$148 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, Dec 6 - Wed, Dec 17
ORD
O'Hare Intl.
LIH
Lihue
$453 Roundtrip, found 3 days ago
$453
Roundtrip
found 3 days ago
Select Delta flight, departing Sat, Dec 6 from O'Hare Intl. to Lihue, returning Wed, Dec 17, priced at $453 found 3 days ago

Airfares from $148 One Way, $277 Round Trip from Chicago to Koloa

Prices starting at $277 for return flights and $148 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.

Tue, Feb 3 - Tue, Feb 10
ORD
Chicago
LIH
Kauai
$277 Roundtrip, found 16 hours ago
$277
Roundtrip
found 16 hours ago
Select Alaska Airlines flight, departing Tue, Feb 3 from Chicago to Kauai, returning Tue, Feb 10, priced at $277 found 16 hours ago
Wed, Feb 25 - Tue, Mar 3
ORD
Chicago
LIH
Kauai
$284 Roundtrip, found 13 hours ago
$284
Roundtrip
found 13 hours ago
Select Alaska Airlines flight, departing Wed, Feb 25 from Chicago to Kauai, returning Tue, Mar 3, priced at $284 found 13 hours ago
Wed, Feb 25 - Tue, Mar 3
ORD
Chicago
LIH
Kauai
$285 Roundtrip, found 13 hours ago
$285
Roundtrip
found 13 hours ago
Select Alaska Airlines flight, departing Wed, Feb 25 from Chicago to Kauai, returning Tue, Mar 3, priced at $285 found 13 hours ago
Wed, Feb 25 - Tue, Mar 3
ORD
Chicago
LIH
Kauai
$285 Roundtrip, found 13 hours ago
$285
Roundtrip
found 13 hours ago
Select Alaska Airlines flight, departing Wed, Feb 25 from Chicago to Kauai, returning Tue, Mar 3, priced at $285 found 13 hours ago
Sun, Jan 18 - Tue, Jan 27
ORD
Chicago
LIH
Kauai
$381 Roundtrip, found 3 days ago
$381
Roundtrip
found 3 days ago
Select Hawaiian Airlines flight, departing Sun, Jan 18 from Chicago to Kauai, returning Tue, Jan 27, priced at $381 found 3 days ago

Koloa economy flight packages

Price found within the past 48 hours. Click for updated prices.
Hanalei Colony Resort
3.5-star property

Hanalei Colony Resort

9.2/10 Wonderful! (624 reviews)

Jan 18 - Jan 26

8 night stay

Chicago (CHI) to Lihue (LIH)

Alaska Airlines • Non-stop roundtrip • Coach
Save 100% on your flight
Price was $2,800, price is now $1,819 per person
$1,819
per person
found 1 hour ago
Awesome place to stay. Good bbq areas, pool, hot tub, and a great place to sit and watch the sunrise over the ocean. Beach access is awesome. Staff was very friendly and helpful.

Reviewed on Apr 4, 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)

Jan 18 - Jan 26

8 night stay

Chicago (CHI) to Lihue (LIH)

Alaska Airlines • Non-stop roundtrip • Coach
Save 100% on your flight
Price was $4,419, price is now $2,697 per person
$2,697
per person
found 1 hour ago
We loved that we could walk to the beach very easily. There are daily activities like yoga, ukulele lessons, etc. The pool and hot tub were nice especially after a day of hiking or surfing. The staff was great, they gave great recommendation on places to see on the island. There was only 2 downsides, one was how expensive the food at the restaurant is in comparison to other places around the island, including other resort restaurants. Second is that the parking is $40/day unless you park the car along the main road and walk back to the resort, which we were never told and figured out ourselves the second to last day we were there. Nonetheless this is a perfect place if you want a relaxing quiet space to vacation. It does not get rowdy, that’s not the vibe as all.

Reviewed on Mar 26, 2025

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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.