$180 Cheap flight deals from Chicago (CHI) to Koloa (LIH)

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This Weekend's Flight Deals from Chicago to Koloa

This weekend's flight prices found within the past 7 days, for the period specified. Prices and availability are subject to change. Additional terms apply.

Sat, Feb 28 - Thu, Mar 5
ORD
O'Hare Intl.
LIH
Lihue
$492 Roundtrip, just found
$492
Roundtrip
just found
Select United flight, departing Sat, Feb 28 from O'Hare Intl. to Lihue, returning Thu, Mar 5, priced at $492 just found
Sat, Feb 28 - Sat, Mar 7
MDW
Midway Intl.
LIH
Lihue
$652 Roundtrip, found 19 hours ago
$652
Roundtrip
found 19 hours ago
Select Southwest Airlines flight, departing Sat, Feb 28 from Midway Intl. to Lihue, returning Sat, Mar 7, priced at $652 found 19 hours ago

Airfares from $180 One Way, $409 Round Trip from Chicago to Koloa

Prices starting at $409 for return flights and $180 for one-way flights to Koloa were the cheapest prices found within the past 7 days, for the period specified. Prices and availability are subject to change. Additional terms apply.

Mon, Mar 9 - Tue, Mar 17
ORD
Chicago
LIH
Kauai
$409 Roundtrip, found 19 hours ago
$409
Roundtrip
found 19 hours ago
Select Alaska Airlines flight, departing Mon, Mar 9 from Chicago to Kauai, returning Tue, Mar 17, priced at $409 found 19 hours ago
Mon, Mar 9 - Tue, Mar 17
ORD
Chicago
LIH
Kauai
$410 Roundtrip, found 19 hours ago
$410
Roundtrip
found 19 hours ago
Select Alaska Airlines flight, departing Mon, Mar 9 from Chicago to Kauai, returning Tue, Mar 17, priced at $410 found 19 hours ago
Sun, Jan 10 - Thu, Jan 14
ORD
Chicago
LIH
Kauai
$413 Roundtrip, found 2 days ago
$413
Roundtrip
found 2 days ago
Select Bargain Flight flight, departing Sun, Jan 10 from Chicago to Kauai, returning Thu, Jan 14, priced at $413 found 2 days ago
Mon, Apr 27 - Fri, May 1
ORD
Chicago
LIH
Kauai
$414 Roundtrip, found 4 days ago
$414
Roundtrip
found 4 days ago
Select Alaska Airlines flight, departing Mon, Apr 27 from Chicago to Kauai, returning Fri, May 1, priced at $414 found 4 days ago
Mon, Apr 27 - Fri, May 1
ORD
Chicago
LIH
Kauai
$414 Roundtrip, found 4 days ago
$414
Roundtrip
found 4 days ago
Select Alaska Airlines flight, departing Mon, Apr 27 from Chicago to Kauai, returning Fri, May 1, priced at $414 found 4 days ago

Koloa economy flight packages

Price found within the past 48 hours. Click for updated prices.
Grand Hyatt Kauai Resort and Spa
4.5-star property

Grand Hyatt Kauai Resort and Spa

9.4/10 Exceptional! (1,005 reviews)

Apr 19 - Apr 24

5 night stay

Chicago (CHI) to Lihue (LIH)

American Airlines • Non-stop • Coach

Lihue (LIH) to Chicago (CHI)

Alaska Airlines • Non-stop • Coach
Price was $3,078, price is now $2,149 per person
$2,149
per person
found 1 day ago
The staff here are outstanding (especially Victor at the Front Desk!); they make you feel welcome, relaxed and taken care of. Photos do not do the property justice as not only is it gorgeous but peaceful, and you can hear the waves from just about anywhere. The rooms are spacious, comfortable and clean. The in-room coffee maker makes a nice cup of coffee - perfect for relaxing on the lanai. Make sure you sign up for the classes before arrival as they will enhance your experience. This resort is a true gem, and the only place I stay when visiting Kauai.

Reviewed on Dec 17, 2025

Kiahuna Plantation Resort Kauai by OUTRIGGER
3.0-star property

Kiahuna Plantation Resort Kauai by OUTRIGGER

8.4/10 Very Good! (973 reviews)

Apr 11 - Apr 18

7 night stay

Chicago (CHI) to Lihue (LIH)

United • Non-stop roundtrip • Coach
Save 100% on your flight
Price was $4,062, price is now $2,713 per person
$2,713
per person
found 3 hours ago
The grounds are well maintained, however, the interior of the Condo was in serious need of upgrades and repairs. We have been staying here for years and as of recent they have cut cleaning services to once a week and towel replacement to once every 4 days. It seems that none of the mony received is reinvested into the condos themselves, we will be looking for other accommodations on our next vist.

Reviewed on Jul 23, 2025

Ko'a Kea Resort on Po'ipu Beach
4.5-star property

Ko'a Kea Resort on Po'ipu Beach

9.4/10 Exceptional! (1,001 reviews)

Apr 5 - Apr 11

6 night stay

Chicago (CHI) to Lihue (LIH)

American Airlines • Non-stop • Coach

Lihue (LIH) to Chicago (CHI)

Alaska Airlines • Non-stop • Coach
Price was $4,078, price is now $2,967 per person
$2,967
per person
found 1 day ago
Another place cancelled our reservation and this hotel was kind enough to let five of us stayed in one room that sleeps 3 people. Staff members were very nice and accomodating.

Reviewed on Jan 8, 2026

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More About Flying To Koloa from Chicago

Route Information for Flights from Chicago to Koloa

Origin Airport IATA Code
CHI
Destination Airport IATA Code
LIH
Distance
Direct Flight Airlines
Earliest Flight Arrival
Latest Flight Arrival

Chicago to Koloa

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Fare, taxes & fees: Fares include all taxes and fees, except baggage fees. Rates shown reflect fares found by other Orbitz users over the past 7 days. Due to rapidly changing airline prices & seat availability, these fares may no longer be available.

Refunds/changes/cancellations: Itinerary changes, if permitted for the fare, will have a $30 service fee charged by Orbitz. Additional airline charges may apply.

Other conditions: Schedules, fares and rules are subject to change without notice. Seats are limited and may not be available on all flights/dates or in all markets. Lower fares may be available. Fares will not be honored retroactively or in exchange for any wholly/partially unused ticket. Tickets are non-transferable and non-refundable. Fare rules are provided for the selected itinerary before booking.