$212 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.

Fri, Apr 10 - Sun, Apr 19
ORD
O'Hare Intl.
LIH
Lihue
$498 Roundtrip, found 11 hours ago
$498
Roundtrip
found 11 hours ago
Select American Airlines flight, departing Fri, Apr 10 from O'Hare Intl. to Lihue, returning Sun, Apr 19, priced at $498 found 11 hours ago

Airfares from $212 One Way, $424 Round Trip from Chicago to Koloa

Prices starting at $424 for return flights and $212 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.

Fri, Nov 27 - Wed, Dec 2
ORD
Chicago
LIH
Kauai
$424 Roundtrip, found 2 hours ago
$424
Roundtrip
found 2 hours ago
Select American Airlines flight, departing Fri, Nov 27 from Chicago to Kauai, returning Wed, Dec 2, priced at $424 found 2 hours ago
Tue, Oct 27 - Fri, Nov 6
ORD
Chicago
LIH
Kauai
$424 Roundtrip, found 5 days ago
$424
Roundtrip
found 5 days ago
Select United flight, departing Tue, Oct 27 from Chicago to Kauai, returning Fri, Nov 6, priced at $424 found 5 days ago
Thu, Aug 20 - Tue, Aug 25
ORD
Chicago
LIH
Kauai
$431 Roundtrip, found 1 day ago
$431
Roundtrip
found 1 day ago
Select Delta flight, departing Thu, Aug 20 from Chicago to Kauai, returning Tue, Aug 25, priced at $431 found 1 day ago
Fri, Nov 27 - Wed, Dec 2
ORD
Chicago
LIH
Kauai
$434 Roundtrip, found 2 hours ago
$434
Roundtrip
found 2 hours ago
Select American Airlines flight, departing Fri, Nov 27 from Chicago to Kauai, returning Wed, Dec 2, priced at $434 found 2 hours ago
Wed, Feb 17 - Wed, Feb 24
ORD
Chicago
LIH
Kauai
$436 Roundtrip, found 2 days ago
$436
Roundtrip
found 2 days ago
Select American Airlines flight, departing Wed, Feb 17 from Chicago to Kauai, returning Wed, Feb 24, priced at $436 found 2 days ago

Koloa economy flight packages

Price found within the past 48 hours. Click for updated prices.
2417 at Lihue Oceanfront Resort
3.5-star property

2417 at Lihue Oceanfront Resort

7/10 Good! (63 reviews)

May 28 - Jun 2

5 night stay

Chicago (ORD) to Lihue (LIH)

United • Non-stop roundtrip • Coach
Price was $1,637, price is now $1,208 per person
$1,208
per person
just found
The facilities were nice, it was a bit frustrating in getting around, it was advertised that there was airport pick up and shuttles to the local shopping centers, but there was not. I didn't rent a car but should have, parking was so expensive, ubers were so expensive and food at the hotel was so expensive. The restaurants would were not accommodating, I brought my grand daughter and she was getting a little home sick and really wanted to have comfort food, but she was too old for the chicken strips and the waiter would not get them for her. He said if he gave her them he would have to charge her more. She would have been happy to get the child's portion.

Reviewed on Jun 26, 2019

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)

May 16 - May 21

5 night stay

Chicago (CHI) to Lihue (LIH)

Southwest Airlines • Non-stop • Coach

Lihue (LIH) to Chicago (CHI)

Delta • Non-stop • Coach
Save 100% on your flight
Price was $2,987, price is now $2,052 per person
$2,052
per person
found 24 hours 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

Waipouli Beach Resorts & Spa Kauai by OUTRIGGER
4.0-star property

Waipouli Beach Resorts & Spa Kauai by OUTRIGGER

8.8/10 Excellent! (1,003 reviews)

May 28 - Jun 2

5 night stay

Chicago (ORD) to Lihue (LIH)

United • Non-stop roundtrip • Coach
Save 100% on your flight
Price was $2,498, price is now $1,766 per person
$1,766
per person
just found
We will liked the condo and how it was layed out and it was convenient to the pool/ocean/parking/etc. I wish there would have been more conveniences in the condo itself (examples: hair dryer, pool toys, cooler, more pans & accessories in the kitchen). We had a great time and loved how quiet and safe it was!

Reviewed on Jan 5, 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.