h 35m
Chicago O'Hare Intl
Mon 4/20
6:00 am-12:22 pm
1 stop11h 22m
$424
LihueChicago
LIH - ORD
LIHORD
Lihue
Wed 4/15
12:55 pm-5:15 am
1 stop11h 20m
Chicago O'Hare Intl
Sun 4/19
7:00 am-3:47 pm
1 stop13h 47m
$424
LihueChicago
LIH - ORD
LIHORD
Lihue
Wed 4/15
8:20 pm-6:52 pm
2 stops17h 32m
Chicago O'Hare Intl
Sun 4/19
7:15 am-5:40 pm
1 stop15h 25m
$430
LihueChicago
LIH - ORD
LIHORD
Lihue
Thu 4/16
8:10 pm-3:00 pm
2 stops13h 50m
Chicago O'Hare Intl
Mon 4/20
6:15 am-4:10 pm
2 stops14h 55m
$475
LihueChicago
LIH - MDW
LIHMDW
Lihue
Wed 4/15
7:10 pm-1:05 pm
2 stops12h 55m
Chicago Midway
Sun 4/19
9:55 am-4:10 pm
1 stop11h 15m
$490
LihueChicago
LIH - MDW
LIHMDW
Lihue
Thu 4/16
8:10 pm-1:45 pm
2 stops12h 35m
Chicago Midway
Mon 4/20
6:55 am-4:10 pm
2 stops14h 15m
$515
LihueChicago
LIH - ORD
LIHORD
Lihue
Thu 4/23
10:26 pm-4:56 pm
1 stop13h 30m
Chicago O'Hare Intl
Mon 4/27
8:50 am-2:04 pm
1 stop34h 14m
$530
LihueChicago
LIH - ORD
LIHORD
Lihue
Thu 4/23
10:26 pm-4:56 pm
1 stop13h 30m
Chicago O'Hare Intl
Mon 4/27
8:50 am-8:29 pm
2 stops16h 39m
$560
LihueChicago
LIH - ORD
LIHORD
Lihue
Fri 5/22
9:51 pm-9:45 pm
1 stop18h 54m
Chicago O'Hare Intl
Sun 5/31
10:27 pm-11:27 am
1 stop18h 00m
$607
LihueChicago
LIH - ORD
LIHORD
Lihue
Thu 4/23
12:55 pm-6:20 am
1 stop12h 25m
Chicago O'Hare Intl
Mon 4/27
10:45 pm-11:23 am
1 stop17h 38m
$636
Showing 1-10 of 28 resultsSorted by cheapest first
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 April 2, 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.
Crew
8.1
Entertainment
7.1
Overall
7.4
Comfort
7.3
Boarding
7.7
Food
6.6
Reviews
1 / 20
8.0
ExcellentAnonymous,Oct 2025
YUL - ORD
Crew
8.1
Entertainment
7.1
Overall
7.4
Comfort
7.3
Boarding
7.7
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
Browse thousands of different options on Cheapflights for your next trip
Toggle through the tabs below to find thousands of options on Cheapflights for your next trip.
Alternative routes
Chicago flight routes
Complete your trip
Flights by cabin class
Other flight options
Popular flights
Alternative routes for Kaua'i to Chicago
See prices for flight routes from nearby airports that may be better suited for you.
Other flights to Chicago
Explore flights to Chicago departing from other origins. Flights are based on user searches made on Cheapflights and were last updated on April 2, 2026.
Complete your trip
Complete your trip to Chicago by adding a car rental and/or hotel reservation to your travel itinerary.
Search flights from Kaua'i to Chicago by cabin class
Find flights from Kaua'i to Chicago, based on your preferred cabin class, be it economy, premium economy, business, or first class.
Kaua'i and Chicago flights
Browse other Kaua'i and Chicago flight options. Last updated on April 2, 2026.
Popular flight searches
Check out other popular destinations found by fellow travelers in 2026
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 April 2, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$468 | Average$651 | FlexibilityNo cancel fee | On-time69% |